E210: How Startups Can Avoid Being Disrupted by OpenAI w/Eric Olson

How do you run a $1B endowment with a lean five-person team — while balancing liquidity, access, and high-conviction relationships? In this episode, I speak with Geeta Kapadia, CFA, Chief Investment Officer at Fordham University, about how she manages a concentrated portfolio of 30–40 manager relationships, the lessons she’s learned resetting the portfolio for liquidity, and why she favors passive equities with selective active bets in emerging markets and developed ex-US. We also dive into the shortcomings of interval funds, when to say yes to continuation vehicles, and how Fordham leverages the Gabelli alumni network and a student venture fund to extend sourcing and diligence reach.

How do you use the SBIC program to access long-dated, low-cost leverage—without blowing up risk? In this episode, I speak with Eric Rosiak, CEO & CIO of Amplify Community Investment Partners, about the mechanics of SBICs, the new accrual debenture license for venture and growth, what top LPs look for, and how policy changes could expand the opportunity set. We dig into eligibility tests, realistic fund sizes, diligence standards (they’re no joke), and why some large platforms now run SBIC sleeves alongside billion-dollar flagships.

What would the bond market look like if it were built today? In this episode, I speak with Dylan Parker, CEO & Co-Founder of Moment, the operating system for fixed income that unifies trading, portfolio construction, and risk/compliance—and automates the workflows wealth platforms run every day. We dig into how fixed income finally went electronic, why half of bond trading still happens by phone or chat, and how Moment can build customized ladders in seconds instead of hours. We also unpack the (surprisingly big) after-tax edge in munis, and Dylan’s lessons from building automated credit trading at Citadel before raising a $36M Series B led by Index Ventures this summer.

What does it take to build an AI-native search engine for science? In this episode, I spoke with Eric Olson, Co-founder & CEO of Consensus, the platform making peer-reviewed research accessible through AI. We covered the company’s journey from Series A to millions of users, the realities of competing with tech giants, and what truly creates defensibility for AI startups. Eric shared his perspective on the “AI talent wars,” building products at hyperspeed, and what truly creates a moat for AI applications. If you allocate to or invest in AI, you’ll want to hear Eric’s frameworks for product strategy, market sizing, and execution speed.

In this episode, I speak with Avy Stein, Founder & Chairman of Cresset—a multi-family office known for its private markets access and co-investing model. We cover Avy’s path from Kirkland & Ellis lawyer to private-equity dealmaker, the Willis-Stein spinout from Continental Bank, why multi-strategy platforms scaled so quickly, how co-invest rights really add alpha (and where adverse selection bites), and the rise of private credit in the middle and lower-middle market. We also get into culture building at scale, how Cresset thinks about alignment with GPs, and Avy’s best career advice from four decades in law, PE, operating, and wealth.

In this episode, I speak with Avy Stein, Founder & Chairman of Cresset—a multi-family office known for its private markets access and co-investing model. We cover Avy’s path from Kirkland & Ellis lawyer to private-equity dealmaker, the Willis-Stein spinout from Continental Bank, why multi-strategy platforms scaled so quickly, how co-invest rights really add alpha (and where adverse selection bites), and the rise of private credit in the middle and lower-middle market. We also get into culture building at scale, how Cresset thinks about alignment with GPs, and Avy’s best career advice from four decades in law, PE, operating, and wealth.

In this episode of How I Invest, I speak with Frank Mihail, CIO of the North Dakota Department of Trust Lands, which manages an $8B sovereign wealth endowment built to fund public schools. Frank shares how his three-person team runs a highly concentrated portfolio with 75% in alternatives, why they prefer evergreen fund structures for liquidity, and how they think about portable alpha, co-investments, and core-satellite strategies. We also discuss the trust’s broader mission: having already distributed $2B to North Dakota schools, with the long-term goal of covering the entire cost of public education.

What happens when AI lets five people build what used to take fifty? Can you scale to eight figures in revenue without ever touching a “Series A treadmill”? In this episode, I talk with Henry Shi, co-founder of Super.com and creator of the Lean AI Leaderboard, about seedstrapping (raising once, then reaching escape velocity), outcome-based pricing, and a new, non-dilutive way to finance lean, profitable startups. We also get into how Henry “vibe-coded” an AI VC tool over a weekend, why survival rates should improve in the lean-AI era, and what founder traits show up again and again among these ultra-efficient companies.

I had the chance to talk with Francis X. Suarez, the 43rd Mayor of Miami, about how his "open-for-business" leadership transformed the city into a global tech and finance hub. We unpack Miami’s “quantum opportunity,” the practical growing pains—housing, schools, transit—and the civic strategy behind international diplomacy and major sports deals. We also explore his run as President of the U.S. Conference of Mayors and his reflections on leadership, resilience, and embracing failure.

Alan Zafran, Founder & Managing Partner at IEQ Capital, joins to unpack how ultra-high-net-worth families and institutions think about risk, cash runways, GP selection, illiquidity, secondaries, LPAC governance, and portfolio strategy amid rising rates and sovereign debt.