Masters of Uncertainty: What do poker and hedge fund management have in common?

Phil Hellmuth Jr., the winningest poker player of all time (17 World Series bracelets), sits down with Itay Vinik (CIO, Equi) and Tory Reiss (CEO, Equi) to explore the parallels between reading people at the poker table and reading markets as an investor.

Phil reveals his lowest moment down to his last $16,000 after losing $236,000 in a single session and how it transformed him into “the most conservative poker player.” He also shares his biggest miss: passing on 5% of Polymarket for $30,000, now worth $700 million.

Meanwhile, Itay breaks down the trade of his career: betting against crowded short-VIX ETFs in 2017, turning a costless options trade into a 500x return when Volmageddon hit on February 5, 2018.

Plus: Why Jeff Yas (Susquehanna) played 60 hours of poker a week before becoming a billionaire, how to fire a winning manager, and why “diversification is the only true free lunch.”

HIGHLIGHTS:
0:00 — Intro: “Masters of Uncertainty”
0:54 — “Phil told us: I’m the ultimate wild card”
1:51 — Phil: “You threatened to take my equity away”
2:39 — Phil sends Equi $2M+ to manage
4:37 — Phil’s lowest moment: Down to $16K, almost went broke
6:06 — “The universe gave me one time”
7:12 — FedExed the check home immediately — “Risk off”
7:37 — “Money management is more important than being great at poker”
8:08 — The 70th percentile poker player who always pays bills
10:49 — Phil’s biggest miss: 5% of Polymarket for $30K = $700M today
12:02 — Prize Picks exit: $4 billion
12:27 — “It’s all about the person” — How Phil picks founders
14:07 — Phil’s founder process: 3 meetings, 3 weeks
15:02 — Itay’s transition: From trading markets to picking managers
16:20 — “How they express asymmetry is more important than strategy”
16:32 — Firing a winning manager: “He’s crushing, but taking excessive risk”
17:09 — “You made a lot of money for us, but you’re taking too many chances”
17:37 — “Sometimes you need to sell your winners”
18:01 — Dan Fleischman, Jeff Assaf, Jacob Diepenbrock, David Maisel shoutouts
19:28 — Jeff Yas: Professional poker player → Billionaire
20:05 — “Poker is limited. It’s a zero-sum game.”
21:06 — Trifecta: Money management + Game theory + Understanding people
22:04 — “My advantage was my network”
23:20 — Itay’s best trade: Betting against short-VIX ETFs
25:04 — “That 10-cent option turned into $50” — Volmageddon (Feb 5, 2018)
25:42 — “Infinitely X the money because it was costless”
26:17 — Itay owns 331 doors in Texas
26:49 — Principles: Bet on people, pot management, convex upside, diversify
27:28 — “Diversification is the only true free lunch”
27:50 — “This disruption is creating a ton of opportunity”

SPEAKERS:

  • Phil Hellmuth Jr. — The Winningest Poker Player of All Time (17 WSOP Bracelets)
  • Itay Vinik — CIO, Equi
  • Tory Reiss — CEO, Equi (Moderator)

Recorded live at Global Alts Miami 2026