Expert Intelligence with Paul Estes

Stop Generating, Start Thinking with Kevin Henrikson

Kevin Henrikson has built and sold companies for hundreds of millions, scaled teams at Microsoft and Instacart, and now runs an AI healthcare startup—and he called complete bullshit on the productivity myth we've all been sold.
The most unmovable meeting on his calendar? 8 PM: GO TO SLEEP. When people want late meetings, he says no. When he travels, his admin moves the sleep block. In his 20s, he was the "code until 2 AM" guy. Now? He protects his ability to think like his business depends on it. Because it does.
But the biggest insight that stuck with me: "If you got in a car accident tomorrow and had to be out for three days, you'd cancel everything. People would understand. You need to give yourself permission to have that car accident periodically."
What You'll Learn:
Why AI is creating chaos instead of productivity—and the one habit that breaks the cycle
The health stack that replaced Kevin's expensive concierge doctor
Why teaching kids to self-regulate with technology beats helicopter parenting every time
How voice AI is solving the work in healthcare that nobody actually wants to do
Why blocking sleep on your calendar might be the most productive decision you'll ever make
Kevin's framework for when to use AI and when to just close all the tabs and think

Writing Is Thinking: AI Slop Is Killing Your Credibility — with Joe Lazer

In a world drowning in AI-generated content, Joe Lazer is betting his career on the one skill machines can't replicate: authentic storytelling. The author of The Storytelling Edge and creator of a popular Substack newsletter walked away from an executive role at a fast-growing startup to pursue what he calls humanity's most essential superpower. In this candid conversation with Paul Estes, Joe reveals why he left stability to write his second book, how he built and sold his first media company, and why the "vortex of mid" is sucking the soul out of modern content.
Understanding which skills will matter when machines can do almost everything else is crucial. Joe shares his framework for using AI ethically in the creative process, explains why neural coupling makes storytelling our most powerful business tool, and offers a radically different vision for preparing the next generation. From the neuroscience of oxytocin to the reputational damage of AI slop, learn why mastering storytelling might be the ultimate competitive advantage in an AI-saturated world.
You'll Learn:
Why AI creates a "vortex of mid" that traps content creators in mediocrity and how to avoid it
The ideation-research-refine framework for using AI as a creative partner without losing your voice
How storytelling triggers neural coupling, making listeners' brains sync with yours to build instant connection and trust
Why the reputational damage from publishing AI-generated content is vastly underestimated by most professionals
Lessons from building and selling a media company at 22 years old
Why soft skills like storytelling, adaptability, and empathy will be lasting competitive advantages
Subscribe to Expert Intelligence so you don't miss future conversations with industry leaders who are navigating the intersection of technology, creativity, and the future of work.
Resources Mentioned:
The Storytelling Edged by Joe Lazer and Shane Snow
Dr. Paul Zak's neuromarketing research (Claremont University)
Kyla Scanlon's newsletter on economics and narrative

Why You Should Embrace Career Pivots with Alyson Griffin

What happens when you realize the career you're in isn't your future? For Alyson Griffin, that moment launched a three-decade journey from Silicon Valley PR agencies to becoming the marketing force behind State Farm's Emmy-nominated Super Bowl campaign and Intel's Cannes Lions-winning drone light show. In this revealing conversation with Paul Estes, Alyson shares how she navigated a dramatic career pivot, brought humanity to one of America's most iconic insurance brands, and is now leading her team through the AI revolution.
From experimenting with AI-generated creative attempts that hilariously failed to building Jake from State Farm into a cultural phenomenon, Alyson offers a masterclass in balancing innovation with authenticity. She opens up about surviving breast cancer in the midst of her executive-level career, and how State Farm's risk-averse culture is learning to embrace cutting-edge technology. Whether you're considering a career transition or leading teams through technological change, this episode delivers actionable wisdom wrapped in honest storytelling.
You'll Learn:
How to recognize when it's time for a dramatic career pivot (and how to find the courage to make it happen)
The critical difference between using AI as a tool versus expecting it to do all the thinking for you
How practicing AI prompting on low-stakes personal projects (like vacation planning) builds skills for high-stakes work applications
Why bringing your whole self to work—including health struggles and vulnerabilities—can strengthen rather than weaken your leadership
How Jake from State Farm became an insurance mascot that people treat like a real celebrity
The reason humanities and critical thinking skills matter more than ever in an AI-driven world
Subscribe to the Expert Intelligence podcast today so you don't miss future conversations with leaders at the forefront of marketing, technology, and business transformation.
Producer: David GrabowskiTheme Music: Aleksey Chistilin

The Truth About AI: Freelancers & Why Systems Matter More than People Think with Chris Dumpleton

While headlines scream about AI replacing call center jobs, Chris Dumpleton reveals a different reality. As an executive at Limitless Technology, he's spent 20 years in telecom and contact centers—today he shares why organizations struggle to implement AI cost-cutting measures and how the gig economy model can create better outcomes for both companies and customers.
With a storied career that includes helping eBay increase seller revenue by 24% using peer-to-peer expert coaching, Chris discusses how Limitless Technology evolved from "taking the Uber business model to contact centers" to becoming a key player in AI training through RLHF (Reinforcement Learning from Human Feedback). Chris explains why outcome-based pricing creates better incentives than traditional employment models and how the same platform that connects customers with brand experts is now connecting AI companies with the specialized knowledge workers needed to train sophisticated language models.
You'll Learn:
Why contact center managers resist AI implementation despite corporate pressure to cut costs
How gig economy experts with real product experience outperform traditionally trained agents
The rating-driven excellence model that makes freelance workers more motivated than employees
The explosive demand for specialized expertise in RLHF and AI model training
Why outcome-based pricing aligns incentives better
Subscribe to Expert Intelligence to get notified when future conversations are published.

Why AI Won't Steal 50% of Jobs with Tom Davenport

Tom Davenport has been watching technology transformations for over 30 years, and he's not joining the AI hype wagon. As a distinguished professor at Babson College and author of 27+ books, Tom brings hard-earned wisdom to the AI conversation that's refreshingly realistic. While Silicon Valley promises instant transformation and a job apocalypse, Tom reveals why real AI success requires the unglamorous work of process redesign, patient leadership, and years of persistent effort.
In this eye-opening conversation, Tom debunks the myth that AI will eliminate 50% of white-collar jobs while sharing practical insights on how organizations can actually capture value from AI. From his "super tech leader" framework to the critical mistake of not planning for entry-level hiring, Tom provides a clear and realistic vision of AI's true potential and timeline.
You'll Learn:
Why AI job replacement predictions have been consistently wrong for decades
How to organize AI initiatives across departments
How to use process mining and redesign to unlock real AI value in your organization
Why citizen development and "vibe coding" are democratizing technology creation
The critical role "boring," entry-level work plays in developing future expertise
Which workflows every business should consider automating first
Why persistence and patience matter more than speed in AI transformation
Subscribe to Expert Intelligence so you don't miss any future conversations — these industry leaders separate signal from noise in this rapidly evolving technological landscape.

Layoffs Aren't the Problem. Employment Strategy Is. — with Brea Starmer

Brea Starmer helped build the future of work out of necessity. As founder of Lions and Tigers, she's unlocking millions in economic opportunity for independent workers, particularly women navigating caregiving responsibilities. When Brea was laid off seven months pregnant, facing workplace discrimination, and having to choose between career ambition and family flexibility, she discovered that the traditional employment system simply wasn't designed for people like her.
What started as personal survival—self-funding her own maternity leave by billing 60 hours a week for 13 weeks—evolved into a movement reshaping how enterprises think about workforce planning. Brea's vision of "no more layoffs" is a practical blueprint for using blended teams of employees and independent workers to build more resilient, flexible organizations that can adapt to rapid change without devastating human costs.
You'll Learn:
How workplace discrimination during pregnancy led to building a multi-million dollar company serving independent workers
Why an "everything's a project" mindset creates more security than traditional employment in today's economy
The critical first question to ask when transitioning from employee to independent work: "Who do you want to serve?"
Why enterprises are struggling with change management
How to leverage your existing network when making the leap to independent work
Subscribe to the Expert Intelligence podcast today so you don't miss future conversations with industry leaders at the forefront of technological transformation.

Start Building: Vibe Coding for Non-Techies with Iwo Szapar

Iwo Szapar saw the future of work early—co-founding Remotely years before the pandemic transformed how we work. Now he's back with groundbreaking research through the AI Maturity Index, analyzing over 250,000 data points across 75 countries to reveal what's really happening with AI adoption in the workplace. The gap between AI winners and everyone else isn't just significant—it's shocking.
In this conversation with Paul Estes, Iwo breaks down the stark reality behind AI adoption, from the top 1% who save 31 hours per week to the bottom 50% saving only six hours. He shares practical frameworks for immediate implementation, introduces "vibe coding" for non-technical professionals, and explains why the traditional consulting model is being disrupted by AI-powered productized services.
You'll Learn:
The shocking productivity gap between top AI users and everyone else (it's over 5x)
Why the biggest AI opportunity lies in decision-making, not just content creation
The simple STEP framework (Segmentation, Transition, Education, Performance) for AI implementation
How "vibe coding" enables anyone to build software without technical expertise
Why productized services are replacing traditional consulting models
The "any task you do twice should be automated" rule that transforms productivity
How to give AI the context it needs to become your most valuable thought partner
Subscribe now so you don't miss any future conversations!

What the AI Shift Means for Your Career with Kelly Monahan

Kelly Monahan, Managing Director of Upwork's Research Institute and co-author of Essential, reveals why 77% of employees feel AI makes work harder, not easier—and what leaders can do about it. In this eye-opening conversation with Paul Estes, Kelly breaks down the real forces behind today's labor market shifts, from inflation and capital costs to the pandemic's lasting impact on customer behavior.
From her research on the frontlines of the future of work, Kelly shares practical frameworks for moving beyond resilience to "anti-fragility"—the ability to adapt and evolve when systems face stress and shock. Whether you're a leader trying to implement AI effectively or a professional wondering how to stay relevant, this conversation offers actionable insights on navigating our rapidly changing work landscape while keeping human creativity and relationships central.
You'll Learn:
Why the AI productivity paradox is happening and how to overcome it
The difference between AI as a tool versus AI as a teammate, and what it means for your workflow
How to move from fragile to anti-fragile thinking when facing career disruption
Why skills are becoming more valuable than degrees and how to credential them effectively
The "configuration mindset" that separates AI power users from frustrated beginners
How to preserve cognitive capacity for creativity in an increasingly automated world
What successful organizational AI strategies look like beyond mere cost-cutting
References Mentioned:
Essential by Christie Smith and Kelly Monahan
Antifragile by Nassim Nicholas Taleb
The Black Swan by Nassim Nicholas Taleb
Thinking, Fast and Slow by Daniel Kahneman
Subscribe to Expert Intelligence so you don't miss future conversations with industry leaders at the forefront of technological transformation. Each episode brings you practical insights to navigate our rapidly evolving digital landscape.
Producer: David Grabowski Theme Music: Aleksey Chistilin

Building Resilience in Uncertain Times with Samia Kornweibel

Generation X professionals are navigating an unprecedented perfect storm: young children at home, peak career responsibilities, and a business landscape in constant flux. Executive coach Samia Kornweibel joins Paul Estes to explore why so many mid-career leaders are experiencing what she calls "career meltdowns"—and how they can build resilience in an era where roles keep shifting.
Fresh from completing her AI coaching certification, Samia shares how she's helping leaders navigate the ethical integration of AI tools while maintaining the human connection that drives real transformation. Using Microsoft's suite of tools and her innovative CHAIR model (Clarity, Humanizing, Aligning, Integrating, Realizing), she demonstrates how coaches can responsibly leverage technology to enhance the coaching relationship.
You'll Learn:
Why Generation X is experiencing "career meltdowns" at the intersection of family, career peak, and rapid change
The "musical chairs" reality of modern corporate life and how to build resilience when stability isn't an option
How to create and maintain psychological safety as an intentional daily practice, not a one-time achievement
The CHAIR model for responsible AI integration in professional coaching and development
Why human accountability and connection remain irreplaceable in an AI-enhanced world
Practical strategies for using tools like Microsoft Viva Insights to enhance coaching conversations and time management
How to move from peripheral AI conversations to focused, ethical implementation
Subscribe to Expert Intelligence so you don't miss future conversations with industry leaders at the forefront of professional development and workplace transformation. Each episode brings you practical insights to navigate our rapidly evolving career landscape.
Producer: David Grabowski Theme Music: Aleksey Chistilin

AI's Role in Personalized Math Tutoring with Peter Relan

Peter Relan, founder of the YouWeb Incubator and initial Discord investor, joins Paul to discuss how AI transforms math education through his latest venture, MathGPT.ai. Growing up in poverty with parents who believed in education's transformative power, Peter is now paying it forward by creating around-the-clock math coaching for students facing critical academic hurdles.
In this eye-opening conversation, Peter reveals how his platform combines AI tutoring with human instructor oversight to address math numeracy challenges while maintaining academic integrity. From Peter's journey as a UCLA math tutor to his vision of personalized learning through AI coaches, discover how technology creates accessible, accurate, and cheat-proof math education that helps students overcome gateway barriers to their chosen careers.
You'll Learn:
How math courses often become gateway blockers that prevent students from entering their chosen careers
Why "innumeracy" is becoming a critical societal challenge comparable to illiteracy
The instructor-led approach that makes MathGPT.ai cheat-proof while still helping students learn
How AI can provide personalized learning experiences based on students' unique interests
Why the future of education lies in the partnership between human wisdom and artificial intelligence
The analytics dashboard that helps instructors identify struggling students in real-time
How AI can automate time-consuming workflows while preserving the irreplaceable human touch in education
Subscribe to the Expert Intelligence podcast so you don't miss future conversations with industry leaders.