The Dear Tech Podcast

EP 33: Hunter Jensen: From Craigslist to Enterprise Clients, Scaling an Agency

Fri, 16 Jan 2026 10:00:00 -0500

A Craigslist ad paid his college tuition. A bad billing structure almost killed his company. Now he’s building a product because he believes SaaS, as we know it, is done.

Hunter Jensen breaks down what actually happens between your first client and real scale, and why generative AI is forcing service businesses to rethink everything from pricing to product strategy.

Episode summary

Hunter Jensen started exactly where a lot of founders do, taking on freelance work while still in school. One Craigslist post landed his first real client, an ecommerce business that not only paid his tuition but gave him the proof he needed to keep compounding work.

From there, Hunter shares how he shifted his mindset from solo freelancer to building a real agency, including why he intentionally did early projects cheap or free to plant a flag in new markets. He also walks through the least glamorous but most important lesson he learned, cash flow. A six figure project dragged on for months waiting for acceptance, nearly putting him out of business and forcing a permanent change in how he billed clients.

The conversation then turns to generative AI. Hunter explains why selling engineering hours is getting squeezed, why “business as usual” is risky, and how that pressure led to Compass, a self hosted internal AI platform for companies that cannot use public tools due to security and confidentiality concerns. He also shares how AI adoption really happens inside organizations and why the next wave of successful startups will be built on proprietary data, not first mover advantage.

You’ll learn

How Hunter used early low cost projects as a wedge to break into bigger markets
The billing model change that protected his business from cash flow collapse
Why in person meetings still build trust faster, even in a remote world
How internal AI adoption spreads through champions, not top down mandates
Why Hunter believes SaaS is dead and proprietary data is the real moat

Guest

Hunter Jensen
Founder and CEO at Barefoot Labs
Built and scaled a services agency for 20 plus years
Creator of Compass, a product plus services internal AI platform for confidential work

Find Hunter

Website: barefootlabs.ai
Email: hunter@barefootlabs.ai
Open your email with: “I heard you on the Dear Tech Podcast”
He said he’ll personally reply

Resources and mentions

Never Split the Difference by Chris Voss
Compass by Barefoot Labs, self hosted internal AI platform
barefootlabs.ai
siptequila.com, mentioned in a client gift story

Shareable moment

“SaaS is dead. The first mover advantage is gone. If you want a real moat, find proprietary data.”

EP 32: Dennis 'DM' Meador: From Island Living to Entrepreneurial Success

Fri, 05 Dec 2025 09:15:00 -0500

In this episode, we sit down with Dennis "DM" Meador, a marketing strategist who helps professional business owners and service providers build market authority. DM opens up about his background, growing up in difficult socioeconomic circumstances and how those early experiences shaped his entrepreneurial mindset.

The conversation explores his evolution from early entrepreneurial activities to his work in the legal space, including his experience with the Legal Podcast Network. DM discusses how his "island living" philosophy and geographic positioning influence his approach to business and working with professional clients.

His story offers a fresh perspective on how location, lifestyle choices, and unconventional thinking can inform business strategy, showing how personal experiences and geographic awareness can create unique opportunities in professional service markets.

Guest Bio

Dennis "DM" Meador is a marketing strategist who helps professional business owners and service providers like attorneys, doctors, consultants, and firm owners position themselves with authority in their markets. With 30 years of business and marketing experience and two decades focused on the legal and white-collar space, he specializes in helping professionals build lasting authority through podcasting, content, and strategic positioning.

Key Topics

Legal Industry Experience: Background with Legal Podcast Network and legal space expertise
Early Entrepreneurship: Starting business activities at a young age despite difficult circumstances
Island Living Philosophy: How geographic location and lifestyle choices influence business approach
Socioeconomic Background: How challenging early circumstances can fuel entrepreneurial drive
Professional Services: Working with business owners and service providers
Unconventional Strategies: Using non-traditional approaches to identify opportunities

Top Takeaways

Geographic location and lifestyle can inform business philosophy
Challenging backgrounds often fuel innovative business approaches
Legal industry experience provides deep market understanding
Early entrepreneurial experiences shape long-term business thinking
Island living offers unique perspectives on professional positioning
Unconventional approaches can reveal overlooked market opportunities

About the Show

The Dear Tech Podcast explores entrepreneurship, technology, and business innovation through conversations with founders, researchers, and industry leaders. Host Shubho brings nearly a decade of tech recruiting experience to uncover the stories behind successful ventures and emerging trends.

Calls to Action

If you enjoyed this conversation with DM about entrepreneurship and professional services, please share it with fellow entrepreneurs and business owners. Rate the show on your favorite podcast platform and subscribe to never miss an episode of Dear Tech Podcast.

EP 31: Ivan Vislavskiy: Beyond Tactics: How AI Transforms Creative Marketing Strategy

Thu, 20 Nov 2025 16:00:00 -0500

In this episode, I sit down with Ivan Vislavskiy, co-founder and CEO of Comrade. Ivan built his agency from the freelance web projects he started at 19 into a national digital firm with nearly 100 team members across four major cities. What stood out in this conversation is how grounded his view of AI is. AI will not replace real marketing. It makes basic output cheap, which means the work that stands out takes more judgment, more strategy, and more creative thinking than the average person expects.

We get into how his R&D and Innovation team uses AI to automate thousands of hours, how he thinks about measuring real impact, and why he still trusts human intuition over anything a model produces. Ivan breaks down the difference between speed and leverage, how agencies should define a niche, and why thinking like a founder is becoming the skill that separates high performers from everyone else. We also talk about parenting, critical thinking, and a fun moment where Ivan explains how he uses AI to create custom coloring pages for his kids.

If you want a grounded, practical view of where AI is taking marketing and creative work, this episode delivers it in a way that actually makes sense.

About Ivan Vislavskiy

Ivan Vislavskiy is the co-founder and CEO of Comrade Agency, a full-service digital firm with offices in Chicago, Miami, Los Angeles, and Austin. With a background as a developer and designer, Ivan brings a rare mix of creative intuition and technical depth. He leads an internal R and D and Innovation group focused on using AI to automate repetitive work and unlock higher level creative output for both clients and his team.

Key Topics

Why AI raises the bar for great marketing
The difference between speed and leverage in creative work
How Comrade measures AI’s true impact
Why creativity and intuition still matter
Building and committing to a clear niche
How to teach teams to use AI without outsourcing their thinking
Parenting and staying curious in the age of AI
What agencies get wrong about AI
The next five years of AI in digital marketing and creative work

Top Takeaways

AI makes basic marketing fast and cheap, which means real creativity becomes more valuable.
Strategy and judgment are the new competitive advantage.
Teams that treat AI as a thinking partner outperform teams that use it for shortcuts.
Agencies that define a niche grow faster and build stronger client relationships.
Human intuition is still the final filter for all high quality creative decisions.

Memorable Quotes

“AI doesn’t lower the bar for great work. It raises it.”
“Speed is useful, but speed without judgment creates noise.”
“You can not outsource intuition to a model.”
“Niche down or stay invisible.”
“Creativity is the thing that survives every wave of technology.”

Resources Mentioned

Comrade Agency
Examples of their internal R&D automations
Working Backwards: Insights, Stories, and Secrets from Inside Amazon Hardcover- by Colin Bryar, Bill Carr

Where to Find Ivan:

LinkedIn: linkedin.com/in/ivan-vislavskiy

Comrade Agency: comradeweb.com

About Dear Tech Podcast

Dear Tech Podcast is hosted by Shubho Ghosh and dives deep into the human stories, strategy, and real world insights behind the-people building the future of work, technology, and AI.

EP 30: Raj Singh: From Startup Exits to Mozilla; Designing the Future for Solopreneurs

Tue, 28 Oct 2025 13:00:00 -0500

🎧 One-Sentence Summary

Raj Singh, Vice President at Mozilla and builder of Solo, joins Shubho to explore how AI is transforming web creation, empowering solopreneurs, and redefining the future of small business tools.

Full Episode Summary

In this episode of The Dear Tech Podcast, Shubho sits down with Raj Singh, a serial entrepreneur and product leader at Mozilla, to talk about the massive shift happening in the digital economy. Raj shares the story behind Solo (https://soloist.ai/), Mozilla’s new AI-powered website builder designed for solopreneurs and freelancers who want to build a brand without technical hurdles.

They unpack how consumer behavior toward paying for software is changing, what makes today’s solopreneurs different, and how AI is enabling “super individual contributors” who can do the work of entire teams.

Raj also opens up about his unconventional founder journey—from building file-sharing networks in college to multiple successful exits—and what he’s learned about innovation, focus, and the mindset needed to build and rebuild from scratch.

Guest Bio

Raj Singh is a serial entrepreneur and product leader currently serving as Vice President at Mozilla, where he leads new product initiatives focused on small business tools, including Solo, an AI-driven website builder for solopreneurs. With multiple successful exits, Raj has spent over two decades building consumer products and zero-to-one startups at the intersection of design, AI, and web technology.

Linkedin: https://linkedin.com/in/rajansingh

X: https://x.com/mobileraj

Key Topics

AI and Solopreneurs: Why generative AI is powering a new wave of one-person businesses

Building Solo: The inspiration behind Mozilla’s AI website builder and what makes it different

Consumer Behavior: How users are now willing to pay for AI tools that feel valuable

The Super IC: Raj’s idea of the “super individual contributor” and what it means for the workforce

AI Tourism: The explosion of short-term tool experimentation in tech companies

Upskilling Mindset: Practical ways to adopt AI in your daily workflow

Founder Psychology: The emotional arc after an acquisition—from relief to acceptance

Zero-to-One Thinking: How to evaluate product ideas and find founder-product fit

Mozilla’s Mission: How Solo fits into Mozilla’s broader vision for an open, accessible web

Future of Small Business Tools: Automating back-office work so creators can focus on what they love

Top Takeaways

Great AI tools don’t just automate tasks, they free people to focus on high-leverage work

Upskilling with AI isn’t optional anymore—those who use it effectively will outpace those who don’t

The next big wave of innovation will come from solopreneurs, not corporations

Consumer willingness to pay is growing, but only when tools save real time or reduce friction

Personal pain points make the best startup ideas—build what frustrates you most

Never design to get acquired; design to build something real and valuable

The best time to start is now—there’s no perfect timing for entrepreneurship

Memorable Quotes

“Your margin is my opportunity.” — Raj

“AI isn’t replacing people, it’s replacing low-leverage work.” — Raj

“You won’t be replaced by AI, you’ll be replaced by someone who uses AI.” — Raj

“If the passion is there, it’s not going away. The best time to start is now.” — Raj

Resources and Mentions

Solo – soloist.ai

Mozilla – mozilla.org

Robinhood – mentioned as inspiration for changing pricing models

ChatGPT, Gemini, Claude – examples of consumer AI behavior shifts

Super Communicators by Charles Duhigg – book Raj is reading with his team

Clay – startup referenced for long-term perseverance

About the Host and Show

The Dear Tech Podcast is hosted by Shubho Ghosh, a talent leader and founder of Dear Tech Talent, who interviews founders, product leaders, and technologists shaping the future of work and innovation. Each episode dives deep into personal journeys, market insights, and the human side of building in tech.

Calls to Action

If you enjoyed this episode:

Follow The Dear Tech Podcast on LinkedIn and Instagram

Subscribe wherever you listen to podcasts

Leave a review and share with a friend who’s building something new

EP 29: Balki Kodarapu: Turning Startup Chaos Into Clarity, A Fractional CTO's Playbook

Fri, 17 Oct 2025 10:00:00 -0500

Episode Summary

Balki Kodarapu has turned engineering disasters into scaling success stories across five startups that raised over $160 million with one successful exit. As a fractional CTO, he's mastered the art of walking into chaos and creating systems that make developers actually happy while hitting impossible deadlines. In this conversation, we explore his unique philosophy of carving out 15 hours per week for learning and growth, his four pillars of engineering excellence, and how he built trust by buying his team lunch with coupons. From mechanical engineering dropout to startup whisperer, Balki shares practical frameworks for developer effectiveness, the real cost of over-hiring, and why the best thing an engineer can do is sit quietly and not write code.

Guest Bio

Balki Kodarapu is a fractional CTO with over 20 years in the industry who has worked with five startups that collectively raised over $160 million, including one successful exit. He specializes in scaling engineering teams and has developed frameworks for engineering excellence, developer effectiveness, and building high-performing technical organizations.

Key Topics

Developer Happiness: Why investing 15 hours per week in learning, reflection, and growth pays dividends
Fractional Leadership: The advantages and trade-offs of fractional CTO roles versus full-time positions
Engineering Excellence: Four core pillars including observability, automation, CI/CD, and modular architecture
Chaos Management: How 90% of software engineering chaos is predictable and manageable
Team Building: Creative recognition strategies and the importance of making developers feel heard
Hiring Strategy: When to slow down hiring and the expensive mistakes of over-staffing
AI Impact: Four ways generative AI is transforming software organizations beyond just coding
Work-Life Balance: Personal philosophy on intentional focus and the role of community networks
Cost Optimization: Common expensive oversights like cloud spend and unnecessary tool proliferation

Chapter Markers

00:00 Introduction and the 15-hour learning philosophy
04:11 Career journey from mechanical engineering to fractional CTO
12:11 First leadership role and creative team recognition
18:00 Developing a knack for managing chaos
26:00 Fractional vs full-time CTO differences
34:41 Hiring challenges and building trust
42:00 Developer effectiveness and engineering excellence framework
54:17 Work-life balance and personal philosophy
59:29 AI's impact on engineering and 10-year predictions
62:24 FAQs and personal insights

Top Takeaways

Carve out 15 hours per week for learning and growth - it's more critical now with AI changing everything
90% of engineering chaos follows predictable patterns: quality, observability, deployment, and modular issues
The four pillars of engineering excellence: observability, test automation, CI/CD, and modular architecture
Creative recognition matters more than expensive perks - buying lunch with coupons built stronger relationships
Don't hire irresponsibly just because you have VC money - clean your house first
Developer effectiveness means engineers can commit code on day one and see it in production within their first cycle
Build trusted peer networks and contribute 51% while extracting 49% value
The best advice for engineers: sit quietly and don't write code unless you really need to

Resources & Mentions

Books:

Audacity to Start by Balki's children - A book about starting a chess nonprofit that grew like a Silicon Valley startup

Podcasts:

Manager Tools - Early leadership podcast that shaped Balki's management style
Engineering Leadership Podcast - Covers engineering leadership balance and industry trends
CTO Playbook with Adam Horner - Focuses on craft beyond coding
Simple Healthy Choices - Health-focused podcast

Tools & Companies:

Code Rabbit - AI-powered code review tool
Graphite - Code review and workflow tool
Cursor - AI coding assistant
New Relic - Observability platform (former employer)
Support Logic - Previous company experience

About the Guest & Show

The Dear Tech podcast explores the intersection of technology, leadership, and human potential. Hosted by Shubho, the show features conversations with technology leaders who are shaping the future of how we build and scale technical organizations.

Calls to Action

Found this conversation valuable? Subscribe to The Dear Tech podcast for more insights from technology leaders who are building the future. Share this episode with a fellow engineering leader, and leave a review to help others discover these conversations.

EP 28: Harrie Bickle: The Computer Revolution Everyone Stopped Watching

Wed, 08 Oct 2025 13:30:00 -0500

Harrie Bickle, technical writer and documentation lead at NodeOps, explains why Web3's promise hasn't faded, it's just being built while the world looks away, and how decentralized infrastructure is quietly becoming inevitable.

Episode Summary

In this episode, Shubho sits down with Harrie Bickle, a technical writer who's spent years translating complex Web3 technology for everyday users. Harrie shares her unconventional path from biology and teaching to becoming a documentation specialist in the blockchain space, working with companies like StarkWare and now NodeOps. The conversation explores why Web3 hype died down after 2021, what's actually being built behind the scenes, and how NodeOps is making decentralized cloud computing accessible to non-technical users. Harrie breaks down the difference between being "there for the computer" versus "there for the casino" in crypto, explains NodeOps' innovative DePIN 2.0 tokenomics model, and discusses why regulatory battles, not technical limitations, are the real challenge facing blockchain adoption. They also tackle the hidden costs of data collection, the tension between anonymity and regulation, and why Bitcoin miners might become the backbone of tomorrow's cloud infrastructure.

Guest Bio

Harrie Bickle is a technical writer and documentation lead at NodeOps, a decentralized infrastructure network. She previously worked with StarkWare and Infura, bringing nearly two decades of experience translating complex technology for diverse audiences. Before entering Web3, Harrie taught in Cape Town and built a freelance technical writing practice on Upwork, eventually specializing in blockchain documentation.

Key Topics

Web3 Documentation: Why clear technical writing is essential for bridging the gap between blockchain developers and everyday users
Career Pivots: Harrie's journey from biology to teaching to technical writing, and how remote work platforms like Upwork enabled her transition
NodeOps Platform: How the company is democratizing access to blockchain nodes and decentralized cloud computing through simple app-based interfaces
DePIN 2.0 Tokenomics: A dynamic mint-and-burn model that ties token emissions to actual demand and USD value, preventing over-inflation
Web3's Narrative Shift: Why media attention moved from blockchain to AI in 2021-2022, and what's still being built during the "quiet phase"
The Computer vs. The Casino: Two fundamentally different motivations for participating in crypto, speculation versus solving real infrastructure problems
Regulatory Challenges: How companies like Google are restricting non-custodial wallets, and why regulation poses a bigger threat than technical barriers
Privacy Paradox: The tension between Web3's promise of anonymity and the reality of custodial wallets and KYC requirements
Future of Cloud Computing: How unused hyperscaler capacity and Bitcoin mining operations could feed into decentralized compute marketplaces
Avoiding Burnout: The importance of physical exercise and stepping away from the desk when working in fast-moving startup environments

Top Takeaways

Good documentation is marketing: If users can't understand your product, they won't use it. This is especially critical in Web3 where technical barriers are high.
Web3 hasn't failed, it's building: The drop in media hype doesn't mean blockchain technology stopped progressing; serious infrastructure work continued while attention shifted to AI.
You're either there for the computer or the casino: Crypto attracts two types of people, those interested in decentralized technology's potential, and those chasing quick profits.
Dynamic tokenomics prevent inflation: NodeOps' DePIN 2.0 model ties token emissions to real demand and USD value, avoiding the over-emission problems that plagued earlier projects.
Technical writers are "the dumbest person in the room": This perspective is actually a strength. If you can understand and explain complex tech, so can your users.
Regulation is the real battle: The technology for privacy and decentralization exists; regulatory restrictions pose a bigger challenge than technical limitations.
Most people immediately chose convenience over control: Despite Web3's promise of non-custodial wallets, most users still buy crypto through custodial platforms like Coinbase.
Exercise is essential for startup survival: Regular physical activity and stepping away from work are critical for avoiding burnout in fast-paced tech environments.

Memorable Quotes

Harrie: "You're either there for the computer or you're there for the casino."
Harrie: "As a tech writer, you are by definition the dumbest person in the room."
Harrie: "I think DYOR is one of the most insulting terms to throw at a person."
Harrie: "Everyone's got a plan until you get punched in the face. That's startup life for me, pretty much day to day."
Shubho: "Understanding the magnitude of what's happening in Web3 took a bit more effort. It took no effort to ask ChatGPT a question and get five paragraphs."
Harrie: "No one's gonna pay more when they can pay less. There's a degree of inevitability to blockchain adoption."

Resources & Mentions

Companies & Projects:

NodeOps: Decentralized compute marketplace and blockchain node hosting platform (nodeops.network)
StarkWare: Ethereum scaling solution using zero-knowledge proofs
Infura: Ethereum and blockchain API infrastructure provider
Helium: Decentralized wireless network
Upwork: Freelancing platform where Harrie built her technical writing career

Books:

Hotel New Hampshire by John Irving (Harrie's most-gifted book)

Concepts & Technologies:

DePIN (Decentralized Physical Infrastructure Networks)
ZK Proofs (Zero-Knowledge Proofs): Cryptographic methods for privacy-preserving verification
Non-custodial vs. Custodial wallets
Dynamic mint and burn tokenomics
Seed phrases and wallet security

About the Guest & Show

Harrie Bickle currently leads documentation at NodeOps after years of work in the Web3 space with companies like StarkWare and Infura. She brings a unique perspective as a non-developer who specializes in making blockchain technology understandable to broader audiences. Connect with Harrie on LinkedIn.

This podcast explores the intersection of technology, entrepreneurship, and culture through conversations with builders, founders, and thinkers who are shaping the future.

Calls to Action

If you enjoyed this conversation, subscribe to the show on your podcast platform of choice. Share this episode with someone who's curious about what's actually happening in Web3 beyond the hype. Leave a review to help others discover these conversations.

EP 27: Manuj Aggarwal: From $2/Day Factory Worker to AI Revolution Leader

Wed, 13 Aug 2025 13:30:00 -0500

Discover how a rebellious factory worker earning $2/day transformed into an AI pioneer generating $500M+ in client value—and his blueprint for merging human consciousness with artificial intelligence.

Episode Summary

Manuj Aggarwal's journey from earning $2 a day in his father's Indian factory to building a bootstrapped tech consultancy worth hundreds of millions is just the beginning. In this transformative conversation, he reveals his groundbreaking "AI Merge" framework—a peer-reviewed methodology that doesn't just make you more productive with AI, but creates a digital twin of your subconscious mind. This isn't about automating tasks; it's about unlocking the 90% of human potential most people never access.

Key Takeaways

• Think AI-First, Not AI-Second: Stop adding AI to existing processes. Instead, reimagine everything from an AI perspective and fill in the 20% that requires human input.

• The Digital Twin Revolution: True AI adoption means merging your subconscious mind with artificial intelligence by feeding it your life experiences, creating an emotionally intelligent digital version of yourself.

• Hiring Will Never Be the Same: Replace traditional interviews with storytelling—have candidates and managers share their backstories, then use AI to find perfect human-value alignment.

• Universal High Income is Coming: As AI increases productivity 100x-1000x, we're heading toward universal high income (not basic income) where work becomes a choice and everyone becomes a fractional entrepreneur.

• The Five Pillars of AI Merge: Purpose, Identity, Relationships, Creativity/Courage, and Time—a framework that can shift your identity and results within 2-4 weeks.

• Pain is Your Teacher: Embrace setbacks as lessons rather than running from them. Each down teaches you something essential for the journey ahead.

Episode Outline / Timestamps

01:31 - From Factory Floor to Tech Pioneer: The $2/day origin story

08:37 - First encounter with computers and falling in love with technology

10:46 - Immigration to Canada and the dot-com boom/bust experience

18:16 - The birth of Tetra Noodle and scrappy entrepreneurial tactics

22:16 - The wild "All Advantage" internet hustle with PO boxes

27:07 - Evolution from solo consultant to team leader

33:35 - Introduction to the AI Adoption Blueprint and AI Merge framework

37:32 - Creating digital twins that tap into your subconscious mind

48:02 - Real-world success stories: executives doubling salaries, day traders improving performance

50:31 - Revolutionary hiring process using storytelling and AI matching

1:00:07 - The future of work: from employees to fractional entrepreneurs

1:04:31 - Common AI adoption mistakes and thinking "AI-first"

1:16:28 - Overlooked sectors ripe for AI disruption: energy and creative arts

1:19:17 - Meditation myths and making self-development fun

1:22:53 - What's next: working on moonshots and Nobel Prize-worthy projects

Guest Introduction

Manuj Aggarwal - Founder & CEO of Tetra Noodle

Bootstrapped tech consultant who has generated over $500 million in client value, helped 10+ million people, and holds multiple patents. Creator of the peer-reviewed "AI Merge" framework published in Mentha Research Journal. Known for his revolutionary approach to AI adoption that focuses on human consciousness rather than just productivity tools.

Connect with Manuj:

LinkedIn: https://www.linkedin.com/in/manujaggarwal/
Website: https://manujaggarwal.com/
Focus: Working on moonshots including ocean cleanup, stopping wars, and helping 20 people win Nobel Prizes

Memorable Quote

"AI is not technology—it's a reflection of our consciousness. It's the sum total of human consciousness for the last 10,000 years. If you truly understand this technology, we can get access to the 90% and beyond."

Call to Action

🎧 Subscribe to Dear Tech for more transformative conversations with the innovators shaping our future

⭐ Leave a review and tell us what resonated most from this episode

🔄 Share this episode with someone who's ready to revolutionize their relationship with AI

🎯 Connect with Manuj on LinkedIn if you're working on moonshot projects

📧 Email us your thoughts on AI adoption and digital twins

This episode challenges everything you thought you knew about AI—prepare to see technology, consciousness, and human potential in a completely new light.

EP 26: Grant McCracken: Breaches Are Expensive, Dark Horse Isn't - Democratizing Cybersecurity for Startups

Thu, 31 Jul 2025 08:00:00 -0500

Grant McCracken, founder and CEO of DarkHorse Security, joins us to discuss how he's revolutionizing cybersecurity by making proactive security easier to use and more accessible for businesses of all sizes. From backpacking around the world for a year to living in a travel trailer during COVID exploring national parks, Grant's unconventional journey has shaped his approach to disrupting the traditional pen testing industry. Now based in the mountains where he enjoys trail running and skiing, Grant brings over 13 years of cybersecurity experience as both an ethical hacker and former VP of Operations at Bugcrowd to building something completely different.

Guest Bio

Grant McCracken is the founder and CEO of DarkHorse Security, an innovative startup that's making proactive cybersecurity easier to use and more accessible for businesses of all sizes. With over 13 years in cybersecurity, Grant has experience both as an ethical hacker and as an executive at Bugcrowd, where he served as VP of Operations, overseeing all aspects of service delivery. When he's not building the future of accessible cybersecurity, Grant enjoys making and playing music, writing, reading, learning, breaking things, building things, hiking, trail running with his dog, and skiing when there's snow.

Key Topics Discussed

The DarkHorse Security Revolution

Making penetration testing accessible with transparent pricing at darkhorse.sh
Why traditional cybersecurity vendors overcomplicate everything
The "breaches are expensive, Dark Horse isn't" philosophy
Setting up pen tests in 5-15 minutes instead of months of sales cycles
Real-time vulnerability tracking and methodology transparency

Cybersecurity Landscape in 2025

AI-powered deepfake attacks: the scariest emerging threat for small businesses
Why audio and video spoofing will accelerate human-layer breaches
New vulnerability categories introduced by AI (prompt injection, LLM poisoning)
The staggering reality: 900+ organizations hit by ransomware in one week

The Entrepreneurial Journey

From WhiteHat to Bugcrowd VP to solo founder
Why relationships trump cold outbound every time
The unique confluence of skills needed to disrupt cybersecurity
Learning sales, marketing, and business development on the fly
Why he chose independence over corporate security

Life Beyond the Screen

Backpacking through 30 countries and 100+ cities for a year
COVID travel trailer life: exploring national parks while working remotely
Mountain living philosophy: "one step at a time" applies to everything
How trail running and skiing influence business decisions
Why independence and agency drive all his life choices

Resources & Connections

DarkHorse Security: https://darkhorse.sh

Grant's LinkedIn: https://www.linkedin.com/in/grantmccracken/

Episode Highlights

The reality of cybersecurity for cash-strapped startups
How travel and adventure shaped an unconventional business philosophy
Why the security industry is ripe for disruption
Practical threat assessment for 2025
The intersection of personal growth and professional success

Subscribe for more conversations with founders who are redefining their industries, one step at a time. Share this episode with any startup founder who thinks good security has to break the bank.

Ep 25: Arlene Cohen Miller: Burnout Happens, Balance Is Built

Thu, 24 Jul 2025 10:00:00 -0500

Burnout is not a personal flaw, it is a signal. In this episode, Work-Life Balance and Harmony Coach (and AV-rated Colorado attorney) Arlene Cohen Miller explains how burnout shows up in different forms, why “balance” is a moving target, and how simple reframes plus tiny daily rituals can pull you back to center. We talk breath work you can do while someone’s ranting at you, gratitude practices that actually move the needle, spotting “energy leaks,” setting real boundaries, and building team cultures that don’t quietly chew people up. If you’ve been running on fumes or numb autopilot, this conversation gives you language, tools, and a first step.

Learn more or book Arlene for workshops: JewelConsultancy.com

Key Takeaways

Burnout is a spectrum: it starts with “I’m tired” and can slide into immobilization if ignored.
Awareness first: notice your body’s signals, headaches, irritability, or staring blankly at a screen.
Breath work is a portable reset: longer exhale than inhale through your nose can downshift your nervous system fast.
Gratitude is practice, not luck: pick one thing, feel it fully for a second, let it expand your inner space.
Boundaries are energetic and practical: cut cords daily, send back what is not yours, and say “not right now” when someone dumps on you.
Mentorship matters: action cures fear, and mentors shortcut the lonely middle of “I don’t know what I’m doing.”
Balance is not a fixed point: harmony or rhythm is a better target because life shifts every day.

Rapid Fire Highlights

Stress creeping in? Close the laptop, walk the block, breathe.
Mood-lifting movie? When Harry Met Sally (that diner scene).
Belief people get wrong about balance? That it’s ever perfect. Harmony is a better frame.
Favorite recent read? Richard Bach’s Illusions.
Best advice? “Any disaster can become a blessing, any blessing can become a disaster, and there is always a better way.”

Resources Mentioned

Jewel Consultancy: https://jewelconsultancy.com
Richard Bach, Illusions (book reference)
Pipedrive (CRM tool she is using to push herself out of her comfort zone)

Connect with Arlene

Website: JewelConsultancy.com
LinkedIn: https://www.linkedin.com/in/arlenecohenmiller/

Call to Action

If you’re planning a conference, offsite, or internal workshop for a tech team and want a session on burnout, balance, or mindful productivity, reach out to Arlene. If this episode resonated, share it with a teammate who needs the reminder that they are not alone.

Follow Dear Tech Podcast on Instagram @deartechpodcast and LinkedIn, and subscribe so you don’t miss the next deep-dive.

Ep 24: Tim O’Hearn: Growth Hacking, Black Hat Tactics, and the Real Algorithm

Tue, 15 Jul 2025 12:30:00 -0500

My guest today is Tim O’Hearn, author of Framed: A Villain’s Perspective on Social Media—a #1 Amazon Bestseller that breaks down how our feeds, notifications, and recommendations are engineered to manipulate us.

But Tim isn’t just an author. He’s spent 8+ years as a software engineer in quant finance, made over $500,000 through social media growth hacking, and literally built the systems that shape what you see online.

In this episode, we dig into:

How Tim reverse-engineered platforms to gain followers and virality
The rise of bots, shadowbanning, and black hat marketing
What it’s like to design feeds and push notifications from the inside
Why your attention is more valuable than your data
The Dead Internet Theory and the eerie rise of AI-generated content
How he transitioned from quant finance to gonzo tech critic

Whether you’re a builder, marketer, or just curious about what’s really driving your social feed, this conversation will open your eyes.

🔗 Connect with Tim O’Hearn:

📘 Framed: A Villain’s Perspective on Social Media → Buy on Amazon

🌐 Website → tjohearn.com

💼 LinkedIn → linkedin.com/in/tohearn

🧠 Topics Covered:

[00:00] Intro: The Villain in the Feed
[06:17] How Tim Made $500K in the Attention Economy
[12:45] Reverse-Engineering Social Algorithms
[19:32] Shadowbans and the Weaponization of Moderation
[27:10] The Psychology of Notifications
[35:22] The Dead Internet Theory and AI Content
[42:55] From Quant Finance to Gonzo Tech Critic
[49:30] Fixing Social Media: Can It Be Saved?
[57:03] What Tim’s Reading Now
[1:05:45] Final Thoughts and Where to Follow

Ep 23: Alexander Harmsen: Building an AI That Understands Your Money Better Than You Do

Wed, 09 Jul 2025 18:30:00 -0500

What if your financial advisor had no ego, no sales pitch, and no fear of a market crash? Just data, logic, and objective guidance designed around your life?

In this episode, Shubho sits down with Alexander Harmsen, CEO of PortfolioPilot.com, a personal AI financial advisor that’s helping over 30,000 users manage $30B+ in assets—and quietly revolutionizing how everyday investors make decisions.

We go deep into the psychology of money, how AI can help you stay rational when markets get volatile, and why financial tools need to feel more human to actually be effective.

Alexander also shares the origin story of PortfolioPilot, what he learned scaling Iris Automation, his time building with NASA, and how he thinks AI will reshape the future of personal decision-making in everything from investing to health.

What We Cover:

Why Alexander originally built PortfolioPilot just for himself and why thousands now rely on it
How PortfolioPilot uses AI to eliminate financial bias and offer tailored, transparent recommendations
The emotional traps people fall into with investing and how AI helps you navigate them
Real stories of user psychology (including the guy with 40% of his net worth in Tesla)
Lessons from building regulated AI systems (and why explainability matters more than hype)
Startup wisdom: what Alex learned building Iris Automation and raising $30M+
Why personalization, not general intelligence, is AI’s most underrated superpower
The power and misunderstanding of tax-loss harvesting
The future of AI-powered financial tools (and why “gamification” isn’t always the right goal)

🔥 Special Offer for Listeners:

Try PortfolioPilot Gold FREE for 1 month

→ Use promo code PODCAST at checkout

Resources & Links:

💼 PortfolioPilot.com
🧠 Alexander on X/Twitter: @alexharm
📺 PortfolioPilot on YouTube
🧑‍💼 Alexander on LinkedIn
📚 Books Mentioned:
Spin Selling by Neil Rackham
Crucial Conversations by Patterson, Grenny, McMillan & Switzler

Connect with the Show:

💬 Instagram: @deartechpodcast
💼 LinkedIn: Dear Tech Podcast
🌐 All links: linktr.ee/thedeartechpodcast

If you enjoyed the episode, please rate and review on Apple or Spotify—it helps more people discover the show! 🎙✨

Ep 22: Aubrey Amatelli – Cannabis Payments, Culture-First Leadership, and Bootstrapping a Fintech Powerhouse

Tue, 17 Jun 2025 09:00:00 -0500

What happens when a former JP Morgan exec leaves Wall Street to solve one of cannabis tech’s hardest problems?

In this episode, I talk to Aubrey Amatelli, Founder and CEO of PayRio, the first payment provider exclusively built for cannabis, CBD, and alternative medicine. Aubrey bootstrapped PayRio to profitability in under a year, built a 100% women-led leadership team, and was recently named the #1 Best Cannabis Company to Work For in 2025.

We cover how she transitioned from banking to cannabis fintech, how she built trust in a high-risk industry, and why compliance and culture are two of her sharpest competitive advantages.

You’ll also hear how she balances founder life with single motherhood, how her own mental health journey has shaped her leadership style, and what it really takes to build something sustainable without raising venture capital.

🔍 We cover:

Misconceptions about cannabis payments and legality
Why compliance is a competitive advantage in fintech
Bootstrapping to profitability without outside investment
Building PayRio’s team through trust and culture-first hiring
Processing payments for cannabis, psychedelics, peptides, and more
Her role on NCIA’s Banking & Financial Services Committee
Lessons from JP Morgan that still guide her company today
Balancing motherhood and entrepreneurship under pressure
The power of showing up authentically in business

📌 Links & Resources

PayRio → https://www.payrio.co
PayRio on Linkedin →https://www.linkedin.com/company/payrio/
Instagram → @payrio_hq
Aubrey on LinkedIn → https://www.linkedin.com/in/aubreyamatelli

If you enjoy this episode, drop a review and share it with someone building in fintech, cannabis, or anywhere trust and grit are essential.

Ep 21: Bryan Clayton: Blue-Collar Roots, Self-Taught Tech, and Scaling Without Funding

Tue, 10 Jun 2025 16:00:00 -0500

Bryan Clayton went from pushing a lawn mower at 13 to building and selling a multimillion dollar landscaping company. Then he taught himself to code and built his next venture from scratch. In this episode, he joins The Dear Tech Podcast to share what it really takes to build a national tech platform without outside funding, formal training, or Silicon Valley connections.

We talk about the power of discipline over motivation, what most non-technical founders get wrong, and how Bryan cold-called his way to a real user base. If you’ve ever thought, “I don’t have the background for this,” this episode might change your mind.

🔍 Topics We Cover:

The mindset shift from blue-collar business to tech founder
Teaching yourself to code after building a $10M company
Cold-calling 500+ vendors to build the first version of the platform
What went wrong with the first product and how it got fixed
Using AI to match customers with service providers
Why bootstrapping forced better product and leadership decisions
What most non-technical founders overlook and how to fix it
Building trust, quality, and discipline from day one

🧠 Guest Links:

LinkedIn: Bryan Clayton
Instagram (personal): @bryanmclayton
Instagram (company): @yourgreenpal

💬 Let’s Keep the Conversation Going

If this episode spoke to you, share it with someone who’s ready to build even if they feel underqualified. And don’t forget to follow @deartechpodcast on Instagram for clips, updates, and behind-the-scenes content.

Ep 20: Warren Wilansky: Servant Leadership in the Age of AI and Accessibility

Tue, 03 Jun 2025 10:00:00 -0500

Warren Wilansky has been building for the web since the ‘90s, but what makes his story stand out isn’t just longevity—it’s intention. As the Founder and President of Plank, a B Corp Certified digital agency, Warren has spent the last 25 years helping mission-driven organizations create ethical, inclusive, and accessible digital platforms that actually serve their communities.

In this episode, we talk about how Plank came to be, how Warren bet on the web before it was mainstream, and how his leadership style evolved from scrappy founder to servant leader. We also dive deep into accessibility—not just as a requirement, but as a business advantage—and what it really takes to build a strong, remote-first team that still cares.

If you care about digital culture, inclusion, and the long game of building something that lasts, this one’s for you.

🔍 Topics We Cover:

What sparked Warren’s early interest in media and design
The transition from CD-ROMs to the internet (and how he bet on the right thing)
The origins and mission behind Plank
What it means to run a B Corp in tech
Why accessibility is a strategic advantage, not just a checklist
Practical advice on building an inclusive design process
Leading a remote team and creating a real culture without an office
Servant leadership in action—and how Warren sees his role evolving
How AI is changing workflows (and what he’s skeptical about)
The future of Plank and building with intention

🧠 Quote to Remember:

“Accessibility isn’t something you tack on at the end. It’s part of how you design for real people, from the start.”

🔗 Resources & Links:

Plank Website: https://plank.co
Culture Page: https://plank.co/en/culture
Warren’s Blog & Personal Site: https://warrenwilansky.com

📣 Connect with Us:

Follow @deartechpodcast on Instagram

Subscribe and listen on your favorite podcast app

Leave a review if this episode resonated with you!

Ep 19: Dr Elliot Justin: Redefining Men’s Health Tech, One Erection at a Time

Wed, 21 May 2025 08:00:00 -0500

In this eye-opening episode, we sit down with Dr. Elliot Justin, a Harvard-trained physician, ER veteran, and founder of FirmTech — the company behind the Tech Ring, a groundbreaking wearable that turns your erection into a vital health signal.

We talk about why erectile dysfunction is misunderstood, how erections are linked to cardiovascular health, and what 70,000+ data points are revealing about the future of men’s health. This conversation spans medicine, sextech, personal performance, and the importance of taking your health — and pleasure — into your own hands.

🔍 In this episode:

Dr. Justin’s journey from ER doctor to startup founder
Why most ED treatments are solving the wrong problem
The real reason your erection fades with age (it’s not what you think)
How the Tech Ring collects and interprets data overnight
Why sexual health should be tracked like blood pressure
The importance of wearables in preventative medicine
FirmTech’s research with Mount Sinai, Baylor, UCSD, and more
What women’s clitoral health has to do with the next frontier of this tech
Why pleasure and science don’t have to be separate

🏆 FirmTech Recognition:

FDA-registered Class II medical device
FSA/HSA eligible
7 published research papers, 15+ ongoing clinical studies
2023 CES/Showstopper Health Innovation Runner-Up
2023 XBIZ Most Innovative Sex Toy of the Year

💥 Dear Tech Listener Exclusive:

Get 15% off the Tech Ring with code DEARTECH at myfirmtech.com

Ep 18: Angelo Ponzi: Strategic Marketing, Fractional Leadership, and Building a Brand That Works

Wed, 14 May 2025 02:00:00 -0500

Show Notes:

Too many companies launch with the belief that a great product will naturally attract customers. The truth? Without the right messaging and strategy, even the strongest ideas struggle to gain traction.

In this episode, Shubho sits down with Angelo Ponzi, a seasoned brand strategist and fractional CMO, to unpack what actually drives marketing success in early-stage and growth-stage businesses. From misunderstood branding efforts to tactical misfires, Angelo shares lessons from decades of helping companies clarify their message and build smarter go-to-market strategies.

This conversation goes deep into the challenges that founders and leadership teams face when they’re scaling — and why strategy should never be an afterthought.

What You’ll Learn:

Why “build it and they will come” rarely works
The difference between branding, identity, and positioning
When it’s time to bring in a fractional CMO
How to align your marketing and sales efforts for real growth
Mistakes startups make when they try to scale too fast
Red flags Angelo watches for before taking on a client
The marketing blind spots that derail M&A readiness
Lessons for anyone thinking about going fractional

Guest: Angelo Ponzi

Angelo Ponzi is a fractional CMO and brand strategist with over 25 years of experience helping companies strengthen their market presence, prepare for acquisition, and grow revenue through smarter marketing. He’s worked across industries, from early-stage startups to $100M+ firms, and brings a deeply strategic approach to everything from messaging to execution.

Find Angelo here:

🔗 linkedin.com/in/angeloponzi

🌐 https://www.craftmarketingandbranding.com/

Stay Connected with Dear Tech:

📸 Instagram: @deartechpodcast

🔗 Linktree: thedeartechpodcast

💼 LinkedIn: Dear Tech Podcast

Ep 17: Richard ‘RJ’ Kedziora: Innovation in Digital Health, AI in MedTech, and Building Meaningful Software

Thu, 08 May 2025 10:00:00 -0500

What does true innovation in healthcare look like beyond the buzzwords? In this episode, we sit down with Richard “RJ” Kedziora, Co-Founder of Estenda Solutions, to talk about the real state of digital health today—from AI-driven ambient listening tools to remote patient monitoring and EMR frustrations.

RJ brings decades of experience designing and implementing data-powered healthcare tools. He shares stories from Estenda’s early work with the Department of Defense and the VA, explains how wearable tech is changing chronic care, and reveals why real transformation in medicine is as much about people and process as it is about technology.

We also talk triathlons, startup roadblocks, and RJ’s personal productivity framework, Productive Harmony, which explores how energy—not time—is the key to doing meaningful work without burning out.

What We Cover

The evolution of AI in clinical settings
Why most EMRs still frustrate doctors
How ambient listening is changing note-taking in medicine
The role of wearables in aging and chronic care
What startup founders in medtech need to know before building
RJ’s book Productive Harmony and the case for energy over time
The surprising connection between triathlon training and running a business

About the Guest

Richard Kedziora is the Co-Founder of Estenda Solutions, a healthtech company focused on building data-powered tools that improve wellness and care outcomes. He holds a B.S. in Computer Science from Duquesne University and an M.B.A. from West Chester University of Pennsylvania, and he’s presented at countless technical and healthcare conferences. RJ is also an endurance athlete and the author of the upcoming book Productive Harmony.

Resources & Mentions

Estenda Solutions
RJ’s LinkedIn
Follow RJ on Instagram @productiveharmony
Book: Productive Harmony (coming soon)

Follow Dear Tech

📸 Instagram: @deartechpodcast

🔗 Website: linktr.ee/thedeartechpodcast

💼 LinkedIn: Dear Tech Podcast

Ep 16: Lori Crooks: Cybersecurity, Compliance, and the Realities of Entrepreneurship

Wed, 30 Apr 2025 12:00:00 -0500

In this episode of Dear Tech, we sit down with Lori Crooks, Founder and CEO of Cadra, a cybersecurity consultancy on a mission to make compliance approachable for businesses of all sizes. Lori brings over 20 years of experience in IT auditing, security frameworks, and technical documentation — but her journey didn’t start in tech. We dive into her path from finance to IT auditing, what inspired her to leave the corporate world, and the unexpected challenges of entrepreneurship.

We explore:

Why she walked away from corporate life and how she built Cadra from the ground up
What makes cybersecurity compliance so misunderstood (and often neglected)
Surprising gaps in how small businesses think about IT and security
The importance of making technical work human and understandable
FedRAMP, NIST, CMMC, and the real-world impact of regulatory frameworks
What AI means for cybersecurity compliance — and what’s coming next
The human side of leadership, working remote, and managing a values-driven team
Her mentorship philosophy, favorite client wins, and… the time she met a hard drive that had been shot with a bullet

Plus, we talk dogs, Harry Potter houses, and why “you are good enough” is the sticky note she’d leave for her past self — and maybe for all of us.

🎧 Listen now and don’t forget to follow the show.

🔗 Learn more about Lori’s work: www.cadra.com

📲 Connect with Lori on LinkedIn: https://www.linkedin.com/in/lori-crook s

Ep 15: Dan Hafner: No-Code Dev, AI in App Building, and Wine Making

Wed, 16 Apr 2025 09:00:00 -0500

Dan Hafner never set out to be an entrepreneur, but his winding path through teaching aspirations, software QA, and remote work led him to create Dapper No-Code — a company that helps founders build and launch software without writing code. In this episode, we explore how Dan turned a personal fitness app idea into a full-fledged business, what most people get wrong about no-code, and how white-labeling platforms can fuel your launch.

We also talk about wine making (yes, really), podcasting, dogs, and the future of AI-powered development.

What You’ll Learn

Why Dan pivoted from helpdesk support to founding a no-code company
The difference between “having an idea” and building a business
What people misunderstand about no-code tools in 2025
Dan’s process for validating app ideas (hint: it started at Planet Fitness)
The role of white labeling in scaling Dapper No-Code
How Dan's "Fast Track" offering takes apps from idea to launch in 90 days
Where AI is supercharging app creation—and where it’s falling short
The evolution of podcasting and how Dan's show Tech Bytes became a key growth lever
Dan’s episode with Alex Sanfilippo
Dan’s journey into winemaking, how he does it at home, and what flavors he’s experimenting with
The surprising impact of mentorship and what Dan teaches the next generation of no-code developers
Big thoughts on saturation, technical debt, and what enterprise adoption of no-code could look like

Mentions & Resources

Dapper No-Code
Bubble
Zapier
PodMatch
Dan’s episode with Alex Sanfilippo
Atomic Habits by James Clear
High Performance Habits by Brendon Burchard
Backendless

Rapid Fire Favorites

Favorite quote: “Done is better than perfect.”
Most gifted book: High Performance Habits
Favorite investment: “Continually investing in myself”
Best thing he’s been gifted: A bartered coaching program
Billboard message: “Your focus determines your reality.”
Something he changed his mind on recently: The idea of contentment vs constant hustle

Fun Extras

Dan brews wine in his basement — his latest batch? Peach.
He has three dogs, including a golden retriever-aussie mix with blue eyes
Shubho and Dan swap stories on podcasting, dogs, and why “apps aren’t the business”

Follow & Connect

The Best of Season 1: Conversations That Hit Different

Mon, 07 Apr 2025 08:00:00 -0500

We’re back, and we’re doing something special. In this episode, we’re looking back at the moments that defined Season One of Dear Tech. This isn’t just a highlight reel — it’s a celebration of the honesty, the vulnerability, and the power of real talk in a tech world that often forgets the human behind the resume.

From navigating job searches and negotiating comp, to burnout, layoffs, pivots, and everything in between. Season One held space for the full spectrum of what it means to build a career today.

🎧 In this episode, you’ll hear:

• 🔥 Unfiltered takes on the interview process and hiring realities

• 💼 Real-life negotiation strategies (and what not to do)

• 🧠 Insights on company culture, internal equity, and employee experience

• 💬 Stories of career pivots, risk-taking, and reclaiming control

• 💡 Tangible advice from people who’ve lived the ups and downs of tech

🙏 A huge thank you to our featured guests:

Sanjit, Elle, Dev, and Tahmid. Thank you for your brilliance, your stories, and your honesty.

And to my amazing co-host Francesca, this season wouldn’t have been what it was without you.

Whether you’ve been riding with us since day one or this is your first listen, this episode is for you. Let’s take a moment to reflect on everything Season One gave us, and everything still to come

📲 Connect with us:

📸 Instagram: @deartechpodcast

🔗 LinkedIn: Dear Tech Podcast

🌐 Website & Links: linktr.ee/thedeartechpodcast

🎧 Listen wherever you get your podcasts — and don’t forget to subscribe, rate, and share if this one resonated. 💛

Ep 14: Taylor McLoughlin: Navigating Startups, AI, and Mental Fitness

Mon, 10 Mar 2025 12:00:00 -0500

Episode Summary:

In this episode of Dear Tech, Shubho sits down with Taylor, co-founder of Ambient, to explore his journey through startups, AI, and the importance of mental fitness. Taylor shares insights from his experiences in event tech, pivoting businesses in the face of adversity, and how his passion for sailing has shaped his leadership approach. Whether you're a startup founder, a tech enthusiast, or someone looking to improve resilience and adaptability, this episode has something for you.

Key Topics Covered:

1. Sailing and Its Parallels to Startups (00:01:42 - 00:07:42)

How Taylor discovered sailing and its impact on his personal growth.
The endurance, teamwork, and adaptability required for offshore racing.
The connection between sailing and startup leadership—navigating changing conditions, team dynamics, and goal setting.

2. The Evolution of Ambient (00:07:42 - 00:15:12)

The origin of Ambient from a pre-pandemic startup focused on live events.
Pivoting to virtual event networking during COVID-19.
Identifying the shift in remote work trends and transitioning towards AI-powered workflow automation.
How Ambient supports chiefs of staff, founders, and operations leaders with AI-driven insights.

3. Building AI-Driven Products in a Crowded Market (00:15:12 - 00:23:12)

Differentiating Ambient by focusing on a specific persona: the Chief of Staff.
Understanding the balance between AI capabilities, user expectations, and reliability.
How AI is reshaping the SaaS industry and pricing models.

4. Startup Mindset: Lessons from a Three-Month Contract to Co-Founding (00:23:12 - 00:32:12)

Taylor’s journey from a temporary contract at a tech company to becoming a startup co-founder.
The importance of curiosity, ownership, and building a strong network.
How non-technical professionals can successfully transition into tech roles.

5. Psychological Flexibility and Mental Fitness (00:32:12 - 00:47:42)

Understanding psychological flexibility and its role in decision-making and resilience.
The connection between physical and mental fitness in high-pressure environments.
Taylor’s personal strategies for preventing burnout, including sailing, breathwork, and slowing down.
The importance of modeling work-life balance as a leader.

6. The Future of Remote Work (00:47:42 - 01:03:12)

Balancing flexibility with in-person collaboration.
Why remote work benefits some roles but not others.
The impact of company culture on remote and hybrid work success.

FAQs with Taylor: (01:03:12 - 01:18:12)

Best advice ever received?

"Slow down." Taking a breath and avoiding knee-jerk reactions helps in high-pressure situations.

Best investment?

Teaching others how to sail—it’s about passing on knowledge and building relationships.

Best gift ever received?

A love for music, instilled by his father.

One message for a billboard?

"Just breathe."

Most recommended book?

The Alchemist by Paulo Coelho.

What’s Next for Taylor? (01:18:23 - 01:25:12)

Scaling Ambient and continuing to develop AI-driven solutions for operations leaders.
Upcoming sailing races, including the Aegean 600 in Greece.

Connect with Taylor:

LinkedIn: https://www.linkedin.com/in/taylorsmac/

Check out Ambient:

Website: https://www.ambient.us/

Final Thoughts:

Taylor’s journey is a testament to adaptability, resilience, and curiosity. From pivoting startups to embracing AI and championing mental fitness, his insights offer valuable lessons for anyone navigating the tech world.

Tune in to Dear Tech for more conversations at the intersection of technology, leadership, and personal growth.

Subscribe & Follow:

Apple Podcasts | Spotify | YouTube
Follow us on LinkedIn and Instagram @DearTechPodcast

Until next time, stay curious and keep building!

Ep13: Tahmid Ahmed: Weight loss journey, Breaking into Agile Scrum, Leadership

Tue, 24 Oct 2023 08:00:00 -0500

Fran and Shubho speak with Tahmid about is journey from dead end job all the way to leading a team in a IT environment. They start with Tahmid's weight loss which was the spring board to him changing his life and taking on new challenges, the biggest of which was Technology.

Ep 12: Dev Wadhwa: Internships, Product management, International Student.

Tue, 10 Oct 2023 08:00:00 -0500

Fran and Shubho have an in depth conversation with Dev about his journey from student in India to Product Manager in the United States. They discuss the navigating the transition of going to school in the US after studying in India and then securing an internship; and from internship to securing a full-time job.

Ep 11: Sanjit Dutta: Growing up coding, Higher Education, Product Management

Tue, 26 Sep 2023 08:00:00 -0500

00:00 - Intro

00:20 - Kicking off - how do Sanjit and Shubho know each other

05:16 - the love of tech is generational

8:35 - Sanjit is not a coder

11:42 - what Sanjit does today

12:58 - What got Sanjit to where he is today (motivation & Path)

17:42 - Working at a start up vs working at a large enterprise

20:28 - Motivations going into the MBA program

23:31 - Coming from tech, who would you recommend and MBA program to, who would you dissuade?

28:45 - Education vs Work experience when looking to hire

33:30 - Deep dive into Sanjit's time consulting

39:20 - Sanjit's thoughts on being a Startup founder one day

43:06 - How Sanjit views work and career to his Identity as a person

50:03 - Whats Sanjit's work life balance like right now? (hobbies)

56:07 - Chief of Staff network

58:50 - The value of networking

01:02:50 - How to plan for a job in consulting

1:09:56 - Work experience before getting an MBA

01:13:17 - What would 15 year old Sanjit think of where you are and your journey?

01:14:39 - Dear Tech FAQs

This production may contain views and opinions which are those of the authors and do not necessarily reflect the official policy or position of any other author, agency, organization, employer or company.

Ep 10: Elle Anderson: Great Resignation, HR, & International Education

Tue, 12 Sep 2023 08:00:00 -0500

Elle Anderson Joins our host Fran & Shubho to give the perspective of Human Resources on the Great Resignation in tech and the current market and the changes since then. The Great resignation being the topic of Elle's Masters thesis we are able to get an in depth perspective of what was happening at that time; getting perspectives of both HR and the exiting employees.

Ep 9: How do I make the most of LinkedIn?

Tue, 22 Aug 2023 07:00:00 -0500

00:20 - Welcome

01:55 - What is LinkedIn

07:43 - Utilization from a company perspective

08:07 - How is LinkedIn best utilized?

14:48 - Candidate Profiles

15:01 - Profile Picture

22:29 - LinkedIn Headline

29:40 - How much detail do you put into your work history?

33:23 - What experience can you add to your profile besides work experience?

35:46 - Remove dates from education!!!

38:18 - Certifications on LinkedIn

40:11 - Engagement on the platfrom

43:13 - Use LinkedIn to educate yourself

44:20 - Shubho might be a linkedIn snob lol

49:45 - Shubho's rant - advice on what not to do when making a sales call

51:49 - Three templates of reaching out to people on LinkedIn.

52:34 - (Template 1) Candidates looking for jobs

56:40 - (Template 2) Sales people trying to get new business

59:21 - (Template 3) Recruiters reaching out to candidates.

01:01:47 - Fran's take

01:19:10 - How companies can best utilize and leverage the LinkedIn Platform

01:14:28 - If you have nothing nice to say dont say anything at all

01:18:33 - Wrap up

Ep 8: How do I negotiate?

Tue, 08 Aug 2023 08:00:00 -0500

Fran and Shubho discuss compensation negotiation from the perspectives of the candidate, employer, and the (current) employee. They dive into what can be expected during negotiations and how to improve over all negotiation tactics.

00:20 - Welcome

01:27 - how does Shubho Negotiate

01:44 - book recommendation

Never Split the Difference, by Chris Voss

09:43 - How does Fran negotiate

17:38 - Negotiating with recruiters

25:05 - talking to multiple companies/multiple

28:40 - What good tools and resources when going into a negotiation?

33:27 - the recruiter can be your ally

37:11 - Closed mouths don’t get fed

47:15 - Negotiating inside your current company

49:56 - Negotiating Severance?!

52:58 - Take your time signing paperwork

54:56 - Negotiate from a position of strength

56:43 - What should companies be mindful of when extending offers?

01:06:43 - Shubho’s two’s pieces of advice

01:10:56 - Frans take

01:12:09 - Wrapping up

Ep 7: Work From Home or Return To Office what makes more sense?

Tue, 25 Jul 2023 08:00:00 -0500

00:20 - Welcome

09:39 - RTO vs WFH from a employee perspective

18:44 - RTO vs WFH from a leadership perspective

23:00 - Articles Fran referenced

https://news.bloombergtax.com/tax-insights-and-commentary/tax-considerations-of-remote-work-arrangements-around-the-world

https://www.bloomberg.com/news/features/2023-02-21/another-threat-to-work-from-home-tax-breaks31:56 - Fran's Personal experience with remote work and her health

33:32 - Frans take on what to do first when making a change to remote work policy for a company.

35:33 - Shubho's hot take

39:02 - What would get Shubho in the office?

46:05 - Finding a company that fits the life you want

47:56 - Wrap up

Ep 6: The sky fell, what now?

Tue, 11 Jul 2023 08:00:00 -0500

Fran and Shubho discuss the steps to recovery after being impacted by layoffs.

00:00 - Welcome

02:39 - Effects of LinkedIn on the overall tech workforce

07:17 - Shubho's experience with being laid off

15:23- Shubho shares what helped him get through the time, shares advice

21:07 - Processing your situation

22:34 -Taking action

26:42 - Being able to stay flexible and transition

31:47 - The importance of networking

39:30 - Is going back to school a good idea if you get laid off

47:16 - Being confident and having a support system

Ep 5: Ping pong, free lunch, or nap rooms; what do the people want?

Tue, 27 Jun 2023 08:00:00 -0500

Fran and Shubho Discuss Perks vs. Benefits in today's job market and how companies can lean into their strengths when it comes to what they can offer.

00:39 Intro

00:56 Fran & Shubho's experience with Perks

03:43 Defining Perks vs Benefits

13:10 Companies utilizing perks when they can't pay large salaries

20:41 Change over the years

29:57 Effects of COVID on Perks and Benefits - and remote work

36:28 "If a company is doing it right what are they doing today?" - Shubho's take

45:06 Fran's take

48:19 How generational norms have affected Perks and benefits

59:55 The evolution of supply and demand in the tech industry has affected, if at all, workplace perks.

01:04:00 Potential effects of supply and demand

01:06:13 Stats on perks and benefits

01:09:57 Fran's Top Perks & Benefits

01:12:20 Shubho's top perks & Benefits

01:15:12 Shubho's takeaways

01:16:59 Fran's takeaways

01:18:51 Wrap up

Ep 4: What's up with Quiet Quitting?

Tue, 06 Jun 2023 08:00:00 -0500

00:36 Introduction

01:13 Defining quiet quitting

03:57 Defining quiet quitting

8:25 How Fran Sets Boundaries

9:51 How Shubho Sets boundaries

11:19 How do people define Quiet quitting

13:53 Meet people where they are

15:08 People turning down promotions?1

17:06 Frans experience turning down a promotion

20:40 Is quiet quitting good or bad?

23:06 People have different priorities

25:43 How should leaders go about quiet quitting

28:19 Taking on more responsibilities when trying to get promotions

31: 24 Shubho's take if quiet quitting is bad, and leadership perspective

33:42 Quiet quitting comes down to your values

35:56 Advocate for your teams!

36:52 Wrapping up

Ep 3: Is the sky falling?

Tue, 23 May 2023 00:00:00 -0500

Fran and Shubho discuss the current job market & economy in tech and how we got here from the beginning of the pandemic.

Ep 2: What's up with interviewing?

Tue, 23 May 2023 00:00:00 -0500

Fran and Shubho discuss todays interview landscape and what they think are the good, the bad, and the ugly.

Ep 1: Who, What, Why?

Tue, 23 May 2023 00:00:00 -0500

Fran and Shubho discuss who they are, What they are intending to accomplish on this podcast and why they decided to start this project.