Live Poker Match!: The Besties Vs. Phil Hellmuth, Alan Keating, and Jason Koon

Watch on YouTube ↗  |  November 29, 2025 at 16:01  |  1:00:12  |  All-In Podcast
Speakers
Jason Koon — Professional poker player
Jason Calacanis — Angel Investor / Founder, LAUNCH
Phil Hellmuth — Professional poker player

Summary

The All-In hosts Chamath Palihapitiya, Jason Calacanis and David Friedberg play a short turbo poker tournament at The Venetian in Las Vegas against professionals Phil Hellmuth, Alan Keating and Jason Koon. The episode is entertainment and table banter: hand commentary, jokes about Hellmuth's tracksuit and sponsorships, stories about the late Stu Ungar and a visit from Molly Bloom. The only substantive discussion is about how poker tournaments should be organised and how much the podcast has grown the game. No stocks, tickers, commodities, crypto or macro views are discussed, and Chamath wins the tournament.

  • A filmed five-minute-level turbo poker tournament hosted at The Venetian in Las Vegas.
  • Players are Chamath Palihapitiya, Jason Calacanis and David Friedberg against Phil Hellmuth, Alan Keating and Jason Koon; David Sacks is absent.
  • Jason Koon argues tournament operators mistreat mainstream players and should offer better venues, reasonable hours and an experience-based format.
  • Jason Calacanis floats an elite All-In branded tournament series and asks whether players would pay a premium for it.
  • Extended banter about Hellmuth's Adidas tracksuit, his sponsorships and an old crowdfunding prank by Calacanis.
  • Poker anecdotes about Stu Ungar, plus a cameo from Molly Bloom, who says she no longer runs games.
  • Jason Koon draws an analogy between taking a priced gamble on pot odds and decision-making in business.
  • No investment, market or company analysis appears in the episode; Hellmuth busts first and Chamath wins.
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