Experimentation as the AI advantage

What role should businesses play in society today?

In this episode of the Unlearn Podcast, I sit down with investor, ecosystem builder, and Foundry Group co-founder Seth Levine to explore how capitalism itself may be evolving. Seth’s latest book, Capital Evolution, examines a fundamental question: can modern capitalism create broader opportunity, stronger communities, and more inclusive ownership?

Our conversation ranges from declining economic mobility and generational uncertainty to the role of values-driven companies and the rise of AI-powered work. We also dive into how leaders can navigate uncertainty—balancing profit, purpose, and technological disruption.

Along the way, Seth shares how a single dinner conversation sparked a two-year research journey, interviewing more than 100 leaders, academics, and entrepreneurs to understand where capitalism may be headed next.

This conversation also builds on ideas we’ve explored before on the podcast—particularly with Seth’s long-time collaborator Brad Feld. In our earlier discussion on Give First leadership, Brad challenged the idea that success comes from extraction, instead arguing that generosity, long-term thinking, and community building are the real drivers of sustainable impact. Together, these conversations offer a powerful lens on how leadership, capitalism, and value creation are being redefined.

If you’re thinking about the future of work, leadership in an AI-powered world, or how organizations can create both economic and societal value, this episode will challenge some assumptions.

Key Takeaways

• Capitalism is already evolving: Many leaders still operate as if we’re in a shareholder-first world—but that model has already shifted. Businesses now face growing pressure to balance profit with broader societal impact.
• Economic mobility is declining: While economies continue to grow in aggregate, fewer people are able to move up financially. This shift is reshaping how younger generations view opportunity and fairness.
• Values-driven companies are becoming more visible: Organizations like Patagonia, Hobby Lobby, and Chick-fil-A show that companies can operate with clear values. What matters most is transparency—being honest about what the organization stands for.
• AI is changing how leaders work: Seth describes using AI tools like Claude as an operating system for his daily work—drafting ideas, exploring questions, and accelerating thinking. Leaders who combine human judgment with machine intelligence can dramatically increase their effectiveness.
• Curiosity and listening are leadership superpowers: One of Seth’s biggest lessons from writing the book was the value of listening to perspectives outside his own experience. Engaging with different viewpoints reveals insights leaders often miss.

Additional Insights

• The danger of misleading economic averages: Seth describes the “Jeff Bezos walks into a bar” problem—where averages distort reality. Aggregate growth can hide widening inequality and declining mobility.
• The difference between values and politics in business: Companies should be clear about their values—but that doesn’t mean every company needs to take political positions. Transparency builds trust with employees, investors, and customers.
• Why younger generations feel uncertain: Many are entering a world shaped by rapid technological change, rising costs of living, and shifting job markets. AI both excites and worries people about what work will look like.
• AI rewards experimentation: The people benefiting most from AI are those who continuously experiment. Treating AI as a collaborator—not just a tool—opens entirely new ways of working.

Episode Highlights

00:00 – Episode Recap

Seth Levine reflects on the changing nature of capitalism and why declining economic mobility, shifting values, and AI-driven disruption are forcing leaders to rethink how businesses create value for society.

02:40 – Guest Introduction: Seth Levine

Barry introduces Seth Levine, co-founder and partner at Foundry Group, entrepreneur advocate, and author of Capital Evolution, a book exploring how capitalism can evolve to create broader opportunity.

05:00 – The Dinner Conversation That Sparked a Book

Seth describes the boardroom conversation that sparked the idea behind Capital Evolution—a question about whether investors would accept lower returns in order to live their values.

07:53 – Why the Capitalism Debate Is Growing

Research for the book revealed that roughly half of people under 40 believe capitalism isn’t working—prompting a deeper exploration of how the system might evolve.

10:33 – Values-Driven Businesses in Practice

Examples like Patagonia and Hobby Lobby show how companies can operate with strong values while still pursuing business success.

19:14 – Generational Anxiety About the Future

Younger generations face growing uncertainty about careers, technology disruption, and economic opportunity.

23:38 – Learning From Different Perspectives

Travel, conversations, and research helped Seth recognize how limited our understanding can be when we stay within familiar social and professional circles.

29:30 – Experimenting With AI at Work

Seth shares how tools like Claude have become part of his daily workflow—helping him explore ideas, draft writing, and accelerate thinking.

33:38 – Why AI Feels Exciting Again

After decades in venture capital, Levine says experimenting with AI tools has reintroduced a sense of novelty and curiosity into his work.

40:51 – The Pattern of Every New Technology

From automobiles to AI, every major technological shift initially sparks fear before becoming normalized.

42:07 – A Simple Leadership Habit: Listen More

Seth encourages leaders to actively seek conversations with people who hold different perspectives—and listen without trying to persuade.

45:00 – Closing Reflections

Barry wraps the conversation, highlighting the importance of curiosity, experimentation, and openness as leaders navigate the evolving relationship between business, society, and technology.

FAQs

Q1. What is Capital Evolution and why is it important?

Capital Evolution describes how capitalism is shifting beyond a shareholder-first model toward creating broader societal value. It’s important because businesses are now expected to balance profit with impact, ownership, and community outcomes.

Q2. Why is economic mobility declining today?

Economic mobility is declining because wealth and opportunity are increasingly concentrated. Even as economies grow overall, fewer people can move up income levels, making it harder for younger generations to improve their financial position.

Q3. What role should businesses play in society today?

Businesses should generate profit while also contributing to society through clear values, responsible decision-making, and long-term thinking. The most effective companies align economic success with positive societal impact.

Q4. How is AI changing leadership and the future of work?

AI is transforming leadership by enhancing decision-making and productivity. Leaders who combine human judgment with AI tools can move faster, process more information, and make better strategic decisions.

Q5. Why are younger generations questioning capitalism?

Younger generations are questioning capitalism due to rising living costs, job uncertainty, and reduced economic mobility. These challenges make traditional systems feel less fair and less effective than in the past.

Useful Resources:

• Seth Levine on LinkedIn - https://www.linkedin.com/in/sethjlevine/ 
• Foundry Website - https://foundry.vc/ 
• Seth Levine Book: Capital Evolution - https://www.amazon.com/Capital-Evolution-New-American-Economy/dp/1637747780 
• Unlearn Episode 160 with Brad Feld - https://barryoreilly.com/explore/podcast/give-first-leadership-brad-feld/ 

Follow the Host:

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

Personal site: https://barryoreilly.com

Facebook: https://www.facebook.com/barryoreillyauthor/

Twitter/X: https://x.com/barryoreilly

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