Show Notes
Bill Perkins (@bp22) is a successful hedge fund manager and entrepreneur. Very few podcasts that I've done have changed my thinking so distinctly. Bill, who started on Wall Street at $16k a year and then found extreme success as an energy trader in Texas, noticed that many of his contemporaries were bad at enjoying life (and, worse, they were unhealthy). Seeking to avoid the same mistakes, he sought to throw away all assumptions and examine happiness as an optimization problem involving the inputs of time, energy, money, and health. The result was his book, Die with Zero. Many of the concepts from the book are covered in the first hour of this podcast. An example of his idiosyncratic advice: he argues that most people should use life annuities as a core retirement vehicle. Why? It eliminates anxiety about outliving your money, it allows you to avoid the worst retirement mistakes (going broke due to risk), and it's a bet on yourself (you get more money the longer you live). I found this advice compelling and I'm writing a blog post on it next week. On the health front, he recently went from 22% to 8% body fat in six months. We discuss his approach in the first twenty minutes.
More from The AI Metagame
In this episode of The AI Metagame, host Brandon Adams sits down with famed forecaster Nate Silver (@NateSilver538) and digital media builder Raf Michalowski to talk about AI slop and where the content industry is headed. At its peak, Raf's pipeline was uploading around 60,000 videos a day to YouTube — roughly 3% of all daily uploads on the platform. He walks through the economics, how platforms end up incentivizing this kind of volume, and what happens when they eventually crack down. Nate works in the part of media where AI doesn't really help — forecasting, accountability, and predictions that can be graded. The conversation maps where human judgment still has a moat, and whether quality can survive when the marginal cost of content is zero.
Episode 4 | The 600,000-Claim Brain: How Lev Milman Uses AI to Map Reality How do you stay ahead of the curve when the "curve" is moving at the speed of light? In this episode, we sit down with Lev Milman, a former U20 US Chess Champion and macro trader, to explore his radical, AI-driven approach to information processing and belief updating.
Episode 3 | The edge belongs to whoever's willing to break things first. Most people are waiting for the safe path. Haralabos Voulgaris handed an AI agent his brokerage API, watched it place $20,000 in unauthorized trades, and responded by building a better confirmation tree — not by shutting it down. We explore what happens when a professional gambler's risk appetite meets the AI frontier — deploying autonomous bots on Polymarket and Schwab, hardening servers against injection attacks, and building a VIX strategy around the conviction that the world is more fragile than consensus believes. Haralabos makes the case that the real AI competition isn't about who has the best model — it's about who owns the physical layer. That China's robotics lead may matter more than America's research lead. And that the consumer surplus from AI doesn't mean much if no one's built the institutions to distribute it.
Episode 2 | Controller | Over-Optimization: Why efficiency kills resilience. A perfectly optimized system is just a fragile one waiting to break. Our guest explains why they stopped optimizing for margins and started optimizing for survival, and what that means when AI moves faster than your org can adapt. We've spent decades chasing efficiency. Removing friction, maximizing output, trimming every edge. But what happens when the system has zero slack left and the ground shifts overnight? This episode unpacks the Controller archetype: the leader who builds tight, optimized machines that work beautifully until they don't. We challenge the Explainer instinct to rationalize away uncertainty, and explore why the smartest move right now might be building in inefficiency on purpose.
Episode 1: Builder | Controller | Premature Abstraction "I built for scale before I understood the problem" In a world where tools allow us to scale instantly, the temptation to build big is overwhelming. But what happens when you scale the wrong thing? The AI Metagame is a twelve-episode series that looks at four archetypes in AI — Builder, Explainer, Interpreter, Narrator — to map where AI creates leverage and where it creates traps. For every great advantage of AI, there are disadvantages lurking. Each episode explores both sides. In our premiere episode, we explore the Builder's most dangerous trap: Premature Abstraction. Modern AI leverage is a double-edged sword — it amplifies errors faster than ever before. True control now requires staying small enough to pivot until the problem itself is fully understood.