How Sam Greenwood Built a 20-Year Career in High Stakes Poker

In episode 68 of the podcast, we sit down with high-stakes tournament pro Sam Greenwood, creator of the popular Substack "Punt of the Day" where he publicly dissects his biggest mistakes. In this deep 3-hour conversation, we explore the evolution of poker strategy, the mental game of high-stakes competition, and the challenge of building a sustainable life around professional poker. We chat about why documenting mistakes is more valuable than celebrating wins, how the solver revolution transformed tournament strategy and separated natural skillsets, the reality of risk management and the costly lessons from COVID-era online poker, what separates elite players at Triton-level competition beyond pure theory, managing performance under pressure across grueling live poker stops, and redefining success from "best in the world" to sustainable excellence with family and balance.