Matt Fried has been one of my closest friends for about 15 years—and this episode is everything I hoped it would be. Equal parts hilarious, inspiring, and useful, this conversation walks through Matt’s wild career path, from graffiti-tagged train rides into art school to sneaker collaborations and startup wins, all the way to building a platform that’s literally helping save lives through faster radiology staffing.

We recorded this at Lure Fishbar (yes, sushi is ordered mid-convo), which is extra meaningful because Matt was with me the night I met Virgil Abloh there—and we retell that story together.

But more importantly, we talk about growing up without selling out. About staying curious. About building sustainable businesses on instinct, obsession, and a touch of madness. And what it really means to create a life—professionally and personally—that you actually enjoy living.

This is one of those episodes I hope makes growing up feel less scary for anyone listening. And I’m really proud to share it with you.

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From Staten Island to Startups & Meeting Virgil with Matt Fried