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Frictionless, Artificial Organizations: Measuring What Matters in the Age of AI

Tue, 03 Mar 2026 21:26:00 -0400

AI can now generate code in seconds. Deployment pipelines are faster than ever. And yet, many teams still feel slow.

In this episode, I sit down with Nicole Forsgren, world-renowned researcher, co-author of Accelerate, and Senior Director of Developer Intelligence at Google. We explore why speed alone doesn’t create performance — and how hidden friction inside systems, culture, and decision-making quietly holds teams back.

Nicole breaks down the SPACE framework, explains why activity metrics create blind spots, and challenges leaders to rethink what productivity really means in the era of AI agents. If you're measuring output but still not seeing impact, this conversation will help you recalibrate.

Key Takeaways

Productivity is multidimensional, not just output: Measuring activity alone creates blind spots. Real performance includes satisfaction, quality, collaboration, and flow.
System constraints determine team speed: Improving individual teams isn’t enough. Performance improves only when bottlenecks across the entire value stream are addressed.
AI accelerates existing systems: Automation increases throughput, but it doesn’t remove friction. Weak processes and structural gaps become more visible as speed increases.
Trust becomes a performance factor in AI workflows: As agents contribute to development, validation systems, guardrails, and confidence mechanisms become essential.
Strategy must come before acceleration: Building the wrong thing faster does not create value. Leaders must define direction before optimizing delivery.

Additional Insights

Organizations scrutinize AI more than human decisions: We often ask whether AI is producing the right output. Yet we rarely question whether human teams are building the right thing either.
AI forces leaders to clarify judgment: Working with agents requires teams to make their assumptions explicit by defining heuristics, edge cases, and decision rules that previously lived in intuition.
Many bottlenecks are decision bottlenecks: Delays often come from postponed decisions, including security reviews, approvals, and quality checks placed late in the workflow.
AI exposes the limits of existing infrastructure: Faster development cycles put pressure on testing systems, CI/CD pipelines, and operational workflows designed for slower environments.

Episode Highlights

00:00 – Episode Recap

Even as AI accelerates development, many teams feel slower than ever — revealing that friction isn’t about code speed but about how systems, culture, and decisions are designed.

02:38 – Guest Introduction: Nicole Forsgren

Barry introduces Nicole Forsgren — researcher, co-author of Accelerate, and Senior Director of Developer Intelligence at Google — whose work has redefined how technology performance is measured.

07:08 – The SPACE Framework Explained

Nicole breaks down Satisfaction, Performance, Activity, Communication, and Efficiency — a practical guardrail to measure productivity across multiple dimensions.

10:19 – Why Optimizing Locally Creates Bottlenecks

Teams often improve within their own scope, only to worsen constraints elsewhere in the system. Real performance requires zooming out.

12:37 – Simple Surveys That Surface Hidden Friction

A few focused questions can quickly reveal productivity barriers — especially when frequency of disruption is measured alongside frustration.

15:51 – Culture, Curiosity, and System Design

Most structural problems come from rational past decisions. Approaching friction with curiosity — not blame — creates safety and clarity.

18:07 – Moving Decisions Upstream

From flaky tests to security reviews, many delays are postponed decisions. The opportunity is shifting confidence-building earlier in the workflow.

22:18 – Making Implicit Judgment Explicit

AI agents force leaders to articulate the heuristics and assumptions they previously ran on instinct — improving both human and machine judgment.

25:48 – Are Humans Building the Right Thing?

We question AI correctness — but rarely apply the same scrutiny to human output. Strategy clarity remains a leadership responsibility.

30:01 – AI Amplifies Existing Bottlenecks

As agents increase throughput, weaknesses in pipelines, testing, and infrastructure become more visible — and more urgent.

32:05 – Removing Friction to Unlock Real Performance

True competitive advantage comes from redesigning systems of work — not just accelerating output.

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Artificial Organizations: Judgment at Speed in the Age of AI

Tue, 17 Feb 2026 21:36:00 -0400

AI isn’t about productivity. It’s about presence.

In this special episode, the tables turn and I’m interviewed by Sham Colegado about my new book, Artificial Organizations. We explore why 95% of AI projects fail, why executives don’t want more tools — they want their life back — and how the real competitive edge isn’t automation, but judgment at speed.

If you’ve been overwhelmed by the explosion of AI tools or unsure where to start, this episode will help you reframe the conversation. This isn’t about doing more. It’s about deciding better — faster, with clarity and confidence — by combining human instinct with machine intelligence.

Key Takeaways

AI Used Only for Productivity Fails: When AI is treated as a cost-cutting tool instead of a transformation system, it rarely creates lasting value.
Presence Is the Real Advantage: The goal isn’t more output. It’s showing up calmer, clearer, and better prepared — so decisions improve.
Decision Velocity + Decision Advantage Wins: Make decisions faster and with better information. Speed without clarity is noise. Clarity without speed is stagnation.
The Future Belongs to Human + Machine Judgment: Executives who combine instinct with machine intelligence will outperform those relying on either alone.

Additional Insights

Executives Don’t Want More Tools — They Want Their Life Back: Leaders aren’t overwhelmed by lack of tools. They’re overwhelmed by fragmented workflows, constant context switching, and decision fatigue. AI must reduce cognitive load, not add to it.
Presence Drives Performance: When AI handles capture and synthesis, leaders show up calmer, more prepared, and more focused. Productivity improves — but performance and clarity are the real unlock.
The Identity Threat of AI: Many executives privately fear incompetence. They don’t want to look behind or uninformed. That hesitation often shows up as skepticism or avoidance.
Decision Velocity Is the New Differentiator: Artificial organizations move faster because they reduce decision latency. Meetings become focused. Context is pre-loaded. Choices are made with confidence.
Traits + Tasks + Tools (T3 Model): Start with how you naturally work best. Then amplify your highest-leverage tasks with the right tools.
Capture, Transcribe, Synthesize, Act: A simple workflow that turns every conversation into a reusable data asset. This loop compounds judgment and accelerates learning over time.

Episode Highlights

00:00 – Episode Recap

Barry explains why AI used purely for productivity fails — and why the real advantage comes from transforming how leaders make decisions.

02:58 – Guest Introduction: Sham Colegado

Barry welcomes Sham Colegado, a key member of the Artificial Organizations team, who interviews Barry about the book and its core ideas.

03:32 – “Executives Don’t Want More AI Tools”

Barry shares the personal burnout moment that sparked a shift from productivity chasing to rethinking how he works.

06:02 – AI’s Real Promise: Presence Over Productivity

Why performance and clarity matter more than output — and how AI can make leaders calmer and more focused.

09:30 – The Identity Threat of AI

Executives reveal a hidden fear of incompetence and why one-on-one learning environments matter.

12:26 – Decision Velocity & Decision Advantage

The two engines of artificial organizations and how reducing decision latency compounds competitive advantage.

15:15 – The Traits, Tasks, Tools Flywheel

How aligning natural strengths with high-leverage work determines which AI tools actually create impact.

19:01 – What the Best AI Adopters Do Differently

Curiosity, experimentation, and comfort with discomfort separate leaders who accelerate from those who stall.

22:46 – The First Workflow to Build

Capture → Transcribe → Synthesize → Act — a simple loop that transforms meetings into strategic assets.

26:05 – The Executive of the Future

The most valuable leaders won’t rely on instinct alone — they’ll pair judgment with machine intelligence to make better decisions faster.

Useful Resources

Artificial Organizations (Book) – https://artificialorganizations.com
Barry O’Reilly – https://barryoreilly.com

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Unlearning Perfectionism While Building Products That Last with Gerry Khouri

Tue, 03 Feb 2026 20:47:00 -0400

What if success isn’t about scaling faster, shipping more, or chasing perfection — but about building something so honest it can last for generations?

In this episode, I sit down with Gerry Khouri, Founder & Managing Director of Bufori, one of the world’s longest-running handcrafted automobile companies. For nearly 40 years, Gerry has gone against almost every rule of modern business — choosing craftsmanship over scale, long-term thinking over short-term returns, and integrity over imitation.

We explore what Gerry had to unlearn to stay in the game for decades: the myth of perfection, the pressure of shareholder expectations, and the idea that success must look a certain way. This conversation is a masterclass in leadership, product thinking, and building businesses that endure.

Key Takeaways

Perfection is a fantasy — luxury is honesty. Products that last are built on integrity, not impossible standards.
Success starts with finishing, not selling. The real win is building something real — everything else is a bonus.
Craftsmanship scales through capability, not volume. Deep skills create optionality and diversification.
The real competition isn’t the market — it’s yourself. Long-term builders focus on self-mastery, not rivals.
Great businesses are built by people who challenge you, not agree with you.

Additional Insights

Gerry built his first car in a garage behind his house — bigger than the house itself — with no external funding.
Bufori operates debt-free after nearly 40 years, an extreme outlier in modern manufacturing.
The company makes more parts in-house than most car manufacturers, turning necessity into innovation.
What started as survival-driven resourcefulness became multiple profit centers through engineering services.
Leadership longevity comes from unlearning ego, listening deeply, and leading by example.

Episode Highlights

00:00 – Episode Recap

Gerry Khouri reflects on a pivotal realization: perfection doesn’t build lasting products — honesty, craftsmanship, and long-term thinking do. This mindset reshaped how he built cars, teams, and a business designed to outlive him.

02:15 – Guest Introduction: Gerry Khouri

Barry introduces Gerry Khouri, founder of Bufori, a handcrafted automobile company that has spent nearly four decades defying the rules of modern manufacturing.

04:14 – Building the First Car Against All Odds

Gerry shares how a backyard hobby, relentless passion, and going against everyone’s advice led him to build his first car from nothing.

07:10 – Redefining What Success Really Means

Success wasn’t about money or validation — it was about starting something and finishing it, no matter the odds.

11:54 – Leading Without Resources

With no books, no mentors, and no capital, Gerry explains how necessity forced invention and deep mastery of craft.

19:50 – Unlearning Perfectionism in a Luxury Business

Why perfection is an illusion, and how focusing on luxury, durability, and intention keeps products moving forward.

23:12 – What Craftsmanship Actually Looks Like

Gerry breaks down what it means to truly “make” a product — from designing for repairability to building for generations.

27:29 – Competing With Yourself, Not the Market

The most dangerous competitor isn’t another company — it’s complacency and losing the hunger to improve.

31:10 – Unlearning Shareholder-First Thinking

Why prioritizing short-term financial returns can destroy long-term craftsmanship and culture.

35:07 – Turning Internal Capabilities Into New Businesses

How Bufori transformed hard-earned internal skills into diversified engineering services.

38:10 – Advice for Founders Scaling Passion Projects

Dream big, be honest with yourself, ignore the noise — and don’t fear hard work or criticism.

42:54 – Building Teams That Challenge You

Why great leaders surround themselves with people who tell them what they need to hear, not what they want to hear.

FAQs

What does it mean to unlearn perfectionism in product building?

Unlearning perfectionism means letting go of the belief that products must be flawless before they can be shipped. In this episode, Gerry Khouri explains why progress, honesty, and durability matter more than chasing an impossible standard of perfection.

How do you build products that last for decades?

Gerry shares that long-lasting products are built through craftsmanship, attention to detail, and designing for repairability and longevity — not speed, shortcuts, or mass production.

Who is Gerry Khouri and why is he notable?

Gerry Khouri is the founder of Bufori, a handcrafted automobile company that has operated for nearly 40 years. He’s known for building bespoke luxury cars by hand and for leading a debt-free business focused on long-term value.

Is perfectionism bad for startups and founders?

Perfectionism can become a liability when it slows decision-making, delays launches, or prevents learning. Gerry explains how redefining excellence allowed him to keep building while maintaining extremely high standards.

What does long-term thinking in business actually look like?

Long-term thinking means designing products, teams, and systems to endure — focusing on durability, skills, culture, and customer trust rather than quarterly results or fast exits.

Useful Resources

Gerry Khouri on LinkedIn - https://www.linkedin.com/in/gerry-khouri-08507788/
Bufori Motor Cars Website - https://bufori.com/

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AI Productivity for Executives: Skyscanner CTO Andrew Phillips

Tue, 20 Jan 2026 21:19:00 -0400

From graduate engineer to CTO, Andrew Phillips’ 16-year journey at Skyscanner is a story of continuous reinvention. He didn’t chase titles—he chased growth, deliberately stepping out of his comfort zone and unlearning the habits that no longer served him. What’s kept him at the company for over a decade isn’t status, but challenge: new teams, unfamiliar problems, and the chance to stay close to the work, even as his scope of leadership expanded.

In this episode, we explore how Andrew is now applying that same mindset to leading in the AI era—personally and professionally. He shares how he’s built a personal AI stack to stay more present, how Skyscanner is blurring traditional team roles to unlock speed, and why “directed autonomy” is more important than ever. For leaders navigating scale, technology, and the desire to make meaningful impact without burning out, Andrew offers a powerful perspective.

Key Takeaways

Growth through discomfort: Andrew’s biggest accelerations came from switching roles and leaving his comfort zone—not climbing a predefined ladder.
AI as a leadership enabler: He uses AI tools to be more present, thoughtful, and effective—especially during high-stakes meetings.
From feature factory to outcome focus: Leaders must reconnect people to impact, not just output.
Directed autonomy: Empowering teams with AI means giving clear goals—not micromanaging the execution.
Unlearning process overreach: Traditional roles, ticketing systems, and rigid handoffs are ripe for reinvention in AI-native organizations.

Additional Insights

The personal AI stack Andrew uses includes ChatGPT, Otter, Cursor, and SpecKit—enabling him to ideate on walks, build apps during board meetings, and maintain strategic presence.
Skyscanner’s senior engineers are back coding, using AI to close the gap between architectural thinking and execution.
AI-driven productivity unlocks don’t just mean faster work—they mean better work-life balance, deeper engagement, and more human leadership.

Episode Highlights

00:00 – Episode Recap

Andrew Phillips shares how stepping into uncertainty—and building his own AI stack—transformed his leadership at Skyscanner. From personal growth to organizational reinvention, he’s leading the charge on what modern technology leadership looks like.

01:35 – Guest Introduction: Andrew Phillips

Barry introduces Andrew Phillips, CTO of Skyscanner, reflecting on their 15-year relationship and Andrew’s rise from graduate engineer to technology leader.

05:45 – The One Trick Pony Moment

Andrew recalls the pivotal moment when a CEO challenged him to move teams and stop playing it safe—triggering his real leadership evolution.

12:33 – Starting with Yourself in AI

Before transforming your company with AI, Andrew urges leaders to start by experimenting personally and learning from the ground up.

15:15 – Writing Better Prompts, Building Better Specs

AI tools thrive on clear direction. Andrew realized that better prompting and crisp product requirements accelerated his results dramatically.

20:01 – Directed Autonomy in the AI Era

Giving AI tools (and people) the “why” rather than micromanaging the “how” builds trust, speed, and better outcomes.

24:56 – Parallel Productivity and Boardroom Apps

How Andrew built an entire app—during a board meeting—by offloading work to AI and staying fully present in the room.

27:13 – Reclaiming Work-Life Balance

AI allows Andrew to unload his mental backlog—using voice notes and assistants so he can be more present at home.

31:21 – Avoiding the AI Cost Trap

Not every solution needs an LLM. Andrew shares how Skyscanner balances innovation with cost and pragmatism.

36:58 – Blurring the Lines Between Roles

Designers writing code, engineers making design tweaks—Andrew explains why role flexibility is a hallmark of high-performing, AI-native teams.

42:32 – Unlearning the Process Fetish

It’s time to rethink JIRA tickets, handoffs, and audits. In a machine-collaborative world, many processes should be automated or eliminated.

43:36 – The CTO’s Excitement for the Next Quarter

Andrew sees a future where everyone—from architects to senior ICs—is back building again, connected to outcomes, not just output.

46:36 – Closing Reflections

Leadership is about presence, purpose, and people. Andrew shares his optimism for what’s possible when teams are empowered to ship and grow.

FAQs

Q1. How is Skyscanner using AI internally?

Teams are using tools like Cursor, ChatGPT, and SpecKit to prototype faster, write code, and automate workflows—blurring traditional role boundaries.

Q2. What is “directed autonomy” and why does it matter?

Directed autonomy means giving teams (and AI) clear goals and guardrails while allowing freedom in how outcomes are achieved. It increases speed, trust, and creativity.

Q3. What does Andrew mean by “blurring the lines between roles”?

At Skyscanner, designers are fixing front-end issues, engineers are influencing product direction, and architects are coding again—enabled by AI tools that lower technical barriers.

Q4. What AI tools does Andrew personally use?

Andrew’s AI stack includes ChatGPT, Cursor, SpecKit, and Otter—used for building apps, drafting comms, and capturing ideas while on the move.

Q5. How does AI help leaders stay present?

By offloading execution to AI (like building apps during meetings or drafting emails from voice notes), leaders can stay focused in key moments and reduce context switching.

Useful Resources

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How Is Visual Intelligence Redefining Human-AI Interaction with Sherry Chang

Tue, 13 Jan 2026 21:44:00 -0400

What if machines could truly see and understand how we move? In this episode, I sit down with Sherry Shang, CEO and co-founder of Neural Lab, a company reimagining how we interact with technology through visual intelligence AI and gesture-based interfaces.

Sherry’s journey from Intel technologist to startup founder began with a pivotal moment during the pandemic. What started as a side project in her living room became Neural Lab—a platform that turns basic webcams into powerful tools for gesture recognition, with no specialized hardware required.

Now, Neural Lab is unlocking new ways to deliver care, boost performance, and support human potential. From sterile surgery rooms to personalized rehab and coaching, touchless interaction is creating fresh possibilities for how we live and work with AI.

Key Takeaways

Computer vision is gaining eyes: Sherry frames visual intelligence as the “missing sense” in AI—complementing language models with sight.
Entrepreneurship is about timing: Sherry waited until her kids were older to build Neural Lab, choosing to innovate on her own terms.
Gesture recognition is real—and ready: Neural Lab’s technology translates hand motions into universal commands with no need for specialized hardware.
Human-centered design is essential: From recognizing intentional gestures to modeling real-world physicality, their design is inspired by how humans naturally interact.
Healthcare leads the way: Use cases like sterile surgical environments are proving to be strong early markets for gesture control.

Additional Insights

Visual intelligence is the missing sense in AI: Sherry describes computer vision as adding "eyes" to AI, enabling machines to interpret physical space just as large language models allow them to process language.
Entrepreneurship is about timing: Sherry chose to start Neural Lab once her children were older, aligning her professional ambitions with personal priorities.
Gesture recognition is real—and ready: Their product works with any basic camera and translates 15 customizable gestures into commands for existing applications—no new hardware required.
Designing for human nuance matters: Neural Lab focuses on distinguishing intentional from unintentional gestures using cues like eye gaze and body motion—mimicking how humans communicate.
Healthcare is an urgent use case: Environments like surgery rooms benefit immediately from touchless interaction, helping maintain sterility and reduce unnecessary patient radiation.
The interface is evolving beyond the mouse: Sherry sees gesture-based interaction as a more natural, immersive input method—moving us beyond traditional tools like keyboards and mice.
Customer feedback drives innovation: From live demos to direct use-case discovery, Neural Lab adapts based on what real users need and how they react in context.
AI can coach, not just compute: Sherry envisions AI-enabled coaching in sports, physical therapy, and even surgery—delivering expert guidance in real time, at scale.

Episode Highlights

00:00 – Episode Recap

Sherry Chang shares how her journey from Intel technologist to founder of Neural Lab began with a desire to create immersive, meaningful technology—and a pivotal moment during the pandemic when gesture-based interaction suddenly became essential.

02:14 – Guest Introduction: Sherry Chang

Barry introduces Sherry Chang, CEO of Neural Lab, former Intel leader, and innovator in computer vision and immersive interaction.

06:27 – Starting Up During the Pandemic

Sherry shares how the idea for Neural Lab came to life in her living room, driven by a vision for safer, touchless human-computer interaction.

09:30 – From Prototype to Minority Report

Barry recalls early demos that felt like science fiction—using just a webcam to control computers with hand gestures.

12:00 – Designing for Intentionality

Sherry explains the challenge of recognizing intentional vs. accidental gestures—and how eye-gaze and motion patterns help filter noise.

14:57 – Gesture as Input Device

They discuss how gestures open new interaction possibilities—from whiteboards to evaluating athletic movements.

18:26 – Finding Product-Market Fit in Healthcare

Sherry shares insights from radiology conferences—surgeons see immediate value in touchless interfaces for sterile environments.

22:21 – Reimagining Clinical Workflows

Gesture-based interaction eliminates the need for voice commands or assistants in the OR—streamlining workflow and reducing risks.

25:35 – The Bigger Picture

Barry reflects on the paradigm shift—freeing people from fixed tools like keyboards to interact with tech naturally.

28:56 – Unlocking Human Potential with AI Coaching

Sherry envisions AI coaches for physical therapy, sports, even surgery—democratizing access to expert feedback and improving outcomes.

33:11 – The AI Augmentation Mindset

Rather than replacing jobs, gesture-based AI enhances human performance and creativity, enabling new ways of working.

35:21 – Closing Reflections

Barry highlights the promise of technologies like Neural Lab—empowering people to interact more intuitively with machines and unlock new capabilities.

FAQs

Q1. What is gesture recognition technology?

Gesture recognition uses computer vision to detect and interpret human body movements—like hand gestures—as input commands to control software or devices.

Q2. How does Neural Lab's gesture control work?

Neural Lab’s system uses any standard camera to detect 15 configurable gestures, translating them into commands compatible with most applications—no special hardware needed.

Q3. Is gesture recognition practical in healthcare?

Yes. Surgeons can use gestures to manipulate images mid-procedure without breaking sterility, improving workflow and reducing radiation exposure.

Q4. Can gesture-based AI help in physical therapy?

Absolutely. It enables real-time coaching, posture correction, and progress tracking for rehab patients—making at-home therapy more effective.

Q5. How is AI augmenting human potential with this tech?

By combining visual intelligence with feedback loops, gesture-based AI allows for elite-level coaching and real-time assistance in fields like sports, surgery, and workplace ergonomics.

Useful Resources

Neural Lab Official Site - https://neural-lab.com/
Connect with Sherry on LinkedIn - https://www.linkedin.com/in/sherryschang/

Investing In Space with Maureen Haverty

Tue, 30 Dec 2025 18:00:00 -0400

Today’s guest is someone I first came across on the Irish People in VC list—and I’m really glad I reached out. Because it turns out Maureen Haverty has one of the most fascinating jobs you can imagine: helping build the future of space. As a Principal at Seraphim Space, the world’s leading space-focused VC firm, she invests globally in technologies pushing the boundaries of what’s possible —and shaping the future of space startup investment.

Maureen began her career in nuclear engineering, earning a PhD from the University of Manchester before making the leap into startups. At Apollo Fusion, she survived a hard pivot into space, ultimately becoming COO and steering the company through a $150M acquisition by Astra. That experience—what she calls a startup “baptism by fire”—now informs how she backs early-stage founders as both investor and board director. Her insights have been featured in The Times, and she’ll soon take the stage at Web Summit to speak on “Space as a Strategic Frontier.”

Key Takeaways

“Build just enough”: Space startups win by testing early and often, not waiting for perfection.
Kill fewer dreams: Rigor matters—but so does nurturing half-formed ideas.
Get to space ASAP: In-orbit validation creates trust and unlocks massive growth.
From Gantt charts to fast loops: High-performing teams test weekly, not quarterly.
Customer conversations still matter: Even in space, talking to users beats assumptions.

Additional Insights

Why VC funding in space is shifting toward earlier MVPs.
The hidden costs of acquisition for startup culture and speed.
How Starship may reshape what's possible—size, cost, and assembly in orbit.
The role of government contracts in fostering a competitive space ecosystem.

Episode Highlights

00:00 – Episode Recap

Maureen Haverty shares how balancing rigor with creativity helped her evolve from nuclear engineer to space startup COO to VC. The key? Learning when to test, when to build, and when to let wild ideas breathe.

01:35 – Guest Introduction: Maureen Haverty

Barry introduces Maureen Haverty, Principal at Seraphim Space and advocate for grounded rigor in an industry literally aiming for the stars.

03:35 – Learning When Not to Kill Ideas

Maureen reflects on being labeled a “dream killer” and how she transformed that mindset to foster innovation with constructive rigor.

07:34 – Applying Rigor Without Stifling Innovation

How Apollo used just-enough testing, internal prototyping, and diverse team strengths to build better, faster.

13:54 – Rethinking MVPs in Space Startups

Why even space companies now push to generate early revenue and test hardware pre-launch.

18:19 – Customers Want Something They Can See

Building a physical, testable product—even a crude one—outperforms pitch decks every time.

20:32 – The $70M Lesson of In-Space Testing

How one flight test flipped customer hesitation into a flood of contracts.

26:12 – Surviving the Shift from Prototype to Production

The real scaling challenge: maintaining culture and customer trust while redesigning for scale.

30:15 – The Hidden Power of Primes and Policy

Why space remains deeply shaped by government buyers—and how that’s changing with new VC-backed players.

35:33 – Starship and the Future of Space

Maureen shares what could shift when larger payloads, faster launch cadences, and orbital assembly become possible.

39:25 – Closing Reflections

Space is finally catching up to the urgency of its people. In an industry where “yesterday” is always the best time to start, speed is the differentiator.

FAQs

What is Maureen Haverty known for?
Maureen Haverty is a Principal at Seraphim Space, the world’s leading venture capital firm focused on space technology. She’s also known for her leadership at Apollo Fusion, where she helped scale the company to a $150M acquisition by Astra.
What does Seraphim Space invest in?
Seraphim Space invests in early-stage space technology startups globally, backing innovations in satellites, launch systems, in-orbit services, and deep tech infrastructure critical to the future of space exploration.
What did Maureen Haverty learn from her time at Apollo Fusion?
Maureen learned the importance of balancing rigor with experimentation. Her experience taught her to support bold ideas without stifling them and to build “just enough” before validating with customers—especially critical in high-stakes industries like space hardware.
How do space startups approach product testing and market validation?
Unlike SaaS startups, space companies face high costs and long timelines. The most successful ones focus on testing early and often, getting hardware into orbit quickly, and talking to customers well before finalizing product designs.
Why is in-space testing so important for space companies?
Even with rigorous ground-based testing standards, nothing builds customer confidence like real in-orbit validation. Maureen shares how one space test led to $70M in contracts within weeks—proving that live demonstrations are a major unlock for credibility and growth.
What trends are shaping the future of the space industry?
Maureen highlights the shift toward faster iteration, more venture-backed growth (vs. acquisition), and the game-changing potential of SpaceX’s Starship, which could enable larger structures, faster launch cycles, and more ambitious projects in orbit.

Useful Resources

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The Octopus Organization with Jana Werner & Phil Le-Brun

Tue, 16 Dec 2025 22:22:00 -0400

Back when I first worked with Jana Werner at Tesco Bank, I saw firsthand how a crisis could be a crucible for innovation and transformation. Her ability to unlock potential in even the most challenged teams was unforgettable. Now, teaming up with Phil Le-Brun—a transformational leader I came to know through his work at McDonald’s—they’ve co-authored The Octopus Organization, a guide for thriving in an age of continuous transformation.

In this episode, we go behind the scenes of their book and explore the anti-patterns that hold organizations back, the behaviors leaders must unlearn, and the mindset shifts required to succeed when change never stops. Whether you’re a CEO, change agent, or team lead, you’ll leave with small, actionable experiments to start evolving your organization—today.

Key Takeaways

Unlearning blame-based leadership: Shifting focus from fixing people to fixing systems unlocks performance and trust.
Spotting anti-patterns in everyday behavior: Habits like jargon, silos, and avoidance subtly block progress.
Embracing uncertainty in leadership: Probabilistic thinking builds better decisions and psychological safety.
Driving transformation through small experiments: Distributed action outperforms top-down mandates.
Leading with curiosity in the age of AI: Execs must actively engage with tech to stay relevant and credible.

Additional Insights

Behind the book: Why The Octopus Organization centers on 36 anti-patterns and how they uncovered them
Real-world leadership stories: Lessons from Tesco Bank, McDonald’s, Amazon, and Ferrari
Transformation fatigue is real: Overengineered change efforts often create fear and resistance
Alignment breakdowns in leadership teams: Many transformations fail because leaders aren't truly on the same page
Reframing performance: Asking “what did you stop doing” reveals deeper impact than traditional goals

Episode Highlights

00:00 – Episode Recap

Jana Werner shares how she took over a struggling tech team, discovered their true strengths, and transformed their performance by rebuilding culture and trust. Phil Le-Brun describes the importance of creating a culture of trust in organizations, allowing people to test ideas and make a real difference.

02:46 – Guest Introduction: Jana Werner & Phil Le-Brun

Barry O'Reilly introduces guests Jana Werner and Phil Le-Brun, describing their collaboration during times of crisis at Tesco Bank, their leadership backgrounds, and their shared vision for adaptive, purpose-driven organizations as captured in their new book.

04:36 – Revitalizing a Demotivated Team at Tesco Bank

Jana Werner narrates how she took over a demotivated technology team, overcame her initial preconceptions, and transformed the group into a top-performing unit by changing culture, empowering individuals, and shifting organizational dynamics.

07:07 – Lessons from McDonald's: Balancing Centralization and Agility

Phil Le-Brun explains McDonald's transformation journey, the need to unify local and corporate efforts, and the financial impact of building trust and alignment.

10:16 – Learning from Industry Leaders

Phil recounts interviews with CEOs like Indra Nooyi and Benedetto Vigna, highlighting that true leadership requires humility, storytelling, and ongoing curiosity.

14:14 – Unlearning the Need for Certainty

Jana Werner discusses shifting away from needing all the answers and embracing uncertainty, drawing on insights from Annie Duke and other leaders.

21:30 – Small Changes, Big Impact

Jana introduces the book's structure around "anti-patterns" and advocates for making small, distributed changes rather than massive, top-down transformations.

26:29 – Leadership Alignment: Avoiding Transformation Pitfalls

Phil highlights the need for alignment among leadership teams and points out common failures in transformation projects due to lack of shared understanding.

29:09 – Becoming "Technology Teenagers"

Phil and Jana emphasize the importance of leaders learning to experiment and engage directly with new technologies, encouraging curiosity and hands-on learning with AI.

32:12 – Start Small and Experiment

Both authors encourage listeners to pick a tip from the book and try it right away—emphasizing the value of experimentation, feedback, and removing old practices to spark growth.

Useful Resources

Jana Werner on LinkedIn - https://www.linkedin.com/in/janawerner1/
Phil Le-Brun on LinkedIn - https://www.linkedin.com/in/phillebrun/
The Octopus Organization – Book by Jana Werner & Phil Le-Brun - https://www.amazon.com/Octopus-Organization-Thriving-Continuous-Transformation-ebook/dp/B0DRZ2MXBR
Related episode: Accelerating Transformation in Crisis – Tesco Bank Case Study - https://barryoreilly.com/explore/articles/accelerating-transformation/
Amy Edmondson – Research on Psychological Safety - https://amycedmondson.com/psychological-safety/
Annie Duke – Thinking in Bets - https://www.annieduke.com/books/
Indra Nooyi – Leadership Insights - https://www.indranooyi.com/

Follow the Host

LinkedIn: Barry O’Reilly
Website: barryoreilly.com
Twitter/X: @barryoreilly
Instagram: @barryoreilly
Facebook: Barry O’Reilly

What Truly Decisive, Agentic Organizations Are Doing? – Steve Elliott

Tue, 02 Dec 2025 22:51:00 -0400

In this episode of The Unlearn Podcast, Barry O’Reilly is joined by Steve Elliott, a serial entrepreneur, product leader, and investor with two decades of experience advising high-growth companies. Steve is the founder of Dotwork, an AI-driven platform that connects strategy to execution, and co-founder of The Uncertainty Project, a community for product leaders focused on better decision-making.

He previously served as Head of Product at Atlassian, where he helped scale Jira Align after selling his company AgileCraft for $166M—earning recognition as a Fortune Best Small Business in America and a finalist for the Ernst & Young Entrepreneur of the Year. With five successful exits under his belt, Steve brings rare depth to the art of building and unbuilding what no longer serves.

In this conversation, Barry and Steve explore how to design for the messy reality of modern work, the role of unlearning in leadership, and how AI is redefining what it means to be a decisive company.

Key Takeaways

From CTO to CEO – Why Steve transitioned from tech leader to founder and the personal growth that came with it.
Scaling after acquisition – The emotional and strategic shifts required when your startup becomes part of a larger machine.
Why strategy execution breaks – Most alignment tools assume order—Steve builds for complexity.
Agentic AI in the enterprise – How Dotwork uses knowledge graphs and AI to surface insight in context, not just dashboards.
Decisive companies – What it really means to help leaders make faster, more confident decisions.

Additional Insights

Unlearning the idea that startups are for the young—Steve didn’t found his first company until his 40s.
How Dotwork is building a “context memory engine” for both executives and AI agents.
The future of AI-native tools isn’t more interfaces—it’s less friction and smarter context delivery.
Why the most valuable enterprise products aren’t flashy—they’re quiet, ambient, and deeply integrated.

Episode Highlights

00:00 – Episode Recap

Steve Elliott shares how each startup exit taught him something new—but also how returning to the founder’s seat means unlearning old assumptions. Now, with Dotwork, he’s not just building a tool—he’s rethinking how organizations make decisions in complexity.

01:45 – Guest Introduction: Steve Elliott

Barry introduces Steve Elliott, founder of AgileCraft (acquired by Atlassian) and CEO of Dotwork, with a track record of five successful exits and a deep focus on enterprise work management.

03:40 – Early career shifts

From a consulting career at PwC to software experiments that took off—how Steve found his way into entrepreneurship.

08:55 – From technologist to founder

The value of combining tech expertise with business empathy—and why startups offer unmatched learning opportunities.

11:05 – Unlearning post-acquisition mindsets

What Steve had to unlearn transitioning from CEO to leader within a larger company—and back again.

13:36 – Building tools for strategic decisions

Why enterprise tools fail to support real-time, strategic decisions—and how Steve is tackling the problem differently.

17:50 – The rise of agentic frameworks

How Dotwork is using knowledge graphs and agentic AI to reflect the dynamic, decentralized nature of modern organizations.

23:31 – Breaking through transformation fatigue

How Dotwork builds trust not through marketing, but by showing real, contextual results fast.

26:23 – Beyond dashboards: AI-native UX

Why true AI-native platforms don’t ask you to log in—they come to you with insight in the moment.

32:44 – Coaching execs on AI

Barry shares his experience coaching executives on AI—and why hands-on experimentation is the only path to mastery.

36:07 – Context engines for agents

Steve explains how Dotwork unintentionally became a context memory platform—crucial for the future of autonomous agents.

40:36 – Magic moments in enterprise UX

When engineering hasn’t seen the reports their software generates—because the platform is that intuitive.

43:17 – Closing Reflections

Steve reflects on the value of doing over theorizing—and the importance of staying close to the problem if you want to innovate meaningfully.

The Human Side of AI: How HR Can Lead the Transformation with Cass Pratt

Wed, 19 Nov 2025 01:49:00 -0400

In this episode of the Unlearn Podcast, I sit down with Cass Pratt, Chief Human Resources Officer at Progyny, to explore how HR is evolving into a design discipline that blends human connection with AI-powered productivity. From building bots to boost employee experience to reshaping how we think about roles in an automated world, Cass shares an honest look at how she’s bringing people along on a transformation journey—with curiosity, experimentation, and heart.

We discuss her pivotal decision to say yes to opportunities beyond her comfort zone, the strategic shifts she's leading inside a fast-scaling company, and why the future of HR is about enhancing humanity, not replacing it. If you’re wondering what leadership looks like when AI meets empathy, this one’s for you.

Key Takeaways

Unlearning expertise-dependence: Cass shifted from relying on experts to co-creating solutions with AI tools before engaging others.
AI as a force for elevation: At Progyny, AI is used to give employees time back, not take roles away—enabling deeper focus on human-centric work.
Low-code leadership: Cass, a self-described non-technical leader, built HR bots and reimagined policies through practical AI applications.
Scaling culture through consistency: AI chatbots improved response times, standardized answers, and gave insight into employee concerns.
Embedding experimentation: Teams are encouraged to ask, "What should I stop doing?"—sparking a culture of reinvention and initiative.

Additional Insights

Progyny’s “Super Fans” initiative reframes AI gains as an opportunity to deepen customer and employee relationships.
Training is done in cohorts to build shared understanding and reduce AI anxiety.
Cross-functional collaboration with junior team members—like the intern who built the HR bot—shows how innovation can come from any level.
Cass uses AI to simplify and globalize complex frameworks like competency models, improving alignment across teams and geographies.

Episode Highlights

00:00 – Episode Recap

Cassandra Pratt shares how embracing discomfort led her to leap into healthcare, build a transformative HR function, and lead with AI—not to eliminate roles, but to elevate people and amplify their impact.

02:37 – Guest Introduction: Cassandra Pratt

Barry introduces Cass Pratt, Chief People Officer at Progyny, a fertility and family-building benefits company scaling rapidly with a human-first, tech-empowered culture.

04:48 – Saying Yes to Growth

Cass reflects on a missed opportunity that taught her the cost of saying no—and set her on a path to jump into unknowns with conviction.

08:04 – Startup Lessons and Leadership Growth

From 50 to 850 employees, Cass shares what it means to grow with a company and embrace mistakes as part of the journey.

11:00 – Diving into AI Without a Tech Background

Despite lacking technical skills, Cass threw herself into generative AI—learning by doing and discovering intuitive ways to drive value.

13:10 – Unlearning the Expert Reflex

Cass rethinks her default of turning to experts first—instead starting with AI to shape stronger ideas and bring others in as collaborators.

15:13 – Redesigning Processes, Not Just Tools

AI opened up opportunities to rethink workflows from scratch, not just automate existing inefficiencies.

20:35 – Making AI Safe and Human

Cass shares how transparent messaging, training, and cultural reinforcement helps ease AI anxieties and keep the focus on people.

25:00 – Building the HR Bot with an Intern

An intern-built benefits chatbot improved response times, consistency, and surfaced new insights—highlighting the power of junior talent and experimentation.

28:41 – Simplifying Competency Models with AI

Cass uses AI to refine complex frameworks, making them scalable across geographies and easier for leaders to apply.

30:00 – Rethinking Work Through Elimination

By asking what should be stopped—not added—Cass surfaces high-leverage opportunities to transform HR workflows.

34:33 – The Two Extremes of HR and AI Adoption

Cass observes a divide: HR teams either lead AI transformation—or risk being the last to catch up.

40:45 – Cross-Functional Collaboration and Culture

AI transformation is a team sport—embedding HR into company-wide initiatives empowers better collaboration and outcomes.

43:38 – Freeing Up Time to Be Present

Cass highlights how AI helps reclaim time for the most human part of HR: being present, listening, and solving meaningful problems together.

Useful Resources

Progyny: https://www.progyny.com
Connect with Cassandra Pratt: LinkedIn
AI Executive Coaching by Barry: https://barryoreilly.com

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LinkedIn: linkedin.com/in/barryoreilly
Website: barryoreilly.com
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Twitter/X: x.com/barryoreilly
Instagram: instagram.com/barryoreilly

How to Create Irresistible Change for Business Transformation with Phil Gilbert

Tue, 04 Nov 2025 22:50:00 -0400

When most leaders think about transformation, they reach for tools and tactics. But real, lasting change doesn’t start with new methods—it starts with culture. In this episode, I sit down with Phil Gilbert, the former General Manager of Design at IBM, who led one of the boldest reinventions in corporate history. After selling his third startup to IBM in 2010, Phil was asked to transform how IBM’s teams worked using design thinking and agile. That effort reshaped the experience of over 400,000 employees and became the subject of a Harvard Business School case study, the documentary The Loop, and coverage in the New York Times and Fortune.

We explore how culture drives outcomes, why the team is the atomic unit of change, and how to design a leadership structure that earns trust and creates momentum. Phil brings sharp insight, rich stories, and practical frameworks drawn from a 45-year career spanning startups, scale-ups, and global enterprises. If you’re leading change—or trying to get others to believe in it—this conversation is your blueprint.

Phil Gilbert is best known for scaling IBM’s global design transformation. He was inducted into the New York Foundation for the Arts Hall of Fame in 2018 and named an Oklahoma Creativity Ambassador in 2019. Since retiring from IBM in 2022, Phil has focused on helping business and military leaders shift culture at scale to improve innovation and team performance.

Key Takeaways

Culture is the system: Real transformation means rewiring people, practices, and places—not just teaching new skills.
Teams are the atomic unit of change: Change doesn’t scale through individual mandates. It scales when cross-functional teams deliver new outcomes.
Design scales empathy: Phil shares how design thinking isn’t just about aesthetics—it’s a tool for scaling understanding and improving systems.
Transformation needs protection: Change teams need structural support and a leadership “shell” that shields them while engaging the broader org.
Momentum beats mandates: Leaders can’t impose change—they must earn it by showing results, listening deeply, and integrating across silos.

Additional Insights

"Every day is a prototype": Phil’s mantra that gives teams permission to change, test, and learn continuously.
The virus model of leadership: To spread new ways of working, Phil designed his leadership team like a virus—with spikes into HR, finance, comms, and IT.
Designers aren’t the barrier—systems are: In companies with weak design reputations, the problem isn’t the designers. It’s the culture around them.
Shadow IT kills transformation: Real progress happens when change leaders partner with CIOs—not work around them.
Most AI efforts are missing the point: Phil argues that AI transformation fails when it focuses on individuals instead of improving team-level outcomes.

Episode Highlights

00:00 - Episode Recap

Barry O’Reilly recaps the episode’s theme, discussing leadership challenges, reclaiming strategic focus, and leveraging frameworks, executive habits, and AI to drive impactful business outcomes.

2:26 - Guest Introduction

Barry introduces Phil Gilbert, renowned for leading a major cultural transformation at IBM through human-centered design. He previews Phil’s new book, “Irresistible Change,” and sets expectations for a discussion on leadership, empathy, and executing change at scale.

3:21 - Official Start of Conversation

Phil Gilbert reflects on pivotal career moments, including his experience founding early startups, the challenge of driving adoption for new technologies, and discovering the power of empathy and design. He introduces his guiding philosophy, “every day is a prototype.”

9:15 - The Power of Prototyping and Embracing Change

Phil explains how prototyping and a willingness to challenge the status quo lead to organizational and personal growth. He shares his “every day is a prototype” mantra and stresses the role of openness in innovation.

13:48 - Culture as a Driver of Outcomes

Phil outlines his formula for driving real change, focusing on people, practices, and places. He discusses his use of journaling and intentional observation to systematically build curiosity and support for change in teams.

20:47 - Designing Transformation at Scale

Phil discusses the challenge of leading IBM’s company-wide design movement. He explains his strategy to reach and influence 400,000 employees and the importance of building a diverse leadership team to support transformative efforts.

31:29 - Practical Tactics for Organizational Change

Phil details the need to integrate HR, tooling, and communications into the transformation process, sharing stories about revamping career ladders and piloting new tools. He emphasizes collaboration and transparency with key stakeholders like HR and CIOs.

37:51 - Lessons for Modern AI Transformation

Phil and Barry examine current challenges with AI change efforts, arguing that teams—not just individuals—are the fundamental units for successful transformation. They discuss why team-level outcomes should guide measurement and strategy for adopting new technologies.

41:09 - Hopes and Irresistible Change for the Future

Phil shares his vision for the next wave of business transformation, especially regarding AI. Drawing inspiration from cloud computing’s impact, he hopes leaders will adopt principles that empower teams to drive industry-defining change.

Useful Resources

Phil Gilbert – Irresistible Change (book): Buy on Amazon
Connect with Phil on LinkedIn: Phil Gilbert
Barry’s blog on AI

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How to Clearly Position What You Do with Anthony Pierri

Tue, 21 Oct 2025 20:56:00 -0400

When it comes to product positioning, clarity isn’t just a communication tool—it’s a strategic advantage. In this episode, I sit down with Anthony Pierri, co-founder of FletchPMM, a product marketing consultancy that’s helped over 400 B2B software startups discover and sharpen their positioning. We explore how founders can unlearn generic marketing advice, clarify their message, and activate their strategy through one often-overlooked asset: their homepage.

Anthony brings practical frameworks, real-world stories, and a refreshing candor to a space that’s often muddled with jargon. This is a must-listen for any founder, PMM, or GTM leader tired of being misunderstood—and ready to focus.

FletchPMM is a product marketing consultancy that helps B2B tech startups nail their positioning and bring it to life through a purpose-built homepage. Alongside co-founder Rob Kaminski, he’s helped more than 400 companies craft focused, champion-centered messaging that converts.

Key Takeaways

Clarity wins: Positioning isn’t about vision—it’s about specificity, segmentation, and telling your champion’s story.
Unlearn the fluff: Ditch the vague benefits and generic promises. Customers need to know what you do and how it helps them.
Focus = traction: Trying to be everything to everyone dilutes your impact. Specialization creates memorability and repeatability.
Your homepage is your positioning: It’s the one asset every stakeholder sees—customers, investors, your team. Make it count.
Position for the champion, not the budget holder: Focus your messaging on the person closest to the problem—not the executive who cuts the check.

Additional Insights

Positioning is pattern recognition: Anthony shares how lessons from church leadership and freelancing helped him recognize early signs of positioning misalignment—even before he had the language for it.
Inbound scale comes from consistency, not creativity: With over 500 companies served, Fletch’s success has come from delivering one service, the same way, every time—not by chasing new ideas or tactics.
Founders often confuse luck with repeatability: Anthony reveals how many early startup wins come from personal networks—and how this masks the real need for scalable positioning and segment focus.
Mispositioning starts with the homepage: Anthony critiques vague, benefits-only messaging like “Make Yes Work”—demonstrating how the lack of a clear product reference point derails understanding and action.
Repositioning is an organizational act: Referencing Klaviyo and Meta, Anthony shows how homepage messaging isn’t just about marketing—it forces internal alignment by making strategic bets visible to every team member.

Episode Highlights

00:00 – Episode Recap

Anthony Pierri shares how a seemingly minor contradiction in a church’s mission statement became his first exposure to a positioning problem—planting the seed for a career built around clarity.

01:30 – Guest Introduction: Anthony Pierri

Barry introduces Anthony, co-founder of FletchPMM, a consultancy that’s helped 400+ B2B software startups craft focused, conversion-driving homepages.

05:09 – The Real Cost of Doing Everything

Why trying to serve every persona or use case is the quickest way to stall traction—and how narrowing your focus builds momentum.

07:14 – Specialization is a Strategic Advantage

Anthony explains how one service, delivered one way, to one segment unlocked a scalable, inbound engine for Fletch.

11:42 – Sales Strategy or Sales Chaos?

The folly of hiring SDRs before narrowing your GTM focus—and why customer acquisition doesn’t scale without segment clarity.

14:03 – Champion-Centric Positioning

Don’t aim for the budget holder—speak to the person closest to the problem. They’ll become your internal advocate.

22:07 – How AI Will Impact Product Positioning

As software creation and discovery become more agent-driven, Anthony sees the same need for ultra-specific, capability-first messaging.

29:19 – Talking About Yourself Without Talking About Yourself

Positioning isn’t self-promotion—it’s about telling a compelling story that reflects your champion’s reality.

35:15 – The “Tell Me More” Effect

Great positioning doesn’t try to say everything. It just gets the right person to say, “Tell me more.”

38:17 – Your Homepage is Your Most Important Asset

The homepage isn’t just a lead gen tool—it’s the most visible alignment document your org has. Make it reflect your real strategy.

44:53 – Changing the Narrative at Scale

Anthony shares why embedding your positioning on the homepage is more powerful (and more visible) than internal decks ever will be.

46:35 – How to Structure a Homepage That Converts

Barry and Anthony unpack how to use messaging anchors, problem framing, and customer-centric storytelling to guide your homepage narrative.

Useful Resources

Follow the Host

Why Brains Need Friends with Dr. Ben Rein

Wed, 08 Oct 2025 00:27:00 -0400

In today’s hyper-connected world, many of us are experiencing a paradox—more digital interactions, but deeper loneliness. In this episode of Unlearn, I sit down with Dr. Ben Rein, neuroscientist and author of Why Brains Need Friends, to unpack why human connection isn’t just emotional—it’s biological. From the neuroscience of loneliness to surprising acts of generosity in mice and minnows, we explore how your brain interprets social disconnection as a threat, and why a full calendar of Zoom calls doesn’t satisfy your social diet.

As someone who experienced this firsthand—working remotely, starting over in a new country—I share my own journey to unlearning the myth of self-sufficiency and redesigning my life to engineer real connection. This conversation is a call to rethink how we connect, show up for each other, and take our social health as seriously as sleep, diet, or exercise.

Key Takeaways

Loneliness Is a Biological Threat: Your brain interprets social disconnection like hunger or pain—not just a mood, but a warning signal.
Small In-Person Moments Matter: Even brief, face-to-face interactions boost mood and cognitive function more than digital ones.
Isolation Damages the Brain: Chronic loneliness raises cortisol, shrinks memory centers, and can shorten your lifespan.
Introverts Still Need People: Social time benefits everyone—introverts just hit their saturation point sooner.
Generosity Is Hardwired: From rats to dolphins, the impulse to connect and give is deeply embedded in our biology.
Connection Requires Unlearning: Independence and solitude aren't always virtues—sometimes they’re survival myths in disguise.

Additional Insights

Social prediction systems in the brain were scrambled by COVID—and many people still haven’t recalibrated.
Most people think they’re worse-than-average at socializing, which fuels avoidance and false self-judgment.
Digital tools remove the social cues—tone, expression, touch—that our brains need to feel emotionally nourished.
Empathy is not automatic—it’s biased and trainable, shaped by exposure to difference and intention.
Rebuilding community isn’t just good for you—it’s essential for physical, mental, and societal health.

Episode Highlights

00:00 – Episode Recap

Ben Rein discusses the importance of socializing, likening it to sleep, diet, and exercise, and emphasizing its role in overall well-being.

02:07 – Guest Introduction: Ben Rein

Barry introduces Dr. Ben Rein, neuroscientist and author, and outlines the episode’s focus on the biological necessity of human connection.

03:43 – How COVID Broke Our Social Predictions

Ben shares his neuroscience background and explores how societal shifts and the pandemic disrupted the brain’s expectations for everyday interaction.

08:23 – Barry’s Story: “You Sound Lonely”

Barry recounts a personal moment of realization and how a friend’s observation pushed him to rebuild his social life with intention.

11:29 – Why We Miss the Signs of Loneliness

Ben explains why loneliness often goes undetected, how it manifests as stress, and why virtual connection isn’t enough.

16:44 – The Hard Work of Making Friends

Barry reflects on the discomfort of building new friendships as an adult—and why it’s worth the effort for mental and emotional health.

21:10 – The Neuroscience of Social Fear

Ben breaks down why we underestimate the value of interaction, how fear holds us back, and the courage it takes to engage.

25:33 – Designing for Connection

Barry shares how he now intentionally schedules social time as part of his weekly routine—and encourages others to do the same.

29:46 – Writing Lessons: Structure Matters

Ben opens up about his writing process and the hard-earned lesson of keeping a book focused on its core idea.

32:58 – Empathy is in Our Nature

Ben shares surprising studies showing kindness and empathy across the animal kingdom—and what humans can learn from them.

39:22 – Closing Reflections

Barry and Ben wrap with a call to action: prioritize connection, embrace kindness, and use what we know to better ourselves and others.

Useful Resources

Why Brains Need Friends by Dr. Ben Rein
Dr. Ben Rein on LinkedIn
Ben’s popular science content on Instagram and TikTok

Follow the Host

Scaling HR For Growth with Grace with Theresa Cantwell

Tue, 23 Sep 2025 22:38:00 -0400

What happens when you stop treating HR as a back-office function and start designing it as a competitive advantage?

Theresa Cantwell, Strategic HR Consultant and Director at GSD HR Consulting, believes scaling a company shouldn't mean burning out your team—or yourself. With nearly two decades leading people strategy at companies like Microsoft, ThoughtWorks, and Equal Experts, Theresa has helped organizations across Europe and Asia grow not just fast, but gracefully.

In this episode, we dive into the most overlooked challenges founders face when they scale: losing visibility, clinging to control, and skipping the crucial step of designing people and culture systems that can actually support growth. From shadow planning and succession strategies to why success itself can be terrifying, Theresa shares powerful tools and real talk every startup leader needs to hear.

If you're moving past 20 employees and want to build a company that lasts—without losing what made it special—this conversation is your playbook.

Key Takeaways

Start HR Strategy Early: Don’t wait for burnout or lawsuits—build people ops into your scaling strategy from day one.
Shadow Planning Is Essential: Prepare for the worst by confronting your team’s shadow behaviors and stress reactions before they sabotage growth.
Succession Planning Isn’t Personal: It's about scalability. Delegate early, document processes, and regularly revisit org design.
Growth Changes Everything: Founders need to let go to level up. What got you here won’t get you there.
AI in HR Is a Tool, Not a Fix: Automate the repetitive, but double down on building trust and strategic visibility.

Additional Insights

HR should be the connective tissue of an organization—not the "issues and tissues" team.
Scaling gracefully requires confronting the emotional toll of growth, including fear of success.
Theresa shares how early experiences at Microsoft and ThoughtWorks shaped her belief in high-trust, high-agency cultures.
Executive coaching and intentional design can prevent burnout and boost retention.

Episode Highlights

00:00 – Episode Recap

Theresa Cantwell unpacks the emotional complexity of growth—from the fear of success to the need for intentional HR design. With experience scaling organizations across continents, she shares how founders can build people-first cultures that thrive under pressure.

01:54 – Guest Introduction: Theresa Cantwell

Theresa is a strategic HR consultant and founder of GSD HR Consulting, with nearly two decades of experience building and scaling agile-aligned cultures in the tech and digital sectors.

04:43 – Pivotal Moment at Microsoft

Seeing a team she’d hired bonding over lunch sparked her transition from recruitment to building cultures that last.

06:28 – ThoughtWorks and Radical Culture Design

Barry reflects on his own onboarding experience and how Theresa helped him understand the unique culture of ThoughtWorks from day one.

09:33 – From Recruiter to Culture Architect

Theresa shares why she shifted from acquisition to engagement, building full lifecycle HR strategies rooted in trust and clarity.

15:29 – When to Start Thinking About People Strategy

At 20 people, you need to get intentional—mission, values, cofounder conflict prep, and hiring bar must be aligned.

18:51 – Shadow Planning Explained

Why leaders must confront their own stress behaviors and prepare for the worst—before it happens.

22:39 – Handling Employee Departures with Grace

How to de-risk talent exits through succession planning and constant market awareness.

26:39 – Scaling Yourself Out of a Job

Helping leaders delegate, prevent burnout, and imagine new roles for themselves as the company grows.

32:16 – When to Start Succession Planning

The earlier, the better—start once you have traction. Document, delegate, and depersonalize the process.

36:17 – AI’s Role in HR

AI can’t replace the human heart of HR—but it can free you to focus on what matters most.

38:50 – Closing Reflections

Barry praises Theresa’s impact and encourages founders at scaling junctures to seek her wisdom and services.

Useful Resources

Follow the Host

How Family Offices Are Disrupting Venture Capital and Private Equity with Ron Diamond

Tue, 09 Sep 2025 22:42:00 -0400

What happens when you stop chasing returns and start investing in purpose?

Ron Diamond, Founder and Chairman of Diamond Wealth, believes the future of finance isn’t just about building wealth—it’s about what that wealth can do. As a trusted advisor to over 100 family offices ranging from $250 million to $30 billion, Ron has spent more than two decades helping ultra-wealthy families align their capital with causes that matter.

In this episode, Ron shares how the collapse of Drexel Burnham shaped his perspective on loyalty, legacy, and leadership—and why “patient capital” is poised to disrupt the short-termism of private equity. We explore how purpose-driven investing is solving real-world challenges, from cancer to climate, and what it takes to build sustainable family office infrastructure in an era of unprecedented generational wealth transfer.

And the timing couldn’t be more relevant: family offices are no longer niche players. The number of single-family offices has surged 31% since 2019, with projections reaching over 10,700 globally by 2030. As trillions of dollars transition to the next generation, Ron offers a front-row seat to the values, strategies, and systems needed to steward that wealth wisely.

Ron is also the Founder, Host, and CEO of Family Office World Media, and helped establish the Family Office Program for TIGER 21, where he chairs a national peer group. He lectures at Oxford, Stanford, Harvard, and the University of Chicago Booth School of Business, and was recently appointed Editor-in-Chief of The National Law Review’s first Family Office newsletter. A LinkedIn Top Voice, TEDx speaker, and former hedge fund founder, Ron began his career on Wall Street at Bear Stearns and Drexel Burnham.

Key Takeaways

People Over Companies: Ron’s experience during Drexel’s collapse taught him that relationships—not institutions—are what endure.
Patient Capital Is a Game-Changer: Family offices can think in decades, not quarters, offering strategic advantage over traditional funds.
Purpose Before Profit: Legacy and social impact must anchor investment decisions.
Professionalization Is Essential: Governance, infrastructure, and talent are what turn capital into capability.
The Ego Barrier: Great wealth doesn’t guarantee great management—humility is crucial for longevity.

Five Core Principles from Ron Diamond

1. Guiding North Star: Profit with Purpose

Anchor investments in something bigger than financial return—personal mission, legacy, or societal impact.

→ Tip: Define your North Star early and align capital accordingly.

2. Trust & Relationships First

Back character over credentials. Trust and personal integrity build more resilient partnerships than models or metrics.

→ Tip: Focus on people, not pitch decks.

3. Patient, Long-Term Capital

Think in decades, not exit cycles. Family offices can outperform by holding steady and avoiding short-termism.

→ Tip: Let compounding do the heavy lifting.

4. Professionalizing Family Offices

Family offices must evolve beyond legacy systems—invest in governance, talent, and infrastructure like any top-tier fund.

→ Tip: Treat talent as a profit center, not a cost.

5. Entrepreneurial Philanthropy

Deploy strategic, venture-style capital into social challenges. Purpose and profit can—and should—coexist.

→ Tip: Apply the same rigor to social impact as you do to your investments.

Episode Highlights

00:00 – Episode Recap

Ron Diamond shares how witnessing the downfall of Drexel Burnham sparked his lifelong belief in prioritizing people over companies—and why loyalty should lie with individuals, not brands.

01:39 – Guest Introduction: Ron Diamond

Barry introduces Ron Diamond, Chairman of Diamond Wealth and Family Office World Media, and a leading voice in purpose-driven capital and governance reform.

05:13 – Building a Family Office Syndicate

Ron explains his “first call alpha” model—aggregating capital from 100+ family offices to invest together in private markets.

08:40 – The North Star Philosophy

From Milken’s prostate cancer initiative to Eric Lefkofsky’s Tempus Labs, Ron shows how personal purpose drives breakthrough impact.

11:41 – Listening to Find Values Alignment

Ron’s secret to identifying values-driven leaders: listen more, talk less—and show up without an agenda.

16:43 – Growth Mindset Over Scarcity

Competing with others is outdated—Ron champions an abundance mindset rooted in collaboration and long-term thinking.

20:32 – The Operational Trap for New Family Offices

Ron breaks down why most new family offices fail and how professionalization—from mission statements to succession—can change that.

23:41 – The Power and Pitfalls of Patient Capital

He explores how family offices can outperform PE firms by holding long-term and avoiding short-term incentives.

32:42 – Creating a Playbook for Next-Gen Wealth

From Booth to Stanford, Ron is building the first structured family office curricula focused on governance, values, and impact.

39:31 – Investing in Talent Like an Institution

Ron outlines why top talent needs equity, not just salary—and why underinvesting in people is the silent killer of family offices.

44:34 – Finance Meets Philanthropy

Why family offices—not government or corporations—will solve many of society’s biggest challenges in the next 20 years.

45:31 – Closing Reflections

Ron shares how listeners can follow his work and why patient capital is the future of both wealth and impact.

🔗 Useful Resources

The Power of Real Conversations with David Homan

Wed, 27 Aug 2025 01:17:00 -0400

What if networking wasn’t about schmoozing but about being seen? David Homan joins me to unlearn the myths of traditional networking and share how vulnerability, deep listening, and small group connection can foster truly meaningful relationships. As a master connector, classical composer, and co-author of Orchestrating Connection, David breaks down the silent skills that build trust, activate communities, and transform the way we gather.

David Homan is the founder and CEO of Orchestrated Connecting, a global community of connectors; Orchestrated Opportunities, an impact-focused advisory firm; and SOAR CONNECT, a start-up focused on the strength of authentic relationships. He hosts the Orchestrated Relationships podcast on developing relationship value, is an active classical composer, and a proud father of two. From middle-class beginnings as the son of a college professor and nonprofit-focused mother, he has built a network that reaches into the most private and powerful circles globally, all while honoring a code of purposeful community building.

Key Takeaways

Small Groups Create Big Impact: Starting events with curated small groups breaks social barriers and sets the stage for authentic connection.
Vulnerability Builds Real Relationships: Opening up—even subtly—invites empathy and depth that surface-level networking can't achieve.
Help Without Keeping Score: Giving without expecting reciprocity strengthens your reputation and extends your reach.
Design Moments That Resonate: Successful events don’t depend on cocktails or keynote speeches—they’re built on meaningful first impressions.
Asking Is a Skill, Not a Weakness: Givers often struggle to ask for support—David’s Impact Ask framework helps mission-driven people share their needs with clarity.

Additional Insights

Most Networking Events Are Designed to Fail: Traditional formats emphasize aesthetics over connection—David redesigns them to foster immediate, meaningful dialogue.
Shared Vulnerability Activates Group Trust: Structured conversations with depth-based prompts unlock faster bonding and community-building.
Music as a Metaphor for Human Connection: David draws from his training as a classical composer to illustrate how relationships, like instruments, must resonate and harmonize.
Clarity Makes Asking Easier: The “Impact Ask” framework simplifies how to articulate passion, purpose, and the kind of help you need.
Your Reputation Travels Faster Than You Do: David’s work shows that investing in authentic relationships amplifies your presence—even when you're not in the room.

Episode Highlights

00:00 – Episode Recap

David Homan reveals how he had to unlearn everything he thought he knew about networking—discovering instead that vulnerability, deep listening, and structured intimacy were the keys to building purposeful community.

01:50 – Guest Introduction: David Homan

Barry introduces David Homan, master connector, startup founder, and co-author of Orchestrating Connection, whose work helps leaders create impact-driven relationships through authentic connection.

02:52 – Why Most Events Miss the Mark

David shares why traditional networking events feel awkward—and how his approach to curated small groups flips the script to create meaningful experiences.

04:49 – Start Small, Go Deep

Barry reflects on the power of small group interactions and how vulnerability accelerates meaningful connections.

08:01 – Sharing Real, Not Polished

David explains the importance of self-worth and courage when choosing to open up authentically in conversation.

10:45 – Creating Connection Through Authenticity

Being real invites empathy—and sets the tone for deeper, more rewarding conversations.

13:18 – Your Reputation When You're Not in the Room

David describes how authentic acts ripple through your network, strengthening your reputation and reach over time.

17:39 – Unlearning Transactional Thinking

Helping someone doesn’t obligate them—it expands your access to their trusted circles.

20:36 – Conducting Communities Like a Composer

David draws on his classical music training to explain how relationships can resonate like instruments in a symphony.

25:16 – Event Design That Actually Works

Purpose-driven event planning means matching people’s needs and asks—not just gathering for the sake of it.

28:13 – Why Givers Struggle to Ask

David outlines the “Impact Ask” framework to help mission-driven people communicate their needs confidently.

31:59 – Fundraising as Shared Mission

Barry reflects on how reframing fundraising as an invitation to join a mission transformed his startup experience.

33:59 – The Future of Community

David offers a hopeful vision: intentional communities built on shared values, layered for systemic change.

35:56 – How to Connect with David

David shares how listeners can join his private, connector-driven community—and what qualities matter most.

Useful Resources

Follow Barry O’Reilly

LinkedIn: https://www.linkedin.com/in/barryoreilly
Website: https://barryoreilly.com
Facebook: https://www.facebook.com/barryoreillyauthor/
Twitter (X): https://x.com/barryoreilly
Instagram: https://www.instagram.com/barryoreilly/

The Sound of Freedom and Healing Trauma with Paul Hutchinson

Tue, 12 Aug 2025 23:21:00 -0400

Paul Hutchinson’s life story reads like a thriller, but his mission is deeply real and urgent. Once a multi-billion dollar fund manager, Paul transformed his life to become an undercover operative, leading more than 70 rescue missions across 15 countries to free thousands of children trapped in sex trafficking. He is the true-life inspiration behind the Sound of Freedom movie and the author of The Sound of Freedom: True Stories That Inspired the Film, offering a raw, unfiltered look at what it takes to confront humanity’s darkest realities and bring hope to the most vulnerable.

This episode goes far beyond heroism. We explore the complexities and personal costs of Paul’s work—from how his background in private equity uniquely positioned him to negotiate with traffickers, to the emotional and psychological toll of seeing trauma up close. Paul also shares vital lessons on protecting your children, what really works in combating trafficking, and why healing—beyond extraction—is the ultimate rescue.

Some stories are tough to face but impossible to turn away from. Paul’s journey is a powerful reminder of resilience, transformation, and what true leadership means when you dare to engage with the hardest truths.

Key Takeaways

Trauma Often Hides in Plain Sight: Early exposure to peer counseling revealed the silent prevalence of abuse and shaped Paul’s lifelong compassion.
Leverage Unique Skills for Impact: Paul’s financial expertise uniquely positioned him to negotiate with traffickers and execute high-stakes rescue missions.
Healing Requires Vulnerability: Emerging therapies like psilocybin can accelerate breakthroughs when used intentionally and safely.
Meditation and Gratitude as Daily Practices: Far from clichés, these tools quiet the mind and strengthen authentic connection.
Impact Extends Beyond Rescue: True change is about rehabilitation, restoring humanity, and creating ripple effects of hope.
Material Success Without Meaning is Hollow: Relationships, purpose, and self-awareness are the real measures of a life well lived.

Additional Insights

Redefine Success on Your Own Terms: Society pushes for more—money, power, status—but real fulfillment comes from understanding what truly matters to you.
Embrace Compassion as a Leadership Skill: Genuine empathy transforms how you influence and inspire others.
Healing is a Collective Journey: Trauma and recovery ripple beyond the individual to impact families and communities.
Courage Requires Vulnerability: Facing your own shadows opens the door to deeper connection and transformation.

Episode Highlights

00:18 – Episode Recap

Paul Hutchinson’s journey from multi-billion dollar fund manager to undercover operative rescuing trafficked children reveals a profound transformation—one fueled by confronting trauma, embracing empathy, and discovering the healing power of vulnerability and plant-based therapies.

02:06 – Guest Introduction: Paul Hutchinson

Barry introduces Paul Hutchinson, former private equity executive turned human trafficking rescuer and author of The Sound of Freedom, sharing raw stories behind one of the largest rescue missions and the personal toll it took.

03:53 – Early Compassion & Peer Leadership

Paul reflects on how his early role as a peer counselor exposed him to hidden childhood traumas, planting the seeds of compassion that would later define his mission.

14:34 – First Undercover Mission & The Rescue of 124 Children

Paul recounts negotiating with traffickers in Colombia, orchestrating a risky sting operation that rescued over a hundred children in a single day.

23:59 – Processing Trauma with Psychedelic Healing

The conversation explores the emotional toll of undercover missions and how Paul and his team used plant-based therapies, like psilocybin, to process PTSD and reclaim their lives.

39:10 – Meditation, Gratitude, and Spiritual Connection

Paul shares his daily practice of meditation and gratitude as foundational tools for lasting transformation and alignment beyond material success.

44:53 – Advice for Deep Healing and Self-Transformation

Paul offers guidance for listeners on beginning their own journey of healing trauma through meditation, breathwork, and embracing vulnerability.

47:26 – Closing Reflections

Paul emphasizes the power of storytelling and awareness to inspire change, thanking Barry for amplifying the voices fighting modern slavery.

Useful Resources

The Sound of Freedom by Paul Hutchinson Amazon Bestseller
The Sound of Freedom movie (inspired by Paul’s missions)
Gabriel Maté – Author of The Myth of Normal (https://drgabormate.com)
Web del x – Plant-based therapy education platform (https://webdelx.com)
Webdelics - https://www.webdelics.com/

Resources from Guest

Get the first 3 chapters of Paul’s book for free: www.soundoffreedombook.com
Liberating Humanity website: liberating-humanity.com
Child Liberation Website: childliberation.org
Youtube - youtube.com/@liberatinghumanity
Instagram - instagram.com/liberating.humanity
Facebook - facebook.com/liberating.humanity
TikTok - tiktok.com/@liberating.humanity
LinkedIn - linkedin.com/in/paulhutch
X - x.com/paulhutchinson

Follow Barry O’Reilly

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Give First and the Ripple Effect of Generosity with Brad Feld

Tue, 29 Jul 2025 23:27:00 -0400

What if generosity—not hustle—is your greatest competitive advantage?

Brad Feld—co-founder of Foundry Group, Mobius Venture Capital, and startup accelerator Techstars—joins Barry to explore the transformative philosophy of “Give First,” a mindset that’s reshaped how founders, investors, and mentors build lasting companies and vibrant startup ecosystems. Brad has spent over three decades cultivating startup communities by putting people before profit and helping others without expecting anything in return.

In this episode, he shares the mindset shifts that fueled Techstars’ global influence, how mentorship evolves from hierarchy to peer learning, and why sustainable success stems from playing the long game. A conversation full of clarity, candor, and challenge—for anyone rethinking what it means to lead, contribute, and create.

Key Takeaways

Generosity Fuels Growth: Giving without expectation of return builds stronger relationships, ecosystems, and companies.
Mentorship is a Two-Way Street: The most impactful mentoring happens when both sides learn, grow, and give.
Play the Long Game: Positive-sum, multi-turn thinking creates more meaningful and lasting impact than transactional wins.
Know Yourself First: Deep self-awareness—not external success metrics—is the foundation of better leadership.

Additional Insights

Redefine Success on Your Own Terms: Society pushes for more—money, power, status—but real fulfillment comes from understanding what truly matters to you.
Build a Network of Givers: Shared values transcend geography. A global community built on generosity leads to collective resilience.
Let Go of the Need for Control: Great mentors—and leaders—create space for co-creation, not dictation.
Disconnect to Reconnect: Time away from constant input helps surface your clearest thinking and truest desires.

Episode Highlights:

00:00 – Episode Recap

Brad Feld reframes mentorship as a shift from a one-way hierarchy to a peer-based relationship.

01:48 – Barry Introduces Brad Feld

Barry introduces Brad's influential work on startup communities and his philosophy of "Give First."

03:12 – Startup Community Origins

Brad shares how the idea of startup communities became a global movement—challenging the belief that tech startups must be in Silicon Valley.

12:54 – The Give First Philosophy

Brad explains why generosity, long-term thinking, and non-transactional relationships are foundational to resilient startup ecosystems.

21:33 – Mentorship as Mutual Growth

A powerful story with mentor Len Fast reveals how Brad came to see mentorship as co-learning rather than knowledge transfer.

27:27 – Knowing Yourself

Brad emphasizes how self-awareness and personal growth are essential to leadership, especially in a world driven by reactive norms.

34:48 – Creating Space for What Matters

A candid discussion on disconnecting from external pressures, valuing inner reflection, and how time off helped Brad refocus on his values.

41:47 – Redesigning Relationships

Brad shares how he and his wife created structure and rules to prioritize their relationship—offering insight into the intersection of discipline and intimacy.

45:41 – Final Reflections

Brad closes with a message on leading through generosity, not transactions—and why playing the long game builds stronger companies and communities.

Episode Resources

Brad Feld on LinkedIn: Brad Feld

Foundry Group on LinkedIn: Foundry Group

Foundry Group website: foundrygroup.com

Techstars website: techstars.com

Why AI-First Digital Product Consultancies Will Win Big with David Tuck

Tue, 15 Jul 2025 21:05:00 -0400

What if becoming a better leader meant letting go of being the expert? In this Unlearn episode, I’m joined by David Tuck, Chief Executive of Waracle, for a thoughtful and human-centered conversation on the mindset shifts required to lead high-performing teams in complex, fast-changing environments.

David’s leadership journey spans over 15 years of agile transformation, commercial growth, and organizational design. He’s held executive roles at Kin + Carta, The App Business, ThoughtWorks, and Scott Logic, and now leads Waracle, a strategic design and technology consultancy that builds trusted digital products for enterprise clients.

Known for his calm conviction and people-first approach, David shares how curiosity, craft, and long-term client intimacy have shaped his leadership philosophy. From stepping back in his career to hone his sales skills, to becoming a CEO who leads experts by asking better questions, David reflects on what it means to grow companies—and yourself—by design.

This episode explores how to lead through inquiry, build trust at scale, and why today’s leaders must become “Chief Unlearn Officers” to stay relevant in an AI-powered world.

Key Takeaways

Craft First, Climb Later: David shares why stepping back from leadership to deepen his sales craft at Waracle gave him the clarity and credibility to lead more effectively.
Lead Without Knowing Everything: CEOs don't need all the answers—they need to ask better questions and create space for their teams to excel.
AI Starts with Literacy: Leaders must understand AI fundamentals to steer transformation and avoid becoming disconnected from how value is created.
From Specialist to Generalist: The CEO role is about orchestration—shifting from doing to enabling across functions and disciplines.
Human Connection Still Wins: At Waracle and beyond, trust, empathy, and meaningful relationships still drive long-term business success in an AI-powered world.

Additional Insights

Redefine Leadership as Service: A CEO’s job is to help others succeed, not to control every decision or be the expert in the room.
Ask Better Questions: Using frameworks like the probing pyramid can unlock better thinking and faster alignment across teams.
Don’t Automate the Human: AI can accelerate delivery, but it can’t replace the emotional intelligence and trust that drive real impact.
Create Space for Reflection: Strategic pauses and structured dialogue lead to more thoughtful, inclusive decisions—especially in hybrid teams.
Unlearn to Move Forward: Leaders need to let go of outdated habits and create the conditions for new thinking to thrive.

Useful Resources

Follow the Host:

LinkedIn: https://www.linkedin.com/in/barryoreilly
Personal site: https://barryoreilly.com
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Email: hello@barryoreilly.com

Bold Go-To-Market Tactics: Just Evil Enough to Win with Alistair Croll

Tue, 01 Jul 2025 22:12:00 -0400

What if the biggest risk in your business isn’t building the product but realizing no one wants it? In this Unlearn episode, I’m joined by Alistair Croll, technologist, entrepreneur, and bestselling author of Lean Analytics, for a candid and clever conversation on rethinking product development, marketing, and demand generation.

Alistair’s work focuses on data-driven innovation and human behavior. He co-authored Just Evil Enough: The Subversive Marketing Handbook, a playbook for bending the rules to win in the attention economy. He has chaired global tech conferences like O’Reilly’s Strata and currently leads Startupfest, where he helps founders turn clever ideas into competitive advantage.

Known for blending insight with humor, Alistair unpacks why subversive creativity, not perfection, often wins. From the “fluency equation” to Burger King’s clever customer acquisition tactics, he reveals how unconventional strategies generate meaningful traction. This episode explores the science of subversive marketing, reframes how we think about product launch risk, and dives into the mindset shifts leaders need to stay relevant in the AI era.

Key Takeaways

Start with Attention, Not Execution: The first job is proving demand, not building features.
The Fluency Equation: Adoption is driven by desire, but also requires lowering inexperience, complexity, and perceived consequence.
Redefine Product-Market Fit: Medium fit — how people find, try, and pay — is just as important as what you offer.
Reverse Your GTM Strategy: Work backward from demand instead of forward from the product.

Additional Insights

Test Before You Build: Demand validation should come before development or scaling.
Have a Disagreement with the World: Bold startups are born from challenging norms, not just meeting expectations.
Use Familiar Behaviors to Drive Adoption: Anchoring new tools to existing habits lowers friction and boosts engagement.
Practice Ethical Persuasion: Subversive tactics work best when they respect users and build long-term trust.

Episode Highlights:

00:00 – Episode Recap

Alistair reframes startup risk with a clever hand-raising test: building isn’t the danger, indifference is.

03:16 – The Beach-Read Business Book

Why Just Evil Enough was built to entertain and educate, and how surprise fuels learning.

07:30 – The Real Startup Risk

Most teams focus on building because it feels safe. But the real risk is customer indifference.

08:41 – Subversive Marketing in Action

The Whopper Detour: How Burger King used playful tactics to achieve strategic goals.

13:20 – The Fluency Equation Explained

A new way to understand user hesitation and remove behavioral friction.

19:14 – AI, Fluency, and Leadership Gaps

Why executives aren’t using AI, even when they know they should.

26:00 – Decision-Making Matrix for Innovation

A two-by-two framework to help teams run smarter experiments with lower risk.

31:01 – The Fourth Miscapitalization

Why companies are still over-investing in engineering in an AI-native era.

35:55 – How to Start with Demand First

Real-world examples of flipping the build-first model by validating before committing.

39:14 – The Subversive Mindset

Disagreeability, creative risk, and how to spot the systems you're trapped inside.

41:36 – Ethical Persuasion

How to avoid crossing the line from clever to manipulative.

Useful Resources:

Alistair Croll on LinkedIn
Just Evil Enough by Alistair Croll & Emily Ross
Lean Analytics by Alistair Croll & Ben Yoskovitz
Unlearn Episode with Emily Ross
Startupfest
Never Split the Difference by Chris Voss
How Minds Change by David McRaney

Follow the Host:

LinkedIn: https://www.linkedin.com/in/barryoreilly
Personal site: https://barryoreilly.com
Facebook: https://www.facebook.com/barryoreillyauthor/
Twitter: https://x.com/barryoreilly
Instagram: https://www.instagram.com/barryoreilly/
Email: hello@barryoreilly.com

Visionaries, Rebels, and Machines: Getting the Best of All with Jamie Dobson (Explicit)

Tue, 17 Jun 2025 22:17:00 -0400

Today on the Unlearn podcast, we welcome Jamie Dobson, technologist, entrepreneur, and a leader known for building systems that connect innovation with purpose. He joins us to share a deeply reflective journey: spanning childhood curiosity, extreme programming, leadership challenges, and the hard truths of building a company with intention.

Jamie Dobson is the co-founder and former CEO of Container Solutions, a consultancy helping organizations adopt cloud-native technologies. A self-proclaimed management nerd and lifelong learner, Jamie’s early career as a software engineer evolved into a calling to improve the world through better people management. He’s the author of Visionaries, Rebels, and Machines, a sweeping narrative on the evolution of computing and leadership. Jamie now advises executives and writes about how systems, both technological and organizational, can be redesigned for the better.

Known for his systems thinking, sharp wit, and grounded view on management, Jamie has spent decades bridging the gap between technological innovation and human-centered leadership. Whether he’s decoding the transistor’s origins or dissecting what makes a high-performing executive team, Jamie is always seeking out better ways to work, grow, and lead with clarity and courage.

This episode explores the mindset shifts required to lead through ambiguity, the costs of integrity in leadership, and how discipline, self-awareness, and naivety can sometimes be your greatest assets.

Key Takeaways

Act on Inspiration Fast: Jamie shares why taking immediate action on a good idea is a rare but powerful leadership move.
Leadership as a Moral Responsibility: Decision-making isn’t just strategic—it’s ethical, emotional, and deeply human.
Naïveté as a Strength: Why approaching challenges with curiosity and a beginner’s mindset can spark unexpected breakthroughs.
Letters to Self as Feedback Loops: How Jamie uses journaling to reflect, recalibrate, and lead with discipline.
Psychological Safety Isn’t Optional: The timeless (and still underused) foundation of every high-performing tech team.
Bullsh*t Detection 101: From recognizing deceptive behavior to building a culture of honesty, trust, and clarity.
Managing Technologists is Solved: The real challenge isn’t how to manage engineers—it’s having the discipline to do what works.

Episode Highlights

00:00 – Episode Recap

Jamie reflects on how childhood curiosity and Maslow’s philosophy laid the groundwork for a career blending tech and leadership.

04:27 – Acting on Inspiration Immediately

Why most people hesitate—and how taking fast, decisive action can be a leadership advantage.

07:42 – Leadership as a Moral Weight

Jamie discusses the emotional cost of doing the right thing and why real leadership isn’t always rewarded.

11:14 – The Loneliness of Idealism

From bold bets to navigating skepticism, Jamie shares what it’s like to hold the line on your values.

15:31 – Shifting Systems, Building Trust

What it really takes to lead teams through technological and cultural transformation—and why trust is the hardest part.

18:41 – Spotting Bullshit in Business

Jamie breaks down how to recognize deception in the workplace—and how to protect your team from it.

23:20 – From Sympathy to Self-Responsibility

Letting go of victimhood narratives and embracing accountability as a leadership discipline.

28:09 – Journaling, Feedback, and Decision Hygiene

Jamie shares the personal practices that help him lead with clarity and consistency.

32:03 – Psychological Safety Still Wins

Despite all the change in tech, one thing remains constant: teams thrive when they feel safe to speak up.

Resources Mentioned

What Happens When You Go All-In in Work and Life on AI with Jeremy Shankle

Tue, 03 Jun 2025 19:39:00 -0400

Today on the podcast, we welcome Jeremy Shankle, full-stack engineer, AI strategist, and early adopter of automation tools across work and life at Nobody Studios.

With decades of experience in web development, startup leadership, and product strategy, Jeremy shares how going all-in on artificial intelligence has transformed how he works, lives, and thinks.

From debugging code to managing projects and planning weekends with his son, Jeremy has embraced AI as a true co-pilot. His story isn’t about replacing people—it’s about unlearning old work patterns, reducing context switching, and building smarter systems for productivity and purpose.

In this episode, we talk about Jeremy’s journey from web design and blockchain to AI-first development, and how adopting a multithreaded mindset helped him balance leadership, creativity, and everyday life in a more focused, high-leverage way.

Jeremy Shankle has worked across large tech organizations, startups, and now contributes to a fast-moving venture studio, helping teams use AI to build better products with fewer people. His thinking blends engineering discipline with human-centered innovation—exploring how tools like GPT-4 and Codex are reshaping the future of work.

Key Takeaways:

Going All-In on AI: Jeremy shares what happened when he decided to run everything through GPT tools—from coding to shopping.
Unlearning Multitasking: Why AI helps him focus more by batching work, parallelizing tasks, and context switching less.
Human First, Tech Forward: How AI frees up space for better thinking, parenting, and problem-solving.
Changing How We Work: Smaller teams, higher output, fewer blockers.
Life OS Upgrade: From weekend planning to debugging code, AI is now part of Jeremy’s daily operating system.

Episode Highlights:

01:50 – Guest Introduction: Jeremy Shankle

Barry introduces Jeremy as a product thinker and engineer at the intersection of AI, software, and strategy.

03:20 – Why Jeremy Went All-In on AI

In December, Jeremy dove deep into agents that search the web and modify code—and he hasn’t looked back.

04:02 – From Tandy 1000 to Tech Trailblazer

At age 5, Jeremy started coding on a Tandy 1000. That early start shaped his approach to learning and tech.

07:49 – Strategic Thinking Without the Switch Costs

AI helps Jeremy stay focused—no more jumping between roles or work personas all day.

10:32 – Fixing Bugs and Finding Basketball Clubs

Jeremy shows how he uses AI to squash code bugs and research activities for his son—at the same time.

15:23 – Smarter Task Management with AI

Jeremy explains how AI-infused project management tools let him create and assign tasks with ease.

22:11 – AI as an Anxiety Reducer

Whether prepping for embassy visits or crafting emails in another language, AI gives Jeremy a calm confidence.

32:31 – Confidence Without the Code Dependency

Barry shares how AI helped him stop second-guessing and start building—without always calling in an expert.

37:48 – AI Made Me Smarter, Not Dumber

By automating the grunt work, Jeremy has more time to understand the why behind every technical decision.

42:35 – What’s Next? Agent-to-Agent Collaboration

Jeremy’s most exciting frontier: AI tools that talk to each other—and get things done without constant prompts.

Resources

Jeremy Shankle
Nobody Studios
OpenAI Codex
GPT-4 with Memory and Deep Research Tools
Tools Mentioned: ChatGPT Pro, Operator, Browser MCP, Codex

FOLLOW THE HOST:

LinkedIn: https://www.linkedin.com/in/barryoreilly
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The Future of Housing and Modular Home Building with John Avrett

Wed, 21 May 2025 01:00:00 -0400

Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast.

____________________________________________________________

Welcome to UNLEARN, the podcast where we talk about bold ideas, fresh thinking, and the mindset shifts needed for real change. Today, I’m excited to welcome John Avrett, former U.S. diplomat, aerospace and electrical engineer, and now Founder and CEO of Hive Modular. With past roles in the U.S. Air Force, U.S. Navy, and Department of State, John is leading a new wave of modular home building in the Philippines, tackling the global housing crisis with factory-made homes and smart design.

John isn’t just a builder; he also loves solving big problems and making homes better for everyone. His journey from engineering and diplomacy to modular homes shows how thinking differently can help fix housing issues in new ways, especially by building smarter and faster in places that need it most.

John has worked across engineering and global trade before starting his company to build homes in a new way. At his factory in the Philippines, his team makes modular houses using a process like a car factory, helping build faster and cheaper. He focuses on smart design and shipping, bringing homes to places that need them, while using skills from aerospace and diplomacy to guide his work.

Key Takeaways:

Fixing Housing Problems: John shares how factory-made homes can help more people.
Starting a Business: What he learned from taking a big risk to follow his dream.
Thinking Differently: Why new ways of thinking are key to solving old problems.
Global Experience: How living and working abroad shaped his big ideas.
Smart Building: How using a car-like factory process makes building homes faster.

Additional Insights:

Mixing Tech and Building: John shows how factory skills can improve home building.
Working in New Markets: What it takes to build homes in places with big needs.
Learning from the Past: How John’s old jobs help him find smart new ways to build.
Solving Real Problems: How he uses design to make homes faster and cheaper.
Adapting to Change: Why being open to new ideas helped grow his company.

Join John Avrett as he shares how bold ideas, smart building, and global thinking can help solve housing needs and spark new ways to grow in today’s world.

Episode Highlights:

[00:10] - Episode Recap

"John Avrett joins to talk about solving housing issues with modular homes and lessons from past careers."

[01:38] - Guest Introduction: John Avrett

"John is an ex-aerospace engineer and U.S. diplomat now building smart, factory-made homes in the Philippines."

[04:48] - Museum Visit Sparks a Big Idea

"A prefab home exhibit opened John’s eyes to a better way of building and inspired his mission."

[07:25] - From Engineer to Diplomat to Builder

"John shares how his global work helped him spot the housing crisis as a real problem to fix."

[10:09] - Why Housing Innovation Fell Behind

"Homes take longer and cost more today than in the 1960s, John explains why change is overdue."

[13:07] - Rethinking Risk to Start a Company

"Leaving a stable job was tough, but learning to see risk in a new way helped John take the leap."

[14:53] - Turning Homes Into a Factory Process

"John explains how car-style production lines and steel frames help build better, faster homes."

[19:42] - Blending Standard Design with Custom Feel

"Standard frames and flexible layouts allow homes to feel unique while staying easy to build."

[22:24] - Labor and Logistics in Home Building

"Even in a factory, homes take skilled work, and every site brings its own tricky challenges."

[27:02] - Strategy, Scaling, and a Life-Changing Book

"John explains how scaling isn’t about more small homes but bigger impact and how a book by Annie Duke helped shape his thinking."

[33:18] - Global Momentum and What’s Next

"John shares why support from countries like Canada and Australia shows prefab housing is gaining ground and how rising costs may push the U.S. to follow soon."

FOLLOW THE GUEST:

LinkedIn Accounts:

John Avrett: https://www.linkedin.com/in/john-avrett-26891944/
Hive Modular: https://www.linkedin.com/company/hivemodular/
US Department of State: https://www.linkedin.com/company/doscareers/
US Navy: https://www.linkedin.com/company/us-navy/
United States Air Force: https://www.linkedin.com/company/united-states-air-force/

Websites:

Hive Modular: https://www.hive-modular.com/
US Department of State: https://www.state.gov/
US Navy: https://www.navy.mil/
United States Air Force: https://www.airforce.com/

FOLLOW THE HOST:

LinkedIn: https://www.linkedin.com/in/barryoreilly
Personal site: https://barryoreilly.com
Facebook: https://www.facebook.com/barryoreillyauthor/
Twitter: https://x.com/barryoreilly
Instagram: https://www.instagram.com/barryoreilly/
Email: hello@barryoreilly.com

The New Science of Self-Actualization for Founders to Reinvent Identity & Find Meaning - Faisal Hoque

Wed, 07 May 2025 01:00:00 -0400

Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast.

____________________________________________________________

Today on the podcast, we welcome Faisal Hoque, author, entrepreneur, and thinker behind Transcend. With over 10 books and years of business leadership, Faisal shares how life, purpose, and challenges have shaped his journey of learning, growth, and helping others.

Known for books like Everything Connects and Transcend, Faisal blends Eastern wisdom with modern leadership. He’s worked with global firms, led startups, and speaks widely on purpose, resilience, and human-centered innovation.

In this episode, we talk about Faisal’s journey of self-growth and leadership, exploring how unlearning, flow states, and personal purpose can reshape how we lead, work, and grow in today’s fast-moving world.

Faisal Hoque is Founder and Managing Partner at Shadoka and NextChapter, Strategic Partner at CACI International Inc., and a Judge and Mentor at MIT. He’s also an investor, board member, and former CEO across various tech and business ventures. A contributor to Fast Company and IMD, he was shortlisted for the 2023 Thinkers50 Distinguished Achievement Award. Faisal is also a public speaker and former Chair of Research and Education at Altea Federation, as well as ex-Product Manager and CTO at GE Capital and Dun & Bradstreet.

Key Takeaways:

Unlearning past beliefs helps us grow and adapt in a changing world.
True purpose comes from small daily actions, not big goals.
Flow, gratitude, and reflection can boost personal and work life.

Additional Insights:

Let go of chasing success and focus on work that feels meaningful.
Use reflection, meditation, and learning to stay sharp and inspired every day.

Join Faisal Hoque as he shares how purpose, reflection, and human connection can guide us to grow and lead in today’s fast-changing world.

Episode Highlights:

[01:00] - Episode Recap

"Faisal Hoque joins the show to talk about purpose, self-actualization, and how life’s challenges shape our leadership."

[01:34] - Guest Introduction: Faisal Hoque

"Faisal is a tech entrepreneur and author of Transcend, blending neuroscience, leadership, and personal growth."

[03:13] - Early Startups and Key Life Lessons

"My second startup failed despite big clients, then I bootstrapped my next one and wrote my first book."

[04:30] - Eastern Roots and the Search for Meaning

"Trips to Japan reconnected me with Eastern philosophy and sparked the idea for Everything Connects."

[06:01] - Redefining Self-Actualization with Purpose

"After life’s ups and downs, I began to ask: What does real success and impact look like for me now?"

[08:13] - Finding Fulfillment in Small Daily Actions

"It’s not about changing the world, it’s about helping one person and finding joy in the process."

[11:02] - The Paradox of Purpose and People in Work

"Mission statements often miss the mark, leaders must connect goals to individual purpose to inspire teams."

[14:08] - Building Regenerative and Connected Cultures

"Good leadership means creating space where people can grow, connect, and even leave to find their calling."

[18:18] - Writing, Reinvention, and Radical Openness

"Writing helps me unlearn and grow. Being open to ideas I disagree with pushes me out of my comfort zone."

[23:30] - Meditation, AI Tools, and Personal Growth

"Daily meditation and tech experiments help me reflect, stay grounded, and find new ways to improve."

[30:01] - Finding Ideas from Life and Observation

"Inspiration comes from watching the world, and writing weekly helps me reflect on change and uncertainty."

[32:51] - Focus on Effectiveness, Not Just Efficiency

"Instead of chasing speed, we must use tech to stay human, be thoughtful, and lift each other up."

FOLLOW THE GUEST:

LinkedIn Accounts:

Faisal Hoque: https://www.linkedin.com/in/faisalhoque/
NextChapter: https://www.linkedin.com/company/nextchapterorg/
Shadoka: https://www.linkedin.com/company/shadoka/
CACI International Inc: https://www.linkedin.com/company/caci-international-inc/
MIT: https://www.linkedin.com/school/mit/
Fast Company: https://www.linkedin.com/company/fast-company/
IMD: https://www.linkedin.com/school/imd-business-school/
Altea Federation: https://www.linkedin.com/company/alteafederation/
GE Capital: https://www.linkedin.com/company/gecapital/
Dun & Broadsheet: https://www.linkedin.com/company/dun-&-bradstreet/

FOLLOW THE HOST:

LinkedIn: https://www.linkedin.com/in/barryoreilly
Personal site: https://barryoreilly.com
Facebook: https://www.facebook.com/barryoreillyauthor/
Twitter: https://x.com/barryoreilly
Instagram: https://www.instagram.com/barryoreilly/
Email: hello@barryoreilly.com

Unlearning Legacy Systems to Build Antifragile AI Operating Models with Ja-Naé Duane

Wed, 23 Apr 2025 01:00:00 -0400

Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast.

____________________________________________________________

Today on the podcast, we welcome Ja-Naé Duane, systems thinker, innovator, and author of Super Shifts. With over 20 years as a behavioral scientist and 4-time entrepreneur, Ja-Naé has guided organizations, governments, and communities through future-focused transformation.

Recognized by outlets like NPR and Businessweek, she’s passionate about reshaping how we live and work in the age of superintelligence, leveraging AR/VR, AI, and blockchain. Ja-Naé has worked with top firms like Deloitte and PWC, and is a sought-after speaker at Singularity University.

In this episode, we explore her transformative frameworks for both personal and organizational growth, highlighting the power of unlearning, integrating systems thinking, and embracing change in a tech-driven world.

Dr. Ja-Naé Duane is a Research Fellow at MIT, Faculty Director of Brown’s Innovation Management program, and a mentor in its Tech Leadership program. She’s also a Council Member at The Stimson Center, an Investor at CollX, and a Co-Founder of The Revolution Factory. At Singularity University, she teaches futures thinking and lectures in Information Systems at Bentley University, where she’s on the Blockchain Advisory Council. She’s the bestselling author of McGraw-Hill and an advisor at Teleportec.

Key Takeaways:

Stress isn’t the enemy; using it intentionally can fuel growth and resilience.
To thrive in the future, we must unlearn outdated systems and develop an antifragile mindset.
Superintelligence and AI are crucial tools for creativity, reflection, and decision-making.

Additional Insights:

Let go of outdated thinking to make room for fresh, innovative approaches.
Use AI and other tools to boost productivity and enhance creativity in your work.

Join Ja-Naé Duane as she discusses transformation, unlearning habits, and creating resilient systems that thrive with technology and nature.

Episode Highlights:

[01:00] - Episode Recap

"Today’s guest is Ja-Naé Duane, author of Super Shifts, discussing personal and organizational transformation in the age of superintelligence."

[01:56] - Guest Introduction: Ja-Naé Duane

"Ja-Naé Duane is a leading behavioral scientist and author, helping individuals and organizations navigate the world of AI and technology."

[03:55] - Inspiration Behind Super Shifts and the Pandemic Pivot

"During COVID-19, I was called to help restart Europe, which sparked the Super Shifts concept."

[06:10] - Exploring Decentralized Systems and Resilience

"We studied nature’s decentralized systems and explored how businesses can adopt similar models to thrive under stress."

[08:33] - Unlearning Comfort and Embracing Stressors

"I realized I was too comfortable. We must introduce stressors to evolve and adapt."

[12:11] - Physical Stressors for Growth and Self-Awareness

"Physical challenges like mountain climbing help build resilience and self-awareness for my work."

[15:29] - Using AI for Productivity and Holistic Living

"We should use AI for efficiency, but also focus on creativity, wellness, and meaningful connections."

[18:56] - Transformative Models and Organizational Impact

"By unlearning old mindsets, the Transform Model helps organizations shift to sustainable, adaptable systems."

[25:07] - Embracing AI for Leadership and Change

"AI can revolutionize leadership and decision-making while keeping us human in how we integrate it."

[30:10] - AI, Time Management, and the Future of Work

"AI tools free up time by automating tasks, but we must rethink how we spend our time and adapt to new ways of working."

[35:40] - Creating Space for Innovation and Long-Term Vision

"Leaders must create space for innovation, even if uncomfortable, to shape the future."

[42:28] - AI Tools, Growth, and Embracing Change

"Our AI-native studio uses automation to streamline tasks, reduce manpower, and embrace discomfort to adapt for future success."

Follow Our Guest

LinkedIn Accounts:

Ja-Naé Duane: https://www.linkedin.com/in/janaeduane/
MIT: https://www.linkedin.com/school/mit/
Brown University School of Professional Studies: https://www.linkedin.com/school/brownsps/
The Revolution Factory: https://www.linkedin.com/company/the-revolution-factory/
Pre-order the First Edition Hardback of Super Shifts today at https://www.target.com/p/supershifts-by-ja-nae-duane-steve-fisher-hardcover/-/A-1001693948

FOLLOW THE HOST:

LinkedIn: https://www.linkedin.com/in/barryoreilly
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Facebook: https://www.facebook.com/barryoreillyauthor/
Twitter: https://x.com/barryoreilly
Instagram: https://www.instagram.com/barryoreilly/
Email: hello@barryoreilly.com

From Fashion to Real Estate, Unlearning to Realign Purpose and Scale with Francesca Cortesi

Wed, 09 Apr 2025 01:00:00 -0400

Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast.

____________________________________________________________

Today on the Unlearn Podcast, I’m thrilled to be joined by Francesca Cortesi, CPO and Founder of Prodotto Collective, a product visionary, transformational leader, and someone who truly understands what it takes to build beloved products and high-performing teams.

Francesca was the Chief Product Officer at Hemnet, Sweden’s leading property platform, where she played a pivotal role in scaling the product organization and driving the company through a successful IPO in 2021. Under her leadership, Hemnet achieved consistent double-digit growth, became one of Sweden’s most appreciated apps, and stood out as a top performer on the Swedish stock exchange.

But her story goes far beyond business metrics. Francesca led cultural shifts too, transitioning the company language to English and increasing female representation in tech, proving that growth and inclusion can go hand in hand.

In this episode, we explore how Francesca thinks about unlearning as a tool for personal and organizational growth, building product excellence at scale, and creating environments where diverse teams thrive.

Key Takeaways:

Changing careers: Francesca switched from fashion in Milan to tech in Sweden after many rejections, showing strong resilience.
Product Management: Asking many questions helped her shift from project management to product management.
Asking for Help: Great leaders don't need to know everything; asking for help builds stronger teams.
Idea company size: Francesca thrives best in scale-up companies (40–400 people), not large corporations.
Unlearning and Growth: Every new role required Francesca to "unlearn" old ways to adapt to new challenges.

Additional Insights:

Changing Roles: Your job changes when your company grows, so be ready for change.
Know your strength: Understand clearly what you’re good at and where you fit best.
Start Fresh: Always approach new tasks like you're learning for the first time.

Get ready for a powerful conversation with Francesca Cortesi on embracing change, scaling with intention, and building inclusive, high-performing product teams that thrive through continuous unlearning and growth.

Episode Highlights:

[01:00] - Episode Recap

"Welcome to the Unlearn Podcast, Exploring career shifts, new leadership styles, and how to build strong product teams."

[02:03] - Guest Introduction: Francesca Cortesi

"Francesca, former Chief Product Officer at Hemnet, helped scale the product and led the company to a successful 2021 IPO."

[03:22] - From Milan Fashion to Stockholm: The First Career Pivot

"I worked in fashion, got a translator job in Sweden, and decided to move."

[07:10] - Facing Rejection and Redefining Identity

"I tried returning to fashion, but it wasn’t working, time to move on."

[10:13] - Discovering Product Management Through Curiosity and Questioning

"I kept asking questions, turns out, that curiosity led me into product management."

[15:20] - What Francesca Had to Unlearn

"As a product manager, I had to leave behind what worked before, it’s always contextual."

[19:56] - Transition from Individual Contributor to Product Leader

"My first leadership role taught me to stop copying others and find my own style."

[24:54] - Why Role Expectations Must Be Rewritten During Scaling

"Too many questions about roles and success? That’s your sign to pause and redefine expectations."

[27:52] - Realizing Where She Thrives: The Scaleup Stage

"My sweet spot? Companies ready to scale after finding product-market fit."

[37:24] - From Operator to Advisor: Unlearning and Redefining Impact

"New roles come with new expectations, especially the ones you set for yourself."

Follow Our Guest:

LinkedIn Accounts:

Francesca Cortesi: https://www.linkedin.com/in/francesca-cortesi/
Prodotto Collective: https://www.linkedin.com/company/prodotto-collective/
Hemnet: https://www.linkedin.com/company/hemnet/

Websites:

Prodotto Collective (Francesca’s Personal Site): https://www.francescacortesi.com/

FOLLOW THE HOST:

LinkedIn: https://www.linkedin.com/in/barryoreilly
Personal site: https://barryoreilly.com
Facebook: https://www.facebook.com/barryoreillyauthor/
Twitter: https://x.com/barryoreilly
Instagram: https://www.instagram.com/barryoreilly/
Email: hello@barryoreilly.com

The Neuroscience of High-Performing Teams for Leaders to Achieve Workplace Success | Dr. Marcia Goddard

Wed, 26 Mar 2025 01:00:00 -0400

Welcome back to the Unlearn podcast! Today, we're exploring neuroscience with Dr. Marcia Goddard, a top neuroscientist and high-performance expert. As the founder of Brain Matters, a LinkedIn Top Voice, TEDx speaker, and a Neuroscientist. She's known for making science practical for business success. Her work with Formula 1, where she studied behavior and culture within teams to develop comprehensive strategies that enhance performance, along with her contributions to Leiden University, and The Contentment Foundation has helped leaders and teams boost performance and teamwork. She is also the Board Advisory Member of Equalture. Tune in for an insightful talk on unlocking human abilities and building creative workplace cultures!

She is a respected neuroscientist who is dedicated to guiding young professionals and bringing fresh ideas into different industries. Dr. Marcia’s work is a valuable resource for anyone aiming to make a big impact in technology and business.

Dr. Marcia Goddard, a neuroscience expert with over 10+ years of experience, applies brain science to boost workplace performance and culture. She has consulted with high-performance teams, including Formula 1 and Fortune 500 companies, optimizing team dynamics. Her thought leadership focuses on psychological safety and inclusion, guiding organizations toward innovation and growth.

Key Takeaways:

Expanding Globally: Dr. Marcia Goddard’s strategies for international growth.
Overcoming Challenges: Solutions for fast-changing industries.
Adapting to Change: Stay flexible, ditch outdated methods.
Personal Experience: Dr. Goddard’s lessons in action.

Additional Insights:

Effective Strategies: Dr. Marcia Goddard on reshaping industries.
Thriving in Growth: Tips for fast-expanding businesses.
Experience to Innovation: Dr. Goddard’s journey to better solutions.

Get ready for an enlightening conversation with Dr. Marcia Goddard on infusing new ideas into business strategies and fostering a culture of innovation and growth.

Episode Highlights:

[00:36] - Episode Precap

"Welcome back to the Unlearn podcast, where we challenge conventional thinking to unlock high performance and breakthrough innovation."

[01:17] - Guest Introduction: Dr. Marcia Goddard

“I'm joined by Dr. Marcia Goddard, a neuroscientist, author, and keynote speaker specializing in applying brain science to workplace performance and culture.”

[02:30] - Navigating Introversion, Networking Opportunities, and Career Growth

"My career was once a series of what I called coincidences, but I no longer believe they were."

[06:46] - Unlearning Misconceptions in Neuroscience

"There are two answers to that. My favorite quote is, 'If the brain were simple enough for us to understand, we would be too simple to understand it.”

[10:26] - Practical Tips for High-Performance

"It's a good question, especially in individual coaching. I think that's what it's related to."

[12:40] - The Importance of Reflection in Decision-Making

"We often tell ourselves we must decide now, but that’s rarely the case."

[15:58] - Enhancing Team Communication

"The most common thing I see at a team level, especially in growing organizations."

[18:44] - Remote Work and Maintaining Connections

"For remote organizations, let’s be clear: I don’t support full-time office work."

[26:04] - Future of High-Performance Teams

"Looking ahead, what excites you most in the industry, and what do you think needs to be unlearned?"

[29:31] - Rethinking Diversity and Inclusion Programs

"We need to unlearn the notion that ticking boxes creates impact and that DEI is just the right thing to do."

[35:52] - Future Trends in Neuroscience and Performance Teams

"Looking ahead, what excites you most about the future of performance teams and neuroscience?"

Follow Our Guest

LinkedIn Accounts:

Dr. Marcia Goddard: https://www.linkedin.com/in/mngoddard/
Brain Matters: https://www.linkedin.com/company/brainmattersconsulting/
Formula 1: https://www.linkedin.com/company/formula-one-management-ltd/
Equalture: https://www.linkedin.com/company/equalture/
The Contentment Foundation: https://www.linkedin.com/company/the-contentment-foundation/
Leiden University - Faculty of Archaeology: https://www.linkedin.com/company/faculty-of-archaeology-university-of-leiden/

Websites:

Brain Matters: https://brainmattersconsulting.com/
Formula 1: https://www.formula1.com/
Equalture: https://www.equalture.com/
The Contentment Foundation: https://www.contentment.org/
Leiden University - Faculty of Archaeology: https://www.universiteitleiden.nl/en/archaeology

____________________________________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

LinkedIn: https://www.linkedin.com/in/barryoreilly
Personal site: https://barryoreilly.com
Facebook: https://www.facebook.com/barryoreillyauthor/
Twitter: https://x.com/barryoreilly
Instagram: https://www.instagram.com/barryoreilly/
Email: hello@barryoreilly.com

Why Playing Too Small Is Stopping Your Finance Career Growth with Kristie Edling-Day

Wed, 12 Mar 2025 01:00:00 -0400

Welcome to UNLEARN, the podcast where we will discuss the transformative journeys, innovative tactics, and the pivotal mindset shifts necessary for authentic progress and development. Today, I'm thrilled to welcome Kristie Edling-Day, the current Executive Vice President and Chief Information Officer of Advisor Technology at LPL Financial, and former Principal and Chief Information Officer at Vanguard, a pioneer in strategic development and information management.

Kristie is not just a leader; she also loves helping young professionals grow and bringing new ideas to different industries. The book ‘Innovate to Elevate: Transforming Markets and Minds in Southeast Asia’ explores groundbreaking insights, offering valuable strategies for those aiming to drive change in technology and business.

Kristie has worked in the Financial Services industry for over 18 years, helping improve technology and develop new products. At LPL Financial, she manages Client Works, a platform that helps over 20,000 advisors with important tools for handling accounts, investments, trading, advisory programs, and compliance. She also leads LPL’s strategy for AI, making sure the company and its advisors have access to the latest in what technology can do both for efficiency and growth.

Key Takeaways:

Growing Businesses Worldwide: Kristie shares how to expand companies across different countries.
Facing Challenges: Tips on handling problems in fast-growing industries.
Learning and Adapting: Why being open to change and unlearning old ways helps with innovation.
Using Personal Experience: How Kristie solves problems based on her own challenges.

Additional Insights:

Smart Strategies and Strong Operations: Kristie explains how these key skills can change industries.
Succeeding in Fast-Growing Markets: How to handle challenges in quickly expanding businesses.
Turning Experience into Innovation: How Kristie uses her own experiences to create better business solutions.

Get ready for an insightful talk with Kristie Edling-Day on bringing fresh ideas into business strategies and building a culture of innovation and growth.

Episode Highlights:

[00:37] - Episode Introduction

"Systems like LPL’s ClientWorks platform are so important and they help over 20,000 advisors manage their work more effectively and stay compliant. "

[01:35] - Guest Introduction: Kristie Edling-Day.

“I did not join Vanguard thinking I wanted to be an executive in technology."

[05:20] - Turning Point in Career Growth Choices and Embracing Uncertainty.

“On my first day at the new job, I realized that I didn't really know the boss or even the names of all the divisions in the company."

[10:05] - Nurturing Passion and Building Effective Leadership Teams

"What are the things you were doing when you chose to stay late, didn't mind, and in fact, were excited or couldn't wait to get up the next day?"

[16:28] - Adjusting to New Roles and Unlearning

"I think it is one of the most profound realizations that two organizations can think about roles and define them very differently."

[24:05] - Discovering Aha Moments in Personal Growth

"Some of the things that helped you, like those aha moments? Now that you have new clarity, what are you doing differently?"

[28:54] - The Need for Unlearning in Industry Evolution

"Things most exciting about in the industry, and what do you think needs to be unlearned? I’ve noticed both individuals and organizations often resist asking for help, preferring to go it alone."

[36:04] - Conclusion and Future Aspirations

"It's been absolutely phenomenal to have you on the show. Thank you for sharing your story so openly and humbly. This is what people love listening to."

Follow Our Guest

LinkedIn Accounts:

Kristie Edling-Day: https://www.linkedin.com/in/kristie-edling-day-10690623/
Vanguard : https://www.linkedin.com/company/vanguard/
LPL Financial : https://www.linkedin.com/company/lpl-financial/

Websites:

Vanguard : https://investor.vanguard.com/corporate-portal

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

LinkedIn: https://www.linkedin.com/in/barryoreilly
Personal site: https://barryoreilly.com
Facebook: https://www.facebook.com/barryoreillyauthor/
Twitter: https://x.com/barryoreilly
Instagram: https://www.instagram.com/barryoreilly/
Email: hello@barryoreilly.com

How to Build a Viral App by Finding Untapped Niches for Explosive Growth | Crystal Gonzalez

Wed, 26 Feb 2025 01:00:00 -0400

Welcome to UNLEARN, the podcast where we explore the transformative experiences, strategies, and mindset shifts essential for true innovation and growth. Today, I’m honored to host Crystal Lee Gonzalez, a trailblazer in strategic growth and innovation across Southeast Asia.

Born and raised in the Philippines, Crystal has spent the last fifteen years shaping and scaling some of the region’s most prominent brands. She is the Co-Founder & CEO of NoneAway and was previously the Co-Founder of PICK.A.ROO. Her leadership has left a significant mark on multiple industries, serving as the Former CEO of Canva Philippines & Southeast Asia, Former President & Managing Director at HonestBee, and Former Regional Head of Southeast Asia at Viber. With a career spanning top-tier organizations, she also held key roles as the Group Account Director at Tribal Worldwide, Head of Branding at Lazada Group, and Marketing Head at YAHOO.

Beyond launching and leading businesses, Crystal finds deep fulfillment in mentoring emerging talent and reshaping industries through innovation. Her expertise is now encapsulated in her upcoming book, Innovate to Elevate: Transforming Markets and Minds in Southeast Asia, a must-read for those looking to make a lasting impact in technology and strategic development.

Key Takeaways:

Scaling Global Startups: Crystal details her strategies for business expansion in Southeast Asia.
Embracing Challenges: Insights into overcoming obstacles in high-growth environments.
Unlearning for Growth: How adapting and unlearning fuels innovation.
Leveraging Personal Experiences: Crystal's approach to creating solutions from personal pain points.

Additional Insights:

The NoneAway Model: Crystal demonstrates how strategic thinking and operational excellence revolutionize real estate.
Adapting in High Growth Markets: Mastering the challenges of rapid expansion and market dynamics.
Innovative Solutions from Personal Insights: How Crystal’s personal experiences inspire practical business innovations.

Prepare for an insightful conversation with Crystal Gonzalez on Bringing fresh ideas to startup strategies and cultivating a culture of innovation and strategic growth.

Episode Highlights:

[00:35] - Episode Introduction

"In the Philippines, there are 120,000 reported scammers in real estate. This is why, even with a legitimate broker, I felt unease and anxiety until I received the keys to my house."

[01:18] - Guest Introduction: Crystal Lee Gonzalez

"Welcome to the Unlearn Podcast. Today, I'm honored to host Crystal Gonzalez, a leader in strategy and growth who has developed and scaled renowned brands across Southeast Asia."

[03:03] - Viber's Launch Story

"It started when I met Talmon, the founder. My first question was simple: Why are you in the Philippines?"

[07:50] - Nurturing Empathy and Innovation

"Okay. So interesting fact. I promise you this is connected to my answer. So my dad and actually my sister, now my younger sister, they're both psychiatrists."

[16:15] - The Role of Relatability in Product Adoption

"When we added more words to our copy and analyzed our data, we changed our messages to offer free chat and calls for your family and friends abroad"

[26:08] - Discussion on Market Needs and Solution Development

"I kid you not, my earliest memories involve playing role-playing games with my childhood friends where I was signing checks."

[31:27] - Vision for a Seamless Real Estate Experience

"I've always promoted and highlighted issues, even if I wasn’t the founder or creator."

[42:11] - Building Trust in Philippine Real Estate: A Digital Solution

"I didn’t feel safe. Despite dealing with legitimate brokers, the anxiety of 120,000 reported real estate scammers in the Philippines lingered until I held the keys. I kept wondering.why hasn’t this been solved yet?"

[53:51] - Conclusion and Future Aspirations

"Just the way you discuss this issue, your previous achievements, and the team you are building indicate you're set to do something truly amazing."

Follow Our Guest

LinkedIn Accounts:

Crystal Lee Gonzalez: https://www.linkedin.com/in/crystalleegonzalez/
NoneAway : https://www.linkedin.com/company/noneaway/
PICK.A.ROO: https://www.linkedin.com/company/pickaroo/
Canva : https://www.linkedin.com/company/canva/
Honestbee: https://www.linkedin.com/company/honestbee/
Viber: https://www.linkedin.com/company/rakuten-viber/
Tribal World : https://www.linkedin.com/company/tribal-worldwide/
Lazada: https://www.linkedin.com/company/lazada/
Yahoo: https://www.linkedin.com/company/yahoo/

Websites:

NoneAway: https://noneaway.com/
PICK.A.ROO: https://pickaroo.com/
Canva: https://www.canva.com/
Honestbee: https://www.honestbee.com/
Viber:https://www.forbusiness.viber.com/
Lazada : https://group.lazada.com/
Yahoo: https://www.yahooinc.com/

_________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

LinkedIn: https://www.linkedin.com/in/barryoreilly
Personal site: https://barryoreilly.com
Facebook: https://www.facebook.com/barryoreillyauthor/
Twitter: https://x.com/barryoreilly
Instagram: https://www.instagram.com/barryoreilly/

How AI is Changing Product Management Forever with Diana Stepner

Wed, 12 Feb 2025 01:00:00 -0400

Welcome to UNLEARN, the podcast where we explore the stories, strategies, and mindset shifts that drive real innovation and growth. Today, I’m glad to be joined by Diana Stepner, a true trailblazer in the world of product management and people-centered leadership.

A Silicon Valley native, Diana has spent over two decades building and leading global product teams for companies like Monster, Cheapflights (later acquired by Kayak), Salesforce, and Razorfish. As Co-Founder, at Product Gold and Former VP of Product Management at Pearson, she has honed her expertise in creating impactful solutions. Along the way, she discovered that while launching great products is exciting, helping people launch their careers is even more rewarding..

Diana’s passion for fostering talent and preparing organizations for the future shines in her new book, Next-Gen Product Management: Future Proof Your Career. It’s a must-read for anyone navigating the rapidly evolving landscape of technology, teams, and innovation.

We dive into her journey, the lessons she’s learned, and the practical advice she has for product leaders looking to thrive in an ever-changing world.

Check out her website at www.dianastepner.com to learn more.

Key Takeaways:

Product vs. Project Management: Diana explains the key differences.
Supercharging Product Managers: How top contributors maximize impact.
Winning with Teams: The power of cross-functional collaboration.
Breaking Into Product Management: Trends shaping new career moves.

Additional Insights:

The Product Gold Framework, Diana shows how adaptability and empathy unlock market opportunities.
Engagement in the Digital Age by mastering attention in a world full of distractions.
Thinking Differently in Business: How challenging norms drives big advancements.

Prepare for an enlightening discussion with Diana Stepner on transforming traditional product strategies and fostering a culture of creativity and innovation.

Episode Highlights:

[00:33] -Episode Introduction

"One of the trends that we're seeing in product management is this rise of a super IC. People are able to do a whole lot more because of AI than they could have done before."

[01:33] - Guest Introduction

"Today, we’re joined by Diana Stepner, an expert in product management and people-centered leadership. Diana has built leading global product teams at companies like Product Gold, Monster, Salesforce, and Razorfish."

[03:08] - Shift from Project to Product Management

"People kept saying, 'Oh, you're a project manager.' And I'm like, 'No, I'm not a project manager. I am a product manager.' Over time, people began to realize that it actually was a skill or an expertise."

[10:44] - The Role of Collaboration in Product Management (corrected from 10:49)

"You need all of those instruments to come together to really make the music sing, and companies still don't realize that."

[16:08] - The Rise of Super ICs

"You're having these people be able to go much farther down the development path than what they did previously. And I think that's fascinating because it makes total sense."

[19:18] - The Evolution of the Mini-CEO & One-Person Unicorns

"For me, it feels like it's the incarnation of the mini-CEO. Now there's this billion-dollar unicorn narrative where one person is expected to do everything with AI."

[27:00] - The Role of Asynchronous Communication & AI in Workflow Efficiency

"It's funny, sometimes people get freaked out when I summarize a meeting in three minutes and email them key points before they've even left the call!"

[30:48] - The Future of Product Management

"I believe we need to evolve, but that also means we need to welcome in the next generation who bring their own unique perspectives."

[35:33] - Conclusion and Next-Gen Product Management Book Promotion

"My book, Next Gen Product Management, is for those who want to future-proof their careers and thrive in this evolving industry."

Follow Our Guest

LinkedIn Accounts:

Diana Stepner: https://www.linkedin.com/in/dianas/
Product Gold : https://www.linkedin.com/company/productgold/
Monster: https://www.linkedin.com/company/monster/
KAYAK: https://www.linkedin.com/company/kayak/
Salesforce: https://www.linkedin.com/company/salesforce/
RazorFish: https://www.linkedin.com/company/razorfish/
Pearson: https://www.linkedin.com/company/pearson/

Websites:

Personal Website: https://www.dianastepner.com
Product Gold: https://www.productgold.com/
Monster: https://www.monster.com/
KAYAK: https://www.kayak.com/
Saleforce: https://www.salesforce.com/ap/
RazorFish: https://www.razorfish.com/
Pearson: https://www.pearson.com/
Get your copy of Next-Gen Product Management today! Order now at https://www.nextgenproductmanagement.com/

_________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

LinkedIn: https://www.linkedin.com/in/barryoreilly
Personal site: https://barryoreilly.com
Facebook: https://www.facebook.com/barryoreillyauthor/
Twitter: https://x.com/barryoreilly
Instagram: https://www.instagram.com/barryoreilly/
Email: hello@barryoreilly.com

How the Attention Economy is Redefining Traditional Marketing with Emily Ross

Wed, 29 Jan 2025 01:00:00 -0400

Welcome to the UNLEARN Podcast! Today, we’re joined by Emily Ross, co-author of Just Evil Enough and a leader in brand strategy and creativity. With a career spanning tech innovation, marketing, and even circus performance, Emily approaches challenges from unconventional angles.

As Director of Brand Strategy at X (formerly Twitter) for EMEA, Emily also serves as an Advisory Board Member at SXSW and GoGreen Routes, an EU funded, pan-European research project on nature-based connectedness, as Co-founder of Resonance Festival (Resonance-Lough Derg), and a mentor to startups across Europe.

In this episode, she shares her approach to subversive marketing, reframing obstacles as opportunities and using bold tactics to achieve extraordinary results. Drawing inspiration from disruptors like Tesla, Emily reveals how creativity and curiosity can transform business outcomes. Whether you’re looking to reimagine your marketing strategies or disrupt the status quo, Emily’s expertise is an invaluable guide.

Key Takeaways:

Unconventional marketing tactics involve reframing challenges and using bold strategies like zero-day exploits to help brands stand out.
The power of creativity lies in applying attention-grabbing skills across industries, as seen through lessons from a diverse career.
Turning flaws into strengths, as seen with Tesla and Space Invaders, shows how weaknesses can become powerful advantages.
Consistency over brilliance emphasizes that success stems from daily effort and experimentation, not rare moments of genius.

Additional Insights:

The Recon Canvas Framework uncovers market opportunities and shows the need for constant adaptability as strategies evolve.
Capturing attention in the digital age requires standout marketing in a noisy, distracted world.
Subversive thinking from Just Evil Enough shows how breaking rules can drive business success.

Get ready for a fascinating conversation with Emily Ross on rethinking traditional approaches, embracing creativity, and crafting strategies that disrupt the status quo!

Episode Highlights:

00:37 - Introducing Emily Ross

"Emily is a powerhouse in brand strategy, creative leadership, and co-author of Just Evil Enough. She’s reshaping how global brands stand out in noisy markets."

03:15 - Lessons from the Circus The Power of Attention

"I spent years as a fire performer, and it taught me that attention is a superpower. Learning to capture and hold attention is a skill every marketer needs."

05:14 - Subversive Marketing Tactics Explained

"Subversive marketing is about being bold, counterintuitive, and creative. It’s not growth hacking, it’s about playing the long game to stay ahead."

09:47 - Turning Bugs Into Features

"The famous Space Invaders bug is a perfect example of how flaws can create differentiation. As the game progressed, it got faster, making it more exciting."

15:10 - The Product-Market Fit Myth

"Product-market fit isn’t real, it’s actually product-medium-market fit. Success lies in how you connect your product to the audience through the right medium."

20:33 - Zero-Day Exploits and Subversive Marketing

“We call those zero day exploits. So in cybersecurity, a zero day hack is one that is a kind of a finite hack."

22:42 - Underdog Success Using Unconventional Tactics

"When smaller forces use unconventional tactics, they can flip the odds. It’s how underdogs win in both marketing and warfare."

29:36 - The Recon Framework and Attention Economy

"One of the most practical pieces of the book is the recon canvas. We are drowning in noise, and Herbert Simon coined the term ‘attention economy’, where the thing in shortest supply becomes the currency of the day."

31:28 - Just Evil Enough: Unexpected Validation

"When I pitched the idea of Just Evil Enough sitting beside Alchemy on the shelf, I never imagined Rory Sutherland would not only read the book but offer such high praise. It was an amazing moment of recognition."

Follow Our Guest

LinkedIn Accounts:

Emily Ross: www.linkedin.com/in/emilyrossonline/
Twitter: www.linkedin.com/company/x-corp/
Resonance Festival (Resonance-Lough Derg): www.linkedin.com/company/resonance-loughderg/
SXSW: www.linkedin.com/company/sxsw/

Websites:

Twitter: https://x.com/
Resonance Festival (Resonance-Lough Derg): www.resonance-loughderg.com/
SXSW: www.sxsw.com/
Pre-order the First Edition Hardback of Just Evil Enough today at www.justevilenough.com/

_________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

LinkedIn: https://www.linkedin.com/in/barryoreilly
Personal site: https://barryoreilly.com
Facebook: https://www.facebook.com/barryoreillyauthor/
Twitter: https://x.com/barryoreilly
Instagram: https://www.instagram.com/barryoreilly/
Email: hello@barryoreilly.com

How Product Managers Can Avoid Startup Failures and Drive Growth with John Cutler

Wed, 15 Jan 2025 01:00:00 -0400

Welcome to the UNLEARN Podcast! Today, we’re joined by a thought leader and prolific voice in product management and organizational design, John Cutler. With a unique ability to navigate the “beautiful mess” of product development, John has spent his career exploring the complex overlaps of product, UX, and strategy.

Currently serving as Head of Product at Dotwork, John has previously held impactful roles such as Senior Director of Product Enablement at Toast and Product Evangelist at Amplitude, where he collaborated with thousands of product teams worldwide. His extensive experience spans B2B SaaS giants like Zendesk, Pendo, and AppFolio, as well as B2C, ad-tech, banking, and media industries.

Known for his insightful writing, John has authored nearly a thousand posts across various platforms, captivating readers with his deep understanding of product dynamics. Whether you’re seeking to level up your product thinking or gain practical tips on team enablement, John’s expertise offers unparalleled insights.

Key Takeaways:

The Beautiful Mess of Product Development: John’s approach to embracing complexity and context in product management to uncover innovative solutions.
Unlearning and Growth: How letting go of rigid practices and adapting to change can unlock greater potential for teams and leaders.
Writing as a Catalyst for learning: The power of consistent writing in shaping ideas, refining strategies, and building meaningful connections in the product community.

Additional Insights:

Product Ecosystems in Flux: John talks about the dynamic nature of product management, highlighting how roles and best practices evolve with organizational and market shifts.
Gamifying the Creative Process: Insights into how John uses tools and techniques to make writing, ideation, and problem-solving more engaging and productive.
Rethinking Organizational Models: Exploring how companies can overcome challenges by reimagining structures, roles, and team dynamics for the modern era.

Get ready for a thought-provoking conversation with John Cutler on embracing complexity, fostering innovation, and mastering the art of unlearning!

Episode Highlights:

00:36 - Episode Introduction

"I don't think we need a product manager for every 4 to 7 people. A software as a service company is much more of a service ecology."

01:15 - Introducing John Cutler

"John is one of the most insightful voices in product management, with a career spanning roles at Toast, Amplitude, and beyond."

03:46 - Discovering the "Beautiful Mess" of Product

"I’ve always been fascinated by the overlaps—where product, UX, and strategy collide in unpredictable ways."

11:27 - The Importance of Writing and Sharing Ideas

"I realized that writing wasn’t just for others—it was for me to process and refine my thinking."

15:59 - Finding Your Path Through Experimentation

"Everybody finds their way if you're willing to experiment and try. It's like software—the rate of iteration and the velocity of creation allow you to refine and improve over time."

33:06 - Lessons in Unlearning

"It’s not just about adopting new practices; it’s about letting go of the ones that no longer serve the team or the context."

40:59 - What Excites John About the Future of the Industry

"The future of product management lies in embracing complexity and experimenting with new ways to scale and deliver value."

Follow Our Guest

LinkedIn Accounts:

John Cutler: www.linkedin.com/in/johnpcutler/
Dotwork: www.linkedin.com/company/dotworklabs/
Toast: www.linkedin.com/company/toast-inc/
Amplitude: www.linkedin.com/company/amplitude-analytics/
Zendesk: www.linkedin.com/company/zendesk/
Pendo: www.linkedin.com/company/pendo-io/

Websites:

_________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

LinkedIn: https://www.linkedin.com/in/barryoreilly
Personal site: https://barryoreilly.com
Facebook: https://www.facebook.com/barryoreillyauthor/
Twitter: https://x.com/barryoreilly
Instagram: https://www.instagram.com/barryoreilly/
Email: hello@barryoreilly.com

Proven Strategies to Create Accountability Without Agency with Lee Vorthman

Wed, 18 Dec 2024 01:00:00 -0400

Welcome to the UNLEARN Podcast! Today, we’re joined by Lee Vorthman, Vice President of Strategic Security Initiatives at Oracle. Lee leads a global team to protect and strengthen Oracle's operations. He is also a Global CISO Advisory Board Member at HMG Strategy and an Advisory Board Member for Phoenix Security.

His career began in the US Navy, and he has since held key roles across defense, technology, cloud, education, and oil & gas industries. Lee’s past roles include Chief Security Officer for Oracle's Advertising group, leading Global Security Engineering at Pearson Education, and serving as Chief Technology Officer for Federal Civilian Agencies at NetApp.

In this episode, Lee shares insights on leveraging technology for growth, navigating cultural transformations, and building resilient organizations.

Key Takeaways:

Mastering Security Fundamentals: Lee highlights the importance of staying grounded in foundational security practices while adopting innovative technologies like AI to address evolving challenges.
Building Trust and Influence: Discover Lee’s techniques for fostering collaboration, psychological safety, and cultural change to drive impactful security initiatives.
The Power of Diverse Skills: Learn why developing a broad skill set across disciplines like engineering, finance, and HR is essential for empathetic leadership and effective problem-solving.

Additional Insights:

Cultural Change in Security: Get ready for a thought-provoking conversation with Lee Vorthman on leadership, innovation, and building resilient organizations!
Balancing Speed and Resilience: Insights on how businesses can prioritize innovation while maintaining strong operational fundamentals.
The Future of Cybersecurity: Exploring emerging trends like AI and their implications for addressing new and complex threats.

Get ready for a thought-provoking conversation with Lee Vorthman on leadership, innovation, and building resilient organizations!

Episode Highlights:

00:36 - Episode Introduction
"We're always going to have new technologies. But that doesn't negate the fact that you still have to master the fundamentals."
01: 03 - Barry introduces Lee Vorthman as a seasoned cybersecurity expert and VP of Strategic Security Initiatives at Oracle.
02:27 - Personal Background and Military Influence
"I grew up in a military household and started in technology before joining the military."
05:33 - Evolution of Security Leadership
"Security leadership now touches every aspect of a business, requiring a broad understanding beyond just technology."
11:15 - Navigating Accountability vs. Ownership
"In the civilian world, I’m accountable for risks I don’t always own, which requires building alliances."
15:05 - Techniques for Overcoming Resistance
"Two techniques I use to convince people: the switcheroo and Jedi mind trick for breaking resistance."
22:35 - Challenges in the Security Industry
"The industry tends to chase shiny new technologies while neglecting critical fundamentals."
28:06 - Excitement About Emerging Technologies
“I love when new technology comes out because it allows security people to put their hats on to make it safe.”
30:25 - Closing Remarks
"It’s been an amazing journey, and I appreciate sharing these stories on the podcast."

Follow Our Guest

LinkedIn Accounts:

Lee Vorthman: https://www.linkedin.com/in/leevorthman/
Oracle:https://www.linkedin.com/company/oracle/
US Navy: https://www.linkedin.com/company/us-navy/
HMG Strategy: https://www.linkedin.com/company/hmg-strategy-llc/
Phoenix Security: https://www.linkedin.com/company/phoenixsecuritycloud/
Evanta, a Gartner Company: https://www.linkedin.com/company/evanta/

Websites:

Lee Vorthman (Blog): https://blog.370security.com/author/lee1fbb48c29971/
Oracle: https://www.oracle.com/
US Navy: https://www.navy.mil/
HMG Strategy: https://hmgstrategy.com/
Phoenix Security: https://phoenix.security/
Evanta, a Gartner Company: https://www.evanta.com/

_________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

LinkedIn: https://www.linkedin.com/in/barryoreilly
Personal site: https://barryoreilly.com
Facebook: https://www.facebook.com/barryoreillyauthor/
Twitter: https://x.com/barryoreilly
Instagram: https://www.instagram.com/barryoreilly/
Email: hello@barryoreilly.com

Why Unlearning Cultural Norms Is Essential for Thriving in Global Leadership with Ani Filipova

Wed, 04 Dec 2024 01:00:00 -0400

Welcome to the UNLEARN Podcast! Today, we’re joined by an inspiring leader in global banking and transformation, Ani Filipova. With over two decades of experience, Ani has made her mark as a former international banking executive, setting up and managing three banks, including Citibank Bulgaria. She also led the transformation of a $2 billion business across 16 countries as Regional COO for Citibank Treasury and Trade Solutions in Asia.

Ani’s path to success was anything but conventional. Fueled by a passion for travel, she overcame rejections and seized every opportunity to explore the world and build a remarkable career. Now, Ani is reshaping her journey through a “portfolio career,” as the Founder & CEO of Change Advisory, drawing from her wealth of experience to inspire others with insights on leadership, transformation, and reinvention.

Key Takeaways:

Exploring Beyond Boundaries: Ani’s journey of growing up behind the Iron Curtain, finding creative ways to explore the world despite restrictions.
Speaking Up and Taking Risks: Strategies Ani used to conquer anxiety, master the art of speaking up, and embrace bold decisions in high-stakes situations.
Global Team Collaboration: Insights on fostering alignment and driving collaboration across diverse teams to achieve success in complex, multinational organizations.

Additional Insights:

Embracing Change: Ani highlights the challenges and rewards of adapting to digital transformation.
Cross-Cultural Collaboration: Understanding local customs as a foundation for trust and teamwork.
Unlearning to Grow: Letting go of old habits to thrive in evolving business landscapes.

Get ready for an inspiring and transformative conversation with Ani Filipova on embracing change, leadership, and the power of reinvention!

Episode Highlights:

00:36 - Episode Introduction

"If you don't speak up, if you don't show your work. If you don't share your opinions, that's not good at all.

01:27 - Introduction to the Episode: Barry introduces Ani Filipova

‘’Ani Filipova, an inspiring leader whose journey spans across continents, industries, and perspectives’’

03:10 - Growing Up Behind the Iron Curtain

"I saw the world through books... Pippi Longstocking inspired me to dream about traveling to far-off places."

12:59 - Leadership Across Cultures

"You can’t pretend to care about people’s aspirations—you have to truly understand what drives them to build trust and alignment."

25:01 - Overcoming Personal Challenges in Leadership

"I realized I needed to stop taking everything personally—it was a turning point that helped me approach challenges more confidently."

27:56 - Speaking Up in Leadership Meetings

"I remember waiting for the right moment to contribute, and when I did, the adrenaline rush was overwhelming, but it was worth it."

37:44 - Adapting Banking to the Digital Era

"Transitioning from three-day payments to three-second transactions required rethinking systems, processes, and customer expectations."

42:11 - The Challenge of Unlearning

"To succeed in today’s fast-changing world, leaders must unlearn old habits and embrace continuous listening and collaboration."

45:33 - Closing Reflections

"It’s about reinvention—helping others see their own potential and embrace transformation in their careers."

Follow Our Guest

LinkedIn Accounts:

Ani Filipova: www.linkedin.com/in/anifilipova
Citibank: www.linkedin.com/company/citi
Change Advisory: www.linkedin.com/company/the-change-advisory
AdVentura Works SA.: www.linkedin.com/company/adventura-works

Websites:

Ani Filipova - Change Advisory: www.anifilipova.me
Citibank: www.citigroup.com/global
AdVentura Works SA.: www.adventura.works

_________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

LinkedIn: https://www.linkedin.com/in/barryoreilly
Personal site: https://barryoreilly.com
Facebook: https://www.facebook.com/barryoreillyauthor/
Twitter: https://x.com/barryoreilly
Instagram: https://www.instagram.com/barryoreilly/
Email: hello@barryoreilly.com

Personalized: Customer Strategy in the Age of AI with David C. Edelman

Wed, 20 Nov 2024 01:00:00 -0400

Welcome to the UNLEARN Podcast! Today, we’re joined by a true pioneer in digital transformation and customer strategy, David C. Edelman. With over three decades at the forefront of marketing and digital transformation, David most recently served as Chief Marketing Officer at Aetna/CVS, where he led transformative shifts in customer engagement. Before that, he co-led McKinsey’s Global Digital Marketing and Sales Practice and held key leadership roles at Digitas and Boston Consulting Group (BCG), advising top executives worldwide.

Now, David is bringing his expertise to Harvard Business School, where he shapes the next generation of leaders and advises CXOs on driving digital agility and building resilient teams. In this episode, he shares insights from his latest book, Personalized: Customer Strategy in the Age of AI.

We’ll explore the different types of AI, where and how to use them, and the evolving role of AI across the C-suite. Get ready for an enlightening conversation with David Edelman on the future of customer strategy in the age of AI.

Key Takeaways:

Personalized Connections with AI: David’s “five promises” framework—Empower, Know, Reach, Show, Delight—guides personalized customer experiences.
AI Beyond Marketing: Personalization extends beyond marketing into a holistic, C-suite-level strategy.
Data to Value: Examples from Aetna using data to simplify interactions and deliver targeted recommendations.
Balancing Innovation and Trust: David stresses trust in AI, focusing on data privacy and ethical personalization.

Additional Insights:

Promise and Pitfalls of AI: Emerging AI tools make data integration accessible, helping smaller companies compete with industry giants.
Managing Expectations: The importance of transparency and data use comfort in creating personalized, non-intrusive customer experiences.
Unlearning Old Mindsets: David encourages that leaders must shift from traditional tactics to a customer-centric, AI-driven approach.

Episode Highlights:

00:00 - Episode Introduction

"If you’re trying to connect with customers using personalization, there are essentially five promises that you’re making to them."

01:35 - Introduction to the Episode: Barry introduces David Edelman, a veteran in digital transformation and customer strategy.

“David has spent over three decades at the cutting edge of marketing and digital transformation.”

03:06 - Early Influences: Creativity and Leadership in Marketing

“I became the music director of my high school show from just simply being a saxophone player.”

08:33 - From Marketing to AI-driven Strategy

“The thing I had to unlearn is that it’s not just about marketing... it’s about strategy and customer experience.”

10:03 - Using AI for Personalization: Shopify and Brinks Case Studies

“So Shopify, who has a free trial and then offers to convert people to paid subscriptions... it’s over 500 combinations.”

19:26 - Educational Personalization: The Aetna Video Initiative

“People don’t understand it, they make mistakes... so we found a provider that could create personalized videos.”

25:25 - The Five Promises of Customer Strategy

“Empower me, know me, reach me, show me, delight me.”

37:59 - Closing Thoughts and The Future of AI in Personalization

“We’ve got to show good things, good experiences that are happening in ways that are trustful and appropriate.”

Follow Our Guest

LinkedIn Accounts:

David C. Edelman: https://www.linkedin.com/in/daveedelman/
Aetna: https://www.linkedin.com/company/aetna/
McKinsey: https://www.linkedin.com/company/mckinsey/
BCG: https://www.linkedin.com/company/boston-consulting-group/
Digitas: https://www.linkedin.com/company/digitas-north-america/
Harvard Business School: https://www.linkedin.com/school/harvard-business-school/

Websites:

Aetna: https://www.aetnacvshealth.com/
McKinsey: https://www.mckinsey.com/
BCG: https://www.bcg.com/
Digitas: https://digitz-digitas.com/
Harvard Business School: https://www.hbs.edu/

_________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

LinkedIn: https://www.linkedin.com/in/barryoreilly
Personal site: https://barryoreilly.com
Facebook: https://www.facebook.com/barryoreillyauthor/
Twitter: https://x.com/barryoreilly
Instagram: https://www.instagram.com/barryoreilly/
Email: hello@barryoreilly.com

Ethical Strategies for Startup Leaders to Avoid Growth Hacking with Andy Budd

Wed, 06 Nov 2024 01:00:00 -0400

Mastering venture capital and ethical growth is essential for startup success. Today’s guest, Andy Budd, shares insights from his journey as Founder and CEO of Clearleft, Venture Partner at SeedCamp, and Founding Member of Adobe’s Design Circle. Andy has evolved from a designer to an investor and advisor, bringing a focus on ethical growth practices and high-impact startup development.

As the author of The Growth Equation, Andy draws on over 20 years of experience to help companies achieve product-market fit and sustainable growth. His work with SeedCamp and other startups focuses on behavioral science and ethical growth strategies to build resilient, user-centered businesses.

In this episode, host Barry O'Reilly explores Andy’s approach to venture capital, leadership, and how his design roots influence his support for founders.

Key Takeaways:

The Transition from Design to Venture Capital: Andy shares his journey from designer to venture capital partner, highlighting the unique insights that his design background brings to his work with startups.

The Importance of Humility in Leadership: Andy emphasizes the value of hiring individuals who excel in areas beyond one’s own expertise, fostering a team culture of shared growth and continuous improvement.

Supporting Startups Through Challenges: Known for working closely with startups facing obstacles, Andy describes how his collaborative approach helps companies pivot, adapt, and ultimately thrive.

Ethical Growth Over “Growth Hacking”: Andy discusses the significance of ethical growth practices, contrasting them with conventional “growth hacking,” and focusing on strategies that promote sustainable and user-centered growth.

Additional Insights:

The Influence of Behavioral Science in Product Development: Andy explains how understanding human behavior enhances product design and growth, encouraging founders to integrate behavioral science for more meaningful user engagement.

The Role of Patience and Empathy in VC: Andy reflects on his approach to venture capital, prioritizing empathy and patience with founders to cultivate trust and strong, lasting partnerships.

The Changing Landscape of Startup Investment: Andy shares his views on how venture capital is evolving, especially as design-thinking and user experience become increasingly vital for high-growth startups.

Episode Highlights:

0:39 - Introduction to the Episode: Barry introduces Andy Budd, Startup Advisor, Investor, and Coach.

“Andy has extensive experience in design and startup advisory.”

03:31 - Transition from Design to Venture Capital

"I've always been inspired by others...there was an agency that really inspired Clearleft back in the day called Adaptive Path."

06:58 - Unlearning Practitioner to Leader

“The main thing I had to unlearn was moving from a practitioner to a leader, where you need to let go and trust others.”

15:56 - Emphasis on Character and Integrity in VC

“If you're rude to the driver or the person at reception, it shows a lot about your character.”

24:34 - The Growth Equation: Helping Founders Find Product-Market Fit

"One of my reviewers said it’s like having a pocket coach. Why spend thousands on an online course when you can get the framework in a book?"

33:32 - Role of Behavioral Science in Growth

"I'd demonstrate it with an example. So an example is economics... economists thought we were rational actors, that we’d make logical decisions about the future, like saving for retirement. But people tend to choose instant gratification, which is where behavioral economics comes in."

37:26 - The Ethical Approach to Product-Led Growth

“Product-led growth has been one of the biggest trends in the last few years, around how we can use our products and the way we design them to attract more users and drive engagement.”

45:13 - Andy’s Thoughts on Growth Hacking vs. Ethical Growth

"A big part of my book is actually about how you look at growth, but in a more moral, reasonable, and acceptable way. I hate the idea of growth hacking."

46:42 - Wrap-up & Final Thoughts: Barry and Andy discuss the ongoing importance of community and knowledge-sharing.

"Everyone, get yourself a copy of The Growth Equation!”

Follow Our Guest

LinkedIn Accounts: Andy Budd, Clearleft, Adobe, Seedcamp

Websites: Andy Budd - Personal Site, Clearleft, Adobe, Seedcamp

_________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

LinkedIn: https://www.linkedin.com/in/barryoreilly
Personal site: https://barryoreilly.com
Facebook: https://www.facebook.com/barryoreillyauthor/
Twitter: https://x.com/barryoreilly
Instagram: https://www.instagram.com/barryoreilly/
Email: hello@barryoreilly.com

Building Relationships to Recruit the World’s Best Talent with Michael A. Morell

Wed, 23 Oct 2024 01:00:00 -0400

Mastering executive search and building lasting business relationships are essential for successful transformations. Today’s guest, Michael A. Morell, shares insights from his journey at Riviera Partners, a top executive search firm, and as a former member of the Technology Advisory Board at Bridgewater Associates.

Michael A. Morell is the Founder and Managing Partner of Riviera Partners, with over two decades of experience in executive search. After starting his career in technology, a poor interview experience sparked his idea to create a better approach to recruiting. Today, Michael and his team help tech companies make high-stakes hires, transforming how top talent is identified and placed in Silicon Valley and beyond. Riviera Partners continues to deliver executive search solutions for some of the most innovative companies around the world.

In this episode, host Barry O’Reilly explores Michael’s approach to executive recruitment, the importance of patience in relationship-building, and how Riviera Partners leverages technology to deliver consistent, high-quality results.

Key Takeaways:

The Power of Patience in Relationship Building: Michael shares why patience is critical in executive search and enterprise sales, where building strong, lasting relationships can lead to long-term success.

Consistent Delivery of High-Quality Experiences: Michael emphasizes how consistent, positive experiences set Riviera Partners apart, explaining how a focus on quality service helped them build a reputable brand in executive recruitment.

The Role of a Clear Vision: Michael discusses the importance of a simple and clear company mission that empowers employees to make decisions aligned with the company’s values.

Adapting to Technological Advances: As technology has evolved, so has Riviera Partners. Michael shares how the firm leverages data and technology to enhance the recruitment process and provide better insights for clients.

Additional Insights:

Learning Through Experience: Michael’s shift from technology to recruitment highlights the value of diverse experiences and risk-taking in meaningful work, as he reflects on the challenges of building Riviera Partners.

The Changing Recruitment Landscape: Michael discusses how tools like LinkedIn have democratized recruitment and shares his excitement about AI and machine learning’s potential to transform executive search.

The Future of Workplace Flexibility: Michael reflects on the pandemic’s impact on remote work, emphasizing the balance between flexible environments and the importance of in-person interactions for leadership roles.

Episode Highlights:

00:40 - Introduction to the Episode: Barry introduces Michael A. Morell, Founder of Riviera Partners

“Michael has over two decades of experience in executive search.”

03:19 - The career transition into recruitment

“About 3 or 4 years into that, I got a random call from a recruiter who said, 'Hey, we’d love to grab coffee.' Long story short, I had coffee, she showed me a couple of opportunities—this was around the 2000 timeframe—and it was just the most awful experience I’ve ever had."

06:34 - Michael applies his long-term sales experience to relationship-building in executive search

“I had the patience to develop these relationships, but I thought, it couldn't be that complicated.”

15:27 - Delivering Consistent, High-Quality Experiences

“For us, it was really about one thing: how do we consistently deliver a great experience?”

24:17 - Navigating the shifts in recruitment technology

“The Rolodex became LinkedIn, and suddenly all the information was democratized. You can start to anticipate changes, but fundamentally, every client and every candidate is unique.”

34:02 - Embracing workplace flexibility and hybrid models

“We went from everyone needing to be on-site to realizing remote could work. Now, we’ve evolved to a hybrid model, balancing in-person and remote roles.”

36:59 - The future of recruitment with AI and machine learning

“I’m excited to see how AI can enhance our processes, from finding insights in data to improving client and candidate experiences.”

Follow Our Guest

LinkedIn: Michael A. Morell, Riviera Partners,Bridgewater Associates.
Websites: Riviera Partners, Bridgewater Associates

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Leading A Top 10 Transformation of the Decade at DBS Bank with David Gledhill

Wed, 09 Oct 2024 01:00:00 -0400

Driving innovation in technology and business transformation demands visionary leadership, seamless integration of business and tech strategies, and a willingness to take risks. Today's guest, David Gledhill, exemplifies these qualities as he shares his experience leading DBS Bank through a remarkable digital transformation and beyond.

David Gledhill is a seasoned technologist and business leader. As the former Group Chief Information Officer at DBS Bank for over 11 years, he spearheaded the bank’s technology and transformation efforts, building a high-performance culture and integrating technology into the core of the business strategy. Under his leadership, DBS achieved global recognition for its digital transformation, and David’s journey has been featured in Harvard Business Review as one of the top global transformations. After his time at DBS, David held a senior role at Lloyds Banking Group, further enhancing his expertise in large-scale transformation. He is now a non-executive director at companies like Singapore Airlines and serves as a senior advisor to McKinsey & Company.

In this episode, host Barry O'Reilly invites David to discuss his leadership journey, from reshaping the technology at DBS to embracing a digital-first strategy. David offers insights on making tough decisions, aligning business with technology, and leading organizations through massive change.

Key Takeaways:

Technology as a Strategic Driver: David emphasizes the shift from viewing technology as a support function to recognizing it as a core driver of business strategy. He explains how leading with a digital-first mindset can unlock new growth opportunities.

]

Bold Decision-Making in Leadership: David shares the importance of making tough decisions early in leadership roles. He describes how scrapping failing projects and resetting strategies allowed DBS to pivot successfully.

Building a High-Performance Culture: David highlights the significance of creating a culture where business and technology teams share accountability. His “two in a box” leadership model at DBS encouraged joint ownership of goals and outcomes.

Learning from Tech Giants: Drawing inspiration from companies like Google and Amazon, David discusses how studying these tech giants helped DBS adopt cutting-edge practices in cloud computing, data analytics, and agile development, setting them apart in the banking industry.

Additional Insights:

Fostering a Culture of Storytelling: David highlights the importance of storytelling in driving organizational change. At DBS, he brought in a journalist to craft compelling narratives around early successes, which helped engage teams and build momentum for transformation.

From Technologist to Strategic Leader: David’s transition from a technical expert to a strategic business leader is a testament to the evolution required in leadership roles. He reflects on how moving from deep technical work to overseeing large-scale business transformation broadened his leadership perspective.

The Role of Technology in the Future of Banking: David reflects on the future of the financial industry, noting that technology will continue to play a critical role in driving innovation and improving customer experiences. He emphasizes the need for continuous adaptation to stay competitive in the fast-changing digital landscape.

Episode Highlights

00:00 - Introduction to the episode

Barry introduces David Gledhill, highlighting his role as former Group CIO of DBS Bank and his contributions to the company’s digital transformation.

04:12 - David on his early career and technical roots

"I started off even when I was 11 or 12, building stuff with electronics and did computing electronics at university."

05:13 - The turning point of joining DBS

"When my career progressed, I became more of an exec... And then back in 2008, an opportunity came to join DBS Bank and become a CIO again, and get really back into tech."

12:21 - Scrapping the core banking system

"They’d spent like $300 million of a $200 million budget. And the estimate was this is going to take another five years and another billion dollars to complete."

12:36 - Rebuilding the technology strategy at DBS

"I had to basically scrap that whole program and restart... it was a total reset of strategy, roadmap, people, everything from scratch."

17:31 - Creating success with the ‘buy, sell, hold’ strategy

"We came up with this what we call the buy, sell, hold diagram... I love the system, and do more with it. Sell it to get rid of it. Hold is kind of meh but it'll keep going for now."

24:21 - The platform model and joint leadership

"We created a ‘two in a box’ leadership model, where a business leader and a tech leader had joint KPIs... business KPIs, customer service levels, tech modernization – everything."

31:47 - The ‘Gandalf’ moment and digital-first strategy

"We looked at Google, Amazon, Netflix, Apple, LinkedIn, Facebook, and I came up with this idea of what if we were the D in Gandalf?"

37:33 - Lessons for the future and technology’s role in business growth

"It’s hugely satisfying when you see that happen... they’re doing some super risky things, which may or may not play out, but that’s great fun to be part of."

Follow Our Guest

LinkedIn: David Gledhill
Website: DBS Bank, Lloyds Banking Group, Singapore Airlines, McKinsey & Company

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Bridging Tech and Healthcare with Richard Lennox- Former COO & Current Health and Senior Director at Skyscanner

Wed, 25 Sep 2024 01:00:00 -0400

Leadership in technology and operations requires a strategic focus on scaling businesses, empowering teams, and driving innovation. Today's guest, Richard Lennox, exemplifies these qualities as he shares his journey from leading Skyscanner through rapid growth to scaling healthcare innovation at Current Health.

Richard Lennox is an experienced technologist and business leader. As Senior Director at Skyscanner, he led the company’s engineering and operations teams through a pivotal period of scaling, focusing on high-performance teams and continuous delivery. After Skyscanner’s successful exit, Richard transitioned to COO at Current Health, where he helped scale the business, focusing on home healthcare delivery through technology. His leadership experience spans multiple industries, making him a valuable mentor and guide for those navigating startup growth and innovation.

In this episode, host Barry O'Reilly invites Richard to discuss his journey, from his early days at Skyscanner to his role at Current Health. Richard provides insights into scaling startups, the importance of data-driven decision-making, and the operational challenges of growing high-performance teams.

Key Takeaways:

Customer Value at the Core: Richard emphasizes the importance of focusing on delivering customer value in all areas of business, whether in technology or healthcare. Customer needs should drive product development and operational strategies.

Scaling High-Performance Teams: Richard discusses how growing from small teams to larger, cross-functional squads allowed for better alignment with business goals at Skyscanner. He shares the challenges and successes of implementing a squad model to foster accountability and autonomy within teams.

Rapid Decision-Making: Making fast decisions and knowing when to reverse them is critical to maintaining agility in a growing company. Richard stresses the importance of empowering teams to make decisions based on data and customer outcomes.

Holistic Leadership: Transitioning from a function-specific mindset to a broader business operations perspective allowed Richard to lead with a focus on scaling the entire organization, not just the technology function.

Additional Insights:

Empowering Teams through Data: Richard highlights the value of real-time data in empowering teams to make informed decisions. At Skyscanner, instrumentation of key metrics allowed teams to focus on customer outcomes and make data-driven decisions at scale.

Transitioning from Tech Leadership to Business Leadership: Richard’s journey from Senior Director at Skyscanner to COO at Current Health showcases the evolution from technical leadership to overseeing broader business operations. He reflects on the mindset shift required to focus on business outcomes over functional expertise.

The Future of Healthcare at Home: Richard shares insights into the growing importance of delivering healthcare in the home environment, using technology to monitor patients remotely and operationalizing care at home programs. This innovation is essential for reducing the burden on hospitals and improving patient outcomes.

Episode Highlights:

00:00 - Download free innovation map
00:41 - Introduction to Richard Lennox
03:36 - Early career and decision to join startups

"I got really lucky early on in my career, joining an early startup, which shaped my thinking about delivering value to customers."

07:48 - Learning from setbacks and focus on customer value

"There has to be a better way to deliver value consistently without causing setbacks for the business."

14:48 - Rapid decision-making and empowering teams

" I think the tricks for scaling are rapid decision making and how you invert the decision when you make it wrong. The more you hang on to a wrong decision, the worse the impact is."

24:21 - Richard’s Transition to COO at Current Health and Leading Healthcare Innovation

"Current Health provides a platform to enable care to be delivered at home."

32:12 - Future of Healthcare at Home and Operational Excellence

"Our job was to operationalize care at home programs, and that required a whole new set of tools and thinking."

38:06 - Wrap Up

Follow Our Guest

LinkedIn: https://www.linkedin.com/in/rlennox/
Website: https://www.currenthealth.com/
https://www.linkedin.com/company/skyscanner/

_________________________________

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Transforming Government Procurement: Paola Santana’s Vision for G-Commerce | Founder at E-Government Innovator

Wed, 11 Sep 2024 01:00:00 -0400

Leadership in government and technology requires not only innovative thinking but also a deep commitment to public service. Today's guest, Paola Santana, exemplifies these qualities as she shares her journey from law and politics to becoming a trailblazer in government technology.

Paola Santana is a lawyer, public procurement expert, and serial tech entrepreneur who is revolutionizing government systems. As the founder and CEO of Glass, she is pioneering G-commerce, a new way for governments to procure goods and services. Her prior experience includes co-founding Matternet, a company leading the way in drone logistics networks. Under her leadership, Matternet worked with the White House, U.S. Congress, and NASA to establish the first U.S. drone regulations, leading to the first drone delivery platform authorized for permanent operations over a populated city.

In this episode, host Barry O'Reilly invites Paola to discuss her remarkable journey, from her early career in law and government to her groundbreaking work in technology. Paola offers insights into the challenges and opportunities of transforming public systems through entrepreneurship, emphasizing the importance of agility, data-driven decision-making, and the crucial role of small businesses in economic development.

Key Takeaways:

Holistic Approach to Innovation: Sustainable change in government systems requires integrating public and private sector strategies, emphasizing agility, and leveraging technology.
The Importance of Small Businesses: Small businesses are the backbone of economic development. Empowering them through government procurement can lead to more dynamic and effective public services.
Procurement as a Catalyst: Effective procurement is essential for materializing government initiatives. It's not just about contracts; it's about ensuring that public funds are spent in ways that truly reflect the needs and priorities of the community.
Embracing Technology: The future of procurement lies in the intersection of e-commerce and government processes. Leveraging data and AI can make government procurement more efficient and aligned with public policy goals.

Additional Insights:

From Law to Tech: Paola's transition from law and public service to tech entrepreneurship highlights the power of interdisciplinary approaches to solving complex public sector challenges.
The Role of AI in Procurement: AI and data analytics are crucial in making government procurement more transparent and efficient, ensuring that public funds are used effectively to meet community needs.
The Value of Persistence: Paola’s journey shows that persistence and a willingness to challenge conventional wisdom can lead to breakthroughs, even in highly regulated sectors like government procurement.

Episode Highlights:

00:00 - Download free innovation map

00:41 - Introduction to Paola Santana

02:05 - Paola’s Career Clarity and Influence

The first thing is that for the level of clarity that someone like me has, where I've always known or carved moments to get very clear on where I wanted to go..."

07:26 - Transition from Law to Tech

"I love this saying attributed to Steve Jobs: You can only connect the dots looking backwards."

21:24 - Founding Glass and the Importance of Transparency

"Glass is literally the name that came very intuitively to me, and I've been unpacking what the name of Glass means."

22:39 - Contrasts Between Public and Private Sectors

"Entrepreneurship is grueling. Like, you know, you either have results or you don't."

47:29 - Small Businesses and Economic Development

"The future of procurement is not procurement. The future of procurement is e-commerce."

Follow Our Guest

LinkedIn: https://www.linkedin.com/in/paolasantanam/
Website: https://www.linkedin.com/company/glassgovtech/

_________________________________

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Email: hello@barryoreilly.com

Brand Safety & Platform Integrity at Spotify, TikTok and Google with from Dave Byrne

Wed, 28 Aug 2024 00:15:00 -0400

Leadership in digital ecosystems requires a commitment to safety, trust, and ethical practices. Our guest today, Dave Byrne, founder of Trust Raise and a member of the Irish Digital Board, shares his journey from major tech giants to establishing a company dedicated to improving the integrity of digital platforms.

Dave Byrne has had an illustrious career, holding significant positions at Google, TikTok, and Spotify, where he spearheaded initiatives in brand safety and platform integrity. Now, as the founder of Trust Raise, he focuses on helping smaller companies navigate the complex landscape of digital safety. His work is driven by a deep commitment to creating ethical digital ecosystems that prioritize user needs and improve industry standards.

Host Barry O'Reilly invites Dave to discuss his career journey, the challenges of maintaining digital safety in a rapidly evolving industry, and the inspiration behind founding Trust raise. Dave shares valuable insights into the importance of adaptability, the evolving role of AI in digital safety, and how smaller companies can leverage his expertise to build safer digital platforms.

Key Takeaways:

Resilience Through Failure: Early career setbacks can teach invaluable lessons about humility, perseverance, and the importance of continuous effort.
Navigating Global Teams: Success in a fast-paced, global environment requires strong relationships, effective collaboration, and the ability to work across different time zones and cultures.
Overcoming 'Golden Handcuffs': Comfort and security in large tech companies can sometimes hinder innovation. Pushing oneself out of the comfort zone is crucial for personal and professional growth.
AI’s Potential in the Workplace: AI has the potential to enhance productivity and creativity. Those who leverage AI effectively will be at the forefront of industry innovation.

Additional Insights:

Personal Reflections on Failure: Dave shared how an early career setback taught him invaluable lessons about resilience, humility, and the importance of continuous effort. This experience has profoundly influenced his work ethic and approach to leadership.
AI's Potential to Revolutionize Work: Dave is optimistic about AI’s potential to enhance productivity and creativity. He believes that those who learn to leverage AI effectively will be at the forefront of the industry, taking on more dynamic roles and contributing to a more innovative tech landscape.
The Importance of Ethical Tech Development: Throughout his career, Dave has been a strong advocate for ethical practices in tech. He stressed the need for companies, big and small, to prioritize user safety and trust, especially as technology continues to evolve rapidly.

Episode Highlights

00:00 - Download my free innovation map
00:39 - Introduction to Dave Byrne
03:00 - Dave’s unexpected start in his career and the impact of failure.

“This career in Google, TikTok, Spotify was not at all planned whatsoever... I actually ended up in Google because I lost a student union election in Trinity College."

07:35 - The rise of brand safety concerns and the 'Apocalypse.'

"The Adpocalypse... Brand safety became something that YouTube started caring about, Meta started caring about."

11:18 - Eroding Brand Perception

“ we're eroding brand perception of our customers. Again, scary things for any business to be facing, never mind the scale of the brands you're going to be working with within Google at the time.."

25:12 - The complexities of the tech ecosystem.

" I think when people think of the digital ecosystem, they think of the Googles, they think of the metas, they think of the TikToks of the world. And yes, they take up a huge amount of people's time and engagement but there are thousands of companies that make up this ecosystem, like just the ad ecosystem itself."

44:38 - The impact of AI on job roles and democratizing work opportunities.

" AI and the tools that we're seeing are democratizing like these skills and like the ability for these folks to actually participate in, in areas where they couldn't have before."

Follow Our Guest

LinkedIn Profile: https://www.linkedin.com/in/davebyrned/
Website: https://www.trust-raise.com/

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Cracking The Code For A Career in Cyber Security with Former FBI Special Agent Dave Mahon

Wed, 14 Aug 2024 01:00:00 -0400

Cybersecurity is an ever-evolving field that requires continuous learning, adaptability, and a deep understanding of both the technological landscape and human behavior. Today’s guest, Dave Mahon, a seasoned cybersecurity expert with extensive experience in both the private and public sectors, shares his journey from the FBI to leading global cybersecurity efforts in the corporate world.

Dave Mahon served as a Senior Advisor for Deloitte, where he was instrumental in developing and executing strategies to safeguard information, technologies, and data. Prior to Deloitte, he was the Global Chief Security Officer for CenturyLink, now Lumen Technologies, and also served as a Special Agent for the FBI, focusing on federal crimes involving cyber threats, terrorism, and more. In this episode, Dave discusses the critical thinking skills he developed over his 20-year career in the FBI and how he applied them in the private sector to tackle emerging cybersecurity challenges.

Host Barry O'Reilly invites Dave to explore his career journey, the lessons he learned, and the importance of mentorship, team building, and strategic thinking in cybersecurity. The conversation delves into the nuances of transitioning from public service to corporate leadership, the evolving nature of cyber threats, and how businesses can better prepare for future challenges.

Key Takeaways:

The Importance of Adaptability in Cybersecurity: As technology and business models evolve, so do the tactics of adversaries. Cybersecurity professionals must continuously adapt to stay ahead.

Holistic Approach to Cybersecurity: Successful cybersecurity strategies involve not just technical defenses but also understanding the motivations and methods of adversaries.

Mentorship and Leadership: Effective leadership in cybersecurity requires understanding the diverse skills and motivations of team members, providing the right guidance, and fostering a culture of continuous learning.

Corporate Culture and Cybersecurity: Transitioning from the public to the private sector requires understanding corporate dynamics, including ROI and business objectives, to effectively integrate security measures.

Additional Insights:

FBI Experience: Dave’s early career in the FBI instilled in him a deep understanding of critical thinking, investigation, and a life of purpose, which he has carried throughout his professional journey.

Adapting to Corporate Culture: Moving from a black-and-white, rules-based environment in the FBI to the nuanced world of corporate security presented unique challenges, particularly in understanding business motivations and the need for clear ROI in security investments.

The Future of Cybersecurity: As organizations move to cloud-based infrastructures and remote work environments, the strategies of cyber adversaries will continue to evolve, requiring constant vigilance and innovation from cybersecurity professionals.

Episode Highlights

00:00 - Introduction to the episode.
00:02:47 - Dave's early life and influences

"There's a couple of key parts of everybody's life... because it starts to set the foundation for how you think about your life going forward and how you're going to make the decisions."

00:03:58 - Joining the FBI and early career challenges

"And all the standard corporations were there that you could imagine... and ultimately get hired by the FBI."

00:07:38 - Undercover work and relocation challenges

"So I literally went undercover for four years... and next thing I know, I was doing computer forensic work."

00:12:35 - Challenges of early cyber investigations

"A couple of things you start to realize around cyber that was so very different... there was a lot of learning."

00:22:15 - Developing leadership skills and understanding team dynamics

"You have to understand people... and what motivated them at what stage they were in their career."

00:39:00 - Evolving cybersecurity threats and the importance of staying ahead

"Bad guys don't go away, they innovate... we need to be moving in cyber to stay ahead."

Follow Our Guest

LinkedIn Profile: https://www.linkedin.com/in/david-mahon-0751074/
Website: https://www.linkedin.com/company/deloitte/

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Email: hello@barryoreilly.com

How Teamwork Drives Success with Rob Smedley, Founder of Smedley Group

Wed, 31 Jul 2024 01:00:00 -0400

Innovation and Inclusivity in Motorsports are about breaking barriers, fostering innovation, and making the sport accessible to all. Today's guest, Rob Smedley, founder and CEO of the Smedley Group, shares his journey from Formula One engineer to entrepreneur, revolutionizing the motorsport industry.

Rob Smedley is known for his work with top Formula One teams like Ferrari and Williams. Using data technology to drive innovation, Rob has now embarked on a new venture to create a global karting league, making motorsports accessible to a wider audience. His career is marked by his commitment to innovation and his belief in the potential of young talent.

Host Barry O'Reilly invites Rob to discuss his path from a disengaged student to a top engineer and now an entrepreneur. Rob shares valuable lessons on embracing discomfort, committing to goals, and continuously innovating. The conversation highlights the importance of inclusivity in motorsports and the exciting future of the Global Karting League.

Key Takeaways:

Embracing Discomfort: Success often involves stepping out of your comfort zone and committing to figuring things out as you go along.
Innovation Culture: True innovation requires a willingness to make mistakes and learn from them. Companies must create environments that foster this mindset.
Making Motorsports Accessible: The Global Karting League aims to democratize motorsports by significantly reducing costs and complexity, making it accessible to a wider demographic.
Building High-Functioning Teams: Success in both engineering and entrepreneurship involves surrounding yourself with high-functioning individuals and creating a synergistic team environment.
Continuous Learning: Whether in the pit or in the boardroom, continuous learning and adaptation are crucial for sustained growth and success.

Additional Insights:

Personal Journey: Rob's unconventional path from a disengaged student to a top engineer and entrepreneur highlights the importance of perseverance and adaptability.
Innovative Approach: Rob’s approach to the Global Karting League demonstrates how rethinking traditional models can lead to significant industry changes.
Team Dynamics: Managing a team of innovators involves balancing different personalities and ensuring that each team member can contribute effectively.

Episode Highlights

00:00 - Introduction to the episode
02:09 - Rob on committing to something and figuring it out

"Commit to something, don't be scared and figure it out as, as you go along."

04:00 - Rob’s academic journey and lack of engagement in school

"I wasn't a great student at school. I absolutely was a terrible student."

09:33 - The importance of innovation and feeling uncomfortable

"If you're not uncomfortable, you're probably not trying hard enough."

18:26 - How Formula One teams innovate

"Innovation is just embedded in the business of Formula One."

25:35 - Democratizing motorsports with the Global Karting League

"We've taken about 95 plus percent of the costs out of it."

36:19 - Transitioning to an entrepreneurial role and learning new skills

"I've had to unlearn coming into what I would call the outside world."

42:25 - What excites Rob about the future of the Global Karting League

"What I'm most excited about is team work, right? I love being part of a really strong, high performing team."

Follow Our Guest

LinkedIn Profile: https://www.linkedin.com/in/rob-smedley/
Website: https://www.smedleygroup.com/about#1

FOLLOW THE HOST:

LinkedIn: https://www.linkedin.com/in/barryoreilly
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Scaling The Heights of Human Performance with Annastiina Hintsa, The CEO of Hintsa Performance

Wed, 17 Jul 2024 05:20:00 -0400

Leadership is about embracing sustainable practices, fostering continuous improvement, and aligning personal values with professional goals. Today's guest, Annastiina Hintsa, CEO of Hintsa Performance, shares her insights on achieving peak performance in both business and sports.

Annastiina Hintsa is the CEO of Hintsa Performance, a world-leading evidence-based coaching company that helps top athletes and business professionals achieve sustainable success. Driven by science and guided by people, their methods have been tested in some of the most challenging business and sporting environments. Annastiina's journey began with her father, Dr. Hintsa, whose pioneering work with athletes like Haile Gebrselassie laid the foundation for their holistic performance model. Annastiina has expanded this legacy, working with over 50% of Formula One drivers and Fortune 500 CEOs, ensuring they reach and maintain high performance.

Host Barry O'Reilly invites Annastiina to discuss her journey and the impact of Hintsa Performance. From her early involvement in the company to her leadership role today, Annastiina shares valuable lessons on balancing professional and personal well-being. The conversation covers the holistic nature of high performance, integrating physical activity, nutrition, mental energy, and more. Annastiina emphasizes the importance of defining personal success and maintaining perspective through life's challenges.

Key Takeaways:

Holistic Performance: Sustainable high performance involves a balance of physical activity, nutrition, sleep, mental energy, general health, and biomechanics.

Defining Success: Personal success should be clearly defined, considering who you are and what you want beyond professional achievements.

Maintaining Balance: Regularly scheduling recovery and downtime, both on a macro (yearly vacations) and micro (daily detachment rituals) level, is crucial for long-term success.

Perspective and Resilience: Building resilience through multiple identity pillars helps maintain performance and happiness despite setbacks.

Continuous Learning and Adaptation: Embracing a mindset of continuous improvement and being open to unlearning outdated practices is key to sustained growth.

Additional Insights:

Personal Influences on Leadership: Annastiina’s father, Dr. Hintsa, played a pivotal role in shaping her understanding of high performance and well-being.

Handling Setbacks: Viewing setbacks as opportunities for growth and maintaining a broad perspective helps in overcoming challenges.

Technology and High Performance: The rapid advancement of technology necessitates leaders to stay mentally, physically, and emotionally prepared for continuous adaptation.

Episode Highlights

00:00 - Introduction to the episode

02:56 - Annastiina on her early career and her father's influence

"I worked with my dad early days. I was employee number three in the very, very early days..."

03:25 - The turning point of joining the family business

"when my father got sick. So he was, uh, he was diagnosed with pancreatic cancer in 2015, passed away 16 months after. And it was a turning point for for me personally"

07:26 - Defining and achieving sustainable high performance

"Our mission is to help people live better lives and as a consequence, perform better..."

27:29 - Importance of balance and avoiding the middle gear

"We get stuck in the middle gear. We get stuck in this kind of like execution mode where we're constantly just, you know, yeah, we're not we're not at our peak. We're also not recovering and resting. We're at this middle gear checking our emails, you know, responding, uh, executing. But when the time comes, when we would actually need to get to that high gear, get to the peak performance"

31:40 - Technology's impact on high performance and the need for human readiness

"how do we make sure that we as humans are ready for that shift?"

36:03 - Practical tips for achieving better performance

"start with the critical questions and you start with that. Do you know who you haven't really think of? Who are you as a person, not just you at work or your job title. How do you actually define success? What is it that you really want? What are the different points of success for you? And then the final question is around sort of control, which is as much as it is about, you know, what are the things that we can control and we can influence."

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Leading with Servant Leadership and Gratitude ft. John Marcante, Vanguard’s former CIO

Wed, 03 Jul 2024 01:15:00 -0400

Leadership is about embracing the process of unlearning outdated practices, fostering a culture of continuous improvement, and aligning your team with visionary goals. Today's guest, with his esteemed 29-year tenure at one of the largest asset managers in the world, Vanguard, shares how he successfully navigated this journey.

John T. Marcante is a renowned technology and business executive with expertise in digital transformation, business strategy, financial planning, and cybersecurity. He is the US CIO in Residence at Deloitte, providing strategic guidance to clients and leadership.

Previously, John was the Global CIO at Vanguard, where he led digital transformation and drove growth to $9 trillion. He modernized Vanguard's technology and promoted an inclusive workplace. He also developed Vanguard’s global advice platform, making financial planning accessible to millions.

John has contributed to the WSJ CIO Journal and Harvard Business Review. His awards include Business Insider Top 50 CIOs and ORBIE CIO of the Year. He holds degrees from The Pennsylvania State University and Saint Joseph’s University.

Host Barry O'Reilly invites John to share his journey at Vanguard and beyond in leadership, culture transformation, and gratitude. Inspired by his father's legacy in technology, John discusses how he aligned tech with business goals at Vanguard. Barry highlights John’s approach to direct client engagement and open feedback. They also explore John’s commitment to servant leadership, maintaining company values, and his future goals of mentoring new leaders and giving back to the community. This episode offers personal insights into what drives effective leadership with gratitude.

Key Takeaways:

Leadership and Transformation: Transformations should align technology initiatives with business goals, led by C-suite executives.

Servant Leadership: Building a culture of servant leadership is crucial for successful transformations.

Client Engagement: Direct client feedback, really listening and a take-action approach are essential for quick and effective improvements.

Maintaining Values: Sticking to core values and supporting clients and employees ensures long-term success and engagement.

Future Aspirations: Coaching future leaders, staying engaged in technology, and giving back to the community are key aspects of making a positive impact.

Additional Insights:

Personal Influences on Leadership: John’s father played a crucial role in sparking his interest in technology and instilling values of gratitude and support.

Handling Client and Employee Relations: Prioritizing core values and employee well-being, even when making tough decisions like firing abusive high-net-worth clients, ensures long-term success.

Learning from Mistakes and Building Trust: Creating an environment of trust and open communication allows employees to voice opinions and make mistakes, fostering innovation and continuous improvement.

Episode Highlights:

00.00 - Introduction to the episode

02:58- John's reflections on recent thoughts and his father's influence on his career

"I think the last thing that popped in my head since we just went through Father's Day, as I was kind of reflecting on my own father…"

05:29- Cultural transformation and leadership at Vanguard

"So I think I go back to a point you just made, which is, if this transformation is a technology transformation, if it's a technology initiative, then it's already lost, right? Because nothing's a technology initiative. Everything is, a business, a client transformation and that alignment..."

05:53- Leadership and servant leadership in transformation

"I always felt like that the transformation was a C-suite and CEO-led transformation. You know, technology, lean, agile. They'll roll out across the company, not just in technology, but across the company really took that level of focus and alignment."

15:00-Engaging and aligning with clients

"if you want to drive engagement and give a group of people an outcome that's meaningful to clients and give them access to clients, and you said, yes, it's a wonderful when they when they could do something, they see the impact."

15:21- Feedback on improving processes and client satisfaction

"And if you have a nimble, very, very nimble foundation that allows you to very quickly take that feedback and turn it."

18:38- Dealing with high-stakes decisions and maintaining company values

"Not every business is good business. Stick to your mission and purpose, and always have your clients' and employees' backs."

20:47 Discussing the importance of mission alignment in leadership

"It's also you feel connected to the mission of the organization. Like what I do every day has to be connected. But the mission, I have to sleep well at night knowing that the company has my back, but more importantly, that I'm actually doing good for society."

21:45- Personal anecdotes on handling client interactions and maintaining values

"this is one of the things I think that, uh, again, it shines about the company. Like sticking to the values, leaning into your principles, I know, and making tough decisions around that.."

23:52- Building Trust Through Commitment to Solutions

"And even if you don't know the answer that you know you're committed to getting the answer, I think you then build trust in the organization."

25.45- Servant leadership and employee engagement

"If your intention isn't good and you make a mistake, well, then we'll deal with that later, right? But if you're doing work for a client and your intention is good that you have nothing to worry about, even if it goes south..."

32:34- Embracing Grace as a Core Mission in Leadership

"I think as a father, that's our mission as a leader. That's our mission. Like, be gracious, you know, be gracious even when someone doesn't hit the record button"

35:09- Transitioning into a new chapter and future plans

"I want to be part of, uh, coaching and developing the next generation of leaders that I want to be part of that team, whatever team that is. Count me in, because that was the best part of my job. Second technology. I mean, like, come on, like, I mean technology, AI, generative AI."

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How AI is Transforming Startup Investment Decisions with William Carbone, CEO & co-founder of Evalify

Wed, 19 Jun 2024 04:30:00 -0400

AI is transforming the world, and William is working on how IP is impacted in an AI world…

William Carbone is an AI expert, former IBMer, and now a seasoned entrepreneur with over a decade of experience in aerospace, quantum computing, and AI.

At IBM, William’s main focus was to identify opportunities, driving business & technology strategies and roadmap for the industries worldwide. He led the Business Development for IBM's Global Automotive, Aerospace & Defense industries.

Currently, William is the CEO and co-founder of Evalify, a flagship venture under Nobody Studios, and the CEO and co-founder of The Adjacent Possible. He also serves as the Program Director for the Master in AI at the Rome Business School (RBS) and advises the European Commission as a senior consultant. From creating an innovation studio to developing cutting-edge tools for intellectual property assessment, His work spans Quantum, Spacetech, AI, and various domains.

In this episode hosted by Barry O’Reilly, William discusses his journey, including his transition from corporate life and the transformative experiences that shaped his entrepreneurial path. He delves into the practical aspects of innovation and intellectual property, offering advice on navigating these complex areas. This episode is packed with insights for anyone looking to improve their approach to entrepreneurship and understand the value of mental health in the process.

Key Takeaways from the episode include:

Entrepreneurial Journey: The transition from corporate life to entrepreneurship involves significant rewiring of the brain and requires navigating uncharted territories with curiosity and resilience.

Parallels with Music: William's self-taught journey as a pianist highlights the importance of playfulness and self-expression, which he parallels with the creative process in entrepreneurship.

Innovation and IP Assessment: William discusses the development of a tool that evaluates the patentability and intellectual property risks of startup ideas, providing investors with quick and affordable insights.

Unlearning Traditional Methods: The necessity of unlearning conventional approaches to intellectual property and embracing new technologies and methodologies to stay competitive.

Mental Health for Founders: The critical importance of mental health for entrepreneurs, with William sharing his experience of attending a silent meditation retreat to find clarity and balance.

Future of Intellectual Property: The potential of AI and advanced tools to democratize access to intellectual property insights, helping entrepreneurs and investors make better-informed decisions.

Additional Insights:

Leadership and Innovation: This episode emphasizes the role of leadership in fostering a culture of innovation and collaboration within startups.

Role of AI in IP: The discussion involves the advancements in AI that have made tools like E-Verify possible, highlighting the transformative potential of these technologies in the intellectual property space.

Practical Applications: This episode provides insights about real-world examples of how the IP assessment tool has helped investors make quicker and more informed decisions, reducing the risk and enhancing the potential for successful investments.

Episode Highlights:

(00:00) Introduction to the episode

(01:25) Importance of rewiring the brain and transformative journey of entrepreneurship

[01:43] “There is no one making things for you… You have to take the tools on the way and find the way.”

(02:23) William shares parallels between learning music and his entrepreneurial journey

[3:53] “Music has always been there for me in the journey, even in difficult times or more challenging situations.”

(05:14) Barry discusses the importance of following curiosity in entrepreneurship

[7:39] “There was a lot of untapped potential in that space, like in billions of dollars that have been spent on patents that have been just never commercialized…”

(08:35) Introduction of E-Verify and its capabilities in de-risking investments

(11:43) The evolution of AI and its impact on intellectual property assessment

[13:22] “But the biggest unlearning there was how to make the industry, to unlearn how they approach LLP. That was the biggest challenge, right.”

(13:23) The challenges and benefits of helping the VC industry unlearn traditional approaches to IP

[14:27] “I would say the biggest challenge for us and for the investors is to understand that the IP can be a valued friend and partner…”

(15:17) Barry shares his experiences with continuous delivery and automation in software development

[17:34] It's not that we're taking the humans out of the process, it's we're allowing them to focus on high-value tasks…”

(19:10) The concept of patent viability assessment and its impact on investment decisions

[21:13] “So these are all great indicators that are simply not available, or maybe no one has the intuition to look for them and find competitors for a startup.”

[22:03] “Some investors will tell you.. revenue speaks louder than IP. Others say, okay, IP is so fundamental.”

(24:13) William's vision for the future of IP and entrepreneurship

[25:29] “There is already a populated market in the direction that you haven't seen before with your business analyst.”

(26:27) The democratization of patent information and its impact on founders and investors

(30:39) William's entrepreneurial journey and the importance of mental health retreats

[30:48] “Actually what is not so much covered is mental health or founders - I would say that's the number one priority.”

(33:29) The importance of balance and intention in life and work

[34:48] “We live in the attention economy, like everything, trying to grab our attention.”

(35:35) Conclusion and final thoughts from Barry and William

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