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A few weeks ago, at Puck’s In the Arena sports conference at The Spiral in New York City, Fanatics founder and C.E.O. Michael Rubin joined Michael Nathanson and me for a candid conversation about his $31 billion digital sports juggernaut and the next frontier of the business. Rubin reflected on how he reinvented the fan merchandise industry, expanded into collectibles and sports betting, and why he’s going all in on live events, from Fanatics Fest to teaming up with Tom Brady for the Fanatics Flag Football Classic in Saudi Arabia. He also addressed the competition with DraftKings and FanDuel, and why “you’re not smart” if you gamble on sports anywhere besides Fanatics. And of course, I asked him about the long-rumored Fanatics I.P.O. As always, this conversation has been slightly edited for length and clarity.