A NEW SERIES FROM THE EDITORS OF FORTUNE AND Sports Illustrated
FOLLOWING ALEX BERNSTEIN'S second season as an NFL offensive lineman, in 1998, he signed up for an internship with Morgan Stanley. It was arranged by his team, the Jets, as part of the organization's effort to get players job experience that would prepare them for life after football.
"On the first day I got up at 5:30 a.m. to lift and do all my off-season training and got to [New York City] by about noon," Bernstein says. "I worked until about 7 p.m., then drove back to my home in Long Island. The next day I woke up again at 5:30 for my workouts and said, 'This is unsustainable.' I never went back."
That single day was the extent of Bernstein's office experience when, two years later, a lingering neck injury ended his football career. "I was newly married, and I was a virtual unknown," he says. "I couldn't do something like buy a Wendy's [franchise]. I could barely afford a Wendy's burger."
In desperation he called a college friend who worked at C-bridge, a software-implementation company based in Cambridge, Mass. It was the frothy heyday of the first dotcom boom, and C-bridge was hiring "anyone who could string a sentence together and went to college," Bernstein says. In August 2000 he became the company's new, 6'3" 340-pound inside sales rep, so low on the company ladder that he wasn't allowed to meet customers in person.
That $55,000-a-year job (counting a $20,000 bonus) was the first in a string of positions he has held in the tech industry, culminating in his cofounding of North Social, a maker of social-media marketing software. In 2011, Vocus Inc. acquired North Social for $25 million, providing Bernstein with more money than he ever would have earned as an undrafted lineman out of Division III Amherst.
During his three-year career with the Ravens, Jets and Browns and one training camp with the Falcons, Bernstein survived on effort. "I stayed on the same schedule as with football, but instead of getting taped at 5:30 a.m. for practice, I showed up at work at 5:30. I had to get a special key card to get access that early since the doors didn't unlock until 7," Bernstein, 39, says from the living room of his 8,020-square-foot Tudor in Alameda, Calif. "Instead of preparing for a game, I devoured every book I could find on business, books about systems integration, how coding worked, the business behind it."
His first few months were humbling. Some of his former NFL teammates shied away from entry-level jobs they deemed beneath them. But Bernstein was young enough—only 24 when he started at C-bridge—and anonymous enough that "I didn't feel like I was too good to start from scratch."
That he started over in Cambridge, away from the social circle of football players he knew in the cities where he'd played, was another key: It forced him to cultivate friendships with his coworkers at C-bridge. "I knew guys who after they were out of the NFL for two or three years were still hanging around old teammates, still talking about getting back into the league," he says. "Their wives would approach my wife because they knew she was a therapist and ask, 'How do I get him to move on?' "
After about four months at C-bridge, Bernstein not only caught up to his peers, his knowledge about the software industry exceeded that of some of his managers. In the fall of 2000 he was named the company's director of strategic alliances, dealing directly with software companies such as Oracle. He and his wife, P.J., relocated to San Francisco, one of the 17 moves they would make (counting his NFL days) in their first five years together.
After the dotcom industry bottomed out in the early 2000s, Bernstein job-hopped. "I had tons of terrible jobs," he says. "But I learned what I was good at and what I liked to do, and that often what you are good at and what you like to do aren't the same thing." Some of the better stops included a sales position at Parametric Technology Corp., where he worked under Mark Cranney, a Silicon Valley veteran and guru; running a start-up in L.A.; and as senior vice president at a division of Virgin.
In 2010, Bernstein cofounded North Social, recognizing early that there was no easy way for small and medium businesses to market on social-media sites such as Facebook. Its first application went live in May of that year, and by November investors were lining up. In February 2011, Vocus acquired the company, and as part of the deal Bernstein remained with North Social for two years to continue to develop the business. He left in September 2013.
Last summer Bernstein took two months off. He dropped his two children, Molly, 12, and Angus, 9, at a summer camp run by a relative in Michigan, and he and his wife chartered a boat and sailed around the Virgin Islands. Then he went to Cape Cod with his kids to meet up with college friends. It was his first significant break from work since the day he walked away from football.
When he did stop playing, he also stopped watching, a decision that he believes was crucial to his success. Shortly after the Falcons released him in 2000, he tried to watch a game, but it was too stressful. "I would see someone playing who I knew I was better than, and it would destroy me inside," he says. "So, I stopped." About 10 years passed before he watched an NFL game again. "Honestly, when I am watching games now, my hands start shaking and I think, Damn, I want to get out there. Just one series, one 14-play drive."
The minute the game is off, however, those feelings subside. Recently he purchased three buildings in distressed areas of Oakland and turned them into technology incubator spaces, a project called InOak. He may invest in the companies that reside there; he may just mentor their founders. "I believe in the social reward of helping convert neighborhoods and building companies and bringing jobs to the area that will help improve Oakland," he says.
Making money is secondary, he adds, which is the kind of outlook one has when he's made it. "In football my goal was to have a 10-year career, the benchmark of manliness," he says. "Some players look back and say, 'I wish I could have played longer.' I look back and think that I got out with enough fuel left in my body to accomplish a lot more."
Bernstein's annual salary at his first tech industry job in 2000.
Amount Vocus paid for Bernstein's company, North Social, in 2011.