When the Scoreboard Changes: A Study in Professional Courage w/ Cullen Roche and Coach Vass on JUST PRESS RECORD

What happens when a 41-year-old football coach realizes his entire understanding of “winning” - not to mention, what he wants from the next phase of life - might be, not “wrong” exactly, but definitely taking him way off of the path his entire life has been on so far?

The first thing that happens is what any of us would do these days: he starts digging around on YouTube, reading everything he can find, getting obsessed. As the questions mount up, he starts cold-reaching out to people. Like me, apparently.

But I need you to know this part, first.

Chris Vasseur, best known as Coach Vass, built a life where games are either won or lost, and scoreboards are the public record your career lives and dies on. Every Friday night, especially in his high school football coaching days, there was a winner and a loser. No hiding, no excuses, no “well it depends on how you look at it.” And, he was good at it (like, really good at it).

His mom got sick. The pandemic was on. He moved from California to Florida to help. Since he had to be there, and since the world was extra weird at that point in 2020, he started to put his defensive coaching processes on the internet to share with others. That’s how the next chapter of his life took off. The Coach Vass Football brand was born.

Because of the situation with his mom, and now his growing business, he found himself with a lot of financial questions. He got information, and it was confusing. So he got an advisor, and that started to help. But, he kept coming up with more questions, and the more he learned, the more he was finding out how much he liked this stuff.

Which is how he ended up finding me.

When I think about going from my attempt at being a musician and recording studio careerist to part-time teller turned financial advisor guy, I think about that cycle of learning too. Vass was already in deep with a bunch of wonky topics, I could tell right away, but it made me reflect on who helped me shape how I understand the world when I was at his phase. One name, in particular, came to mind: Cullen Roche. Cullen’s the ultimate outside-the-box thinker. And, like Vass, he also started off as an outsider, which, I wondered if Vass even knew about.

Personally, in the post-global financial crisis period, Cullen’s writing helped me understand (and, as I learned from previously interviewing him, he was further developing his understanding too, in real time) how the modern financial system works. He helped me understand why all stuff I had very quickly learned prior to the financial crisis had flaws. While he wasn’t fixing up some new crystal ball, he was explaining nuance in a way that attracted me to his work (then at Pragmatic Capitalism) that I’ll forever be grateful for.

So when Coach Vass came to me with questions about a future career in finance and a seemingly unquenchable knowledge to learn, I knew I had to introduce him to Cullen.

And that’s exactly what Just Press Record is built for.

There were so many angles to explore with them. The whole idea of how football coaches chase perfect execution of plays and money managers seek to avoid catastrophic mistakes - where one profession directly rewards excellence and the other rewards disciplined restraint - it’s kind of an amazingly flipped scoreboard logic that I’ve rarely heard discussed.

Cullen and Vass took it there. Vass asked Cullen how crazy it would be to leave a domain where he’s already mastered the rules. Cullen asked Vass what he knew about moving from a “you must win” game to a “just don’t lose” game.

They both talked, at detail, about the impostor syndrome present at every stage of professional development. Cullen explained how he has no formal training in most of the areas he’s now known for exploring, but the crashes and client experiences, they got him to where he is today. Vass echoed his own lack of formal training, but explained his fascination with pattern recognition emerging after thousands and thousands of high-stakes decisions.

This conversation isn’t only about finding the courage to switch careers at 41, and if or when it’s too late to find new sources of confidence. This conversation is about recognizing that the expertise you imagine exists in someone else today is overrated. Fresh eyes on old problems can be more valuable than credentials. But, only if you start, only if you love it, and only if you’re willing to work really, really hard at it.

Sometimes, the best way to learn what all the sections are on a new scoreboard is to admit you don’t understand the game yet, and then to just start playing.

I don’t know if Vass will have a successful career in finance, just like I don’t know if Cullen’s next book will be a best-seller.

But, what I am positive of, is that when people love to do something, and the love is more important to their identity than whatever other label people want to throw on the topic of interest, or the prior experts who have done it all before, or whatever businesses have already been built - there’s room.

It’s never too late to change, so long as you’re following a path you love. Listen to what happens when Cullen Roche meets Chris Vasseur, for the first time ever, on Just Press Record: