Generating Alpha Podcast

This week, I had the pleasure of sitting down with Anthony Scaramucci, a true embodiment of resilience, reinvention, and grit. Best known as the founder and managing partner of SkyBridge Capital, Anthony’s journey has taken him from humble beginnings in Long Island to the highest levels of Wall Street and a brief but unforgettable turn in Washington, D.C.

Anthony’s story is one of constant evolution. After starting his career at Goldman Sachs, he took the leap to build his own firm, navigating market cycles, public scrutiny, and personal setbacks along the way. What stands out most about Anthony is his unwavering belief in the power of authenticity. Whether in finance, politics, or media, he’s never been afraid to speak his mind or challenge the status quo—and he’s built a business culture at SkyBridge that reflects those same values.

Our conversation touched on his upbringing, his biggest wins and losses, and the philosophy that’s kept him grounded through it all. We talked about what it really means to be an outsider, how to cultivate courage and curiosity throughout your life, and why staying true to yourself is the ultimate competitive edge.

Anthony’s energy, self-awareness, and candor make him a rare figure in any industry—and his ability to keep pushing forward, no matter the obstacles, is both inspiring and instructive.

I hope you enjoy this episode as much as I did.

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: @zulaufconsulting

Felix's LinkedIn: https://www.linkedin.com/company/27109806/admin/dashboard/

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!

Today, I had the honor of sitting down with Alan Schwartz, a distinguished leader in finance and investment banking. Best known for his tenure as the CEO of Bear Stearns, Alan has had a remarkable career at the highest levels of Wall Street, navigating some of the most challenging moments in financial history.

Alan began his career after earning his degree from Duke University, joining First Boston before moving to Bear Stearns in 1976. Over the next three decades, he rose through the ranks, eventually becoming CEO in 2007, just months before the 2008 financial crisis. As the firm faced unprecedented turmoil, Alan played a critical role in its final days, ultimately overseeing its sale to JPMorgan Chase.

Following his time at Bear Stearns, Alan transitioned to Guggenheim Partners, where he currently serves as Executive Chairman, helping to build one of the most respected financial services firms in the world.

In this episode, we discuss Alan’s journey, his perspectives on leadership, connecting the dots, and the lessons he’s learned from navigating crises. He also shares invaluable insights on the evolution of investment banking, and advice for those looking to build lasting careers in finance.

Today, we had the privilege of speaking with Michael Mauboussin, one of the most respected minds in value investing. With a career spanning decades in finance, Michael has been at the forefront of applying behavioral science, probability, and market efficiency to investment strategy.

Michael began his career after earning his degree from Georgetown University, later becoming a longtime Chief Investment Strategist at Legg Mason Capital Management. He has since held senior roles at Credit Suisse and Morgan Stanley, where he has shaped investment thinking with his deep research into expected value, skill vs. luck, and the psychology of markets.

Beyond his professional work, Michael is a prolific author, having written several essential books, including The Success Equation and More Than You Know, which explore how to make better decisions in uncertain environments. He also serves as an adjunct professor at Columbia Business School, where he teaches and mentors the next generation of investors.

In this episode, we dive into Michael’s journey, his perspectives, and his advice for investors at every level. Whether you’re a professional or just starting out, this conversation is packed with insights that will change how you approach investing. We hope you enjoy!