Think You Have a Cool Side Hustle? This $100 Million Company Founder Is Also a Boxing Manager

David Segura is a tech founder in Detroit. And the manager of up-and-coming welterweight Domonique Dolton.

Segura’s grandfather fled the Mexican Revolution in 1917 for work on the assembly lines in Detroit–“from the state of Michoacán to the state of Michigan,” he used to say. Segura’s first job out of the University of Michigan was at Ford, but not on the factory floor; he had a computer science degree.

David Segura, 47, grew up going to fight nights at the Palace in Auburn Hills, Michigan, with his dad. This night, he’s in a ringside seat at the Dort Federal Credit Union Event Center in nearby Flint, watching his boxer take on an undefeated opponent, Jamontay Clark.

CREDIT: Ike Edeani

When he quit three years later, at 25, to start his own software development firm, his blue-collar dad thought he was nuts. Segura’s first two customers sold hot dogs and tortillas; today, Vision IT has 850 employees worldwide, a roster of Fortune 500 clients (including Ford), and more than $100 million in revenue. “You get to a point in your career when you’ve had some success,” says Segura, “and you’re in a position to really impact someone else.”

Domonique Dolton.

CREDIT: Ike Edeani

Segura spends about 20 hours a month working with Dolton–helping book fights, manage a social media presence, and choose appropriate endorsements, among them clothier Detroit Vs Everybody. So far, he’s invested $35,000 in travel, training, and marketing, and he’s yet to see a return. But that could change. Champions fight for seven-figure purses and sign lucrative endorsement deals, and the manager takes a cut.

CREDIT: Ike Edeani

“You can’t cheat the grind,” Dolton says. Segura knows. Since he started hanging out with Dolton at Detroit’s legendary Kronk Gym (where icons Sugar Ray Leonard and Thomas Hearns have trained) and shadowing Dolton’s brutal workouts, he’s lost 35 pounds. “It has transformed me physically,” Segura says, “and got me thinking more like a fighter thinks.”

CREDIT: Ike Edeani

Not to be overlooked, says Segura, is the “awesome cool factor” of managing a professional boxer–even one appearing on the undercard this night in Flint. Segura enlisted his staff at Vision IT to work on logos and marketing materials (“They’re having a blast”), and entertained clients ringside.

CREDIT: Ike Edeani

Dolton, who entered the fight with a 19-1-1 record, dropped 10 pounds for the weigh-in–then put 15 back on in the hours leading up to the opening bell. Two factors beyond his control: Clark’s 6’2″ to 5’10” height advantage and a reach that’s 10 inches longer. Dolton drew blood but couldn’t deliver a knockout. One judge called it even, while the other two gave it to Clark.

CREDIT: Ike Edeani

“As an entrepreneur, and in boxing, you’re investing in people,” Segura says. And you take your knocks. “There are times when you get a setback,” Segura told Dolton after the loss. “You improve, and you learn, and you come back stronger.”

Not Every Business Challenge Will be Solved on the First Attempt: Mistakes Are the First Step to Success

Last winter I put together a group of San Francisco Bay Area folks who wanted to climb 14,179-foot Mt. Shasta in California. Our intentions to take on a new challenge were good, but our timing was miserable. As we checked into the ranger station to get our permits, we were told that the mountain was essentially shut down, with blizzard conditions and 60 mph winds forecast the next several days. Of course we listened respectfully and an hour later were strapping on our crampons and headed up a mountain in near whiteout conditions.
It was after sunset when we reached a flat snow field at 10,443 feet (halfway on the trek to the summit) and pitched our tents. Temperatures dropped and darkness brought a considerable increase in winds.  

Inside our down bags, we were snug and warm, but the group’s mood was a bit dour as we started to accept that the weather was unlikely to improve for our planned 4 a.m. start up the glacier. In all probability, there would be no summit attempt at all. A few in our group talked about the trip being a failure, then goodheartedly laughed it off and added, “Maybe next time.”

As the lanterns went out, I laid back in my sleeping bag (sleep comes slowly when you can hear the wind barreling down the mountain) and I thought about how little I was personally bothered by the fact that we weren’t going to reach our goal the next day. I knew I wanted this as bad as the rest of the group. I’d planned the trip, recruited climbers (none of whom I’d met before), and done all the group prep. Slowly I realized that maybe my comfort with failing to reach this trip’s goal was in part that as a marketer who works with small businesses, I’m well acquainted with proverbial explorations into the “wilderness” that often initially fail to reach an ultimate goal.

With more than a dozen years’ experience in marketing, there are certainly areas and projects that are always winners. But sticking to certainty will leave a lot of opportunity for growth and new revenue on the table. So most successful businesses adopt a scientific approach of test and measure. And with this approach, failure is a critical step towards every summit. I can honestly say that there are times when I’ve been most excited by a failed promotion that taught me something critical about customer attitude and behavior.
For the intuitive small business owner, navigating a fast-moving industry, a well-measured failure or miss of goals (the key phrase being “well-measured”) can provide insights that will drive future success well beyond what we first thought possible. Failure is not to be feared. It should be measured, evaluated, recorded, and then used to inform the next move forward.

Failure educates and creates resolve, and ultimately should be celebrated. The business that fails first, fast and frequently is often the one that is also spectacularly successful. It’s fairly typical that your customers, competitors and industry will take note of your final “instant success” and marvel at how easy you made it look, and give little consideration for the bumps, bruises and cold nights on a mountain ledge you may have suffered along the way.

At least that’s what’s hoping as this year I watch the winter storms bearing down on us. It’s time to take another look at this Shasta puzzle and see if I can put last year’s lessons to good use.