The interview

The interview

CoachUp CEO John Kelley catches me up on how his startup is doing. It's the prelude to our hour-plus workout and basketball lesson.

Photo by Ryan Light

Warm-ups

Warm-ups

CoachUp coach Brandon Ball shares some tips in between exercises. Jumping rope was my most humbling performance of the day.

Photo by Ryan Light

Commence the sweating

Commence the sweating

The early drills were about getting the blood flowing and testing our balance and endurance.

Photo by Ryan Light

More drills

More drills

I'm already out of breath, and we haven't even touched a basketball yet.

Photo by Ryan Light

Hand-eye coordination

Hand-eye coordination

You try dribbling a basketball with your left hand (without looking down), catching another ball with your other hand, and throwing it back.

Photo by Ryan Light

Check it out

Check it out

We got this.

Photo by Ryan Light

Score

Score

A successful right-handed layup. (At least, I think this one went in.) My coaches back home would be proud.

Photo by Ryan Light

John Kelley sinks one

John Kelley sinks one

I'm thinking he dunks it next time.

Photo by Ryan Light

Xconomy Boston — 

As I step onto the basketball court, I feel a flash of giddiness mixed with a tinge of nervousness. Just like when I was a kid, warming up before a game.

I’m dressed in dark silver athletic shorts and a worn-out Marquette University basketball T-shirt with the sleeves cut off. My laptop is stowed in my backpack, along with a pair of black sneakers and a stretched-out headband, both waiting to be called to duty after months gathering dust in my closet.

I drove to this gym in Waltham, MA, to meet with John Kelley, CEO of Boston-based startup CoachUp. His company runs an online service that connects athletes of all ages with private coaches in a variety of sports, and I’m about to embark upon what is probably the most intense product review Xconomy has ever conducted. Kelley has graciously agreed to sacrifice his body and join me in a basketball torture training session with CoachUp coach and former professional basketball player Brandon Ball. (See photos above, and read more and watch video highlights below on page 2.)

“I couldn’t sleep last night,” Kelley says before our workout, and I’m not sure whether he’s joking. “I’m still nervous. I’m like, ‘Let’s do a golf lesson.’ [But] I’ll take one for the team. I’ll do anything for CoachUp.”

Before we get started, I pull out my laptop and chat with Kelley courtside about how business is going, CoachUp’s efforts to broaden its appeal, and plans to incorporate more video technology in its online platform. Consider it a mental warm-up to our hour-plus workout.

The Evolving Fitness Industry

It’s Xconomy’s first in-depth interview with Kelley since he became CoachUp CEO in early 2015, succeeding co-founder and former pro basketball player Jordan Fliegel.

Kelley, previously a top marketing exec at The Princeton Review, Monster.com, and other firms, says he’s having fun running CoachUp at a crucial juncture. The five-year-old company, which employs over 30 people, has shown there’s ample demand for its online matching service. Around 20,000 private coaches are on its platform, and they have led more than 250,000 training sessions since CoachUp got started, Kelley says. (CoachUp makes money primarily by taking a cut of what clients pay coaches for each lesson.)

Kelley won’t share exact revenues, but he says they’re on track to grow by a percentage in the “high double digits” this year.

Kelley says the plan now is to enhance CoachUp’s offerings and expand its use among people outside of the service’s core demographic of athletes ages 12 to 18.

To that end, the company created CoachUp Play, a service for groups of kids ages 4 to 10, aimed at introducing them to sports and encouraging healthy habits and teamwork.

CoachUp is also getting more interest from adults, Kelley says. Frustration with traditional monthly gym memberships is causing people to switch to alternative services such as ClassPass and CoachUp, which allow them to perform a variety of workouts led by trained instructors, he says.

“The whole fitness industry is undergoing an evolution,” Kelley says. Adults have an “interest in trying different things and changing it up frequently. I think we play into that very well, particularly because we’ve got all kinds of coaches in all kinds of sports.”

Kelley says kids tend to use CoachUp for team sports, such as basketball and soccer, while adults mainly hire coaches in what he calls “lifestyle sports,” such as golf, tennis, yoga, and strength and conditioning workouts.

“We’re now beginning to really expand our messaging and product to appeal more to younger kids and older folks like me,” Kelley says.

Building Coaches Up

CoachUp is also trying to make its platform more useful for its network of coaches, beyond the benefits of helping them connect with clients and handling back-office work like scheduling sessions, managing billing and payments, and other services. The company is adding video capabilities that will enable coaches to upload recordings of sessions to the CoachUp site so they can go over critiques with clients and give better feedback, Kelley says. That’s especially useful for helping athletes see how they can improve the technique of their golf swing or their jump shot, for example.

Coaches will also be able to post promotional videos on their CoachUp profile page, which might help potential clients get a better sense of their experience and personality, Kelley says. Many of CoachUp’s coaches have other jobs, but some of them accumulate enough clients that they can coach full-time, he adds.

But the biggest opportunity Kelley sees for video technology is amassing an online library of coaching tutorials, where athletes can brush up on tips for, say, improving their crossover dribble, and other coaches can learn best practices from their peers.

“Certainly you can find things on Google and YouTube, but there’s no authoritative source,” he says.

He thinks CoachUp is well positioned to be that go-to resource because it already has an established network of coaches and athletes. “We envision a future where we have a vibrant community of coaches who are bringing their own content into the system,” Kelley says. “They are also looking to build their brand.”

Brandon Ball is one of CoachUp’s success stories. After playing collegiate basketball and earning a bachelor degree in business administration and marketing at Michigan Tech, he played professionally for several minor league teams. Around 2012, he made the difficult decision to quit because he wasn’t making enough money to comfortably buy a house and start saving for the future, he tells me after our training session.

He became a real estate agent, but continued playing basketball in recreational leagues and giving private lessons on the side, finding clients mainly through word of mouth, he says. Then he got recruited to be a CoachUp coach by a friend—company co-founder Fliegel.

Ball became one of the most popular coaches on the platform, building up enough clients that he could financially support himself primarily through giving lessons, he says. In 2014, he was hired by CoachUp to help market the company locally, provide feedback about the service, and help other coaches learn how to use the platform’s tools, he says.

Ball says he’s fortunate to have found a way to turn his love for basketball into a career. The coaching sessions don’t feel like work to him.

“Not only are you touching kids’ lives and helping kids build confidence and just really being able to give back, but I get to earn an income doing my passion,” Ball says. “The things that I really enjoy are motivating and pushing people and getting them to understand that we’re capable of much more than we believe of ourselves.”

Pushing Limits

Coach Ball’s motivational skills are on full display during my session with Kelley. Any delusions I had that Ball might go easy on us—maybe a friendly game of Horse?—were quickly erased.

He starts us off with a series of stretches, followed by grueling cardio exercises that test our coordination and endurance. About 11 minutes in, we’re already sweating profusely and in serious need of electrolytes and a breather. We haven’t even touched a basketball yet.

Kelley was a good sport to agree to a basketball session. He says he didn’t play it much when he was younger.

“You’ll see why,” Kelley quips before our workout begins. “It’ll be good for laughs. You’ve got to have a sense of humor in this business.”

Meanwhile, I played organized basketball for years growing up, starting with Saturday morning youth camps at the YMCA in Muskegon, MI, and sticking with it through my junior year of high school. That year I rode the pine on the varsity team, an unsurprising role for a relatively slow guy with a serviceable three-point shot.

Since then, I haven’t shot hoops more than a couple times a year, and I’m rusty during the CoachUp session. Kelley and I both have our fair share of humbling moments, mostly missed layups and clumsy ball handling. My most embarrassing drill was my laughable attempt at jumping rope during warm-ups—how have I never figured out how to do that for longer than five seconds?

But Ball keeps our spirits up by praising us when we get things right, patiently offering helpful tips and demonstrations of proper form when we falter, and choosing the right moments to push us harder than we think we can handle. Kelley and I bark “good work” and other supportive words at each other (when we can muster the breath), and we exchange high fives or bump fists between drills.

“Focus on technique, all right? Don’t worry about fatigue,” Ball says to us during one break, as we all bump fists.

Slowly but surely, some of the skills drilled into my head years ago start coming back to me, and I find a comfortable rhythm—just in time for the session to end. Our last exercise is a shooting competition. We each get 60 seconds to make as many baskets as we can from different spots on the court, with more points being awarded for trickier and longer shots.

I decide to challenge myself. I start with some easy layups and shots from the free throw line, sinking a few from each location. Then I venture to the wings (brick city) and beyond the three-point line (more bricks). I finish with 15 points.

Kelley opts for a wiser strategy: shoot as many one-point layups as possible in 60 seconds. He gets to 15 points with time to spare, and politely misses the rest of his shots on purpose so we can tie.

It’s a fitting end to our workout. Kelley and I only just met, but there’s something about sports—and shared physical suffering—that brings people together.

I’m not looking to hire a personal coach or athletic trainer right now, but I tell Kelley and Ball it was a great workout and I wouldn’t mind doing it again.

“I would definitely watch Jeff do it again,” Kelley responds, drawing a laugh from me.

Don’t worry, John. Next time I’ll be the good sport who swallows his pride—we’ll do a golf lesson.

[Thanks to CoachUp employees Ryan Light, who shot and edited the above photos; Ben Hillman, who filmed and edited the video; and Ben Nadeau, who oversaw audio and held the boom microphone during filming.]