E425: What 30,000 Founders Taught Me About AI, Judgment & Top Founders

What if passive investing is actually one of the biggest active forces shaping markets today? In this episode, I sit down with Michael Green, Founder and CIO at Tier1 Alpha Asset Management. Michael challenges the conventional view that stock prices primarily reflect fundamentals, arguing that the transaction itself moves prices and that the rise of passive investing has fundamentally changed who trades, why they trade, and how markets respond to capital flows.

Peter Hecht, Managing Director at AQR Capital Management, explains why diversification has to be measured by underlying risk rather than the number of investments you own. At AQR, diversification is a core principle: thousands of relatively small, uncorrelated investment decisions can collectively create an attractive return for a given level of risk.

What happens when a private equity firm refuses to chase every new opportunity and spends 30 years getting better at one thing? David sits down with Michael Fisch, co-founder and CEO of American Securities, to unpack how the firm grew from a $71.4 million first fund to $23 billion in AUM without abandoning the investment discipline that got it there. Michael explains how private equity evolved from a sub-$1 billion institutional market into a multi-trillion-dollar industry, why American Securities resisted the temptation to expand into every adjacent asset class, and why seeing more deals matters almost as much as knowing which ones to reject.

David sits down with Byron Ling of Twelve Below to unpack the judgment required to invest at the earliest stages of technology. After roughly 30,000 founder meetings over the past decade, Byron believes the strongest signals rarely appear on a résumé. He looks for an almost biological drive to win, second-level thinking, exceptional learning velocity, clear communication, authenticity, and a sense of urgency that makes a founder difficult to compete against.

What can 32 years as a university CIO teach you about identifying exceptional investors before everyone else does? David sits down with Scott Malpass, Co-Founder and Managing Partner of Grafton Street Partners and former Chief Investment Officer of the University of Notre Dame, to discuss the patterns he learned from evaluating thousands of investment firms and building decades-long relationships with some of the world’s leading managers.

David sits down with Bryon Hargis, co-founder of Castelion, to unpack why rebuilding America’s defense manufacturing capacity has become a national security imperative. Bryon explains why decades of consolidation and outsourcing weakened the defense industrial base, why America could struggle against an adversary with significantly greater manufacturing capacity, and why Castelion is betting that deterrence ultimately requires weapons that can be produced affordably by the thousands.

Why do so many GPs misunderstand what institutional LPs actually care about? David sits down with John-Austin Saviano, an Backing & Building Challenger Investment Firms and Former Endowment CIO, argues that one of the biggest mistakes GPs make is overemphasizing track record. Great LPs care less about the headline returns than how those returns were generated. They want to understand the investment process, whether it is repeatable, and whether the people and market conditions that produced past performance still exist today.

What if the biggest edge in private equity isn’t finding better deals, but designing better incentives? In this episode, I sit down with Jack Purcell, Managing Partner at Ridgemont Equity Partners, to unpack how alignment helped turn a Bank of America spinout with fewer than 15 people into a private equity firm managing more than $11 billion. Jack explains why Ridgemont invests significant GP capital alongside its LPs, why more than two-thirds of the team participates economically in its funds, and how a nine-person unanimous investment committee uses a proprietary 40-point scorecard to evaluate deals.

What if the biggest AI investment opportunity isn’t AI companies, but the infrastructure required to make AI possible? David sits down with Stuart Waugh, Managing Partner of Northleaf Capital Partners, to explore why the AI boom is creating massive demand for power, data centers, communications networks, and other essential infrastructure. Stuart explains why Northleaf estimates roughly $40 trillion of infrastructure investment will be needed across its addressable markets over the next decade, and why governments increasingly need private capital to help fund it.

Venture capital was designed around a relatively simple model: invest in a startup, help it grow, and eventually exit through an acquisition or IPO. David sits down with Benjamin Black Powerlaw Corp. (Nasdaq: PWRL), Akkadian Ventures, Ben invests in growth-stage technology companies while providing alternative liquidity to founders, employees, angel investors, and venture funds. In this episode, Ben and David unpack the evolution of the venture secondary market, why great companies staying private longer creates an entirely different opportunity set, how sophisticated investors price illiquid private-company shares, and why liquidity itself is becoming a critical piece of venture capital infrastructure. The result is a different way to think about private markets: the investment opportunity doesn't end after the primary financing round.