E303: What Blackjack Taught Me About Investing w/Ari Levy

Why has liquidity across private markets broken down and what does it mean for institutional portfolios? David Weisburd speaks with Alex Ambroz about collapsing distributions, the rise of continuation vehicles and secondaries, and why many allocators are facing a structural mismatch between models and reality. They explore whether “private is the new public,” how incentives shape GP behavior, and what LPs must change to adapt to a new normal of prolonged illiquidity.

What happens when AI stops assisting humans and starts replacing decision-making itself? David Weisburd speaks with Camilo Acosta about the rise of agentic AI, why incumbents still leave massive openings for startups, and how AI will reshape labor, venture capital, and entire asset classes. Camilo explains how investing ahead of regulation, betting on founders over ideas, and building for a fully agentic future define the next era of venture.

What happens when capital markets move from batch processing to real time? David Weisburd sits down with Yuval Rooz to discuss his path from Citadel and DRW to founding Digital Asset and building the Canton Network. Yuval explains why blockchain is less about crypto speculation and more about upgrading the infrastructure of global capital markets—unlocking 24/7 settlement, asset utility, and new forms of liquidity across public and private markets.

How do you compete with Sequoia and Andreessen while running a $650M fund and still expect to outperform? In this episode, I sit down with Glenn Solomon, Managing Partner at Notable Capital, to break down how focused early-stage investing can outperform mega-platform venture funds. Glenn explains why 70%+ of venture dollars now go into mega-rounds over $100M, why Notable stays disciplined at seed and Series A, and how delivering “unscalable” founder support creates real edge. We also go deep on Anthropic, the so-called “software apocalypse,” AGI narratives, and where durable alpha exists in an AI-dominated world.

Why does execution velocity matter more than pedigree at the earliest stages of company building? David Weisburd speaks with Eric Bahn about the concept of “hustle,” why early judgments about founders tend to persist, and how throughput, learning speed, and grit outperform traditional signals in pre-seed investing. Eric explains Hustle Fund’s wide-net strategy, its community-driven platform model, and how changing startup timelines are reshaping venture economics.

Why are vertical AI applications emerging as some of the most defensible opportunities in technology today? David Weisburd speaks with Nick Beim about why context—not raw intelligence—is becoming the key driver of AI performance, and how vertical software is reshaping wealth management, legal services, and defense. Nick shares how legacy infrastructure, industry economics, and human-centered workflows create enduring opportunities for AI-driven transformation.

How should investors think about risk when traditional measures like volatility fall short? David Weisburd speaks with Jeff Blazek about portfolio construction across institutions and family offices, why drawdown matters more than standard deviation, and how allocators should balance public and private markets. Jeff shares first-principles thinking on liquidity, behavioral risk, and building resilient portfolios across market cycles.

How should investors think about risk when traditional measures like volatility fall short? David Weisburd speaks with Jeff Blazek about portfolio construction across institutions and family offices, why drawdown matters more than standard deviation, and how allocators should balance public and private markets. Jeff shares first-principles thinking on liquidity, behavioral risk, and building resilient portfolios across market cycles.

Where does real edge still exist in public markets and how do you size risk when certainty doesn’t exist? In this episode, I talk with Ari Levy, Founder and CIO of Lakeview Investment Group, about applying probability theory, arbitrage, and disciplined position sizing to public equity investing. Ari explains how early lessons from card counting and game theory shaped his approach to risk, why small-cap markets remain structurally inefficient, and how activism, arbitrage, and management access can create asymmetric outcomes—without blowing up the portfolio.

What actually creates sustainable alpha in endowment portfolios and why do most investors mistake activity for edge? In this episode, I talk with Larry Kochard about building investment programs that endure across cycles. Drawing on his experience as CIO at Georgetown and the University of Virginia and later at Makena Capital, Larry explains why preparation before crises matters more than heroics during them, how governance and stakeholder buy-in reduce behavioral mistakes, and where real alpha still exists in increasingly efficient markets. We unpack liquidity discipline, rebalancing under stress, manager sizing, and why “people are upstream of everything.”