Generating Alpha Podcast

This week on Generating Alpha, I’m joined by Paul Krugman — Nobel Prize-winning economist, prolific writer, and one of the most influential economic thinkers of our time. Over the past five decades, Krugman has helped shape modern economics through both his academic work and his role as a leading public intellectual.

He first rose to prominence for his work on international trade and currency crises, which earned him the Nobel in 2008. But beyond academia, Krugman became a household name through his long-running New York Times column — which he concluded in 2024 — where he blended economic insight with sharp commentary on fiscal policy, globalization, inequality, and politics.

In this conversation, we talk about Krugman’s early life in Utica, the roots of his interest in economics, and the key — sometimes serendipitous — milestones in his career. We dive into his views on the global and U.S. economies, the evolution of trade policy, the rise of Wall Street’s influence, and the challenges of inequality and populism. He also shares what policymakers often get wrong, how he balances analysis with advocacy, and his advice for the next generation.

Paul brings a rare combination of clarity, experience, and conviction to economic issues that are often misunderstood. His perspective challenges assumptions and offers a powerful lens into how the world really works.

This week on Generating Alpha, I’m joined by Michael Rees — Co-President of Blue Owl Capital and the visionary founder behind Dyal Capital, the platform that pioneered GP stakes investing and reshaped the landscape of alternative asset management.

Michael launched Dyal Capital with a bold and unconventional insight: that owning minority stakes in leading asset managers could create durable, long-term value in a space historically focused on short-term performance. Over the past decade, under Michael’s leadership, Dyal has invested in some of the most elite and influential firms in alternatives—including Silver Lake, Sixth Street, Vista Equity Partners, H.I.G. Capital, and many others.

In 2021, Dyal merged with Owl Rock to form Blue Owl Capital, where Michael now helps lead one of the fastest-growing alternative investment platforms in the world—managing over $270 billion across private credit, GP stakes, and real estate strategies.

In this wide-ranging conversation, we talk about Michael’s early career at Lehman Brothers, the genesis of Dyal Capital, and how he built an institutional platform that redefined how investors think about the business of asset management itself. We also explore the key qualities that separate great firms from good ones, what he’s learned from working with some of the sharpest minds in finance, and how Blue Owl is positioning itself for the future of alternatives.

Michael’s story is one of innovation, resilience, and a relentless focus on building lasting value—offering powerful lessons for anyone navigating the evolving worlds of investing, entrepreneurship, and financial strategy.

This week on Generating Alpha, I’m joined by Annie Duke — a former professional poker player turned cognitive scientist, bestselling author, and one of the world’s foremost experts on decision-making under uncertainty. Over the course of her career, Annie has helped everyone from investors to CEOs to policymakers improve how they think about risk, probabilities, and knowing when to double down — and when to walk away.

Annie’s journey is anything but traditional. She left a PhD program in cognitive psychology at the University of Pennsylvania and went on to become one of the most successful poker players in the world, winning millions — including a World Series of Poker championship. After retiring from poker, she dedicated herself to teaching others how to make better decisions in environments where luck and skill collide.

She’s the author of multiple bestselling books, including Thinking in Bets, How to Decide, and Quit, which have become required reading for decision-makers in finance, business, and beyond. Her work sits at the intersection of psychology, game theory, and behavioral finance.

In this conversation, we explore how to make smarter decisions under uncertainty, the common mistakes even the smartest investors make, how to know when quitting is actually the most rational choice, and the frameworks she’s developed that anyone can apply — whether at the poker table, in markets, or in life.

This week on Generating Alpha, I’m joined by Joseph Edelman — founder and CEO of Perceptive Advisors, and arguably the most successful biotech investor of the past two decades. Over the last 25 years, Joe has built Perceptive into one of the most dominant and respected healthcare-focused investment firms in the world — with a track record that rivals the best human-managed funds in modern history.

Joe launched Perceptive in 1999 with a simple but highly differentiated insight: that deep scientific expertise, paired with bold and patient capital, could drive outsized returns in one of the most complex and volatile corners of financial markets. Since then, he’s backed some of the most transformative biotech and life sciences companies — businesses pioneering breakthroughs in gene therapy, rare diseases, oncology, and cutting-edge therapeutics.

In this rare conversation — his first-ever podcast appearance — we dive into his upbringing, how his passion for science shaped his worldview, the founding story of Perceptive, and how he navigates an industry defined by uncertainty, asymmetric outcomes, and extreme volatility. We also talk about what separates great investors in highly specialized spaces, how he thinks about risk, and the mindset that’s driven one of the most remarkable investing careers of the past quarter century.

Joe’s story is one of conviction, intellectual rigor, and staying true to a focused mission — offering a masterclass in long-term thinking for anyone in investing, entrepreneurship, or science-driven industries.

This week on Generating Alpha, I’m joined by Anthony Pompliano — a former soldier turned tech executive, investor, and one of the most influential voices in Bitcoin and digital finance. Known to millions simply as “Pomp,” Anthony has built a uniquely powerful presence at the intersection of technology, investing, and media.

After serving in the U.S. Army, Anthony transitioned into the private sector with roles at Facebook and Snapchat during periods of explosive growth. He later co-founded Morgan Creek Digital, an investment firm focused on blockchain technology and digital assets. Over the past several years, he’s become one of the most widely followed advocates for Bitcoin and decentralized systems — building an audience that spans Wall Street, Silicon Valley, and everyday retail investors. Through his daily newsletter and top-ranked podcast, he’s played a major role in shaping how a new generation understands money, innovation, and financial sovereignty.

In our conversation, we talk about how his upbringing and military background helped shape his work ethic and worldview, lessons he took from working directly with leaders like Mark Zuckerberg and Sheryl Sandberg, and how he came to see Bitcoin not just as technology, but as an ideology. We also explore what separates great founders and the mindset he uses to stay sharp in rapidly evolving markets.

Anthony’s journey is a testament to conviction, clarity of thought, and the power of building in public — and his perspective offers real value for anyone navigating the future of finance, media, or entrepreneurship.

This week, I had the honor of sitting down with Roger Altman—an icon of American finance whose influence spans Wall Street, Washington, and beyond. Roger began his career at Lehman Brothers, where he became the youngest-ever general partner in the firm’s history. In the 1980s, he played a key role in the founding chapter of Blackstone, working alongside Pete Peterson and Stephen Schwarzman as they shaped what would become one of the world’s largest alternative asset managers. But Roger’s contributions didn’t end in the private sector.

He twice served in the U.S. Treasury Department, including as Deputy Secretary under President Clinton, helping steer the country through critical fiscal and economic decisions. Then in 1995, he founded Evercore with a vision for a firm that would combine world-class financial advice with independence, integrity, and client-first values. Since then, Evercore has grown into a $10 billion company that has advised on over $5 trillion in transactions—earning a place among the most respected firms on Wall Street.

In our conversation, Roger shares reflections from a career that has intersected with nearly every major financial and political turning point of the last 50 years. We explore his early days at Lehman, his transition into public service, and the values that guided him as he built Evercore from scratch. He opens up about the lessons that skills that have aided him in the competitive enviornment of Wall Street, and the advice he’d give to a 15-year-old trying to make sense of the world today.

In this episode, I sat down with Tully Friedman—one of the true pioneers of private equity—for his first-ever podcast appearance. Tully co-founded Hellman & Friedman, a firm that helped define the modern buyout era, and later launched Friedman, Fleischer & Lowe, where he’s led investments in middle-market businesses with a highly focused and values-driven approach. Before that, he made his mark at Salomon Brothers during the firm’s golden age in the 1970s, gaining an early education in high-stakes finance at one of Wall Street’s most legendary institutions.

Over the course of our conversation, Tully shares how his early life and legal training shaped his worldview, the principles behind building two successful investment firms, and how he evaluates leadership and long-term value. We also discuss his partnership with the late Warren Hellman, his definition of a “great investment,” and the non-negotiable values he’s never sacrificed for returns.

This episode is full of timeless lessons on judgment, talent, integrity, and scale—told by someone who has quietly influenced generations of investors behind the scenes.

If you have not already, I urge you to subscribe or follow the podcast and share it if you enjoyed this conversation.

This week, I had the rare opportunity to sit down with Asher Edelman—one of the most legendary and unconventional figures to ever emerge from Wall Street. A pioneer of corporate raiding in the 1980s and widely recognized as one of the real-life inspirations for Gordon Gekko, Asher built a reputation for bold, high-stakes takeovers that redefined the balance of power between shareholders and management. After founding Edelman & Co., he became known not just for his financial acumen, but for the psychological precision with which he approached every deal—often guided by his monthly reading of The Art of War.

Beyond finance, Asher has had an extraordinary second act in the art world, where he's become a prominent dealer, collector, and curator with a keen eye for value and authenticity. He recorded this conversation in his Switzerland office, surrounded by pieces from his personal art collection, which he graciously walked me through.In this episode, we explored his early days on Wall Street in the 1950s, his most memorable corporate battles, and the traits that separated survivors from legends. He also shared insights on the current state of activism, including his candid take on an investor he believes doesn’t live up to the title. Asher’s perspective is sharp, original, and completely unfiltered—this is a rare glimpse into a mind that has shaped both markets and culture for over half a century.

P.S. I apologize for the choppiness at some parts of the interview, I had some technical difficulties on my end.

This week, I had the pleasure of sitting down with Scott Bok—a deeply thoughtful leader whose journey from Grand Rapids, Michigan to the top of Wall Street reflects quiet determination, intellectual rigor, and a deep commitment to principled leadership.

Best known for his long tenure as CEO of Greenhill & Co., Scott has helped shape the modern M&A landscape.Scott’s story is one of steady ascent. After earning his law degree from Penn, he began his career at Wachtell, Lipton, Rosen & Katz before moving to Morgan Stanley, where he spent over a decade navigating the fast-evolving world of investment banking. He later joined Greenhill in its early years and eventually led the firm through its IPO, the global financial crisis, and its recent sale to Mizuho—all while fostering a culture that prioritized independence, trust, and long-term thinking.

Our conversation touched on his early influences, the defining moments of his career, and the lessons he's drawn from decades of advising CEOs and boards on high-stakes decisions. Scott brings a rare blend of humility and insight, and his reflections offer valuable guidance not only for those in finance, but for anyone striving to lead with clarity and integrity.I hope you enjoy this episode as much as I did.

This week, I had the pleasure of sitting down with Dan Ariely, one of the most influential voices in behavioral economics and a pioneer in understanding the irrational forces that drive human behavior. A bestselling author whose books—including Predictably Irrational, The Honest Truth About Dishonesty, and Dollars and Sense—have sold millions of copies worldwide, Dan has helped reshape how leaders across business, healthcare, and policy think about decision-making. His TED Talks have garnered over 10 million views, and his research at Duke University continues to inspire both academic and corporate communities around the globe.Dan’s personal story is as powerful as his professional work. After surviving a traumatic accident as a teen in Israel, he became deeply fascinated by how people experience pain, make choices, and navigate complexity—insights that fuel his mission to design systems that support better, more human decisions.While this podcast usually features financial leaders, I knew I had to bring Dan on because understanding the why behind decisions is just as critical as the strategies themselves. In our conversation, we explored his early life, the behavioral patterns that shape utility and trust, and what it takes to create environments where both employees and ideas can thrive.Dan’s blend of scientific insight, practical wisdom, and human empathy makes this episode uniquely powerful—and one I believe every leader should hear.