CoachUp founder Jordan Fliegel with NBA forward (and CoachUp athlete) Nerlens Noel.

Even in a city obsessed with its teams, being a sports startup in Boston can be a rough life. It requires all of the usual traits found in other sectors, but with the added touch of a built-in passionate demographic of customers. Still, the sports tech startup scene in Boston is one of the most fascinating places of its kind in the country. The community includes CoachUp, a site for booking private coaching, and PlayLocal, which lets users find tennis courts and other players online. Here’s some advice and lessons learned from entrepreneurs involved with the two Boston-based companies:

Jordan Fliegel, CoachUp

Founded as a private coaching service that has grown to be the largest of its kind in the United States—with more than 15,000 coaches now a part of it—CoachUp is an example of a Boston startup that has thrived in the local market. Company founder and president Jordan Fliegel offered some thoughts on the sports startup scene in Boston, as well as advice for those thinking of jumping into it.

“Hiring is definitely easier than it is for big data,” Fliegel said in regards to luring talent into the sports tech scene. Clearly, sports sells itself to a large demographic. This is not lost on the CoachUp founder.

“It’s fun,” he said. “It’s something that you’re passionate about. It gives you energy. It gives your team energy everyday to show up to work on something that you enjoy.”

Fliegel is also a proponent of a familiar route: Athletes who are transitioning from their playing days into the business world. Of course, it’s not for everyone. But for those who have some versatility in their skill set, it can make all the difference.

“I think the third thing, this has served me well personally, is just having the combination of being an athlete and knowing something about technology, business and fundraising,” Fliegel said. “And being able to bridge those worlds. It’s kind of a rare background I think, but if you are one of those people, that can serve you very well.”

Naturally, Fliegel (as a founder of a growing company) thinks that sports startups are often unsuccessful because they don’t reach for the correctly sized market.

“A lot of people with ideas in sports, it’s very small actually,” he said. “They’re sort of thinking about the professional teams and ‘wouldn’t it be cool if they had some data thing that allowed teams to better manager their athletes?'”

To make, especially in funding terms, entrepreneurs have to think bigger.

“I think those kind of ideas that are kind of limited to selling to professional athletes. And professional teams just really aren’t a big enough market to really excite venture firms.”

One way to avoid the trouble of attracting venture firms? In Fliegel’s experience, it was partly due to CoachUp getting a product out there quickly, showcasing their business model.

“Right away we had revenue,” he recalled. “We had a traction. We had a product. We had a team. So that became a fundable business.”

One more piece of advice for all of the would-be sports entrepreneurs out there: Don’t just try hitting up Mark Cuban. Chances are, it won’t work.

“I actually don’t think Mark Cuban really likes sports tech as an industry,” Fliegel said. “He tends to avoid it, it seems.”

Anmol Wassan, PlayLocal

Having launched in Boston in 2015 after a very thoughtful process of experimentation in surrounding towns and cities, PlayLocal’s model met with success by all accounts. And co-founder Anmol Wassan recently sat down with BostInno to talk about some of the lessons that he’s learned in this time. Wassan was quick to point out that the company is still far from what can be called a success, but was willing to share some more basic information for others who are just getting started.

“We’re in no position to be giving out advice from a PlayLocal perspective,” Wassan said, admitting that the company has a long way to go. “What I can share is insights on how we went about it and where we found success, which could help people out.”

“Most people start with ‘I want to do an app,’ or ‘I want to do a something or other,’ right? Forget about that.”

Wassan, who got his MBA from Babson, said that one of the most important things he did was to simply go out and interact in different environment to get comfortable recognizing everyday needs.

“You’re expected to do a lot of research,” he explained. “Not just secondhand research in terms of markets and problems and all that, but they actually required you to do service and go out and talk to people.”

In that, it allows for the most fundamental aspect of developing a startup.

“First you identify the problem,” said Wassan. “You know, what are the must-haves? What are the need-to-haves. They’re very encouraging not to think about it as a product or a service. Most people start with ‘I want to do an app,’ or ‘I want to do a something or other,’ right? Forget about that.”

In Wassan’s eyes, the important part is establish a “hierarchy of needs,” as he was taught at Babson. After identifying a problem that could be feasibly solved, other steps are taken (discerning if there’s a market for it, as an example) before anything else is done toward establishing even a basic concept for a startup.

Challenging existing notions, even (and especially) their own, are fundamentally important steps in finding the right model.

Anmol Wassan (left), with fellow PlayLocal co-founder Brent Colson.

“They keep encouraging us at every step to keep on thinking of design and continue to validate all our assumptions in the market,” Wassan noted. “So as you are thinking about what you want to do, you keep going out to the market, not just to companies that are similar, but also the companies that have failed in the space. That was a huge advantage for us.”

When PlayLocal (then called Reserve a Game) began, it launched in areas around Boston. Each of the markets was picked because it presented a different challenge and different audience. Again, it showcases a fundamental startup lesson: test your business in different climates as much as possible to measure its potential.

“We went with four cities with four different business models,” Wassan said. “Quincy, Winchester, Arlington and Wellesley. So you know, Quincy, more of a city feel. Arlington is close enough to the city you know and Wellesley is out in the ‘burbs for all our different models.”

While Wassan is clearly aware that an education program tailored to becoming an entrepreneur isn’t absolutely vital, he left Babson as a major proponent.

“There are obviously very smart people everywhere, so absolutely,” he says regarding entrepreneurial potential without specific schooling. “I don’t want to discount that at all. But it does help to have the structure and network obviously, to support you. If you have that, you just get to things faster.”

The last piece of advice Wassan offered revealed the degree to which he is at once a member of the sports startup community as well as a fundamental sports fan. Talking about the necessity for pushing yourself and your startup everyday, Wassan cited a phrase, explaining it with a touch of New England Patriots wisdom.

“I want to make new mistakes every day,” he said of staying aggressive in his startup life. “It’s like ‘Do your job’ that Bill Belichick says, the unspoken word is ‘do your job well,’ right? So you want to make new mistakes every day, the unspoken part is you’re not making mistakes again. So that execution is important, but you’re trying things enough that it’s sort of pushing people and saying ‘hey, is this something?'”

Image via CoachUp