How this entrepreneur made the move from corporate life to startup founder

Chris Clark thought he landed his dream job with manufacturer Wilson’s Sporting Goods. As a global product line manager, the former college tennis player oversaw the development of the brand’s signature tennis balls and “W” rackets.

But he found the role unfulfilling, and the feeling lingered with him through new roles at Kraft Heinz and a sports team-building startup. “Sometimes in life we chase dollars, and it takes a while to know once you get the dollars, it’s not really everything is all cracked up to be if you’re not happy,” he told Founder Brew.

Clark kept up a personal tennis habit throughout his career journey. “The one thing that had always followed me throughout my career was racket sports and tennis,” he said. “Even in corporate, I was always teaching a little bit, still playing, still engaging in the game, still very much a part of my life.”

So when he was furloughed by the startup during the Covid-19 pandemic, Clark’s wife encouraged him to turn his side hustle—teaching tennis lessons for $60 a session—into a full-fledged business.

“At that point, my wife was just like, ‘Why don’t you try? Why don’t you make this tennis thing real? Instead of just teaching lessons, build a company, build an empire,’” he said.

Clark built Toss and Spin, a Chicago-based platform for racket sports, offering group classes, specialty coaching, and B2B branded experiences across both tennis and pickleball. He operated with a “brick-by-brick” mentality when starting out. At first, Clark leaned on his marketing skills, before worrying too much about the parts of the business he didn’t know yet.

“My gift is moving very quickly. My curse is moving very quickly. So once I decided, it was like, ‘We’re going to figure this out,’” he told Founder Brew.

Over six years later, Clark reflects on what he’s learned about being his own boss, building a trusted circle, and his recommendation to others sitting on the fence.

The following interview has been edited for length and clarity.

Why do you think it’s both a gift and a curse to move quickly?

It’s a gift because if I see an opportunity, I’ll put it together quickly. I know what to do, how to do it. The curse part of it can be sometimes in really challenging situations that are uncomfortable, you’ll move too quickly.

Did you have an experience early on that taught you to slow down a little bit?

There’s always an experience every year where little mistakes are made, and I’m like, “That’s a rookie mistake. You went too fast, or this wasn’t done correctly.”

We did a deal with the [Chicago] Bulls, but I wanted to push it through really quickly…We would have missed the timing if we had to wait for a contract, so I didn’t. I was like, “Whatever. You don’t need to do a contract.” Good press, all these cool things come out about it, and then the Bulls cancel, and I didn’t have a contract, so I got burned there.

But the good learning there was A: Never do anything without a contract for that reason. Then B: Even some things that seem really good, you really have to analyze. Is it the right move for your business? I think that’s the moral of the story.

What were some of the lessons you learned not having a boss?

I always laugh because people are like, “I can’t wait to be my own boss,” and you’ll quickly learn like being your own boss isn’t cracked up to what everybody says it is, and being the No. 1 person isn’t all cracked up to what people think it is. There’s value in being two and three and four because it never all fully falls on you…You constantly have to be a student of your own business. You can never think that you know more, that you’ve learned everything.

What does it mean to be a student of your business?

It means continuous learning, and it means continuously networking and picking people’s brains…There’s a lot of people who just want you to win. They like you. They just want to see you win, so if you ask for help, they will help you. Take them for a coffee. It doesn’t always have to be like, “Hey, I’m going to pay you $5,000. I’m going to pay $2,000.” People will do it. “Hey, can I take you for a coffee?” And normally, I have a group of people who I take my biggest problems to, and I say, “Can we grab a coffee?”

Who’s your trusted group?

There’s a couple different people who have sold large companies that are really drawn to Toss and Spin. There are people who have large franchises across the country. My parents are in that group. They’ve been very successful in the corporate world. It’s like a group of five to six people. I’m like, “You’re in HR. What do you think about this problem?” or, “You’re in legal. Hey, can I ask you this question?”

What was the best investment you made in your company in the first year?

The very first investment that I think really helped was investing in a platform that allowed Toss and Spin to come up on Google search…If you Google “tennis classes near me” or “tennis classes New York,” the one thing you’ll find out that is very important: A lot of racket sports organizations don’t run ads on Google. In Chicago, there are much larger entities and clubs than Toss and Spin, but we’re the first thing that will come up because they don’t run the ads. We learned that early on. We got real solid on search, and then it made it easier for us to acquire customers because we were able to get early reviews…It wasn’t much. It was like 99 bucks a month.

What’s your advice for someone considering starting their own company?

Do it. Do it quickly while you’re thinking about it, because you really don’t have anything to lose, and you never want to look back and say, “I wish I would have.” Because as a 39-year-old person turning 40—which when I was 20, 40 felt a long way away—time flies fast. But I also say, if you do jump into entrepreneurship, be ready for pain and be ready for lots of it, and prolonged periods of being misunderstood. People will think you’re crazy. I laugh when I say it, but it’s a lot. You have to really go back and think, “Why am even doing this? I could just go get a plush corporate job and ride into the sunset.” But, for me, it’s about pushing myself to be the best I can be and seeing how far I can push it. Again, it’s about not looking back and saying, “Five years ago, I really wish I would have done that.” I won’t have any regrets.