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December 1, 2025 78 mins

There's a good chance that you already know Tony from his work on Around the Horn, the primetime ESPN sports debate show that aired its final episode in May and that Tony hosted for nearly 5,000 episodes, a track record longer than Oprah's that began in 2004 when Tony, then just 25 years old, was called up as a temporary fill-in host the day after Super Bowl XXXVIII, which is remembered more for its halftime wardrobe malfunction than its game winning field goal. Rewatching this episode, I'm amazed by how natural Tony is at facilitating the debate between four seasoned sports journalists, bringing out their voices while still holding them accountable. It's the first day on the job that he's been dreaming of for 20 years and that he'll hold for 20 more. 

Fast forward to today, Tony is raising three young kids with his wife, Samiya, while also navigating a major midlife career transition. As he settles into a spot on my living room sofa, Tony reflects on the waters of the East River, visible from his home in Brooklyn, and the waters of the Hudson River visible from my home on the Upper West Side. These rivers, as my ten year old recently taught me, are both estuaries, bodies of water where the river's freshwater current meets the ocean's saltwater tide to create a surreal environment where the steady state is constant change - much like life itself. It's a poetic prelude to our conversation, which covers Tony's reflections on his career and the vision for what he's building; perspective and advice from his experiences with anxiety and grief; life-changing discovery of self-love; present moment where being intentional and celebrating the surreal go hand-in-hand; and what youth sports teaches our kids.

I'm grateful to be sharing this conversation with you. Special thanks to Andrew, Dim Sum Dad, for introducing me to Tony.


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