Skip to main content

Michael Redd reveals the other thing he learned from Ray Allen and Kobe Bryant outside basketball

Michael Redd has already achieved a lot in business, but he still lives by the lessons he learned from Ray Allen and Kobe Bryant
Michael Redd on what he learned from Ray Allen and Kobe Bryant

Michael Redd, Ray Allen, and Kobe Bryant

Making smart investments is something not all NBA stars are able to do after their career. We’ve seen an array of them blow their fortune and go broke. Fortunately for former Milwaukee Bucks star Michael Redd, growing his money is one of his other skills besides basketball.

Learning from successful people

Redd spent his childhood years in Columbus, Ohio. And even though basketball is his passion, Redd always envisioned himself becoming a successful businessman. To do so, he knew right away that he would need to be around successful people and take a leaf from their book. And that’s exactly what he did during his 12-year NBA career.

Redd’s mentality has always been “you don’t make money without losing money.” Therefore, he is well aware that there will always be risks along the way. So to limit the setbacks, Redd listened to the advice of perennial NBA superstars who already have a stellar resume in growing their fortune, specifically Ray Allen and Kobe Bryant.

“The main thing I’ve focused on in my investment career is, how can I keep money and put myself around people who are smarter than me and learn from them? I did that in my playing career,” Redd told Boardroom. “I learned so much from Ray Allen. He was a mentor of mine when I came into the NBA. I learned from the great Kobe Bryant, who became a brother to me. We worked out every day during our Olympic time together.”

“I always try and surround myself with people who are better than me,” he continued. “I think it speaks a lot to someone’s character when they’re always the top dog in the room. You want to surround yourself with people who are better than you, smarter than you, so you can raise your level. Those stories are out there, but not enough stories are out there about what positives are happening with guys that transition.”

Living by it

Like a true good businessman, Redd also knew that time is of the essence. So after learning the trade, the one-time NBA All-Star decided that he’d start investing his money sooner rather than later.

Scroll to Continue

Recommended Articles

In 2008, while still playing in the league, Redd tested the waters and founded The Wave, a non-profit organization centered on promoting entrepreneurship and economic development. Four years later, injuries prompted him to end his career. But not his business.

A year after officially retiring from the NBA, Redd focused on amplifying his business by expanding The Wave and turning it into The Wave Venture Innovation Group. Around the time, he also co-founded TwentyTwo Ventures, where he serves as the C.E.O. to this day. On top of that, he also became a venture partner at Third Wave Digital, Israeli investment company OurCrowd, and the ADvantage Sports Tech Fund, a corporation supported by the family of Adidas founder Adi Dassler.

Indeed, Redd has already achieved a lot, but the lessons he learned from Allen and Bryant did not only benefit him in the formative years of his business ventures. Instead of slowing down a bit and just watching his money grow, Redd continued to live by it, something his ADvantage Sports co-partner Jeremy Pressman, saw firsthand.

"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 told Bleacher Report in 2020. "I think he brings that to just about everything he does in life, including venture investing."

Humility is key

To date, Redd has invested his money in over 100 companies, mostly in the sports technology and media industries. He also keeps himself busy hosting the “Betting On Yourself” podcast, where he invites successful businessmen to inspire up-and-coming entrepreneurs by talking about how they were able to reach the top.

While Redd indeed has a lot to share in the podcast, he already once revealed the key to success. And according to him, it all starts with humility.

"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 told Bleacher Report. "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.”

If we come to think of it, many players see the NBA as the peak of their dreams. But for an ambitious man like Michael Redd, it was just the beginning, the starting point of a long journey where the opportunities are endless.

Laker center Shaquille O'Neal

“He bought a new Rolex for every single guy on the team” — former Laker Mark Madsen reveals Shaquille O'Neal's generosity

Just when Madsen thought Shaq buying him a car would finish the shopping spree, O'Neal decided to buy every Laker a brand new Rollie.

LeBron James admits he started taking care of his body pretty late in his career

LeBron shares his top three players of all time: "This is tough!"

Back in 2014, LeBron had a lot of trouble picking just three guys.


Tracy McGrady calls out Rudy Gobert: "What the f**k are you doing in the off-season?"

T-Mac just can comprehend Gobert hasn't added any moves to his offensive game over the years.

Chicago Bulls guard Michael Jordan

Michael Jordan once went from judging a dunk contest to destroying the winner in street clothes

MJ's future teammate Jo Jo English was one of the first people to learn an important lesson - never talk trash to Black Jesus.

Chris Bosh

Chris Bosh promotes healthy eating that keeps him in prime shape despite being retired — “It gives me the energy I need to go forward”

Fully aware his NBA days are behind him, Chris Bosh explained why he still eats healthy and works out every day.

Chicago Bulls guard Michael Jordan goes up against Utah Jazz player Bryon Russell

“There's no 'Jordan rules' when you play 1-on-1“ — Bryon Russell claims Michael Jordan 'chickened out' from a 1-on-1 challenge

After being called out by Michael Jordan during his Hall of Fame speech, Bryon Russell hit back and challenged MJ to a 1-on-1 game. According to Russell, Jordan "chickened out."

Lower Merion High School senior Kobe Bryant

Kobe Bryant had a “kill list” of 56 players who were ranked above him in high school

Trust Kobe Bryant to make any rankings lists (that has him as an underdog) look foolish