Fall Reading List 2025

Fall has been a season of decision-making and risk for me, both in what I’ve been reading and thinking about. Following up on my summer reading list, here’s what’s been on rotation this fall. Unlike the summer’s eclectic mix of fish history and F1 engineering, this season had an unintentional theme: how smart people think about uncertainty, probability, and building things that last.

Thinking in Bets

by Annie Duke

Professional poker player turned decision strategist Annie Duke makes a compelling case that we should think about decisions the way poker players think about hands. Life isn’t chess where perfect information leads to perfect outcomes. It’s poker, where you make the best decision you can with incomplete information and then accept that sometimes you’ll still lose.

The core insight is brutally simple: separate decision quality from outcome quality. You can make a great decision and still get a bad result. You can make a terrible decision and get lucky. Duke argues that once we accept this, we can start making better decisions by focusing on the process rather than being results-oriented.

What I found most useful was her framework for dealing with uncertainty. Instead of “I’m right” or “I’m wrong,” think in terms of confidence levels. “I’m 70% sure this is the right call” is a more honest and useful way to think about most decisions we face.

Born to be Wired

by John Malone

The autobiography of the cable industry’s most successful dealmaker and the man who basically invented modern cable television. Malone ran TCI (Tele-Communications Inc.) and turned it into the largest cable company in America through an endless series of acquisitions, financial engineering, and what can only be described as aggressive tax optimization.

The book is part memoir, part business strategy manual for how to build an empire through leverage and deal-making. Malone’s approach to capital allocation was unconventional to say the least. While other CEOs focused on earnings, he focused on cash flow and used every financial tool available to defer taxes and reinvest in growth.

What struck me most was how Malone thought about risk differently than most executives. He was comfortable with enormous amounts of debt because he understood the asset values and cash flows at a level that gave him confidence when others saw only danger. Whether you agree with his methods or not, watching someone operate at that level of financial sophistication is fascinating.

I grew up on cable industry war stories so it was particularly fun to hear familiar tales from a new-to-me perspective.

The Missing Billionaires

by Victor Haghani and James White

A former bond trader and a finance professor team up to answer a simple question: why aren’t there more billionaires? Not in the sense of “why is wealth inequality so bad” but rather “why do so many smart, successful investors fail to compound their wealth the way they theoretically should?”

The answer, they argue, comes down to a mathematical principle called the Kelly Criterion and our psychological inability to follow it. The Kelly Criterion tells you the optimal amount to bet when you have an edge, balancing growth with the risk of ruin. Most people either bet too much (and eventually blow up) or too little (and never reach their potential).

The book walks through numerous case studies of brilliant investors who made fatal mistakes by over-betting their edge. Long-Term Capital Management gets a detailed treatment, as does the 2008 financial crisis. The authors argue that following Kelly-optimal betting strategies requires an almost inhuman level of discipline because it often means betting less than your gut tells you to when you’re confident you’re right.

This one pairs beautifully with “Thinking in Bets.” Duke teaches you how to think about decisions under uncertainty. Haghani and White teach you how much to bet once you’ve made your decision.

If you read this blog often you know I’ve got a special interest in bankroll allocation strategies so this one was a joy for me.

Wrap Up

Three very different books that ended up telling a coherent story about decision-making, risk management, and the gap between what we know we should do and what we actually do. If you’re interested in any of these topics, all three are worth your time.