Part I: The Season of Misalignment

I made my first startup investment in 2010—just a few years into my NFL career.

It wasn’t some master-planned strategic move. I was following the signal everyone else seemed to be picking up:

“You’re a pro athlete. You should be investing in startups.”

So, I did. Alongside a handful of other players. Small checks. Syndicated deals. The kind where influence amplified the impact, and everyone felt like they were playing the game the right way.

From the outside, it looked like a smart move.

But from the inside, it felt... off. I didn’t know the space. I didn’t know the players.

And the outcomes—if they ever came—would take 7 to 10 years to materialize. That doesn’t seem like a long time until you factor in the average career only lasts 3.5 years.

That didn’t align with how I’d built anything up to that point. I came from a world where success came through work, not passive bets. I couldn’t just hope something panned out. I needed to understand the rules. I needed to know how to contribute.

That’s when the misalignment started to show up.

Seeing founders that mirrored my journey

As I started asking more questions, I stopped seeing myself as just a passive investor—and started seeing something deeper.

Entrepreneurs were navigating the same uphill battle I faced as an underdog draft pick.

They had to pitch a vision before anyone believed in them. They had to build something out of nothing. They had to grow into the role while already being expected to perform.

That’s what it means to build something real.

And that insight gave me a new level of respect—and relevance—as an investor.

I knew what it felt like to bet on yourself when no one else saw the blueprint. And I wanted to support founders with more than a check.

But the ecosystem didn’t make space for that.

Athletes were still seen as logos, not lenses. Capital without context. Exposure without expertise.

And that realization triggered the next chapter of the journey.

Change the system from within

I figured the best way to shift the narrative was to give athletes tools to become better investors—not just better check writers.

Over the years, I met a couple colleagues that saw value in that idea. As we continued to build a relationship and friendship, we joined forces. We created a partnership with Columbia Business School to build and launch an executive education program: Venture Investing and Entrepreneurship for Professional Athletes.

Real curriculum. Real access. Real structure.

My belief was simple:

Athletes could learn how to evaluate opportunities, understand deal flow, and advocate for their own ideas.

They didn’t need a finance degree—they needed a filter. A baseline. Something to build confidence and command more ownership in rooms that weren’t designed for them.

I thought the support would come.

The NFL Players Association had a tuition reimbursement program—why wouldn’t they want their athletes to use those benefits on a program at Columbia — especially when they were working with players to break in the to venture capital world?

Financial advisors were already helping athletes with investment decisions—why wouldn’t they want their clients to have better tools to protect themselves?

But that’s not what happened.

The PA never got behind it. Financial advisors pushed back—educating athletes meant fewer fees, less control.

What I thought would be a win for the whole ecosystem revealed something else:

There was no incentive to engage athletes beyond the surface.

The perception of support was enough to keep the engine running.

I wasn’t angry. I wasn’t even surprised. But it opened my eyes. I was trying to fix a system that said one thing in public, but operated another way behind closed doors.

There was a lot of contentment on the surface — so I went in deeper.

Stepping into the fire—again

If no one was going to help athletes build real financial understanding on the surface, I wanted to go to the source.

I got licensed. I joined a financial services firm. I became the source.

I believed I could bridge the gap between private investing, public markets, and personal growth. I had the lived experience, the strategic lens, and the ability to translate complex dynamics into practical decisions.

This was the next evolution of the work. Or so I thought.

What I didn’t realize was how deeply misaligned I’d be with the industry’s business model.

I wasn’t there to accumulate AUM. I was there to support people. And real support means answering questions that don’t fit inside a neat compliance-approved script.

I had clients trying to build cash-flowing businesses to complement their portfolios—exactly what you’d want a client to do. But compliance saw it as “selling away.” They tracked my emails. Flagged my conversations.

It became clear:

I wasn’t being treated like a trusted advisor. I was being treated like a liability.

So, within two years, I left. Not because I lost faith in the mission—but because I realized I couldn’t pursue it in a system that didn’t value holistic thinking.

Sometimes the misalignment is the message

By that point, I was tired and frustrated.

I’d tried to provide something the ecosystem claimed it wanted. I’d tried to play by the existing rules. And it kept leading me to rooms that didn’t make space for who I really was—or what I really brought to the table.

So I stepped away from investing altogether.

I didn’t know what was next. But I knew I couldn’t keep forcing alignment where there was none. And that space—the willingness to step back—would open up everything else that followed. But that’s Part II of the story…

Closing Thoughts

This first chapter was about building and confirming conviction.

The ideas I had back then weren’t wrong. They were just early. The timing was off. The context wasn’t ready. I wasn’t fully ready.

But I kept moving. I kept learning. I kept stacking the experiences that would eventually become the foundation for something more complete.

Sometimes, the long way around is the only way forward. Especially when the thing you’re building hasn’t existed yet.

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