Now Tim Glomb spends his days as an AI transformationist, and he's not selling hype.

In this episode, Tim joins Sara and Dan to talk about what actually happens when a company adopts AI seriously (spoiler: it's not "slap it on top"), why the open web's foundation is quietly crumbling, and how a small bar owner turned empty seats into free beer and $200 nights using a simple text campaign. We also get into his dad's tear-jerking ChatGPT moment, AI-generated music, and why he worries more about social media than about any AI model.

Key takeaways:

• Most companies are putting "AI paint" on broken processes instead of rebuilding the foundation
• The open-source code holding up the entire internet is maintained by a shrinking handful of people
• Small, local businesses can scale further and faster than ever using AI plus real business acumen
• A simple photo-and-text workflow turned empty bar seats into real revenue
• Context is everything when prompting AI, vague questions get vague, even misleading answers
• Tim's dad had an emotional breakthrough using ChatGPT to redesign his bathroom
• Suno.com lets anyone turn a memory or a person into an original song in minutes
• Nuclear energy, especially microfusion, may be the real answer to AI's energy demands
• Some questions (therapy, sensitive personal decisions) simply aren't ones you should hand to AI alone

00:00 Cold open

00:46 Meet Tim Glomb

01:50 The biggest AI misconception execs have

03:15 "AI paint" on a junk car

04:31 Where human glue lives in a business

07:16 Becoming the operator, not getting replaced

09:02 Code review bottlenecks from AI-written code

10:48 The internet's crumbling open-source foundation

13:27 His dad's ChatGPT bathroom breakthrough

15:50 A resurgence for local economies

18:43 One small business, one big AI use case

21:02 Turning a bar's empty seats into $200

25:15 Advice for kids choosing a career path

29:14 The therapy question you shouldn't ask AI

32:10 Why context changes everything you ask AI

36:03 Scanning food with the Yuka app

38:09 Estrogenic compounds, wastewater, and AI research

40:04 AI's real climate cost

41:07 Betting on nuclear fusion energy

44:08 Making AI-generated songs with Suno

48:09 Why he blames the music industry, not AI

Connect with Tim Glomb: https://www.linkedin.com/in/timglomb/

Follow Sara: https://www.linkedin.com/in/saralynneroberts/

Follow Dan: https://www.linkedin.com/in/danroberts27/

Email the show: hello@promptlyspeakingpod.com

Key takeaways:

• Judgment, not data access, is what separates a good product decision from an obvious one
• A CNN customization feature that tested well in feedback flopped with 20 million real users
• "You don't bring a presentation anymore, you bring a prototype" is becoming the new baseline
• PMs are experiencing a new kind of fatigue: constant bombardment with fast AI-built options
• Curiosity, more than credentials, is what Cliff screens for when hiring product people
• Demo days and hackathons help channel company-wide building without losing focus
• Cliff built his own AI accountability agent to track workouts, meditation, and eating patterns
• Stepping away from screens, and away from AI itself, is still essential to good thinking

00:00 Cold open: judgment over AI hype

00:50 Meet Cliff Barrett

01:05 What a product manager actually does

01:51 The Airbnb product management debate

03:07 Biggest risk: trusting AI's "right" answer

03:26 The CNN newsfeed test that flopped

04:42 How Iterable used AI for marketers

05:45 Why you still need to ask "why"

06:50 Market analysis, data, and stakeholder input

07:25 PM fatigue and decision overload

08:01 The case for thinking time and naps

09:33 Skills for the next generation of PMs

10:22 The Nokia to Apple mobile shift

11:02 Prototypes over presentations

11:27 Building HTML sites at Glean

12:00 Everyone adopts AI at a different pace

13:29 Discernment: what actually matters in a demo

14:16 Step one for product leaders right now

15:19 When everyone can build, how do you focus

16:20 Running successful demo days

18:10 What makes Cliff want to join a company

19:36 Agents marketing to agents

21:08 Why product managers still matter

22:00 Cliff's personal AI accountability agent

24:01 What the historical look-back actually reveals

26:34 How Cliff screens for curiosity in hiring

28:40 Avoiding burnout as a builder

31:00 Using AI to simplify information overload

32:03 AI as a thinking partner, not therapy

34:07 Final advice for product leaders

Follow Sara & Dan:

Sara: https://www.linkedin.com/in/saralynneroberts/

Dan: https://www.linkedin.com/in/danroberts27/

Email the show: hello@promptlyspeakingpod.com

For our first ever in-person guest, we sat down with Larame Spence, who has spent years tutoring, running a private school, and building AI learning tools. His take flips the usual fear: the most powerful use of AI in education right now isn't sitting a kid in front of a chatbot, it's using AI as the source a parent, tutor, or teacher works through with the student, so the human stays in the loop.

Key takeaways:

• Why AI works best as the tutor's source material, not the tutor
• The MIT study where feedback labeled "human" beat identical feedback labeled "AI"
• Building a whole curriculum around one kid's obsession (the all-golf student)
• The calculator question, and what we lose and gain with every new tool
• "Confidently wrong" AI, and teaching kids to check their resources
• How a vetted library plus retrieval makes AI answers more trustworthy
• The privacy trade-off of an AI that learns exactly how your child thinks
• Why struggle, not ease, is where the real learning lives

This one will change how you think about AI and your kids.

Connect with Larame Spence: https://www.linkedin.com/in/laramespence/

Follow Sara & Dan:

Sara: https://www.linkedin.com/in/saralynneroberts/

Dan: https://www.linkedin.com/in/danroberts27/

Email the show: hello@promptlyspeakingpod.com

00:00 The scary parts of offloading to AI

01:30 Our first in-person guest

02:30 How education is going to change

03:30 AI as the source, not the tutor

05:30 Tutoring Algebra 2 with an AI

07:30 The MIT human vs AI feedback study

10:30 Spotting AI-generated content

12:00 Helping kids across a language barrier

14:00 The Dominican Republic email workflow

16:30 Will we still learn other languages?

18:30 Tailoring the lesson to each student

21:30 Asking questions without feeling dumb

24:00 Rethinking how we assess students

26:00 The calculator question

29:00 The brain is a muscle

31:30 Advice for nervous parents

33:00 The all-golf student

36:00 Personalizing a lesson by interest

38:30 Measuring student confidence

40:30 Confidently wrong: the star ceiling

43:30 Teaching kids to check their resources

46:00 Cutting hallucinations: tools and retrieval

49:30 How the teacher's role changes

53:00 Does AI help long-term recall?

55:30 Why they built the interactives first

58:30 The privacy trade-off for kids

60:30 Higher ed and the path to a job

63:30 The God code and earned struggle

66:30 Brandon Sanderson and the experience of a book

69:00 Sycophantic AI and why struggle matters

73:00 One takeaway, and don't underestimate Nano Banana

Brian went from running a digital marketing agency with a team of content creators to replacing that whole function with AI the month ChatGPT arrived, and growing a YouTube following of 25,000 by simply giving away what he figured out. In this conversation we get tactical: the email workflow he runs for about $30 a month, why he builds his own tools instead of renting someone else's wrapper, what "disposable software" means, when to use a project versus a gem, and the one thing he thinks actually lasts. Playfulness.

Key takeaways:

• Why Brian replaced content creators with AI in January 2023
• The email-triage workflow anyone can build for ~$30/month
• Build vs. buy: the case for owning your own automation
• "Disposable software": agents that build throwaway tools on demand
• Projects vs. gems vs. custom GPTs, and when each one fits
• How to get unstuck by asking a different model
• The skill Brian says will still matter in six months

Connect with Brian Albert: https://www.linkedin.com/in/brian-albert-executive/

Follow Sara & Dan:

Sara: https://www.linkedin.com/in/saralynneroberts/

Dan: https://www.linkedin.com/in/danroberts27/

Email the show: hello@promptlyspeakingpod.com

00:00 You can do anything with AI

00:47 Only 0.04% automate with AI

02:46 How Brian feels about this moment

04:07 Firing the content team in 2023

05:04 Six friends, then 25,000 followers

06:17 Giving everything away for free

07:39 A first agentic email workflow

09:42 Is it actually hard to build?

12:39 The real monthly cost, about $30

16:54 Build it yourself vs. buy the product

19:48 Add the next step to the automation

22:11 Was Brian always technical?

22:58 Starting with a PRD

25:29 A voice-driven book-writing app

26:02 Getting unstuck by asking another model

27:56 Disposable software, explained

30:45 Building apps vs. a whole eng team

30:54 Cowork and scheduled agents

36:01 Is this feeding the AI slop problem?

38:54 Unique perspective, value, adjust

41:22 Spotting AI writing, the do-not-use list

43:01 One thing to go do right now

45:07 Projects vs. gems vs. custom GPTs

47:25 The skill worth investing in, playfulness

50:36 Wrap up

Jason Stover, Executive Vice President at SSA Group and the builder behind Scout — SSA's internal AI platform — joins Sara and Dan to share how a people-first philosophy is driving one of the most thoughtful AI adoption strategies in the hospitality industry. From getting laid off teams through COVID, to discovering ChatGPT and not sleeping for weeks, to accidentally sending an AI-written email that almost got him flipped off by a colleague, Jason's story is equal parts honest, funny, and genuinely inspiring.

Key takeaways:

• Why the hospitality industry may be more AI-resistant than most — and why that's a strategic advantage
• How Scout was born, and what makes it different from generic AI tools
• The fight-flight-freeze response to AI adoption, and how to move your team past it
• Why AI adoption strategy starts with one question: "How does this impact me?"
• The email incident that changed how Jason thinks about AI communication forever
• How SSA is using behavioral psychology to personalize the AI experience for each employee
• What it really means to lead with empathy when rolling out new technology
• Why giving a long-tenured employee a four-day week might be the best ROI AI can deliver
• Jason's honest take on the future of work and the industries most at risk
• The number one piece of advice for any business leader who is still dancing around the AI topic

Connect with Jason Stover: https://www.linkedin.com/in/jason-stover-4b6b7a1b/

Follow Sara & Dan: Sara: https://www.linkedin.com/in/saralynneroberts/

Dan: https://www.linkedin.com/in/danroberts27/

Email the show: hello@promptlyspeakingpod.com

00:00 Episode preview & intro

01:15 Jason's parallel path: people & tech

01:43 Digital scales & predictive analytics

03:11 How Jason stays curious about AI

03:51 The YouTube channels he follows

04:44 EVP blocking Fridays for AI discovery

04:54 Journey from dishwasher to VP at SSA

06:38 The pivot: stepping down to focus on AI

06:47 COVID, layoffs, and the ChatGPT moment

09:47 Why it's always about people, not just AI

10:21 Meet Scout — SSA's internal AI platform

10:56 Tank Stover: the persona that started it all

14:08 Early feedback: fight, flight, or freeze

15:33 How employees are actually using Scout

17:26 Building career paths with AI in hospitality

18:10 Building trust in AI tools with frontline staff

18:47 The million-dollar question: transparency

19:55 What most CIOs get wrong about rollout

20:46 Trips and falls along the way

20:57 The email incident that changed everything

24:17 Rethinking who to bring AI to first

26:05 Repurposing saved hours for human connection

27:14 AI helping us be more human

27:41 Tangible vs. soft ROI of AI investment

28:47 The four-day workweek conversation

31:59 How Scout connects siloed departments

33:21 Crystal ball: the future of SSA with AI

36:15 Demographics, retention & daily pay

39:10 Leading with empathy — advice for leaders

39:31 Stop freezing: come up with a strategy

40:39 What Jason admires about Anthropic & Claude

41:13 A united leadership team behind the vision

42:16 Advice for young people navigating AI

43:04 Behavioral Essentials & personalizing Scout

46:20 The data trust problem

46:40 Using AI to discover your own strengths

47:18 Where to find SSA & closing thoughts

47:41 Outro

Aaron Trockman is a partner manager at Glean who had zero formal coding experience — and then built PartnerSync, a fully functional partner automation platform used daily across his sales organization, in about 10 hours using AI tools. In this episode, Sara and Dan sit down with Aaron to unpack exactly how he did it, what tools he used, what it actually cost, and what it means for the future of work. Aaron's story is a clear signal: AI is democratizing product development, and professionals who embrace these tools will have a massive advantage.

Key Takeaways:

• Aaron built a working MVP for around $30 in AI credits using Base44, then migrated to Lovable + Supabase.
• His AI workflow: dump the problem into Glean → generate a prompt with Prompt Cowboy → build in Lovable → debug with Gemini/ChatGPT.
• The tool he built, PartnerSync, replaced a capability they were evaluating from Crossbeam at significant additional cost.
• Key principle: assess complexity and margin for error before committing — internal tools with ~5–10% error tolerance are ideal for vibe coding.
• AI is democratizing product development — a team of one can now ship what once required a team of five.
• The future of work isn't AI replacing jobs — it's people who use AI replacing people who don't.
• The platform play is shifting: companies are building custom internal tooling instead of buying bloated SaaS they only use 30–40% of.
• Prompting tips: assign AI a persona (researcher, UX engineer), tell it to forget its last approach, and switch tools when you hit a wall.
• Job security comes from making your team more effective — not just from being able to build.
• Aaron's one action for listeners: take your biggest problem right now and ask ChatGPT, Gemini, or Glean how to solve it. Just start.

Connect with Aaron Trockman: https://www.linkedin.com/in/aarontrockman/

Sara: https://www.linkedin.com/in/saralynneroberts/

Dan: https://www.linkedin.com/in/danroberts27/

Email the show: hello@promptlyspeakingpod.com

00:00 Intro & cold open

00:47 What is Glean? Sara's pitch

02:06 Aaron's role: partner manager

02:54 Building PartnerSync — the story

04:57 Replacing a $$$$ SaaS tool for $30

06:06 The AI workflow: start to finish

07:11 Prompt Cowboy & prompt engineering

07:52 Base44 vs Lovable — why he switched

08:57 What is throttling? Plain language

09:46 Total cost: under $100 to MVP

10:33 Sara's Lovable build attempt

12:13 When AI lies about APIs

12:50 AI = brilliant dev with ADHD

14:55 How to scope AI-built projects

16:25 ISVs, internal use & margin for error

16:54 How to push through roadblocks

17:57 Prompting as building a team of one

18:53 Three hours on a multi-model build

20:40 Job security in the AI era

21:46 AI democratizes product development

24:47 How AI changed Aaron's mindset

25:41 Someone using AI will take your job

26:24 What Aaron wants to build next

27:39 Scope: too big vs. your wheelhouse

29:56 The future of SaaS & the platform play

31:21 One action to take in 30 minutes

32:16 Outro

In this episode, Sara gives a brief tour of their home & recording spaces, highlighting the challenges they've faced and the changes they plan to make.

Subscribe so that you don't miss new episodes! Be back soon!!

In this episode of Promptly Speaking, Sara and Dan sit down with Sreeveni Kancharla (“Sree”), CIO at SailPoint, to unpack what the AI revolution really means for leaders, employees, and the next generation entering the workforce.

Sree brings a rare, grounded perspective from the front lines of enterprise transformation, balancing innovation, governance, productivity, and humanity in a world where AI agents are becoming part of everyday work.

💡 Topics We Cover:

1. How AI is reshaping the workforce and where the real opportunities are
2. Why AI shouldn’t replace people, but amplify them
3. How leaders should think about productivity, governance, and strategy
4. Why junior employees still matter in an AI-driven world
5. How AI can support personal life decisions, learning, and creativity
6. The importance of human judgment, critical thinking, and boundaries
7. Why embracing AI is no longer optional, but blind trust is dangerous

⏱ Timestamps:

00:00 AI, Job Displacement, and Opportunity

00:43 Introducing Sree and Her Role as CIO

02:01 Why AI Is Different From Past Tech Revolutions

02:41 The Pressure on Leaders to Define AI Strategy

04:39 Junior Roles, Internships, and the Future Workforce

08:09 Why Human-in-the-Loop Still Matters

15:20 Using AI in Personal Life: Healthcare, Family, and Trust

18:20 AI as a Creative and Learning Tool

24:38 How AI Empowers the Next Generation

26:50 Rethinking Business Processes with AI Agents

31:51 Productivity, Strategic Thinking, and Leadership Time

36:49 Learning Habits, Curiosity, and Staying Relevant

39:08 Final Advice: How to Start Embracing AI Today

How to Find Sree:

LinkedIn: https://www.linkedin.com/in/sreeveni-kancharla/

Follow Sara & Dan:

Sara: https://www.linkedin.com/in/saralynneroberts/

Dan: https://www.linkedin.com/in/danroberts27/

Email: hello@promptlyspeakingpod.com

In the final Promptly Speaking episode of 2025, Sara and Dan take a moment to reflect on what they've learned from their guests, and through their own experimentation with AI in life & work.

Now, more than ever, it's important that we stop and take a moment to think about where we're trying to go in this world of technology that's moving so fast.

⏱ Timestamps:

01:23 Embracing AI in Daily Life

04:07 The Power of Continuous Learning

04:36 Optimizing Business Processes with AI1

3:44 Real-World Applications of AI

16:38 Reflecting on the Future

22:34 Humanizing Technology

Follow Sara & Dan:

Sara: https://www.linkedin.com/in/saralynneroberts/

Dan: https://www.linkedin.com/in/danroberts27/

Email: hello@promptlyspeakingpod.com

In this episode of Promptly Speaking, Sara and Dan speak with Scott Barghaan, a longtime enterprise sales leader whose career spans EMC and Salesforce, and who now teaches future business leaders at the Kellogg School of Management. Scott unpacks how AI is actually reshaping the practice of sales, not through flashy tools or automated outreach, but through better preparation, deeper customer context, and higher expectations for judgment. He explains how executives are often pressured to adopt AI before clearly defining the problem they are trying to solve, and why AI delivers real value only when it is applied to concrete constraints around scale, cost, and margin rather than introduced as a solution in search of a use case. The conversation explores how buyers are showing up differently, how great sellers adapt without losing authenticity, and what practical, grounded AI adoption looks like for teams of any size.

💡 Topics We Cover:

- Why buyers now enter sales conversations later, more informed, and more skeptical

- Board-level pressure to adopt AI and how it shapes executive decision-making- Why starting with tools instead of problems leads to disappointment

- Using AI to prepare for better conversations, not replace sellers

- Customer context as the real advantage in modern sales

- Where AI genuinely helps sales teams today and where it can backfire

- The risk of AI-assisted communication sounding polished but hollow

- Buying committees, political capital, and why “helping buyers buy” matters more than ever

- How small teams can pilot AI, measure impact, and scale responsibly

- Teaching sales and leadership during a major technology shift

⏱ Timestamps:

00:00 Introduction to AI, sales, and executive pressure

01:04 Scott’s career journey from enterprise sales to academia

02:41 Advising AI startups and supporting non-profits

04:49 Customer-centric selling in the AI era

08:42 How the role of the salesperson is changing

11:16 Leveraging AI for research, preparation, and insight

25:28 Why buying is harder than selling

31:15 Convincing executives to embrace AI thoughtfully

33:02 Why this technology shift feels different

33:50 AI’s role in business transformation

34:29 Challenges and opportunities with AI adoption

35:21 What successful AI implementation actually looks like

36:42 Addressing fear, risk, and resistance around AI

41:03 Lessons from teaching at Kellogg

46:03 Final reflections and practical takeaways

How to Find Scott:

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

Kellogg: https://www.kellogg.northwestern.edu/academics-research/faculty/barghaan-scott/

Follow Sara & Dan:

Sara: https://www.linkedin.com/in/saralynneroberts/

Dan: https://www.linkedin.com/in/danroberts27/

Email: hello@promptlyspeakingpod.com

The conversation goes beyond diagnostics to focus on where AI is already making meaningful progress in healthcare today, particularly in reducing administrative burden through tools like ambient documentation and message triage. Together, they explore the barriers to AI adoption in healthcare, including privacy, liability, fragmented data systems, and regulation, as well as the growing role of clinicians in shaping AI products.

The episode closes with practical advice for patients on how generative AI can be used responsibly right now to better understand medical bills, insurance documents, and care options, while acknowledging the real tradeoffs around data privacy and trust.

💡 Topics Covered:

• Why humans are surprisingly bad at diagnosing common conditions
• How AI can reduce diagnostic variability without replacing clinicians
• Pediatric ear infections as a global health problem
• AI in low-resource and rural healthcare settings
• Administrative burnout and “pajama time” for clinicians
• Ambient scribes and inbox triage as early AI wins
• Payers vs providers and how healthcare actually works
• Accountability and liability when AI is involved in care
• Why healthcare AI moves slower than other industries
• How patients can use generative AI today without over-trusting it

⏱ Timestamps:

00:00 Introduction to ear infections and AI in healthcare

00:44 Meet Matt Crowson: from ENT surgeon to AI advocate

01:36 Payers vs providers and how the healthcare system functions

02:39 AI and administrative burden in clinical work

04:55 Privacy, safety, and regulatory barriers to AI adoption

09:37 What a Chief Medical Officer does in an AI company

13:37 AI in rural healthcare and pediatric ear infection case study

26:35 Accountability and liability in AI-assisted care

26:51 The scalpel analogy and human responsibility

29:57 AI’s potential impact on healthcare costs

30:41 Generative AI and patient empowerment

36:10 What the future of AI in healthcare may realistically look like

36:40 How AI tools are implemented inside hospitals

38:35 Real-world AI deployments and auditing41:14 Vendor and healthcare system partnerships

42:01 Practical advice for patients using generative AI

45:07 Final reflections

How to Find Matt:

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

Follow Sara & Dan:

Sara: https://www.linkedin.com/in/saralynneroberts/

Dan: https://www.linkedin.com/in/danroberts27/

Email: ⁠hello@promptlyspeakingpod.com⁠

Neil breaks down why this wave of technology is unlike any before it, why white-collar roles are more exposed than people think, and why the next five to seven years will reshape entire industries. He dives into how AI is transforming marketing, legal work, medicine, and manufacturing in very different ways — from one-person teams running $60M campaigns to diagnostic models outperforming specialists — and what that means for your career trajectory.

He also shares his latest venture, The American Dream Index, a data-driven tool that quantifies what it truly costs to build a stable, middle-class life in America — and why so many people feel like they’re falling behind.

💡 You’ll learn:

• Why AI is moving faster than any disruption in modern history
• Which roles are most vulnerable over the next few years
• The real skill divide: entrepreneurial thinkers vs handle-turners
• How marketing, law, medicine, and manufacturing are being reshaped by ai
• What separates people who adapt from those who get left behind
• Why curiosity, experimentation, and communication are the new power skills
• How Neil is using AI to map the American dream — and why it’s drifting out of reach for many

🧠 Whether you’re an operator, a leader, or just trying to stay ahead, this conversation offers clear-eyed insight into a future that’s arriving much faster than most people expect.

⏱ Timestamps:

00:00 Disruptive Technology: Why This Wave Is Different

00:19 The American Dream and Shifting Goalposts

00:37 Meet Neil Shepherd

02:05 AI’s Acceleration and Job Disruption

06:27 Marketing’s Massive Transformation

08:58 Career Advice in the Age of AI

15:39 AI in Medicine

19:34 The Future of Robotics and Manufacturing

22:52 Entrepreneurs vs Handle-Turners

23:27 What Job Security Really Looks Like Now

24:11 Adapting to Technological Change

27:04 Introducing the American Dream Index

29:05 Meaning, Purpose, and Mid-Career Reinvention

33:32 Curiosity, Experimentation, and Adaptability

38:37 The Communication Skill That Now Sets You Apart

43:36 Final Thoughts and What to Do Next

How to Find Neil:

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

American Dream Index: www.americandreamindex.com

Follow Sara & Dan:

Sara: https://www.linkedin.com/in/saralynneroberts/

Dan: https://www.linkedin.com/in/danroberts27/

Email: ⁠hello@promptlyspeakingpod.com⁠

And how do you keep your voice — your taste — when machines want to average everything out?

In this episode, Sara and Dan sit down with Simone Stolzoff — author of The Good Enough Job and the upcoming How to Not Know — to talk about the real skills we need in an age of nonstop change: uncertainty tolerance, identity beyond work, and the confidence to experiment even when everything feels foggy.

But we go deeper:

• What does originality look like when AI can draft anything?
• How do writers protect the parts of their work that only come from human judgment?
• What’s worth delegating to AI — and what should never leave your hands?

Simone breaks down how he uses AI to push his ideas, not replace them, why first drafts should still come from humans, and why taste, discernment, and creative rejection might be the most important skills of the next decade.

💡 You’ll learn:

• How writing is actually evolving in a world of large models
• Why taste is the new competitive edge
• How to use AI as a developmental editor without flattening your voice
• The danger of tying your identity to work in a volatile economy
• Why uncertainty isn’t a threat — it’s what gives life meaning
• The mindset shift that reduces anxiety and increases agency
• How to anchor yourself as everything around you changes

🔥 If you’re navigating AI, career uncertainty, creative work, or the pressure to “figure it all out,” this episode will give you clarity — and momentum.

⏱ Timestamps:

00:00 Introduction: The AI Awakening

00:21 Navigating Uncertainty in a Polycrisis World

00:52 A Confession and Reconnecting with an Old Friend

02:15 The Good Enough Job: Rethinking Work and Identity

04:10 Generative AI: Transforming the Creative Process

11:10 How to Not Know: Embracing Uncertainty

20:07 The Future of Work: Autonomy and Adaptation

24:39 Segmenters vs. Integrators: Work-Life Boundaries

25:32 The Role of Generative AI in Work Autonomy

26:29 Transitioning to Self-Employment

28:10 Balancing Self-Employment: Pros and Cons

31:45 Building and Finding Community as an Entrepreneur

36:33 Embracing Uncertainty in Work and Life

39:43 Action Bias: Moving Forward with Generative AI

How to Find Simone:

Website: https://www.simonestolzoff.com/

LinkedIn: https://www.linkedin.com/in/simone-stolzoff-5a16b648/

X: https://x.com/SimoneStolzoff

Instagram: https://www.instagram.com/thepizza_bagel/

TED Talk: https://youtu.be/cfKFbh8LPvU?si=yXlz4FzgHK3OPNH7

Follow Sara & Dan:

Sara: https://www.linkedin.com/in/saralynneroberts/

Dan: https://www.linkedin.com/in/danroberts27/

Email: hello@promptlyspeakingpod.com

In this episode of Promptly Speaking, Sara and Dan sit down with Sara Filipčić, a researcher, founder of Be Human(e), and expert in childhood social–emotional development. Her work spans the Yale Center for Emotional Intelligence, EdTech innovation, and early field research in Japan on human–robot dynamics.

Together, they explore how technology is reshaping childhood, how AI companions are influencing the way kids build relationships, and what parents can do to create safer, more resilient, and more connected homes.

💡 You’ll learn:

- Why connection offline builds resilience online

- Why fear-based parenting and strict restriction tend to backfire

- How to gradually and intentionally introduce technology at every developmental stage

- How to co-view and co-play apps and games with your child

- What digital citizenship actually means — and why it matters

- How loneliness fuels reliance on AI companions

- Red flags to watch for when kids (or adults) turn to chatbots for emotional validation

- How cultures like Japan are approaching human–machine relationships differently

- The crucial role of psychological safety and open communication

- How parents can rebuild trust after digital missteps

🧠 Whether you’re excited about AI or terrified of it, this episode offers a grounded, research-informed roadmap for parenting in a tech-saturated world.

⏱ Timestamps:

00:19 – Meet Sara Filipčić

00:59 – Childhood development, cyberbullying, and tech’s impact

01:53 – Teaching emotional intelligence human-to-human and human-to-machine

02:47 – From Croatia to the U.S.

03:03 – Building Humane & the mission of healthy human–machine relationships

04:00 – Why fear-based parenting backfires

05:08 – The dangers of restriction without conversation

07:47 – How to gradually introduce tech in age-appropriate ways

13:21 – AI companions: what parents need to know

18:45 – Loneliness, identity, and anthropomorphism

23:01 – Modeling healthy tech behavior as adults

27:34 – Co-viewing, co-playing, and why it matters

32:47 – Teaching kids to question online content

33:34 – Parental guilt, self-forgiveness, and rebuilding trust

34:05 – Digital citizenship explained (privacy, safety, digital footprints)

36:40 – What Japan can teach us about human–machine symbiosis

41:54 – The future of AI companions and realistic robotics

43:20 – Why self-awareness is the most important skill kids need

47:55 – Final advice for parents

📚 Resources & Links Mentioned:

Find Sara Filipčić:

- Substack: www.substack.com/@humanerobot25

- Instagram: www.instagram.com/filipcic.sara/

- LinkedIn: https://www.linkedin.com/in/filipcicsara/

- Website: https://behumane.ai/

Parenting & Tech Resources:

- Common Sense Media: age ratings + app guidance (https://www.commonsensemedia.org/)

- Gingko: developmental-stage-aware AI with human therapist loop (https://www.gingko.ai/)

- Little Otter: teletherapy platform built by mother & daughter duo (https://www.littleotterhealth.com/)

⚠️ Safety Note:

This episode references suicide, predators, and mental health challenges. If you or someone you know is struggling, call or text 988 in the U.S. for free, confidential support.

Follow Sara & Dan:

Sara: https://www.linkedin.com/in/saralynneroberts/

Dan: https://www.linkedin.com/in/danroberts27/

Email: hello@promptlyspeakingpod.com

In this episode of Promptly Speaking, Sara and Dan explore how AI is reshaping not only how we think - but how we feel.

From chatbots like Replika and Character.AI to Instagram’s synthetic influencers, they unpack what happens when emotional AI starts filling our social gaps - and what we lose when simulated empathy replaces real human friction.

This episode contains brief discussion of suicide and loneliness in the context of AI companionship. If you or someone you know is struggling, please reach out to the Suicide and Crisis Lifeline by calling or texting 988 (U.S.) for free, confidential support.

💡 You’ll learn:

- How AI companions are changing our emotional landscape

- Why loneliness isn’t always a problem to fix - and what it can teach us

- The difference between empathy and sympathy (and why it matters)

- When it’s healthy to lean on AI for support - and when it’s time to log off

- Practical ways to stay grounded, connected, and human in an AI-driven world

🧠 Whether you’re curious about emotional AI or concerned about its impact, this conversation dives deep into the psychology of connection - and how to keep your humanity intact as technology gets more personal.

⏱️ Timestamps:

00:27 – AI and Mental Health: The New Frontier

00:52 – The Role of AI Companions

01:54 – Loneliness and Technology

02:27 – The Importance of Human Connection

07:22 – Empathy vs. Sympathy

08:25 – The Impact of AI on Friendships

12:48 – Using AI for Emotional Support

14:48 – Final Thoughts and Takeaways

19:33 – Closing Remarks

Follow Sara & Dan:

Sara: ⁠https://www.linkedin.com/in/saralynneroberts/⁠

Dan: https://www.linkedin.com/in/danroberts27/

Email: ⁠hello@promptlyspeakingpod.com

In this episode of Promptly Speaking, hosts Sara and Dan Roberts sit down with Dr. Ravit Dotan, PhD - a practical philosopher and AI ethicist - to unpack the cognitive, ethical, and emotional effects of our growing reliance on AI.

💡 You’ll learn:

- Why using AI can actually reduce brain engagement - and how to prevent it

- How to apply ethical reasoning in everyday AI use

- The “Chef Approach” to AI - a framework that keeps humans in control

- What skills will matter most in the next decade of AI-driven work

🧠 Whether you’re an AI optimist or a cautious skeptic, this episode explores how to stay curious, ethical, and fully awake in the age of intelligent machines.

⏱️ Timestamps:

00:00 – Welcome to Promptly Speaking

00:20 – Meet Dr. Ravit Dotan: From philosophy to AI ethics

03:50 – The gray zones of AI ethics

07:49 – What AI does to your brain

16:58 – How to brainstorm *with* AI (not let it think for you)

25:16 – Ethical adoption in business

30:37 – How to build trust into AI workflows

36:12 – The “Chef Approach” explained

39:35 – Custom chatbots, agents, and the next frontier

45:42 – The skills your brain needs for the future of work

51:11 – Final reflections

Dr Ravit Dotan:

https://www.linkedin.com/in/ravit-dotan/

https://www.techbetter.ai/

Follow Sara & Dan:

Sara: ⁠https://www.linkedin.com/in/saralynneroberts/⁠

Dan: https://www.linkedin.com/in/danroberts27/

Email: ⁠hello@promptlyspeakingpod.com

In this episode of Promptly Speaking, hosts Sara and Dan Roberts explore how generative AI tools like ChatGPT are rewiring our brains. Drawing on new research from MIT, Science Advances, and Harvard Business Review, they unpack how these tools influence creativity, focus, and intrinsic motivation.

You’ll hear how AI can raise productivity while lowering originality, why brain engagement drops when we outsource thinking, and what that means for our ability to learn, create, and stay mentally sharp.

💡 You’ll learn:

- What MIT discovered about how AI impacts neural engagement

- Why using AI can boost quality but reduce creativity

- How to stay mentally active when tools do the “thinking” for you

- The hidden trade-off between efficiency and satisfaction

- Simple strategies to use AI without losing your edge

🔥 Whether you’re an AI optimist or skeptic, this episode offers a grounded look at how to keep your brain — and your creativity — alive in the age of automation.

⏱️ Timestamps:

00:28 – Personal experiences with AI in daily life

05:27 – MIT study: how ChatGPT lowers brain engagement

10:51 – Can AI make us more creative—or just more average?

14:53 – The “Google Effect” and how memory changes with technology

16:00 – The productivity paradox: getting more done but caring less

19:08 – Intrinsic motivation and AI fatigue

24:46 – Balancing AI assistance with human intuition

26:32 – Final reflections and takeaways

Follow Sara & Dan:

Sara: linkedin.com/in/saralynneroberts/

Dan: linkedin.com/in/danroberts27

Email: ⁠hello@promptlyspeakingpod.com⁠

📚 References & Further Reading

1. Sparrow, Liu & Wegner (2011) — Google Effects on Memory: Cognitive Consequences of Having Information at Our Fingertips. Science.

https://scholar.harvard.edu/files/dwegner/files/sparrow_et_al._2011.pdf

2. MIT Media Lab (2024) — EEG study on neural engagement during essay writing with ChatGPT and Google (reported by Time).

https://time.com/7295195/ai-chatgpt-google-learning-school/

3. Doshi & Hauser (2024) — Generative AI Enhances Individual Creativity but Reduces Collective Diversity. Science Advances.

https://www.science.org/doi/10.1126/sciadv.adn5290

4. Harvard Business Review (2025) — GenAI Makes People More Productive—and Less Motivated.

https://hbr.org/2025/05/research-gen-ai-makes-people-more-productive-and-less-motivated

5. Science (2023) — Experimental Evidence on the Productivity Effects of Generative AI.

https://www.science.org/doi/10.1126/science.adh2586

6. Nature Scientific Reports (2025) — Cognitive Offloading in AI-Assisted Work: Impacts on Engagement and Attention.

https://www.nature.com/articles/s41598-025-98385-2

7. arXiv preprint (2025) — Large Language Models and the Human Mind.

https://arxiv.org/pdf/2506.08872v1

8. arXiv preprint (2023) — Programming with ChatGPT: Impacts on Developer Speed and Code Quality.

https://arxiv.org/abs/2302.06590

9. Nature Machine Intelligence (2022) — AI-Enabled Peer Support Improves Empathy in Mental Health Conversations.

https://www.nature.com/articles/s42256-022-00593-2

10. Academy of Management Journal (2022) — Augmented Creativity: How AI Tools Help Customer Support Agents Innovate.

https://journals.aom.org/doi/abs/10.5465/amj.2022.0426

11. MDPI – Societies Journal (2024) — AI Use and Critical Thinking: Evidence from 666 Participants.

https://www.mdpi.com/2075-4698/15/1/6

12. IE Center for Health & Well-Being (2024) — AI’s Cognitive Implications: The Decline of Our Thinking Skills.

https://www.ie.edu/center-for-health-and-well-being/blog/ais-cognitive-implications-the-decline-of-our-thinking-skills/

13. Frontiers in AI (2022) — Cognitive Offloading and the Rewiring of Human Thought.

https://www.frontiersin.org/journals/artificial-intelligence

14. Forbes (Knapp, 2025) — Prototype Study Suggests AI Tools Decrease Critical Thinking Skills.

https://www.forbes.com/sites/alexknapp/2025/01/10/the-prototype-study-suggests-ai-tools-decrease-critical-thinking-skills/

15. PMC Article (2025) — Technological Overreliance and Cognitive Decline: Lessons from Prior Tech Revolutions.

https://pmc.ncbi.nlm.nih.gov/articles/PMC9329671/

In this episode of Promptly Speaking, Sara and Dan sit down with Jess Ramos — data analyst turned entrepreneur and one of LinkedIn’s most influential voices, with nearly half a million followers.

Jess shares how one viral post changed the course of her career, why she believes everyone should understand data, and how she’s using AI and ChatGPT to make analytics more human — and more accessible.

💡 You’ll learn:

- How Jess went from a corporate desk to full-time entrepreneurship

- Why learning SQL still matters (even in the age of AI)

- How she uses ChatGPT to simplify data, spark creativity, and scale faster

- The mindset shift that turns online influence into real business results

- Why taking imperfect action beats waiting for the perfect plan

🔥 Whether you’re curious about AI, building your personal brand, or finding the courage to bet on yourself — this episode is a masterclass in turning data and creativity into opportunity.

⏱️ Timestamps:

00:19 Meet Jess Ramos: Data Analyst Turned Entrepreneur

00:58 Understanding Data Analytics and SQL

02:27 Jess's Journey: From Viral Post to Thriving Business

05:33 Balancing a 9-to-5 Job and Building a Business

11:38 The Leap to Full-Time Entrepreneurship

16:01 Discovering the Power of ChatGPT

18:19 Jess's AI Toolkit

18:51 Exploring Notion AI

19:27 AI Meeting Notes and Task Trackers

21:12 Using AI for Personal Projects

23:40 The Importance of Learning SQL

25:49 Generative AI and Cognitive Skills

30:52 Advice for Aspiring Entrepreneurs

35:00 Final Thoughts and Social Media Plugs

Jess Ramos:

https://www.youtube.com/@JessRamosData

https://www.linkedin.com/in/jessramosmsba/

https://www.instagram.com/jessramosdata/

https://www.tiktok.com/@jessramosdata

https://linktr.ee/jessramosdata

Follow Sara & Dan:

Sara: ⁠https://www.linkedin.com/in/saralynneroberts/⁠

Dan: https://www.linkedin.com/in/danroberts27/

Email: ⁠hello@promptlyspeakingpod.com

In this episode of Promptly Speaking, Sara and Dan build on insights from their conversation with Tiago Forte to explore how context-aware AI is reshaping the way we think, work, and create.

They break down the difference between deterministic and non-deterministic systems — and why that subtle distinction defines the future of intelligent tools. From winning competitive RFPs to solving frustrating real-life problems, they share how context-driven AI can turn data into insight and action.

💡 You’ll learn:

- What makes AI context-aware (and why that’s a big deal)

- How deterministic vs. non-deterministic systems shape decision-making

- Why grounding, context windows, and multimodal AI are revolutionizing human–machine interaction

- The growing tension between personalization and data privacy

- How to experiment with AI in ways that create real-world impact

🎯 Whether you’re curious about the tech itself or how to use it practically, this episode reveals how good data — combined with critical reasoning — can turn AI from a novelty into a true advantage.

⏱️ Timestamps:

00:33 Reflecting on Tiago's Insights

01:56 Understanding AI Terminology

03:44 Winning Business with AI

06:05 Using AI for Personal Projects

11:27 Financial Caution with AI

16:47 Practical AI Applications

23:32 Conclusion and Takeaways

Follow Sara & Dan:

Sara: ⁠https://www.linkedin.com/in/saralynneroberts/⁠

Dan: https://www.linkedin.com/in/danroberts27/

Email: ⁠hello@promptlyspeakingpod.com⁠

Listen as Forte debunks common misconceptions about AI, reveals surprising industry applications, and outlines how AI can act as a thought partner rather than a simple task automator.

From cutting-edge projects at a sugar mill in Guatemala to AI’s potential to reshape personal finance and recruiting, this episode is packed with insights that challenge conventional thinking and inspire new possibilities.

⏱️ Timestamps:

00:23 Meet Tiago Forte: Productivity Expert

01:04 Misconceptions About AI

03:33 AI as a Thought Partner

04:27 Accuracy and Citations in AI

07:33 Defining AI: A Mirror to Humanity

09:04 Fear of AI and Projections

10:38 Backlash and Sacred Cows

16:22 Adapting to Change in Business

16:32 Generational Shifts in Business

22:31 Global Technological Divide

23:12 Case Study: AI in a Guatemalan Sugar Mill

24:07 AI Adoption in Various Teams

24:36 Top-Down vs. Bottom-Up AI Implementation

25:12 Experimentation and Business Culture

26:57 Unique AI Use Cases Across Industries

28:57 Transformational AI in Small Businesses

32:13 AI in Recruitment and Candidate Sourcing

36:03 AI as a Financial Thought Partner

40:46 Finding Your AI Spark

42:43 Conclusion and Final Thoughts

Tiago Forte:

⁠https://www.youtube.com/@TiagoForte⁠

⁠https://www.buildingasecondbrain.com/⁠

Follow Sara & Dan:

Sara: ⁠https://www.linkedin.com/in/saralynneroberts/⁠

Dan: ⁠https://www.linkedin.com/in/danroberts27/

Email: ⁠hello@promptlyspeakingpod.com

In this episode, they discuss why they started the podcast, their personal backgrounds in tech, and their aim to demystify AI for the everyday person. With insights from various industries and a focus on the human-AI partnership, they seek to provide practical advice and hope amidst the rapid technological changes.

Tune in, stay informed, and be part of the conversation. Send your thoughts to hello@promptlyspeakingpod.com. New episodes every Tuesday!

⏱️ Timestamps:

00:24 Why Another AI Podcast?

01:06 The Rapid Evolution of AI

02:06 Podcast Format and Guest Insights

02:46 Human-AI Collaboration

04:17 The Future of Work with AI

05:37 Getting Started with AI Tools

06:43 Engage with Us!

Follow Sara & Dan Roberts:

Sara: https://www.linkedin.com/in/saralynneroberts/

Dan: https://www.linkedin.com/in/danroberts27/

Email: promptlyspeakingpod@gmail.com

Promptly Speaking dives into how artificial intelligence is reshaping the way we live, work, and think, one human story at a time.

Meet Sara & Dan Roberts — Sara’s an entrepreneur who’s helped scale some of Silicon Valley’s hottest startups. Dan’s a tech sales leader at Glean, where he talks every day with companies figuring out how to bring AI into their business.

Together, they’re exploring how AI is changing everything.

Follow now and get ready for the official launch on October 21 — and a first look at the stories shaping the AI era.