What do most people regret at the end of their careers? According to legendary venture capitalist Bill Gurley, it’s not the failures — it’s the risks they never took.

In this wide-ranging episode of The Puck, Jim Baer sits down with Gurley — longtime Benchmark partner, early Uber board member, and author of Running Down a Dream — for a candid conversation on boldness, bubbles, AI speculation, venture capital cycles, and America’s structural challenges.

Gurley reflects on:

- Why “boldness regret” weighs heavier than failure

- How to turn passion into mastery — and why most people don’t

- The resume arms race and why young people feel trapped

- AI: real revolution or speculative excess? (Hint: both)

- Venture capital’s evolution — from discipline to burn-at-all-costs

- Why five-year AI forecasts may set companies up to stumble

- Regulatory capture in healthcare and education

- State-by-state competition as America’s hidden advantage

From Austin’s music scene to Silicon Valley’s capital cycles, Gurley delivers battle-tested insights from decades at the center of tech’s biggest waves.

If you care about careers, markets, AI, or the future of the U.S. economy, this episode is essential listening.

What does it take to build trust on the internet—at global scale?

In Episode 111 of The Puck: Venture Capital & Beyond, Jim Baer sits down with Jimmy Wales, co-founder of Wikipedia, to explore why trust—not technology—is the true foundation of open systems.

Wales reflects on Wikipedia’s evolution from a scrappy experiment into one of the most trusted information sources in the world, and why neutrality, transparency, and purpose matter more than algorithms or scale. The conversation centers on ideas from his new book, The Seven Rules of Trust, including how institutions earn trust, how they lose it, and what it takes to build systems that last.

Baer and Wales also dive into:

Why trust across journalism, politics, and business is collapsing

How Wikipedia governs bias without a single “editor-in-chief”

The role of funding models in preserving independence

Why AI systems struggle with transparency and attribution

What the decline of local journalism means for democracy

How open debate—done fairly—can be a path toward social cohesion

In a world increasingly shaped by algorithms, outrage, and information overload, this episode offers a sober, thoughtful look at how trust is built—and why it remains indispensable.

In this episode of The Puck, Jim Baer sits down with Jack Goldstone—the Hazel Chair Professor of Public Policy at George Mason University and one of the world’s foremost scholars on revolutions and social change. Goldstone has advised the National Intelligence Council, the World Bank, and the U.S. State and Defense Departments. His latest book, Revolutions: A Very Short Introduction, distills decades of research into why societies unravel—or endure.

Jim and Jack explore how rising debt, political polarization, elite fragmentation, and declining public trust mirror the early stages of historic revolutionary periods. They discuss China’s global ambitions, the impact of social media algorithms, the stagnation facing America’s working class, and what it would take to restore stability and rebuild a shared national purpose. Goldstone offers a candid assessment of where the U.S. stands in 2025—and why compassionate, unifying leadership will be essential to avoid deeper turmoil.

A wide-ranging and timely conversation about the forces reshaping democracy, the risks ahead, and the paths that might still lead America toward renewal.

Global macro strategist Vincent Deluard joins Jim Baer for a direct, data-driven conversation about the new economic regime taking shape in the U.S. and around the world. Deluard explains why fiscal dominance now outweighs monetary policy, why inflation is proving sticky, and how generational inequality, asset bubbles, and rising deficits are reshaping politics and markets.

A concise, unfiltered look at the forces shaping the next decade of markets, democracy, and everyday life.

On this week's episode, Jim talks with Matthew Continetti about the real story of the American Right—how conservatism evolved, why populism exploded, and what’s coming next. Sharp history, clear analysis, and a roadmap for understanding today’s politics.

Jim Baer talks with Francis Fukuyama — author of The End of History and the Last Man — about the fragility of liberal democracy in an age of rising authoritarianism and deepening polarization.

They discuss political decay in the U.S., geopolitical threats from Russia and China, and the outsized influence of social media. Fukuyama also shares a practical vision for rebuilding effective governance through an “abundance agenda” that cuts through gridlock and proves democracy can still deliver.

In this episode of The Puck, Jim Baer sits down with acclaimed author and journalist Oliver Burkeman, whose books Four Thousand Weeks and The Antidote have reshaped how we think about time, productivity, and perfectionism.

Oliver introduces ideas from his forthcoming book Meditations for Mortals, exploring how embracing our human limitations—rather than denying them—opens the path to deeper meaning and accomplishment. From the illusion of “getting on top of everything,” to the paradox of slowing down in a productivity-obsessed culture, Oliver offers insights drawn from philosophy, spirituality, and his own journey.

Together, Jim and Oliver reflect on mortality, imperfectionism, and how practices like patience, Sabbath rest, and journaling can help us live saner, more fulfilling lives.

Musician turned therapist Dan Koch joins The Puck: Venture Capital & Beyond to share his remarkable journey from touring in a rock band to pioneering research on spiritual abuse. We explore how faith and psychology intersect, why polarization is so hard to overcome, and why Dan believes ‘reality itself can be the medicine.’ A conversation about healing, curiosity, and hope in a divided world.

As violence flares in Gaza and the Middle East teeters on the edge of a wider crisis, The Puck turns to Aaron David Miller — a senior fellow at the Carnegie Endowment for International Peace; a former State department analyst and negotiator in Republican and Democratic Administrations — for an unflinching look at the road ahead. In this urgent conversation, we explore the hard lessons of history, the role of U.S. leverage, the realities of Israeli and Palestinian leadership, and whether there’s any realistic path to a lasting peace after October 7th. A candid, deeply informed discussion that cuts through political soundbites to the heart of one of the world’s most intractable conflicts.

As violence flares in Gaza and the Middle East teeters on the edge of a wider crisis, The Puck turns to Aaron David Miller — Global Fellow at the Wilson Center and veteran U.S. negotiator — for an unflinching look at the road ahead. In this urgent conversation, we explore the hard lessons of history, the role of U.S. leverage, the realities of Israeli and Palestinian leadership, and whether there’s any realistic path to a lasting peace after October 7th. A candid, deeply informed discussion that cuts through political soundbites to the heart of one of the world’s most intractable conflicts.