E244: Structural Alpha vs. Storytelling w/Alan McKnight
What separates elite CIOs from everyone else?
In this solo-style deep-dive conversation, I sit down with Alan McKnight, Executive Vice President and Chief Investment Officer at Regions Asset Management, to unpack how one of the industry's most respected allocators makes decisions across public and private markets. Alan oversees investment strategy, risk management, and portfolio construction across the firm's full platform — and brings decades of experience from leadership roles at Truist, SunTrust, Equitable, and Morgan Stanley.
We get into the realities of managing capital across different client types, how CIOs should think about illiquidity versus opportunity, where structural alpha truly comes from, and the process-driven framework Alan uses to separate skill from luck. If you're an allocator, founder, CIO, or LP, this episode lays out one of the cleanest mental models you'll hear on building durable long-term returns.
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57:52
E243: The Gift Hidden Inside The Biggest Crisis
What happens when you’re forced to face your biggest fear?
In this solo episode, David Weisburd shares a deeply personal reflection on how moments of crisis can become the crucible that forges strength, resilience, and clarity. Drawing inspiration from Lloyd Blankfein’s reflections on the 2008 financial crisis, David explores why confronting your greatest fears—rather than avoiding them—can transform you into a more powerful, anti-fragile version of yourself.
From Joe Rogan’s public reckoning to founders who rebuilt stronger after near-death moments, this episode unpacks the paradox of hardship: how the moments that almost break you often become the foundation for your greatest breakthroughs.
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E242: How an 18-Year-Old Harvard Dropout Raised $47M
Can a 23-year-old Harvard dropout build the next billion-dollar company?
In this episode, I talk with Steven Wang, founder and CEO of dub, a U.S. copy-trading platform that lets you automatically mirror the portfolios of real investors and traders. We get into why he thinks most retail investors won’t get good at stock picking, why the future is about picking people, not tickers, and how dub is trying to turn social-media-driven, mimetic trading into better financial outcomes. We also cover the retail trading boom, meme stocks, the “retail army,” what dub’s top creators actually do to generate alpha, and how a creator-led marketplace for strategies could reshape how the next generation builds wealth.
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41:58
E241: How Spirits Became a $1 Trillion Alternative Asset Class
How do you turn whiskey barrels into an institutional asset class?
In this episode, I sit down with Giuseppe Infusino, Chief Investment Officer and Managing Partner at InvestBev Group, to explore how a real asset like aged whiskey is quietly becoming one of the most uncorrelated and profitable investments in alternative markets. From his early years at RVK advising multi-billion-dollar allocators to managing institutional portfolios in a niche category few understand, Giuseppe shares how InvestBev has built an entirely new asset class from the ground up.
We discuss the economics of whiskey aging, how barrel pricing creates asymmetric returns, and why alcohol performs differently across economic cycles. This conversation breaks down incentives, alpha generation, and how to educate LPs on emerging strategies long before they go mainstream.
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E240: The Edge: Risk, Discipline, and Judgment in Venture
What separates great investors from generational ones—and how do you actually find the next Elon Musk?
In this episode, I sit down with Mike Annunziata, Founder & Managing Partner of Also Capital, a solo GP fund backing the world’s most ambitious hard tech founders. Before launching Also Capital, Mike spent years at the Cornell University Endowment, helping allocate over $1 billion across venture and private equity managers—giving him a front-row seat to what “world-class” really looks like.
We talk about how LPs identify the next top-decile fund managers, why the best founders are like amateur pilots, and how to find the tiny behavioral tells that separate the merely ambitious from the truly elite. From identifying credibility under pressure to understanding the physics of hard tech investing, Mike shares a rare, insider’s look at the art of backing outliers.
How I Invest with David Weisburd is a podcast that interviews the world's leading institutional investors. Previous guests include The Ford Foundation, Northwestern University Endowment, CalPERS, Stepstone, and other top limited partners.
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