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Michael Redd: Lessons Learned in a Life After Basketball

The Milwaukee Bucks legend always envisioned himself as a businessman. Now, living that reality, his greatest investment is in people.

As a young kid growing up on the West Side of Columbus, OH, Michael Redd always saw himself one day being a businessman. Now, aged 42, those childhood visions are a reality.

Drafted 43rd overall in the 2000 NBA Draft by the Milwaukee Bucks, Redd went on to play 11 of his 12-year career in Milwaukee, where he averaged 20 points, 4 rebounds, and 2.3 assists across 578 games (427 starts). He spent the 2011-12 campaign with the Phoenix Suns before announcing his retirement in 2013. Afterward, he founded The Wave Venture Innovation Group. He then co-founded TwentyTwo, where he serves as Chairman and has invested in over 100 companies largely in the technology and media sectors.

He is additionally a venture partner at Third Wave Digital and the Advantage Sports Tech Fund as well as the host of the “Betting On Yourself” podcast, where he speaks with successful entrepreneurs and athletes on taking success into their own hands.

In a Q-&-A with Boardroom, Redd discussed the fondest memories and lessons learned during his NBA career, the role veterans played in his success on and off the court, and what tools he’s utilized from his playing days to find success in his second act.

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CHRIS CASON: The Bucks welcomed you back as they received their championship rings to begin the season. With the things you accomplished with that organization and the way you poured into the Milwaukee community, what was it like to be a part of that celebration?

MICHAEL REDD: It was amazing. I was there for 11 years and many nights and seasons, we hoped that we had the success that they experienced last season. I re-signed back with the Bucks when I could’ve been a free agent, for that very reason — to win a championship in Milwaukee. I told [reigning Finals MVP] Giannis [Antetokounmpo] how proud I was of him for staying and seeing it through because you don’t see that nowadays with guys going to different teams.

Those guys have been in Milwaukee for a long time, and I’m so happy for the owners, [former Bucks owner] Senator Kohl, and the legacy that he left with the Bucks. It was an incredible and emotional night across the board. A lot of the people that worked in the organization when I was there are still there. People were crying and just really overjoyed. The fans of Milwaukee have been great for a long time, and they deserve it. 

CC: What would you say was the most memorable moment in your career, and the best lesson you learned?

MR: The most memorable moment of my athletic career was the Olympic team in 2008, the Redeem Team. It was an amazing experience. To win a gold medal, represent our country, was amazing, and to do it with the best players in the world was surreal. To this day, I pinch myself, like “Did I really play for that team?”

There are a ton of lessons to take away from my experience. I think the relationships are the biggest thing I took away more than anything. There’s such a bond amongst NBA, NFL, NHL players, and guys who play sports that you can never forget. The bus rides, locker room conversations, the jokes, it’s something that’s hard to replicate. The NBA is a fraternity, and once you join that fraternity, you’re in there for life. We all know what each [other] is going through. It’s a special group of people to be a part of. The aspect of teamwork is something I’ve taken away and applied throughout my life. 

CC: In sports, we often hear more about the athletes who have financial troubles post-career than those who find success. Did those stories resonate with you while you were playing?

MR: It’s interesting because everyone, whether you play sports or don’t, we all make bad investments, whether it be in people or companies. I think it becomes more glorified when an athlete has done it, but there are guys who have never played sports in their life who have made bad investments.

You don’t make money without losing money, and that’s just the reality. Learning what not to do has been a key for me. Not wanting to be a statistic or boxed in those numbers. 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. 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. 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. 

It’s hard to transition from being a senior level in one space in life to being a junior level, or lower than that. When you retire, you’re leaving something you’ve done your entire life. There’s a whole lot of psychological rewiring that has to happen for a lot of us. There are a lot of nuances to retiring. We know going into it that professional sports is finite, but we never really are prepared psychologically. There are a lot of programs out there to help guys transition, but from a psychological standpoint, you have to be able to transition as well. 

CC: You came into the league when veterans were grown men and had a lot of life experience. How pivotal were those vets to your career and do you see players like that still being an asset now?

MR: It was everything. Veterans shape your career, and I still believe that. I had a great group of guys that held me accountable on and off the court. They showed me the ropes with family life, how to save your money, things like reading The Wall Street Journal. There’s something to be said about having life skills and mentors that can help shape the course of your career. The league has definitely gotten younger, but I think more than anything, there were things you could learn about life in the locker room when you have guys in their 30s and late 20s — guys who are married, who’ve been in the league for 10-plus years. You can learn so much from those guys, and it can help your career compared to just having a young group. 

It’s interesting because the young group is exciting to watch on the court, but how are those guys developing off the court? Who is helping mentor them? I had guys who had been through wars in the [NBA] Finals. They had been in playoff situations, had kids, were married. They pulled me out of the city to live out in the suburbs. As a young guy, who does that? All of the veterans told me I didn’t need to be in the city. I needed to live out there where there was peace and quiet, and I could focus on my craft and my life. I will never forget those guys because they shaped the course of my career and I tried to pass that down to the young guys before I retired. 

CC: Did you know investing was always what you wanted to do after you were done playing? 

MR: It’s interesting because there are a lot of lanes in the world I’m in now, but ever since high school, I always wanted to be in business. I had a knack for it, as far as wanting to be a part of it [and] having a suit and a briefcase. The limited exposure that I had to Wall Street and any kind of business was appealing to me. When I got to the NBA, the narrative has always been about how much the guys that play make. I was intrigued by the guys that were paying us and what they did. I always wondered, How do you buy an NBA franchise? The NBA in the 2000s was shifting more towards venture, private equity, hedge fund, and tech guys buying these franchises. That was eye-opening to me, and I said, ‘That’s the world I want to be in [in] some capacity.’ 

All the more, there’s a lack of diversity in those worlds. I wanted to somehow leverage what I did in the NBA to get into the world that I’m in now. You have a better chance of being struck by lightning than playing in the NBA and transitioning to this world. It’s a rare thing, and I’m humbled by these opportunities and the doors that have been opened for me as well. 

CC: In just looking at your portfolio, some of the things you’ve done with 22 Ventures, there is a theme of assisting, teaching and accessibility. Why are those principles so important to you?

MR: It stems back to a lot of the mentors I’ve had in my life. They were more concerned about me than what I produced on the court. I grew up in a Christian household — Biblical principles that are interwoven into my belief system and principles as an investor and a business leader. I’ve always cared about people. We want to invest in people to grow companies, and that’s legit. We certainly want to be able to see someone become healthier as a person and as they become healthier as a person — mind, soul, body, and spirit — we believe that the product and business will be healthy. 

That’s an organic and intentional play because, far too often, the person is overlooked when it comes to business transactions. I care more about the personal aspect than I do about the product because the product will be a secondary consequence of the health of the CEO and leader. 

CC: When you see the guys now who are realizing the power of their individual brands and leveraging that while playing, how does that make you feel?

MR: I’m really proud that the current players have become more business savvy. I think social media has accelerated that over the last 10, 15 years. Now guys are thinking of themselves as entities and brands, and how do I leverage that brand to ownership? That was my thinking 10-plus years ago. I’m seeing more guys now that are understanding their worth. They realize they can help a business and company by having equity in the company, and that’s been the wave that’s been happening. LeBron [James] has done an incredible job, and there are several others — Carmelo [Anthony], Kevin Durant. Kobe [Bryant] was doing it, God rest his soul. The best way to extend your brand beyond basketball is ownership. It’s better to have that equity than just an endorsement check. 

CC: I know you’re approached by current players on advice in getting into the VC world. What do you tell them?

MR: First, be the best basketball player you can be. That may sound counter to what we’re talking about, but the greater you become as a player, the greater the success of the team, which leads to better visibility. That gives you greater exposure to whatever you want to engage yourself into post-[playing] career. Your game opens doors. Your abilities and what you accomplish on the court, that single focus of being a great basketball player allows you the freedom to pick different lanes and different opportunities you want to engage in post-career. 

Secondly, begin to study the different lanes you want to go into. Study venture, hedge funds, real estate, angel investing, and what those different lanes represent. In your downtime, immerse yourself in studying those worlds. 

Also, begin to collect cards. I say cards, but now you have IG and all these different platforms. When you look at our game, there’s so much interest from business leaders from around the world, and there’s really not anyone you can’t get access to while you’re playing. Take advantage of that and leverage that. There are business people that are fans who are clamoring to meet these players, and when they meet them, that can spark a relationship. 

CC: What are some of your personal and professional goals this year?

MR: Personally, to continue to grow as a person, a husband, and a father. To continue to grow in my faith. Those are foundations to my continued evolving. From a business standpoint, continuing to grow infrastructure. I’m a team-orientated guy and I believe in tools.

I told our CEO, John Weaver, that I want to continue to help him get help. I want to make sure he has the right people and the right infrastructure to continue to grow and expand. I’m always looking to bring on talented people to be a part of what we’re doing. 

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