Follow the Fortunes

Almost every insurance policy ever written pays out when something goes wrong. Game Point Capital writes policies that pay out when a team wins.

Will Hall and his brother Jack started it with no experience in insurance and nobody they knew in sport. Ten years on it's an MGA writing contractual bonus, coach buyout and NIL cover — and in 2024 it paid the University of Connecticut $2.77m after the men repeated as national champions and the women reached the Final Four. On how you price a bonus when there's no loss history to price it from, how you hedge a $54m coach buyout without handing the buyer the trigger, and why the cheapest place to lay off a sports risk right now might be a prediction market rather than a reinsurer.

Guest: Will Hall, co-founder and CEO of Game Point Capital.

Chapters

- 00:06 — Introduction

- 00:44 — Insurance that pays out when you win

- 01:37 — "You kick in when something goes right"

- 01:57 — A nine-billion-dollar market, and the liability nobody funds

- 02:32 — Two brothers, and a text message about Grigor Dimitrov

- 03:53 — "We were probably dumb"

- 04:19 — Lloyd's coverholder to MGA, and the friend from kindergarten

- 04:50 — Pricing a bonus with no loss triangle

- 05:40 — Why every quote has a shelf life

- 06:19 — UConn 2024: $5.6m of bonuses triggered, $2.77m paid

- 07:45 — $228m of buyout money in a single coaching carousel

- 09:12 — Hedging a buyout without creating a moral hazard

- 10:48 — Limits: "we haven't signed a hundred-million-dollar risk policy"

- 11:04 — NIL, the House settlement, and a $48.8m hard cap

- 12:08 — "You're gonna get sued again and again"

- 13:15 — Coaches are CEOs, paid the opposite way round

- 13:55 — Kalshi, and hedging at roughly half price

- 15:39 — Where the discount comes from, and where it doesn't

- 17:23 — Venue risk: the unresolved legal status of event contracts

- 18:19 — "You're rounding — it's like zero percent is hedged"

- 19:09 — The next Covid, and the wrong takeaway from the last one

- 20:27 — One per cent

Links

- Game Point Capital

- Kalshi / Game Point Capital partnership and pricing figures, February 2026

- "UConn insured basketball coach bonuses and saved nearly $3M," Stamford Advocate, April 2024

- 2025 coaching carousel buyout tracking, Yahoo Sports

- Protect College Sports Act of 2026, Senate Commerce section-by-section summary

Follow the Fortunes covers the risk behind the return in sport. Hosted by Phil Schmidt.

Views expressed by guests are their own. Nothing here is insurance, investment or legal advice.

RedBird Capital owns AC Milan, a Formula One team, and — through Fenway — Liverpool FC and the Boston Red Sox. It also owns a sports insurance business that doesn't cover any of this.

Bishop Street Underwriters has been buying into American amateur sport since 2023: nine operating companies now, $650m of premium last year, $800m targeted this year. Jim Arnold and George Wilson run its sports and entertainment division. On why you buy two competitors and use each to fix the other's weakness, what a founder-friendly sponsor does differently with a family business, and why flag football is now one of the more interesting underwriting problems in the market.

Guests: Jim Arnold, President of Sports & Entertainment (previously with Guy Carpenter and Markel) and George Wilson, SVP and Head of Distribution (previously with RT Specialty, AIG, and Great American) at Bishop Street Underwriters.

• 00:05 — Introduction
• 01:47 — "You must insure Messi and LeBron. Now tell us what you actually do."
• 03:01 — The size of the youth sports market
• 03:50 — Jim Arnold: law, claims, Markel, and why operations
• 05:13 — George Wilson: "I don't want to sell and I don't want to be involved in insurance"
• 07:06 — Bishop Street: nine operating companies in three years
• 08:22 — Why a panel of carriers rather than one balance sheet
• 09:13 — F.L. Dean, SportUnderwriters.com, SportsCanadaUnderwriters.com
• 10:17 — The mirror image: what each agency base asked for
• 12:15 — "We acquired literally John Dean"
• 12:50 — Why both brands survive
• 13:36 — What the RedBird and Weatherford connection delivers
• 15:26 — AI at the submission, not at the decision
• 16:27 — Emerging sports, and underwriting with no loss history
• 17:53 — The centralisation opportunity in governing bodies
• 18:32 — What private equity brings

• Bishop Street / White Mountains, $125m investment
• "Bishop Street plots next moves," Program Manager, June 2026
• RedBird / Weatherford launch Collegiate Athletic Solutions

Follow the Fortunes covers the risk behind the return in sport. Hosted by Phil Schmidt.

Views expressed by guests are their own. Nothing here is insurance, investment or legal advice.

The capital moving through sport, and risk it's exposed to. Host Phil Schmidt talks with the investors, owners, executives, and underwriters doing the deals — where the money comes from, what can go wrong, and who carries it.