BONUS* Arik Armstead on Investing Beyond Football

Summary

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Podcast Summary

Money And Wealth with John Hope Bryant

Episode: BONUS* Arik Armstead on Investing Beyond Football
Date: May 8, 2026
Host: John Hope Bryant (Black Effect Podcast Network/iHeartPodcasts)
Guest: Arik Armstead, NFL Pro (Jacksonville Jaguars, formerly San Francisco 49ers)

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Overview of Episode’s Main Theme

In this bonus episode, John Hope Bryant welcomes NFL player Arik Armstead to discuss investing and wealth-building strategies beyond a football career. The conversation centers on Armstead’s recent involvement as an early investor in the new Pro Flag Football League, highlighting the importance of relationship-building, proactive investment, and legacy planning. The episode serves as a practical guide and inspiration for listeners—especially from the Black community—on leveraging opportunities and partnerships to build generational wealth outside of traditional careers.

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Key Discussion Points & Insights

1. Introduction: Arik Armstead’s Off-Field Ambitions

• [02:49] John Hope Bryant introduces Arik Armstead as a living legend, NFL star, Walter Payton Man of the Year, and now an investor.
• Focus is set on Armstead's endeavors off the football field, specifically his investments with long-term impact for his family and community.

2. Investing in the Pro Flag Football League

• [03:42-06:18]
  • Arik announces his landmark investment in the newly announced Pro Flag Football League—a league developed in partnership with Tomorrow Sports and the NFL.
  • This is his largest private equity commitment to date.
  • Armstead highlights the sport’s growing global reach, predicting flag football’s rise in popularity and inclusion.
  • He links this investment opportunity to years of networking, relationship-building, and providing value to others:

    "Years and years prior, things that I invested in, in time that I spent in relationships, I built… fast forwarded 8 years, provide[d] an opportunity to invest…” (Arik Armstead, 06:18)

3. The Power of Relationships and Timing

• [06:20-08:12]
  • Armstead underscores the role his connection with Byron Dieter (Bessemer Capital) played in getting early access to the deal.
  • He stresses being present, authentic, and value-driven in networking:

    "Being in the right rooms… adding value where opportunities were presented… reputation and relationship building and all those things presented an opportunity years and years later that not everyone was afforded to." (Arik Armstead, 07:47)

  • Notes that the investment is “very much a legacy investment,” especially meaningful as the league launches with female athletes at the forefront.

4. Creating Legacy and Equity

• [08:10-08:20]
  • Armstead points out his desire to leave a legacy for his children, especially as the league gives prominence to women.
  • This moment is both personal and forward-thinking.

5. Deal Structure & Players’ Participation

• [08:20-11:00]

  • Bryant asks for non-confidential details about the deal:

    • Tomorrow Sports will operate the league, with firms like Bessemer, Silver Lake, and others as principal investors.
    • Curtis Martin, former NFL great, and his private equity firm Ludus helped ensure player involvement.
    • Convincing the NFL (Roger Goodell) to open opportunities for players to invest.

  • Armstead emphasizes the value of being seen as seriously interested in business, not just appearance at events.

    “On the NFL side…it was awesome, you know, working with Curtis Martin and his private equity firm Ludus…players need to be involved… I got the call to be one of those players… and that goes back to… relationship building and being in the right place at the right time and showing up and presenting yourself at the right time.” (Arik Armstead, 09:53-10:38)

6. The Pre-IPO Opportunity and Mindset

• [11:00-11:54]

  • Bryant breaks down the concept: Armstead’s investment is equivalent to a “pre-IPO environment”—exclusive, early-access investing.

  • Stresses the critical importance of surrounding oneself with enterprising and successful people:

    "If you hang around nine broke people, you'll be the tenth… Right rooms, right places, right spaces, talking about the right things and the right mindset." (John Hope Bryant, 11:00)

  • “Capital stack” is defined as the layers of financial investment in such deals.

7. Memorable, Authentic Exchange

• [11:54-12:00]
  • Light-hearted banter about NFL Commissioner Roger Goodell’s reputation and personality:

    “You know what they say about redheads. They might as well… be Black.” (Arik Armstead, 11:54)

  • Bryant responds in kind, preserving the good-natured, direct tone of the show.

8. Closing Messages: Role Modeling and Legacy

• [12:00-12:41]

  • Bryant thanks Armstead for embodying the principles discussed: investing intelligently, building wealth beyond salary, and paving a generational path.

    “Building wealth in your sleep, things like this, investment in flag football. Eric, thanks for being a role model and living what you say.” (John Hope Bryant, 12:37)

  • Armstead closes with a humble commitment:

    "Trying to keep leading the way." (Arik Armstead, 12:41)

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Notable Quotes & Memorable Moments

• On Relationships Leading to Wealth:

  "Years and years prior, things that I invested in, in time that I spent in relationships, I built… fast forwarded 8 years, provide[d] an opportunity to invest…” (Arik Armstead, 06:18)

• On Mindset and Association:

  "If you hang around nine broke people, you'll be the tenth…"
  "Right rooms, right places, right spaces, talking about the right things and the right mindset." (John Hope Bryant, 11:00)

• On Building Legacy:

  "This investment, I feel, is very much a legacy investment. I have two daughters and I have a son as well, but I have two daughters. And this. The league is launching with Women's First." (Arik Armstead, 08:10)

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Key Timestamps

• 02:49: Introduction—Arik Armstead, his legacy, and hunger for opportunity
• 03:42: Armstead describes his investment in the Pro Flag Football League
• 06:20: Relationships’ impact on investment access
• 08:10: Significance for daughters and the league’s focus on women
• 09:14: Deal structure, major backers—Tomorrow Sports, Bessemer, Silver Lake
• 09:54: Players’ involvement enabled by Curtis Martin and Ludus
• 11:00: Lessons on mindset, pre-IPO deals, and capital stacking
• 11:54: Banter about Roger Goodell
• 12:37: Closing recognition for Armstead’s example

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Conclusion

This energizing, straightforward conversation illustrates how professional athletes—and anyone—can parlay connections, reputation, and strategic thinking into wealth-building ventures that last generations. Armstead’s path shows that real equity and legacy come from active participation, authentic networking, and never being satisfied with just playing on the field. Bryant’s warm, candid hosting keeps the episode practical, challenging, and empowering.

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For more episodes: Listen to Money and Wealth with John Hope Bryant on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

Transcript

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[John Hope Bryant]

welcome to Money and wealth with John Hope Bryant, a production of the Black Effect Podcast Network and iheartradio Foreign.

[Podcast Host]

O'.

[John Hope Bryant]

Brien. And this is the Money and Wealth podcast episode season three on iHeartRadio and Black Effect Network. We have with us Eric Armstead, who is a NFL pro and in some ways a working living legend. And he's won the Walter Payton man of the Year award. He's a first round draft pick for the San Francisco 49ers. He's now with the Jacksonville Jaguars. You know him because he always rubs his belly after every good play. He's always hungry, but he's hungry not just on the field. This is a bonus episode talking about what he does off the field to expand his field of play. The investments he makes, not just the life he lives. Eric, tell us about unique and important investments you made that you think might have legacy and lineage tied to it.

[Eric Armstead]

Yeah, thank you for the intro. And just recently I was fortunate enough to invest in the new, just announced last week, Pro Flag Football League in partnership with Tomorrow Sports and the NFL. And although it's a cool, exciting opportunity and one that right now I haven't really made too often, this is probably the largest investment I've made into a singular private equity deal to date. But really excited about the opportunity and where Flag football is headed. You know, the times are changing and football in itself is becoming a global game. And so when I had the, the opportunity and, and I was presented the opportunity to invest into this league, which I feel very fortunate for because not everyone was brought in that early, I really began to think about this opportunity. But how years and years prior, things that I invested in, in time that I spent in relationships, I built really fast forwarded 8 years, provide an opportunity to invest, to make this investment. And there are a number of people involved. I built a great relationship, a relation, I built a great relationship with a gentleman named Byron Dieter, who's with Bessemer Capital. And me and Byron have, you know, been friends and, and done business together for going on about eight years now and just building and nurturing that relationship and trying to add value to him and his firm and, you know, just trying to be a sponge. Byron and Bessemer actually ended up becoming one of the lead investment partners in this league. And so throughout the process, he was picking my brain, asking me about what I thought about Flag in the future for the, for the sport.

[John Hope Bryant]

Yep.

[Eric Armstead]

And so that was one way I was able to learn and then also too, just being connected. You can look up the list of people that. Of players that invested into the league. And it's, It's a very, you know, short, exclusive list which I'm humbled to be a part of. And that was purely all about connections and relationships as well, too, being in the right rooms, you know, adding value where. Where opportunities were presented at the league level and partners and building relationships and going to events and. And being myself and letting everyone know who I was and what I was about and what I stood for. And in all that, you know, reputation and relationship building and all those things presented an opportunity years and years later that not everyone was afforded to. And so I'm really excited about this investment and where this league is headed. It really, for me personally shows that. That I am moving the right way, that when I do present myself to the world and, and. And meet people, that something is. Something is sticking and it's opening up doors and knocking down barriers for me. And this investment, I feel, is. Is very much a legacy investment. I have two daughters and I have a son as well, but I have two daughters. And this. The league is launching with Women's First.

[John Hope Bryant]

Wow.

[Eric Armstead]

A big. A big initiative. I don't actually. I don't know if I can say that, but I think I can.

[John Hope Bryant]

Well, you just said it. Well, no. Well, I'm gonna save you. We'll pivot on that. Let me ask you this question because we'll see ahead further, the league's press release. Because I played flag football growing up, everybody can relate to this story. This is a really cool thing that I think you've done. And I think that what the. With the. The principles of this business enterprise, what they saw was somebody who was more interested in partnership conversation than party conversation. And so your focus in your integrity brought you in off the field of play to the field of business in the minds of some people who took you seriously. Without giving any confidential information, can you quickly tell the audience how this deal was structured? So you. It's. It's. It's the who the partners who are the backers, the financiers, the bankers. Where, you know, where does it operate? And without getting into getting the confidential. I think this is how do we make the money.

[Eric Armstead]

It's public information. There is Tomorrow Sports will be the operator and there are six big firm that will lead that investment. On that side, I think Bessemer, Silver Lake and a num. A number of others firms that came together to and will be the lead investors on this.

[John Hope Bryant]

Everybody knows best of it does investment management, family office management, things like that private banking and then Silver Lake is private equity. Etc. Continue. Yep.

[Eric Armstead]

And on the NFL side, which was awesome, you know, working with Curtis Martin and his private equity firm, Ludus, we were able to have conversations and he had conversations with Roger Goodell and NFL that, you know, players need to be involved. And so we were able to have some players be able to invest. And I was fortunate enough to. That I got the call to. To be one of those players that had an opportunity and an allocation to invest. And I'm really excited, like I said, about the opportunity. And that goes back to, like I said, relationship building and being in the right place at the right time and showing up and presenting yourself at the right time as well too, and creating opportunities for yourself in that space that people see you in that light and they bring you in on those conversations.

[John Hope Bryant]

Yep. And as I love to say, if you hang around nine broke people, you'll be the ten. What he said is basically the opposite of that. Right rooms, right places, right spaces, talking about the right things and the right mindset. And essentially what he just described was what you might call in a traditional sense, a pre IPO environment where he was brought in to an investment because before it became public, before it became publicly available or even available to mainstream investors, somebody selected him to be. As part of the original capital stack. You can look up what capital stack means, but it's a, it's a. It's the literally the stack of types of money that goes into a deal. Debt and equity. And. And so he's got a real shot at success at this. And I think if anything has a shot of success is dang on flag football. And the fact that in my. And Roger Goodell, she's a wonderful, wonderful human being. I love that brother. Call him an honorary black man, but if the NFL's.

[Eric Armstead]

You know what they say, you know what they say about redheads. They might as well. They might as well be black.

[John Hope Bryant]

Okay, well, that's a whole nother conversation. Roger, I'm sure will appreciate that he is a good brother. So look, this has been great and I'm glad you took this time to give the people a. A super vitamin of a targeted deal. Who's involved, what you're doing off the field to make money during the day, his salary from NFL, but building wealth in your sleep, things like this, investment in flag football. Eric, thanks for being a role model and living. Living what you say.

[Eric Armstead]

I appreciate that. And trying to keep leading the way.

[John Hope Bryant]

And you will. I'll see you in the field of Play Money and Wealth with John o' Brien is a production of the Black Effect Podcast Network. For more podcasts from the Black Effect Podcast network, visit the iHeartRadio app, Apple Podcasts, or wherever you listen to your favorite shows.

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