#63 - The (Improbable) story of Michael Iavarone's Rise to a Horse Racing Legend.

Michael Iavarone’s done what most horse people only dream about, he’s won the Kentucky Derby. He’s been in this game at the highest level, from Big Brown taking him to the presipice of racing to many G1 wins, but he didn’t grow up in it.

He came from a working-class family, started out getting crushed at the betting windows, and somehow figured out how to buy the right horses at the right time.

This one’s full of wild stories, buying million-dollar horses days before a race, flying around the world to race in Hong Kong and Dubai, and the highs and heartbreaks that come with it. But what stuck with me most is how much Michael still loves the game. Even after all the pressure, all the wins, all the money spent, he’s still out there watching morning works like it’s the best part of his day.

Key Topics we discussed:

• Why Michael only buys horses that have already raced, and how that’s helped him win big

• The story behind Big Brown and how it felt to win two legs of the Triple Crown

• What it’s like to wire a million dollars for a horse just days before the Breeders’ Cup

• Why elite horses have to be mentally tough, not just talented

• How horse racing pulled him back in after he stepped away

Follow Michael on Instagram: @michael.iavarone

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