The Matt King Show – Episode 016: Anthony Tolliver | 13 Years in the NBA… But This Is What Actually Built Wealth

Release Date: June 11, 2025
Host: Matt King (GoBundance)
Guest: Anthony Tolliver

Episode Overview

This episode dives into the remarkable journey of Anthony Tolliver, a 13-year NBA veteran who played for 11 teams and got cut nine times, but whose sustainable wealth and legacy were forged off the court. The conversation explores how his upbringing, mindset, investment strategy, and relentless work ethic led to a diversified business portfolio and a purposeful life after sports. The dialogue is honest, practical, and filled with memorable lessons about transitioning identity, leadership, generational wealth, and the power of networks like GoBundance.

Key Discussion Points & Insights

1. Early Adversity and Work Ethic

• Resilience in the Face of Rejection
  • Tolliver was cut nine times from NBA teams, but each setback fueled his resolve:

    "There's doubts every single time. Yeah, whenever somebody says you're not good enough...This might be my last opportunity." (00:04)

• Family as Foundation
  • Tolliver attributes his work ethic to both parents. His mother, a teacher, juggled multiple jobs and introduced him to real estate by keeping and renting out her first home (02:54).

    "She kept that house. Instead of selling it...we go across town and collect money from the people that live in that house...So it was normal. It’s like, yes, of course, you own other houses besides your own and you collect money from them." (02:54)

  • He saw relentless hustle in both parents, shaping his view on “working at something I want to do.” (04:21)

2. Basketball as a Tool—Not an Identity

• From a young age, basketball was a means to an end, not who he was:

  "Basketball was never my identity...I looked at it as a tool. I'm going to use it to my, me and my family's advantage for as long as I can. And when it stops, that's okay." (00:24, 65:08)

• He realized in college that professional basketball could create “generational money,” shifting his focus from the sport itself to the wealth-building opportunities it offered (05:01).

3. Breaking Into and Sticking in the NBA

• The Challenge of Making It and Staying

  • Tolliver recounts the anxiety of getting cut, and his first NBA camp with the Cavaliers, which included being matched up with LeBron James (08:25):

    "They have me matching up against LeBron. Why? Because we're the same size. I'm like, but we're not the same at all." (08:51)

  • His persistence paid off:

    "At the eyeglasses store...I just had a moment. I was like, holy crap, I just made the team. Now it was short lived. I got cut the next day...but at that point I made the team. So technically I made the NBA. So technically you can't tell me nothing." (11:06–11:32)

• Role Player and Relentlessness

  • Tolliver recognized he wasn’t the best athlete or shooter, but could be “relentless,” quickly learn systems, and fill gaps on any team.

    "What can I be? I can be relentless. I can be a hard worker. I can be the guy who doesn't mess up...that became my calling card." (14:56)

4. Transferring the Athlete’s Mindset to Business

• Forever a Student

  "I'm a forever learner. I'm going to be 80 years old trying to solve problems." (19:34)

  • Tolliver’s curiosity led him to research and invest in over 50 companies across real estate, startups, and private equity (59:51).

• Knowing Roles & Partnership

  "I knew I wasn't the CEO of any of these businesses. I need a great person who's going to be the operator...I just built my entire portfolio and entire business structure on partnership and role playing." (20:27, 21:16)

• Problem Solving

  "Solve big problems, typically, it's going to be bigger paydays...I just try to solve problems, you know, especially in business." (81:01, 82:19)

5. Leadership by Example (Sports, Business, and Parenting)

• Tolliver’s most profound leadership lessons came from Tim Duncan during his time with the San Antonio Spurs:

  "One of the best leaders I've ever seen. I'm not sure if he ever said five words to me...but it was clear. The expectation was clear as day." (33:05–34:02)
  "Leadership is way more than just words. It's walking the walk more than it's talking the talk." (36:39)

• He has seen the opposite: vocal but uninvolved leaders get ignored (37:12).

• Parenting Parallel

  "If I treat my wife and kids with respect, even if I never say treat others with respect, they're gonna pick that up." (38:04)

• On Empathy

  "You don't know what to...His wife might have just had a miscarriage...I went back two weeks after my mom passed. I'm on the court trying to perform, and I can't make a shot...So there's just a level of empathy that I have for guys who are struggling on the court, because I literally give them the benefit of the doubt every single time. And it's not just them. It's people." (66:58–68:11)

6. Transitioning Out of the NBA

• Identity Beyond the Game

  "My identity was never the NBA...I was always Anthony Tolliver who happened to play in the NBA, but you weren't an NBA player named Anthony Tolliver." (64:04)

  • He made the post-NBA transition easier by building his portfolio and identity on business interests outside basketball from year one.
  • He encourages athletes to treat money as a tool, not an obsession (65:08).

7. Building and Sustaining Wealth: Principles and Stories

• Diversification

  "If you're all in on one thing, well, then you're subject to that one thing. And that's where, you know, the diversification is very important." (79:52)

  • Covid destroyed one business investment but multiplied returns in another (Big Blanket), reinforcing the need to spread risk (77:00–79:39).

• Network Value (GoBundance & Beyond)

  "There's value in brain trusts...the value of the loose ties is worth every penny that we pay." (71:22, 72:25, 74:37)

8. Legacy, Generational Wealth & Social Responsibility

• Tolliver is passionate about building a legacy for his children and broader community, especially as part of the first African American generation with real access to wealth-building:

  "My dad was 19 when Martin Luther King got killed...he did not have the opportunity to build wealth. So...I'm part of the first generations of African Americans that...I don't feel like there's any limits on what I can go do for my family. So there's a certain level of responsibility that I feel..." (85:04–86:19)

• For Tolliver, money is just one part of generational wealth; the bigger legacy is the example and opportunities left behind (84:55–88:41).

Memorable Quotes & Moments (With Timestamps)

• On Getting Cut 9 Times and Resilience:

  "There's doubts every single time...whenever somebody says you're not good enough...this might be my last opportunity." (00:04)

• Business, Not Sports, Built Wealth:

  "It’s not about the money...it’s about the legacy...a foundation for my family, for my kids and their kids and their kids to be able to build upon." (00:45, 84:23)

• Turning Lessons Into Legacy:

  "The real game wasn't on the court. It was who you become when the lights go off." (01:08)

• Tim Duncan's Silent Leadership:

  "Not sure if he ever said five words to me...but it was clear...the expectation was clear as day." (33:05–34:02)
  "Leadership is way more than just words. It's walking the walk more than it's talking the talk." (36:39)

• On Being Starstruck:

  "Every day...I was StarStruck by seeing LeBron. Even though he's literally my age." (40:30)
  "Meeting Michael Jordan for the first time, I was just like, what the heck? Like, this is crazy, right? This is awesome. But there's very few people I've met that had like an aura. And he's one of them, a true aura around that man." (41:36–42:54)

• On Kobe Bryant:

  "Relentlessness. I compare him to a lion...he would sacrifice at all for the win." (45:28)
  "His work ethic in basketball has influenced probably more business than most any...business influencer." (46:16)

• On Empathy and Life Off the Court:

  "Whenever I...was driving and...there's this car that just like, saw me, sped up...instead of being like, yeah...my first thought was not like, f you. It was like, man, that guy might be having a bad day. And what was awesome is my daughter got a chance to see that..." (68:10–69:22)

• On Not Getting Lost in the 'Best' Player Arguments:

  "If you say Michael would only be a DeMaro DeRozan in today's game. I'm like, oh my gosh, what a disrespect...you're discounting both of their greatnesses." (54:17–54:23)
  "Doesn't matter, because there's no right or wrong answer." (54:44–54:48)

• On Getting into Business Transition:

  "It was something that I never really made a transition because from year one, I began, I guess, my journey as a businessman, as a real estate investor..." (59:51)

• On GoBundance:

  "The value of the loose ties is worth every penny that we pay...it's just, it became such a cool way to expand my network." (72:11, 73:13)

• On Building Generational Wealth and Responsibility:

  "For me, especially being African American...I'm part of one of the first generations that...I don't feel like there's any limits on what I can go do for my family. So there's a certain level of responsibility that I feel that I have." (85:04–86:23)

Timestamps for Key Segments

• Work Ethic & Family Influence: 00:45–04:57
• Making and Sticking in the NBA: 06:34–12:13
• Starstruck Moments & Meeting Legends: 40:30–46:16
• Business Philosophy & Diversification: 59:51–80:31
• Lessons from Tim Duncan & Leadership: 32:47–37:48
• Empathy, Identity, and Life After Sports: 64:04–68:10
• GoBundance Value & Networking: 70:01–74:37
• On Legacy & Wealth—Social Impact: 84:55–88:41

Final Takeaways

• Legacy over Income: Tolliver repeatedly emphasizes that wealth exists to create a foundation for future generations—money is a tool, not the final prize.
• Stay Humble and Curious: Whether in basketball or business, embracing a “forever learner” mindset pays dividends.
• Diversify and Adapt: No career or investment is guaranteed, and quick pivots plus diversified interests can turn catastrophe into opportunity.
• Surround Yourself with Greatness: The power of networks and learning from the best (in sports and business) is unmatched.
• Empathy and Perspective: Carrying grace toward others, whether on the court, at home, or in business, makes one a better leader and creates a richer legacy.

"I just try to solve problems...to build a foundation for my family, for my kids and their kids and their kids to be able to build upon." — Anthony Tolliver (84:23)