How did a tennis player ranked 864th in the world find a career in comedy? He learned how to lose

New York Times

30-05-2025

Editor's Note: This story is a part of Peak, The Athletic's new desk covering leadership, personal development and success through the lens of sports. Peak aims to connect readers to ideas they can implement in their own personal and professional lives. Follow Peak here.
You may know Michael Kosta as a stand-up comedian and rotating host of 'The Daily Show' on Comedy Central. But two decades ago, he had another title: The 864th-ranked men's singles tennis player in the world.
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The story of Kosta's time as a professional tennis player is the subject of his new memoir, 'Lucky Loser: Adventures in Tennis & Comedy,' published earlier this year. The book is a sometimes funny, sometimes poignant (and sometimes NSFW) tale about falling in love with a sport, chasing a dream and how ultimately losing a lot provided the tools for a second career.
I reached out to Kosta with a simple pitch: Let's talk about losing and how we handle it.
It turned out to be a conversation about the importance of our parents in building self-belief, why timing can be everything, and how to bounce back from a brutal loss.
So I want to ask you about losing. But we should note, before you were a 'failed' tennis player, you won a lot. Did becoming a 'loser' change you in any fundamental way?
You know, it's like a, I'm allowed to say I'm a loser, but no one else is type of thing. Because in that first 95 percent of my time as a tennis player, I was a winner, right? So when you start losing so much, which is what happens when you're pro, it is very jarring. It's not like I was a mediocre tennis player my whole life, and then I kind of understood the mechanics and rhythms of losing. It was a huge transition: 'Oh, s—, I'm not the number one player in the world. I'm losing a lot.' And it was a hard adjustment.
Did you feel like it changed your identity or the way you look at the world?
It humbled me and it toughened me up, but it doesn't eliminate your self-belief. It doesn't make you a coward or change my ability to believe in myself, because you still have to have those things to try to win a few matches at least in pro tennis, and obviously those lessons that you learn helped me a lot in my next career.
You wrote in the book how it gave you a sort of armor to pursue comedy and take risks.
I remember these older comics living in Michigan, 10, 15 years ahead of me. Maybe they were kind of trying to insult me, and I didn't pick up on it, but they would say: 'Hey, you know, I saw you yesterday and that looked like kind of a rough set, but you're back out here again today?' It gave me this armor that I almost didn't take it personally. And in a lot of ways, that's tennis.
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I remember winning or losing in college, and our coach would sometimes make us run afterwards. Even if you won, you had to remember that you were capable of a higher level. And when you lost, you could see the running as punishment, but it was really just, this is a very long-form process. So that little thing that happened today in comedy, you bombed the set, that wasn't the success or failure. The success is continuing in the process of improvement.
Which sounds very, very cliche. But you know what? It's cliche for a reason.
I've always thought tennis seems like the most vulnerable sport in terms of losing. What do you think of that?
Yeah, I agree. I think you're alone. Your face is not covered. There's no one to turn to. It's individual — look, HDTV has made it even worse. It's like in basketball, we really love basketball players because we can really see their faces. Tennis, more so, there's nobody else for the camera to show. It is incredibly vulnerable. It hurts a lot, and one of the more unique things about the sport of tennis — if you're in the finals and you lose, you have to stand there and do the ceremony with the winner. What other sport does the losing player or team stand out there? Losing is an indelible part of a tennis player's life.
Roger Federer gave a speech last year in which he noted that he only won 54 percent of his points during his career. And you're thinking, 'Wow, one of the best players ever wins 54 percent of points.' Almost half the time, he's failing.
I thought it was a great thing to share with young people — that there's going to be a lot of failure, a lot of grit. The other thing that I took from that speech and morphed it into comedy in some ways was that timing is everything. You say that in comedy: Timing is everything.
He only won 54 percent of his points, but I would love to see how he did on break points, match points. He always brought his best at the right time. And that's an important part of comedy, too. Like, you can have a rough five minutes in your set. You can lose the audience. But as long as you get them back by the end, I think that's kind of most important.
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So when you're up on stage and a joke doesn't go very well, it's the sports thing of thinking, 'All right, next joke, next joke…'
Not even next joke. More like, 'This is a long match. You got another 52 minutes to go. You got a lot of time here.' And that was very much a tennis thing. That was very much similar to the self-talk you do in tennis. You get broken, you're down 2-0 in the first set. It's very easy to start thinking about, like, 'When's the next flight out of here?' But it's like, 'This is a long match. You can break back and get right back on serve.'
In the book, you mentioned a match you lost when you were playing professionally, where afterward you just kind of went over to the track next door to the court and started running. What other rituals did you have after tough losses? Did anything make you feel better?
Practicing always helped. But it was very hard to do that. I remember traveling with Raven Klaasen, who became a top-10 doubles player in the world. He helped mature me in a way that was like, 'You're not practicing fast enough after a loss.' And I thought, 'Oh, well, it's because I'm really sad about my loss.' And he was like, 'That's kind of the point. Get over it. Get out there and keep practicing.'
I used to keep what I call a 'lessons journal,' and it was a loss journal. After I would lose, I would write down what I learned from that match. But I gave up on that. I didn't like that. I felt like I was over-analyzing the losses. I mean, sometimes you just lose. Sometimes the guy plays good. Sometimes you play bad. Sometimes it's windy. Sometimes you're jet lagged. I thought I was kind of digging into these failures too heavily.
Yeah, a few years ago, some researchers were looking at failure. And the conventional wisdom is that failure is motivating. But they argued that people don't learn as much from their failures as we actually think because it can be so de-motivating. They argued that people still should try to learn from failure, of course, but one of the best ways to do that is actually to talk about them. When you finished playing your career, did you struggle to talk about the losing?
I think I'm still trying to tell people about it — that's why I wrote the book.
And honestly, as I've gotten older, I would say about losing — and this is true for comedy, too — instead of wallowing in or analyzing the defeat, it's really just like, 'Keep going. Just go do another set, go play another match, go do cross-court backhands. Go find an open mic.' And I think the best players — and Roger is definitely this way — they let it go. Their memory is short.
One of the things that I learned about myself in writing this book was this match that I blew in South Korea. I mean, it affected me sooooo much. It still does. I still think about it. And it's like, now as I've gotten older and I've studied more people that have had success in comedy, it's like, 'Hey man, that hurt you too much. That should have just been a f—– up match. You blew it, water off a duck's back, keep going.' But the fact that it stuck with me so long is telling that I was taking these losses too personally for something that really wasn't.
Why do you think you did that?
Well, that's a good therapy question. Probably attaching too much (self) worth to outcome, still hoping my parents pay attention to me at the dinner table, wanting my picture in the paper. A lot of good reasons.
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One of the things I always think about: Anytime I've moved up in my career or gotten to the next level, it feels like, yes, I've arrived — a reward for my hard work. And then what ends up happening is that I realize I have a whole new group of people to compare myself to.
Who are actually better than your last group.
Exactly. Tennis feels like the ultimate example of that. Because not only is there a group of people. They actually keep the ranking in the form of a ladder. Did you struggle with comparing yourself to other players?
Yeah, even on my mirror to this day, in my bathroom, in my handwriting, it says, 'Comparison is the thief of joy.' Some smart person said that. I have to remind myself of that to this day.
When I was playing tennis, there was this thing called 'Steve G Tennis.' It was an internet message board and he would post all of the results around the world. So if I was picking between going to Montreal or Mexico and I picked Mexico, I would lose in the first round or whatever. And then I would quickly go on Steve G and see that the Montreal draw was really weak and I would go, 'Damn it, I blew it!' So many players would do this, and I remember finally thinking, 'This is not helping me. This is hurting me.'
Why did that quote connect?
I remember as soon as I heard it, it connected with me and reminded me of my tennis days. There's Instagram and TikTok as a comedian now. How do I not pay attention to all my other peers? Every time I open up these apps, it's showing me everything they've done. So I just thought that was a good reminder: 'Don't focus on them. Focus on you.'
You mentioned that when you were playing tennis, you would write jokes in your journal.
I would always do this thing in my journal that would just say like, 'This is something that made me laugh today.' That was just a thing from a very early age that I started to do, when my mom would put me to bed when I was really young. We would just talk about something that made us laugh today. I've tried to do this with my daughters today. But my daughters usually tell me, 'Go away, Dad.'
Then when I started playing pro tennis, it was less about, 'What's one thing that made me laugh today?' And it was more, 'What are funny ideas or jokes that happened throughout this experience?' So I guess I just leveled it up a little more. Now, why? I didn't think I was gonna be a comedian. I wasn't seeing it as comedy training. It just helped me.
Did playing tennis and the experience of all of that losing in a short period inform your writing?
It gave me a lot of time to write and gave me a lot of time to go experience stuff. So, I'm in the Netherlands. I've got six and a half days till the next tournament. Probably what I should have been doing is just staying at the courts every day and practicing. But I would take the train in Amsterdam, or I would go try to find something interesting and those experiences of cultivating my life outside of tennis really help you as a comedian.
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To circle back to something you said at the beginning: You said you were able to still hold on to belief while losing, and whether it was belief that you're going to win the next match or belief that you can succeed in comedy in a new career. This might be another therapy question. But where does that belief come from? How does somebody build up belief?
That's a very good question because you can't just say it comes from external reward. I think external reward is helpful, but we all know people who have had a lot of external rewards who are still self-conscious and not fulfilled. It has to come from within, and it's incredibly important to have self-belief. And self-belief is really the only reason I think anybody does anything. You have to believe you can do it. It probably comes from some form of unconditional support and love from one of your parents. (Laughs).
For me, one of the biggest, most helpful tools I used as a tennis player that I also use now as a comedian is that I remind myself of previous achievements. For instance, a tennis example: All right, it's 5-4 in the third (set), I'm serving for the match. I'm feeling nervous. This guy's return is great. I can't believe I'm even in this position. He's ranked so much higher than me.
I'll say, 'Self-belief, Michael. You did this. You served out this match a year ago in Toronto. Two years ago, to win the doubles future (event), you did this before. In high school, you won the state tournament with this exact same score.'
And I do that with comedy every time. 'Oh my God, this crowd is tough. Oh, they were certainly hard on the opener. What am I doing here? You're gonna really open with a Trump joke? Half these people might have voted for this guy.'
It's like, 'Michael, relax, you crushed two weeks ago, and you felt the exact same thing.'
I was watching the PGA Championship and after Scottie Scheffler won, his dad gave him a hug. Some TV mics picked up his dad saying how proud he was. It's interesting to think that self-belief really can come from those people who believe in you unconditionally.
Yeah, and I think probably as you are forming into a human. Because we know adults who hear it to this day, and it doesn't resonate. But I think when children are being formed, their personalities are being formed, you've got to tell them that they're enough, that you can do it, you can do hard things. And you might be able to get that from other people or places, but for me, that seems like a pretty natural answer.
(Illustration: Dan Goldfarb / The Athletic; Jeff Kravitz/FilmMagic/Getty Images)