Part II: Fighting Uphill to Position Your Value

After two years and two cohorts of students, we wound down the Columbia program. When I stepped away, I had a choice to make.

I still believed athletes deserved more—more understanding, more access, more ownership. But it was clear the institutions and advisors around them weren’t interested in creating that space.

After coming up empty in my search for financial firms that put their clients holistic need first, I decided I wanted to bring that approach into the room myself.

So I decided to get licensed and become a financial advisor myself. I thought that was the solution. Turns out, it was the start of a much deeper rooted challenge.

Sometimes the vision makes sense — the system doesn’t.

When I joined my firm, I wasn’t trying to be a traditional advisor that provided solutions from the outside looking in. I had a unique lens, and I wanted to use it.

I had experience in private investing, a growing understanding of public markets. Most important from my perspective, I had a decade of navigating the psychology of an athlete. The high pressure stakes to get it right in a short, high-earning window.

I’d been the client. I’d lived the complexity. I had a unique understanding of what it took to build long-term financial health for people whose careers—and cash flow—didn’t follow a linear path.

To me, financial advising was about far more than managing portfolios — especially for my peer group. It was about helping people solve problems that impacted every area of their lives.

Interestingly enough, that’s where the tension started.

Serving PEOPLE in a system focused on ASSETS

I had a client who wanted to start an entrepreneurial venture—a small operating business, not a vanity project. He wanted to build a portfolio of vending machines. It was legitimate, low risk move to generate cash flow and start building a a bridge to the second chapter before his first one closed.

As an advisor, he was a dream client.

He came to me for support. Not capital. Not a co-sign. Just perspective. And I gave it to him—because that’s what I believed a good advisor does.

Turns out, my firm considered that conversation was considered “selling away.”

The firm started tracking emails. Reading into conversations, trying to find the line where support became liability. Eventually the sent a warning shot that alluded to the ‘business practices of former athletes’ as a liability to watch out for.

That was the moment it clicked:

This wasn’t about helping clients succeed. This was about managing risk for the firm—and protecting AUM.

To my firm, the people I worked with were names on a spreadsheet. Their complexity was a threat to the model, not an opportunity to add value.

In that moment, I knew I couldn’t stay. It wasn’t going to be feasible to add value inside a container that saw compliance as the priority.

The hardest part wasn’t leaving. It was accepting the fact that the very thing I thought made me valuable—my ability to meet people at the intersection of identity, transition, and strategy—had no place in that environment.

The truth?

I wasn’t trying to “sell” clients on anything. I was trying to help them think differently. Build differently. Move differently.

That kind of support couldn’t be automated. And it would never be compliance-friendly. In reality, my goal was to get clients to a point where they didn’t ‘need me’ as a crutch, but viewed me as a valuable advisor.

I knew my vision wasn’t going to change — the ‘why’ was too important. I also knew the firm was not going to flex at all. Once I became a liability in their eyes, it was only a matter of time before a gray areas became an issue. So I left.

And that opened up a new question: If the work I wanted to do wasn’t allowed in traditional finance, where did it belong?

Stepping out of the game—and into alignment

For the first time in over a decade, I walked away from the investing world. No spreadsheets. No cap tables. No client portfolios.

I had no intentions on going back into a space that only saw pieces of the man, not my entire being.

But, my mission — to meet people where they are and help guide them to where they want to go — was not going to change.

It led me into an opportunity in executive coaching. At first, it didn’t feel like I fit. But once I got comfortable, it felt like home.

It was the first time in years I could bring my whole self into the room—without needing to play a role or present an identity that made other people comfortable.

All the things that had been liabilities in other spaces?

Now they were my leverage:

• My lens as an athlete;

• My experiences in venture;

• My belief in human potential;

• My obsession with transition as a process, not a moment.

That’s what made the work real.

Being > Performing

In coaching rooms, I was tasked with supporting key executives at Nike and Jordan Brand with one-on-one coaching. I also facilitated workshops for McKinsey and Microsoft, and helped leaders make decisions that shaped billion-dollar organizations.

It took me a while to realize I didn’t need to ‘perform professionalism',’ I just needed to tell the truth through my lens.

I didn’t need to posture.

I needed to listen, learn to ask engaging questions, and reflect back what people already knew, but couldn’t see clearly yet.

That’s when it clicked. This is directly aligned with the work I had been trying to do in financial services — help people align their decisions with their values.

My mission wasn’t the wrong mission — I’d just been doing it in the wrong container.

Bringing it back home

After three years of supporting corporate executives, I knew I wanted to bring this work to my peers — Athletes and Entrepreneurs.

From experience, these groups were navigating change without a playbook. They felt the weight of performance, but didn’t always have the support to match it. Most had no HR or benefit packages that offered executive coaching and professional development.

But coaching wasn’t familiar to those audiences. At least not in this form.

They’d seen “life coaches.” They’d seen motivational content. But few had been exposed to executive coaching that centered identity, mindset, and long-term clarity.

So I had to learn how to present it — not as a curriculum or a checklist, but as a thought partnership and strategic advisory relationship.

That’s when I landed my first two clients—a newly retired NFL player and a high-profile entrepreneur. Both were navigating identity shifts. Both needed space to think. And both saw value in a thought partner who could meet them at eye level.

That’s when things started to come full circle.

Closing Thoughts

This chapter wasn’t a pivot to something new. It was a full circle return to the kind of work I’d been trying to do all along: Support people at the intersection of ambition, identity, and transformation.

But this time, it wasn’t inside a system that limited my voice. It was on a platform that honored it.

The takeaway?

Sometimes the problem isn’t your approach. It’s the container you’re trying to force it into. Sometimes the model is too small for the impact you’re built to make.

That’s what I had to learn before CVP ever had a name.

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