Pickleball Dating’s founder on finding a niche and building a community

There are many similarities between building muscle and building a business, and entrepreneur Jyl Steinback knows how to do both well.

After starting her career as a fitness instructor, Steinback branched into fitness programs and cookbooks. Through her nonprofit, Shape Up Us, she has also brought wellness education into schools in Scottsdale, Arizona, which introduced her to pickleball.

As she became more involved in the sport, she spotted a potential business opportunity to help people develop more than their physique: People who play pickleball regularly might want to date someone who shares their passion for the game. That idea became Pickleball Dating.

But building a dating app has presented a different challenge from her previous ventures. Steinback launched the app earlier this summer. Her next hurdle is building a large enough user base in the same geographic areas to make connections—and turning that audience into a sustainable business.

In a conversation with Founder Brew, Steinback shares how she identified an underserved niche market, why she believes playing together can reveal compatibility, and the daily habit she uses to push her business forward.

This interview has been edited for length and clarity.

What is it about playing pickleball together that you think can reveal compatibility in a way dating apps can’t?

I love pickleball because you can learn so much about somebody on the court, versus when I looked on a dating app, it was just who they are until you talk to them. Are you talking to the right person? Are they faking it? What’s going on there? Pickleball, you’re there…There’s a lot of things called red flags, green flags, on the pickleball court. A green flag would be somebody that comes on the court and after you make a point, you tap paddles. A red flag…he’ll hit his paddle to my butt, and I’m like, “No, no, no. This is our first game.” To me, that tells about somebody, as far as respect…You learn a lot about that person that doesn’t come out in the app that’s online or even a conversation. [It] speeds it up and just makes it real in real life time.

You’ve decided to offer users 90 days free rather than charge them upfront. What are you hoping to learn during that period, and how will you know when people are willing to pay?

We were going to start really low, at like $14.95, $14.99, and I decided no. I want to just start 90 days free to get people on, so I did change that perspective of it. That was probably pretty much one thing that’s different about our app too than other apps out there—we really hone in on pickleball. Are you beginner, intermediate, advanced? People know a lot of people are very snobby in the pickleball world, like tennis, and they don’t want to play the beginner. Our app is also: “Do you want to come in and just meet a friend, or do you want that romance, or do you want that soulmate?”

What advice would you give founders who see an audience or community with clear interest but aren’t sure how to turn that interest into a viable business?

I’d always go with the numbers and the growth that the business is having, and also take a look at how many people, for example, in pickleball—what I looked at was how many people are coming on board or jumping on the ship with pickleball…from paddles to balls to clothing, you name it—and nobody was doing this niche. So, what is the niche in your market that somebody’s not covering? That would be my biggest “aha” [moment].

What have you learned about yourself as a founder through building this business?

My middle name is tenacity and persistent, and I think sleep’s overrated.

I’m best at three in the morning, and so I just get up and do the task. But my thought to everybody, what I do, will do, is call somebody that you’re afraid to call first in the morning, so it’s over, so you don’t have to think about it all day. Do the dessert first. No, you can’t wait to eat the dessert, so just eat it. But you’re like, “No, I have to wait.” But then you’re thinking about it all day long. What I also do myself is I’ll make one call a day that I don’t want to make, but that’s five calls a week. That adds up.

The other thing I have to say to people: There’s no such thing as “no.” It’s just “not right now,” because when I’ve gone back to many companies in a year or two years, even one—I’ve been trying to do work with this one company for seven years, and he just answered yesterday. Okay, it wasn’t his time. They had to build their business. They had to do what they needed to do. A no doesn’t mean no. It means next, but it also means put it on your record for six months, then a year, and keep going.