Startups and Sports: 3 Lessons From CoachUp’s Jordan Fliegel

Sports have universal appeal, but they resonate particularly strongly with startups. So what can entrepreneurs learn from successful sports teams and players?

First, that they share a common bond. Entrepreneurs and athletes “both like creating, and they both like being part of small teams,” says Jordan Fliegel, the CEO and founder of CoachUp. “They also like seeing results and mentoring each other.”

Boston-based CoachUp is a two-year-old tech startup that connects athletes with private coaches. Any level of athlete—from grade-school to high-school to pro—can use CoachUp to find the right local coach and track their sessions; on the other side of the market, coaches can use the startup’s software to help manage their business. CoachUp has signed up 12,000-plus coaches and over 100,000 athletes, Fliegel says.

Fliegel (pictured above) grew up in Cambridge, MA, and became a serious basketball player, thanks in large part to private coaches. He played college ball at Bowdoin, and professionally for two years in Israel and Europe. After that he went to business school, worked at an online marketplace, and then caught the startup bug.

His experience as an athlete and a coach led him to start CoachUp, which has raised just under $10 million from VCs including General Catalyst, Point Judith Capital, Data Point Capital, and Founder Collective, as well as angel investors like Paul English, Dharmesh Shah, Semyon Dukach, Mike Dornbrook, and Boston Bruins president Cam Neely (he’s a friend of General Catalyst’s David Fialkow).

I asked Fliegel about what he’s learned as a first-time CEO. “Similar to sports, you’re always trying to play up a level,” he says. That means interacting with more experienced players and surrounding yourself with the best possible talent, team, and advisors.

It also means learning from mistakes. Fliegel says he’s been guilty of trying to do too much, or not communicating well enough at times. “You have to be ruthless in focusing,” he says. “It’s a daily ongoing challenge.”

In the end, he says, leading a startup is about “how do you constantly improve, and comparing yourself to the best companies.” As in athletics and other endeavors, the key is “putting in the time and effort when no one’s watching,” he says.

It’s still early for CoachUp, but the startup has grown to 25 employees and is part of a consumer-tech trend to watch in Boston, particularly in the Seaport area.

So here are three lessons from different sports, all applied to startups, from CoachUp’s CEO:

1. Basketball

Interesting story: Fliegel first met Bill Aulet, the head of MIT’s entrepreneurship center, when he was seven years old and Aulet (also a former basketball player) was coaching kids at the Tobin school in Cambridge. That was the first time Fliegel played basketball. He would later play pickup ball with Aulet on Sundays, usually in Waltham.

“It was old-man basketball,” Fliegel says. “If you lose, you’re in Waltham and it sucks, you’re watching old guys play.”

So the key was “how do you pick your team to make sure you guys hold the court, but you also enjoy playing with them?” Lesson for startups: choose your team wisely, or be prepared to watch from the sideline.

2. Boxing

About a year ago, Fliegel started weekly boxing sessions with a personal trainer. One of the lessons he applies from the sweet science is rolling with the punches.

As a startup, you know you’re going to get hit, but you “lean into it, absorb it, and set up your next punch,” he says. “Be calm and relaxed in that moment. Startups are so hard, there’s always the next milestone. You’re in the battle—be in it, be present, and know that there’s nine rounds.” (More from Fliegel on boxing in this blog post.)

3. Football

Here, the lesson is in the structure of the team and the role of each player. When a play is called, everyone from the offensive linemen to the wide receivers, running backs, and quarterback have to do their job—all requiring different strengths and skill sets—otherwise it won’t work.

“When you build a company, how do you make sure you have your receivers and your linemen, and everyone’s on the same page, and everyone does the right thing?” he says.

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