The AI Metagame

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.

Alex Hutchinson (@sweatscience) is my favorite fitness journalist. This podcast was an absolute pleasure. We had the opportunity to explore his outstanding new book, The Explorer's Gene. We also discuss, in detail, his 2018 NY Times bestseller Endure: Mind, Body, and the Curiously Elastic Limits of Human Performance. I rate this book among my top ten favorite works of non-fiction.

Jared Dillian (@dailydirtnap) publishes daily market commentary (The Daily Dirtnap, www.jareddillian.com). He hosts a twice weekly podcast called Be Smart. He has a popular Substack (https://substack.com/profile/450570-jared-dillian), and he's the author of Street Freak and All the Evil of This World. His latest book, Those Bastards: 69 Essays on Life, Creativity, and Meaning, was published in late March.

Scott Fawcett (@scottfawcett) is the creator of the DECADE golf system and he has coached Will Zalatoris, Stewart Cink, Keith Mitchell, and many others. In the first hour, we do a deep dive into golf analytics. He describes his career in professional golf, his early discovery of the PGA Tour's Shotlink Data and Mark Broadie's Strokes Gained Metric, his development of the DECADE system, and his experience coaching PGA players. At the one hour and three minute mark, we are joined by David Epstein (@DavidEpstein), author of the bestselling books Range and The Sports Gene. The three of us discuss talent in sports, similarities between golf and poker, "tilt" in golf and poker, the history of game theory in poker, and the emotional make-up of poker players.

Daniel Negreanu (@realkidpoker) is fresh off a $3.3 million win in the Super High Roller Bowl. Perhaps the most famous poker player on the planet, he is ranked #3 on the all-time money list. We start with a discussion of the new era in poker ("the Solver era") and some recent adjustments he's made in his game. We move on to some deep history - his move from Canada to Vegas; his early years with Phil Ivey, Allen Cunningham, and John Juanda; some very big gambling in the early years; and the "pump-up years" in the poker economy after WSOP 2003, Rounders, and the Andy Beal games. He tells some great golf-gambling stories from the late 2000s, and he explains how his competitive goals shifted from cash games to tournaments. Daniel goes through his WSOP routine each year, which includes a prep period, followed by extreme intensity during the WSOP (where he often gains ten to fifteen pounds), and then a long rest period.

David Benefield (@DWBenefield) is a poker legend with an incredible story. He started poker at age 16 after watching the movie Rounders. He dominated the biggest games online from ages 21-26. By his own estimate, he worked 100 hours a week during those years. In 2010, he went back to school at St John's University and then Columbia University (transfer after sophomore year). After his first semester at Columbia, he took a year and a half off to play the biggest poker game in the world in Macau. He also made the Main Event final table during this sabbatical. He ultimately finished his degree at Columbia, and then became increasingly interested in the cryptocurrency sphere. Today he employs eight people in a cryptocurrency-focused fund, based out of Dallas.

Brad Delong is an economic historian at UC-Berkeley. A former Deputy Assistant Secretary of the Treasury in the Clinton Administration, he frequently writes about policy issues on Twitter as @delong, where he has over 80,000 followers, and on his popular blog Grasping Reality (https://braddelong.substack.com). He is the author of a new book, Slouching Towards Utopia, that has been widely lauded as the most important book in economic history in many years.

Shaun Deeb is, far and away, the most successful player at the World Series of Poker over the past decade (when evaluated based on WSOP leaderboard points). We discuss, among other things: his daily routine, WSOP fantasy poker, his view on tournament edges, his rise in poker (playing at Turning Stone in NY as an 18yr old) to his near fall (playing in Mexico post Black Friday), mixing family and poker, and his philosophies about learning in poker.

Eric Olson (@IPlayedD1) is the co-founder of Consensus, a leading start-up in natural language processing. I was interested in learning about the specific topic of AI/machine learning in the social sciences, and Eric was a brilliant guide in this area. Eric is a former football player at Northwestern who graduated with a master's in predictive analytics. With co-founder Christian Salem, he build Consensus, a search engine that uses AI to extract findings from scientific research.

Patrik Antonius is one of the biggest winners in the history of poker. Even seasoned poker fans will be shocked by some of stories in this pod. We cover all aspects of his approach; we deep-dive into health, the mental game of poker, fun off the felt (especially crazy prop bets), and key aspects of Pat's personal poker history.

Edward Chancellor is a British financial historian, financial journalist, and former investment strategist. He wrote the bestselling book Devil Take the Hindmost: A History of Financial Speculation in 1999 and Crunch-Time for Credit in 2005. He has just published The Price of Time: The Real Story of Interest, which I rate as the best book I've read this year. Fortune has called Chancellor "one of the greatest financial historians alive, and the Financial Analysts Journal called him "one of the greatest financial writers of our era." Our chat mostly covers The Price of Time. Jim Grant says this work is "A masterpiece of history, analysis--and property understated outrage."

Matt Kalish (@mattkalish) is the Co-Founder and President of Draftkings. A computer science major from Columbia, Matt is a passionate gamer who also has one of the largest personal collections of NFTs in the world. In this podcast, we take a deep-dive into the new Reignmakers project at Draftkings, where players assemble fantasy teams using player NFTs that they have purchased and compete for tens of millions in prizes.

Peter Jennings (@CSURAM88) is one of the most successful daily fantasy sports players of all times. Notably, he won the first ever six-figure DFS prize, as well as the first ever $1 million Draftkings live final. He is a popular podcaster, and an extremely successful sports entrepreneur and investor. He co-founded Fantasy Labs (sold to Action Network), as well as Lucky Trader HQ (an analytics company focused on NFTs), and he has invested in many top companies in the gaming, analytics, and crytpo spaces.

Hugh Hendry was the founder and Chief Investment Officer of the macro hedge fund Eclectica Asset Management. After strong returns before and during the Great Financial Crisis, he became a popular figure in the financial media. He retired in 2017 to run a luxury hotel in St Barts, but has lately been increasingly active in financial media, tweeting as @hendry_hugh (60k followers) and podcasting (The Acid Capitalist).

Ben Hunt (@epsilontheory) earned a PhD in Government from Harvard in 1991. He was a research academic for a decade before founding two technology companies. He then worked in investment management for a decade, before starting a content community at www.epsilontheory.com in 2013. Epsilon Theory quickly found a large audience of over 100,000 email subscribers. For the past several years, Epsilon Theory has been a vibrant, paywalled content community. We discuss three primary topics in this podcast. In the first 50 minutes, we discuss Ben's recent long piece on Fed policy, "NGMI". Ben makes it clear that his stance on risk assets has mostly changed from one of bullishness to one of bearishness, based on his view that there has been a sustained change in the Fed narrative. We then move on to discuss Ben's long piece on cryptocurrency, "The MacGuffin, Part 1". We end with fifteen minutes on the current state of the paid content space (Ben surprised me by being bearish on Substack and the micropayments model).

Kyle Boddy (@drivelinebases) is the founder of Driveline Baseball, the best data-driven baseball development program in the world. I recently taught a course in sports analytics at the University of Miami, and Kyle was gracious enough to provide materials to Nikolai Yakovenko for a guest lecture on "What Makes Good Pitching?" The material is fascinating and surprising for anyone with the slightest interest in baseball. Much of that material is covered in the first half of the podcast. Other podcast topics include: Kyle's transition from poker to sports analytics, the early coaching experience that led to the development of Driveline, the new Driveline metric Stuff+ (which quantifies pitch effectiveness), his recent experience with the Cincinnati Reds, and his future ambitions.

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.

Doomberg (@DoombergT) has become a star of Substack and financial Twitter. Doomberg's in-depth, smoothly written pieces have quickly found a regular audience of nearly 100k per post. We spend the first third of this podcast chatting about his most popular post ("Dollars Ex Machina", on crypto). The second third of the podcast explores his general philosophy on investing, and the last third covers his recent pieces on commodity shortages, including the most recent piece, "Farmers on the Brink" (about likely upcoming food shortages).

Jared Dillian (@dailydirtnap) publishes daily market commentary (The Daily Dirtnap, www.jareddillian.com). He hosts a twice weekly podcast called Be Smart, and he's the author of Street Freak and All the Evil of This World.