The boys finally get comedian, former ATP player, and professional roast master Michael Kosta on the pod—and it’s everything you’d hope for. Kosta spills on his days grinding the Challenger circuit, the exact moment he knew pro tennis wasn’t for him, and how he pivoted to roasting players instead of playing them.

He dishes on the real differences between tennis and stand-up, why tennis players are the worst at taking jokes, and the time he absolutely bombed on stage. Plus, Kosta gives the inside scoop on his new book, Lucky Loser, where he breaks down the absurdity of life on tour, from wild travel mishaps to the worst hotel rooms he’s ever stayed in.

00:00 Introduction to Michael Costa

00:52 Michael's Tennis Journey

01:36 The Transition to Comedy

02:56 Insights from the Book

03:53 Comparing Tennis and Comedy

06:38 College Tennis Experience

09:57 Funding a Tennis Career

13:31 Comedy Beginnings and Challenges

17:40 The Tough Choices in Comedy and Tennis

17:53 The Delusional Self-Belief

18:26 The Grind of Professional Tennis

19:07 Never Giving Up on Comedy

19:34 Comparing Comedy to Tennis

20:00 The Grand Slam of Comedy

21:00 The Challenges of Stand-Up Comedy

23:45 Learning from the Best

25:16 Pre-Show Routines

26:25 Trading Careers and Hollywood Tennis

29:54 The Emmy Dilemma

30:55 Wrapping Up and What's Next

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Lucky Loser: Adventures in Tennis and Comedy

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