Follow the Fortunes

Phil Schmidt
  • 5.0 (1)
  • Business

Insurance executive and underwriter Phil Schmidt interviews the people who finance, build, and protect the business of sport. Guests include private equity and credit investors, team owners, league executives, underwriters, and the lawyers who structure the deals. Each episode covers the risk behind the return: where the capital comes from, what can go wrong, and who ends up carrying it.

Episodes

  1. 10h ago

    002 RedBird Capital’s Bishop Street Underwriters with Jim Arnold and George Wilson

    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. Chapters00:05 — Introduction01:47 — "You must insure Messi and LeBron. Now tell us what you actually do."03:01 — The size of the youth sports market03:50 — Jim Arnold: law, claims, Markel, and why operations05:13 — 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 years08:22 — Why a panel of carriers rather than one balance sheet09:13 — F.L. Dean, SportUnderwriters.com, SportsCanadaUnderwriters.com 10:17 — The mirror image: what each agency base asked for12:15 — "We acquired literally John Dean"12:50 — Why both brands survive13:36 — What the RedBird and Weatherford connection delivers15:26 — AI at the submission, not at the decision16:27 — Emerging sports, and underwriting with no loss history17:53 — The centralisation opportunity in governing bodies18:32 — What private equity brings LinksBishop 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.

  2. Season 1, Episode 1 Trailer

    Follow the Fortunes Trailer

    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.

Trailer

About

Insurance executive and underwriter Phil Schmidt interviews the people who finance, build, and protect the business of sport. Guests include private equity and credit investors, team owners, league executives, underwriters, and the lawyers who structure the deals. Each episode covers the risk behind the return: where the capital comes from, what can go wrong, and who ends up carrying it.

Information

  • Creator
    Phil Schmidt
  • Years Active
    2026
  • Episodes
    2
  • Rating
    Clean
  • Copyright
    © 2026 Phil Schmidt