Fifteen years in startup boardrooms. I was the guy who could spot a cash flow problem from a mile away. But I was also bored out of my mind, and the guy who could spend every Sunday reverse-engineering NFL salary tax calculations instead of watching the actual game.

When I finally admitted I cared more about sports cap structures than software valuations, everyone said I was crazy. "You don't know anyone in sports." "You never played professionally." "Start over at your age?"

I made the jump a few years back. And yes, I had my share of rough patches—wrong fits, bad timing, the usual. But today I can tell you it was all worth it and I don’t regret a thing, because I'm doing what I’m passionate about. Work hours don’t exist because I love what I do, and after a while, I realized that financial models are just financial models, whether you're projecting software revenue or revenue for a startup league.

Your skills already translate. You just need to stop apologizing for where you learned them.

Here are five honest lessons from my transition that might help you make your own jump.

Sports organizations don't need another fanboy or person who can recite WAR statistics. They need someone who can explain why they're hemorrhaging cash every quarter. They need financial models that former players running the front office can actually read. They need expense tracking that checks out.

The sports industry surprisingly runs years behind other sectors when it comes to financial operations. Your routine quarterly reporting process could transform how they make decisions. That Excel model you've built a hundred times might be exactly what they've never seen.

Stop trying to be a sports expert. Be the business expert they desperately need.

Passion without skills? You're a fan with opinions. Skills without passion? You're a spreadsheet jockey counting someone else's dream. 

Put them together and you've got a career.

Traditional CFOs walk into sports franchises and treat them like widget factories. They miss why a team might take a financial hit for community goodwill. Sports fans land finance roles and get starstruck into bad decisions because they can't separate emotion from analysis.

The job looks like 90% spreadsheets, 10% talking about sports. That 10% makes the other 90% worth it.

Your passion gets you in the room. Your skills keep you there. Run a DCF analysis on a stadium deal while genuinely caring about Sunday’s game. Speak fluent finance and translate it for people who measure success in championships and packed stands. Love sports enough to protect its business side from terrible decisions.

Everyone camps out at sports business conferences hoping to hand their resume to a team president. Spoiler: so are 500 other people.

The network that matters lives outside sports. Tech people who’ve scaled revenue. People in tech, real estate, retail, hospitality, and yes, finance. They know people in the sports world from business, not because they both love basketball. Their credibility opens doors you can’t reach from a conference name tag.

Approach conversations differently. Nobody cares that you want to work in sports. They care if you can solve their problems. Frame your experience as transferable solutions. Your e-commerce background speaks to ticket sales. Your corporate finance work translates to team valuations.

Stop fighting through the crowded front entrance. Find the side door where fewer people knock, and your skills make you valuable.​​​​​​​​​​​​​​​​

Most sports organizations can’t justify paying a full-time CFO $300k plus benefits. They can justify paying for senior expertise when they need it.

Sports run seasonally and project-based. Teams need heavy financial work during the season and contract negotiations, then go quiet. Leagues spike around media rights deals. Agencies ramp for draft season. Stadium projects demand six months of intensity followed by maintenance mode. You show up for the heavy lifting and leave when it’s quiet.

You bring ideas from outside their bubble. A team exec who’s only worked in baseball doesn’t know how retail fixed their merchandise problem or how tech companies structure revenue shares. You’ve seen it. You also carry zero political baggage. You’re not competing for the GM role or trying to build an empire. You can tell the owner their new facility loses money without risking your career.

The model works because sports organizations get senior talent without senior overhead, and you get variety without tying your fate to one business’s performance.​​​​​​​​​​​​​​​​

Finally, the skills that kept me working had nothing to do with my finance know-how.

Financial modeling and GAAP knowledge get you through the door. Sure. And like I said, those are valuable commodities in sports. But others competing for work in the industry have those credentials. 

What separates you from the pack is knowing how to read a room full of strong personalities, managing egos, and knowing when to push back versus when to shut up and listen. Emotional intelligence, if you will. 

You translate balance sheets into plain English. You explain why the financially smart move contradicts someone’s gut without making them feel stupid. You understand that ROI sometimes means brand equity that pays off three years later.  

“We can’t afford that” or “Your sponsorship structure doesn’t work” lands differently depending on how you say it. Technical skills open doors. Reading people and managing relationships keeps you in the game.​​​​​​​​​​​​​​​​

Ultimately, if I want to be the best sports CFO I can be, that means being part therapist, part translator, and part coach, just with a finance degree.

I spent fifteen years doing finance for startups before admitting I’d rather build models for sports organizations. Zero connections. Zero industry experience. Just skills that worked the same whether I was analyzing SaaS metrics or stadium revenue.

You’ve got your own version of this story. Different industry, same doubt. “Too late.” “Wrong background.” “Don’t know anyone.”

Here’s what I learned: the people already doing what you want to do aren’t smarter or better connected. They just stopped waiting for the perfect moment and started moving. I treated my background like an asset instead of a liability. Turns out good work translates. Financial models are financial models. Problem-solving is problem-solving.

The gap between where you are and where you want to be is smaller than the story you’re telling yourself. You already know how to do the work. You’re just doing it in the wrong place.

Start one conversation. See what happens.​​​​​​​​​​​​​​​​