Michael Redd recalls the feeling when his Milwaukee Bucks advanced to the Eastern Conference Finals during his rookie season. Though he sat behind the team's star at the time, Ray Allen, he couldn't help but think of his time and moments to come in the future. "'Oh, this is normal. It's the Eastern Conference Finals. Wow, great start," Redd said during a recent telephone call.

Redd, taken in the second round of the 2000 draft out of Ohio State, eventually blossomed into a franchise cornerstone in Milwaukee, making an All-Star team in 2004 and, four years later, claiming an Olympic gold medal in Beijing. But he never again qualified for the conference finals before twice-torn ACL and MCL injuries in his left knee ended his playing days after 12 years in the NBA.

Still, he entered each season with renewed optimism, a trait that is aiding Redd in his new line of work as a venture partner. "I've used a lot of optimism bias that I had when I played toward now failed opportunities or a loss in business," Redd said. "Staying positive. Grit, resiliency, tenacity—those elements, those characteristics you have to have in investing as well as in business."

Redd recently joined ADvantage Sports Tech Fund, a firm backed by the family of Adidas founder, Adi Dassler, and Israeli investment group OurCrowd with a goal to source and advance new sports analytics, technologies and development. Jeremy Pressman, a partner at ADvantage, described Redd as a natural leader. He recalled an instance when one of their portfolio companies sought information on breaking into the U.S. market. Redd quickly put together a brief pitch. "We're talking from requests to action was a matter of weeks, two weeks, if that, to getting meetings with key decision-makers or in this case the relevant sports teams and stakeholders," Pressman said.

"He's been quite actively involved with business development and marketing activities; kind of right off the bat, he hit the ground running with that same energy and attention that he brought as an athlete on the court," Pressman said. "I think he brings that to just about everything he does in life, including venture investing."

For Redd, the decision wasn't merely about finding a financial opportunity but connecting with his life as an athlete.

"Sometimes I'm like, Man, I'm about five years late, 10 years late—with all the advancement, with analytics, the merger of sports and data, the convergence of wellness and athletics," Redd said. "I had two ACLs that kind of derailed my career, but where technology is now 10 years later, six years later, I think you're going to see more Tom Bradys and more Vince Carters in the years to come because we have the technology and the data and the metrics to help have these careers be prolonged."

ADvantage is just the latest financial move for Redd, whose investment career is more than a decade old.

In 2008, when Redd was still playing (and winning an Olympic gold medal), he started The Wave, a non-profit group focused on fostering entrepreneurship and economic development. (After he retired, Redd founded The Wave Venture Innovation Group, which operated largely in the tech and media sectors, and 22 Ventures, a firm dedicated to support entrepreneurs and company leaders.)

"I was locked in, like most athletes are, but it wasn't until mortality begins to set in and you can kind of see the end coming—which I still believe it came prematurely for me—but you know, at some point, it's going to end," Redd said. "So, basketball was not my identity. It was something that I did. I enjoyed it. I loved it with all my heart, but that wasn't the extent of what I could be and who I could become for the next 50 years after basketball. … There was more to me than just playing ball. And I think most athletes are recognizing that now."

After retiring from the NBA in 2013, Redd returned to Columbus, Ohio, and re-ingrained himself with the city's community.

He decompressed, played golf, travelled and spent time with his family. In 2014, Redd expanded his portfolio when he was named a partner by NCT Ventures, a Columbus-based company that provides financial backing for entrepreneurs, largely in the Midwest.

"Transitioning is part of life," Redd said of moving beyond his basketball career. "Change is a part of life, but it's the adjustment to change and the adjustment to transition, which is the challenging part. If your identity is wrapped up in what you do, it's going to be really ultra-hard for most athletes to end, because the spotlight is not as bright as it was compared to when you were playing, and if that's the case, you have a hard time after retirement. … There's nothing that can replace the fourth quarter of the playoffs or the championship or the gold medal ... but you can channel it into other things, and that competitive nature, those skill sets that you had when you played ... are applicable to everything after basketball as well."

He thought about what he enjoys doing and how to channel that.

"I had a curiosity of what was next, particularly with sports tech, but overall a passion for entrepreneurs. After all, us as young athletes are entrepreneurial in our mindsets when we leave school early and be risk-takers on our own careers."

He first sought to learn everything he could in angel investing.

"You're a gold medalist in your professional sport, but you're a junior executive or you have a junior perspective when it comes to a different space," Redd said. "Humility is key as you transition. Just because you were an expert as a professional in one space, it doesn't mean you are that in another space. Putting yourself around people who are smarter than you is important. But the transition psychologically, it's a great challenge for a lot of people because those skill sets that you had, they never go away. The body gets older, but your mind and your skill sets are still there."

Redd has contributed to more than 85 companies, the bulk in media and technology. "I just really basically had a number of things thrown at me in real estate, different other opportunities," he said "I really found more of a passion in the world that I'm in now. So, really got my feet wet with the local venture capital firm here in town and learned a lot. Still learning a lot six years later."

Part of that learning curve is coming to terms with the notion that losses are a cost of doing business. "Some of the failures I've had in business or investments, it's been, 'OK, that didn't work. What's next? How do I pivot?'" Redd said. "Compared to if you have a one-game winner-take-all game in the playoffs, there is no tomorrow."

A little more than a decade ago, Sports Illustrated estimated that 60 percent of former NBA players are broke within five years of retirement. Redd and others are part of a wave of former athletes who are taking ownership and autonomy in their post-playing days after leveraging opportunities to learn the corporate world while playing. Among them, Junior Bridgeman, who played for 12 seasons in the NBA, owned more than 100 Wendy's and Chili's restaurants before becoming president and CEO of Bridgeman Foods, Inc., and Jamal Mashburn, also a 12-year NBA veteran, owns restaurant franchises and car dealerships all around Kentucky.

"There's all kinds of great stories," Redd said. "Now it's become more of a thing for athletes to begin to think of themselves as a brand. So, by no means am I a trailblazer; I've been more stealth and discreet about what I've done over the last six, seven years. But I'm so proud to see guys now take themselves more seriously—more than just the endorser of a company. You may have shares and upside, you may have equity, you may have ownership."

Currently, Redd is dividing his time between being a janitor, cook, husband, teacher and principal while at home with his wife and two children during the pandemic.

"It's been interesting on a lot of levels because we've never been home—and I think a lot of people can attest to this—we've never been home this long consistently day by day, night by night, never ever," Redd said. "So it's been really interesting with them. They have not destroyed each other, which is a good thing. They are somewhat having fun with each other. We're trying to be creative with them by playing with them and having fun and getting outside. But it's been unique discovering their transition in life. Our kids are getting older now, and there's a perspective now that I have at where they are compared to where they were as babies and it's been fun. We usually, my wife and I usually observe them anyway, but we've had more time to observe their personalities or tendencies."

Redd hopes that his ventures can be part of the healing process once the country starts to emerge from the coronavirus pandemic.

"Everything is uncertain right now, and I think it's a matter of everyone—angel investors—it's really a new reality that's upon us," he said. "There is focus on pain right now; figuring out the pain and how to make people's lives better is going to be a new focus. That's always been the focus of life and innovation and creativity. But even more so now."

Jonathan Abrams is a senior writer for B/R Mag. A former staff writer at Grantland and sports reporter at the New York Times and Los Angeles Times, Abrams is also the bestselling author of All the Pieces Matter: The Inside Story of The Wire—available right here, right now. Follow him on Twitter, @jpdabrams.