Adam Grossman sits down with George Barrios — former Chief Financial & Strategy Officer and Co-President of WWE, co-founder of ISOS Capital, board member and investor in Global Sport Group, and author of the new book Sometimes Wrong, But Never in Doubt.

George helped take WWE from a company worth less than a billion dollars to a valuation north of nine billion, architected its merger with UFC, and — alongside his longtime partner Michelle Wilson — wrote a playbook that reframed how the sports industry thinks about intellectual property, content, and the fight for a fan's time. In this wide-ranging conversation, he unpacks the WWE Network gamble, the "swamp of despair" that forged an 18-year partnership, getting fired in 2020, the triumphant return to negotiate the UFC deal, and why he believes AI is foundational technology on the scale of the integrated circuit — not the internet.

Chapters

• (00:00) Welcome & introductions Adam welcomes George to the show and sets the table for the conversation.
• (00:58) A "not so long" career — Time Warner to WWE to ISOS George traces the arc: early finance, management, and strategy roles at Time Warner, HBO, and the New York Times Company, the move to WWE, and the founding of ISOS Capital and Global Sport Group.
• (03:55) The book — Sometimes Wrong, But Never in Doubt Where the title came from, the Harvard-surgeon origin story, and why confidence rooted in preparation isn't the same as bravado.
• (08:41) The IP unlock: it's not sport, it's live The 12–18 months of consumer research and first-principles thinking that led to repositioning WWE around live, tribal, passionate, multi-generational content — and the "content factory" strategy.
• (09:22) Launching the WWE Network Cannibalizing a hugely profitable pay-per-view business to build an SVOD service for the most passionate fans — the criticism, the cannibalization fears, and the climb past two million subscribers.
• (13:03) Working with Vince McMahon What it was actually like — not the loud TV persona, but a stoic who was hard to read — and selling him on "killing the baby" of the pay-per-view business he created.
• (19:13) The "swamp of despair" The emotional journey of doing something big: naysayers, public-market pressure, and the three-to-four-year wait for the economics to manifest.
• (22:49) The Michelle Wilson partnership How two high-powered executives built an 18-year partnership, why the co-CEO model is so hard, and the Venn diagram of intellect, integrity, and energy.
• (30:40) Getting fired — January 2020 The wind-down with Vince, the decision to leave, the abrupt ending, and the stock drop that followed.
• (39:05) The dinner, the call, and the return Reconnecting with Vince in 2020, the 2023 phone call to bring back "the A team," and rejoining the board.
• (43:06) Architecting the UFC merger The strategic process, the conviction around scale ("one plus one is more than two"), and why the deal has looked better every day since.
• (48:22) What "data-driven" really means The difference between dabbling in data and doing the hard work — cross-platform content measurement, data engineering vs. analysis, and building the infrastructure from scratch
• (51:51) Closing question: Artificial intelligence Why George thinks AI is foundational like the integrated circuit, the danger of "dabbling," sports' competitive moat, and the discipline of not duct-taping AI onto an old business model.
• (55:35) Where to find the book & wrap-up