Generating Alpha Podcast

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.

Anthony Scaramucci, founder and managing partner of SkyBridge Capital, shares his extraordinary journey from humble beginnings in Long Island to Wall Street and a brief stint in Washington. He candidly discusses the financial anxieties of his youth, the lessons learned from being fired at Goldman Sachs, and the importance of resilience and authenticity in overcoming failures. Scaramucci emphasizes the value of curiosity and embracing one's outsider status, while offering advice on reading, taking risks, and staying true to oneself in pursuit of passion.

This week, I had the distinct honor of speaking with Howard Marks, one of the most respected and insightful investors of our time, and the co-founder and co-chairman of Oaktree Capital Management. Known for his deeply analytical memos and disciplined approach to risk, Howard has helped shape the landscape of investing.Howard’s career began in equity research at Citibank in 1968, where he witnessed firsthand the boom and bust of the Nifty Fifty era. He later transitioned into high-yield and distressed debt, eventually co-founding one of the first distressed debt funds at TCW in 1988 with Bruce Karsh. In 1995, the two left to launch Oaktree Capital Management, which has since grown into one of the world’s leading alternative asset managers—with a distinct culture focused on risk control, intellectual honesty, and long-term thinking.In our conversation, we explored the defining chapters of Howard’s career—from building conviction around a then-niche strategy, to the building of Oaktree. Along the way, we discussed what makes a great investor, the importance of price, and how Howard and Bruce Karsh built one of the most effective partnerships in modern finance.And on a more personal level, we reflected on his childhood, the influence of the late Charlie Munger, and what advice he’d give to a 15-year-old navigating the world today.Howard’s clarity of thought, long-term orientation, and humility make him a rare voice in the industry—and I came away from this conversation with a deeper appreciation for the philosophy behind Oaktree and Howard's success.I hope you enjoy this episode as much as I did.

This week, I had the distinct honor of speaking with Barry Ritholtz, one of the most original and influential voices in modern finance, and the co-founder, chairman, and CIO of Ritholtz Wealth Management. With a career that has spanned law, trading, strategy, and media, Barry’s unique path has given him a perspective that few in the industry can match.After beginning his professional life as a lawyer, Barry made the unconventional leap into finance—first as a trader, then as a strategist, and ultimately as the architect of one of the fastest-growing wealth management firms in the U.S. Alongside Josh Brown, he built Ritholtz Wealth Management on the foundation of transparency, evidence-based investing, and a deep respect for behavioral finance.Barry’s latest book, How Not to Invest, is a culmination of decades of experience studying markets, investor psychology, and systemic failures. Rather than offering yet another formula for beating the market, the book takes a different approach—highlighting the most common mistakes investors make and the thinking traps that lead to underperformance. Organized into three categories—bad ideas, bad numbers, and bad behavior—it’s a guide for avoiding the pitfalls that derail so many investment journeys.In our conversation, we covered Barry’s unconventional upbringing, the twists and turns of his career, and the mental models that have shaped his approach to investing and decision-making. We also dug into the principles behind his book, his thoughts on media consumption, and how young people can navigate their own paths in an increasingly noisy world.I hope you enjoy this episode as much as I did.

This week, I had the distinct honor of speaking with Felix Zulauf, a legendary figure in the world of macro investing and the founder of Zulauf Consulting. With over four decades of experience navigating the complexities of global markets, Felix has cemented his place as one of the most insightful and influential voices in finance.He began his career at Swiss Bank before joining UBS, where he rose to become Head of Global Asset Management. In 1990, he struck out on his own to launch Zulauf Asset Management, a fund that managed billions and delivered consistent, long-term outperformance. A longtime member of the Barron’s Roundtable, Felix is known for his sharp macro insights, contrarian thinking, and ability to anticipate major turning points in markets well before they occur.Beyond his impressive track record, what sets Felix apart is his global mindset and philosophical approach to investing. Over the years, he's cultivated a deep understanding of how politics, economics, and psychology intersect to drive market behavior. His insights have shaped how many professionals view the world.In this episode, we spoke about his early years growing up in Switzerland, his path from commercial banking to global strategist, and the motivations behind founding his own firm. We explored how he developed his mental framework and the evolution of his investing process.We also discussed the unique challenges and advantages of managing money independently versus within large institutions, the key geopolitical forces driving markets today, and how he continues to stay sharp after 40+ years in the business.Hope you enjoy this conversation as much as I did.Felix's YouTube: @zulaufconsultingFelix's LinkedIn: https://www.linkedin.com/company/27109806/admin/dashboard/

This week, I had the honor of speaking with Annie Lamont, one of the most respected investors in healthcare and fintech. As the Co-Founder and Managing Partner of Oak HC/FT, Annie has built a reputation for identifying and backing transformative companies that have reshaped industries. With over 30 years in venture capital, she has led investments in some of the most innovative companies in healthcare, financial services, and technology. Annie’s journey began with a strong foundation—after attending Stanford, she started her career at Hambrecht & Quist, where she gained exposure to high-growth technology and healthcare companies. She later joined Oak Investment Partners, where she spent decades honing her investment philosophy before co-founding Oak HC/FT, a firm dedicated to healthcare and fintech innovation. In this conversation, we dive into Annie’s early career, the lessons she learned navigating venture capital as a young investor, and the turning points that led her to build Oak HC/FT. She shares how she evaluates new industries, her approach to investing in cutting-edge fintech and healthcare startups, and how the increasing overlap between these sectors is shaping the future. We also discuss the principles that guide her investments, the biggest changes in venture capital over the last two decades, and the qualities that define great entrepreneurs. Finally, Annie offers invaluable advice on breaking into venture capital, navigating market cycles, and the lessons she would share with her younger self. This episode is packed with insights from one of the most influential investors in the industry—I hope you enjoy it!

This week, I had the privilege of sitting down with Tim Draper, a legendary venture capitalist, entrepreneur, and advocate for innovation and freedom. As the founder of Draper Fisher Jurvetson (DFJ), Draper Associates, and Draper University, Tim has played a pivotal role in shaping the startup ecosystem, backing companies like Tesla, SpaceX, Baidu, Coinbase, Robinhood, Skype, and Twitch.Coming from a long line of investors—his grandfather was the first venture capitalist in Silicon Valley—Tim has spent decades pushing boundaries in finance, technology, and education. He was an early advocate for Bitcoin, making headlines in 2014 when he purchased 29,656 BTC in a U.S. Marshals auction.Beyond investing, Tim has championed entrepreneurial education through Draper University, where he helps young founders develop real-world skills. He is also known for his bold ideas, including his controversial proposal to split California into multiple states, and his strong views on decentralization and the future of innovation.In our conversation, we dive into his upbringing, how he built his venture capital empire, and the big bets he believes will shape the future. Tim shares his insights on Bitcoin, AI, and investing in transformative technologies, as well as his advice for young entrepreneurs looking to break into the world of business and venture capital.This episode is packed with incredible stories, valuable lessons, and bold ideas—I hope you enjoy it!

This Wednesday, I had the privilege of speaking with Bob Prince, one of the most influential macro investors of our time. As Co-Chief Investment Officer at Bridgewater Associates, the world’s largest hedge fund, Bob has spent decades refining the firm’s systematic approach to global markets, risk management, and economic forecasting.Bob joined Bridgewater in the 1980s, working alongside Ray Dalio to develop the firm’s renowned All Weather strategy—a risk-balanced investment approach designed to perform across economic cycles. Over the years, he has been a key architect of Bridgewater’s macroeconomic insights and portfolio construction methods, helping institutions and governments navigate volatile markets. His ability to bridge economic theory with practical investing has made him one of the most respected voices in finance.In our longest episode yet, we dive deep into Bob’s journey—from his early career and formative experiences to the evolution of Bridgewater and the principles behind its success. He shares insights on leadership, decision-making, and the role of humility in investing, along with lessons learned from working with some of the greatest minds in finance.We also discuss what he’s watching in today’s macro environment, and his advice for the next generation. Thanks for tuning in and I hope you enjoy!