4 football lessons a former pro athlete turned into fundraising gold

Nearly every first-time founder runs into hiccups and must pivot quickly to pick up new skills — and I thank my nontraditional background for helping me power through. 

I spent my life in sports, playing football from age 8 through 27. While other founders learned about finance in college, I was learning how to spot the body language of a linebacker disguising a blitz. 

So when I leaped to launching a startup, I had a lot of business learning to catch up on, especially around fundraising. When I started Rego to help commercial buildings participate in the circular economy, I leaned on key lessons I learned while playing sports to navigate raising money for the first time. 

While Rego still has a long way to go, and raising a pre-seed round doesn’t equal success, there are four key lessons from sports that I believe can help other founders navigate their first raise.

Commit for the long haul to become a ‘pro’ 

Long before athletes play in the big leagues, they’re little kids shooting their first basketball shot, swinging their first baseball bat or scoring their first little league touchdown.  

From their first try to playing on a global stage, it takes years — often over a decade — as they work through middle school, high school and college to have a fraction of a chance of making it professional.  They train late nights after school and on weekends, fight setbacks and failures, and get cut from teams.  

For example, I started playing football at age 8 in 1998, then through college, and then in a now-defunct arena league in 2014. 

After football, I transitioned to playing rugby sevens, a faster version of the sport played in the Olympics. By the time I  “retired” in 2017, I had spent nearly two decades in sports. During that time, the world experienced the dot-com bubble, the war on terror, and the 2008 financial crisis — all before I ever earned a dime for playing the game. 

I had a lot to catch up on to become a founder. 

In startups, the same long-term commitment applies. From day one, I knew it would take at least a decade to see success. 

Investors want to see founders with that mindset, too. Like in sports, you must prove yourself before opportunities follow. 

My co-founder, Brandon Castagna and I learned this firsthand after dozens and dozens of failed pitches. It wasn’t until we got opportunities with programs like Techstars and the PACT Capital conference that we started gaining traction. 

Build a strong behind-the-scenes team for support

In sports, you have two teams: a primary one, and the behind-the-scenes support team. 

Your team is your fellow players, but your support team includes your coaches, equipment staff, physical trainers and more.  Any athlete can tell you the importance of a strong support team. For example, you quickly find out the impact of a good trainer who can treat or prevent a rolled ankle after you’ve dealt with a bad one. 

The same goes for startups. It’s easy to talk about hiring a great core team, but founders often overlook the importance of a great support team — legal advisors, accountants and mentors. 

When my co-founder and I navigated due diligence for the first time, we relied on experienced professionals like Ballard Spahr for legal advice and Wipfli for accounting, along with mentors from the PACT Mentor Connect program. I credit them for helping us land the pre-seed.

Keep a close eye on the competition

In sports, watching film is essential. You learn about your opponents, refine team strategies and use that to improve your own game.  

As an undersized running back in college, my coaches had me watch videos of larger players in the position to improve my game. I later found out most coaches encourage only watching players of your size but that just creates copycats. 

My coaches used this film strategy to help me and my teammates break past limiting beliefs and look for opportunities to be better players than we thought possible.  

In fundraising, it’s tempting to create a competition slide and simply be one feature better than your rivals. But this approach limits your growth. 

We studied companies outside our industry to learn how they raised pre-seed rounds and adapted those lessons to Rego. The goal is to define your category, not just compete within it. 

Mistakes are a good thing

In sports, making new mistakes is a sign of growth. My coaches pushed us to avoid making the same mistake twice, forcing us to constantly improve. Learning from your mistakes is a common mantra, but making new mistakes drives progress. 

For example, each football team has slight variations in its “play calls,” or offensive approaches, which typically involve a directional assignment to each player. As a player joining a new team, coaches will give you the opportunity to go the “wrong” direction once. But they need you to get it right 100% of the time afterward so that you can start learning more complex play calls. 

This mindset applies to fundraising as well. Investors want to see your company moving forward, learning and adapting. Making new mistakes and not repeating the old ones shows growth and a willingness to improve.