Why Athlete Entrepreneurs Are Often the Hardest Clients to Work With — and the Best
We work with a lot of former athletes at Ripples Edge. Founders who played college sports, competed at a high level, spent years inside a culture that rewarded discipline, coachability, and an almost irrational willingness to outwork the room.
They are, without question, some of the most rewarding clients we work with.
They're also, almost universally, the ones who take the longest to let go of the thing that's holding them back.
This isn't a criticism. It's an observation — and it comes with a lot of respect. Because the qualities that make athlete entrepreneurs hard to advise are the exact same qualities that made them exceptional competitors and that drove them to build something worth advising on in the first place.
“Athlete entrepreneurs don’t fail because they lack drive. They hit ceilings because they trust their own effort more than their systems — and eventually, effort runs out.”
We work with a lot of former athletes at Ripples Edge. Founders who played college sports, competed at a high level, spent years inside a culture that rewarded discipline, coachability, and an almost irrational willingness to outwork the room.
They are, without question, some of the most rewarding clients we work with.
They're also, almost universally, the ones who take the longest to let go of the thing that's holding them back.
This isn't a criticism. It's an observation — and it comes with a lot of respect. Because the qualities that make athlete entrepreneurs hard to advise are the exact same qualities that made them exceptional competitors and that drove them to build something worth advising on in the first place.
What makes them exceptional
Let's start here, because it matters.
Athlete entrepreneurs show up differently than most founders. They understand systems intuitively — the idea that individual effort only goes so far, and that a well-designed play beats individual brilliance in a close game. They know what it feels like to be coached, to receive hard feedback, and to come back the next day and implement it. They've failed publicly and kept going. They understand that peak performance isn't accidental — it's the result of preparation, iteration, and a willingness to do the unglamorous work.
In a business context, that translates to founders who execute. Who follow through. Who, when they commit to something, mean it. Who know how to be part of a team even when they're leading it.
Those are not small things. We work with founders who have all the ambition in the world and none of the follow-through. Give us a former athlete every time.
Where it gets complicated
Here's the pattern we see, consistently, across almost every athlete entrepreneur we've worked with.
They built the business the same way they won games: by being the best person on the floor. Outworking everyone, making every call, jumping in whenever the execution wasn't up to their standard. And for a long time, that worked. Because in the early stages of a business, that kind of drive is exactly what you need.
The problem is that it doesn't scale. And more importantly — it doesn't transfer.
A business where the founder is still the closer, still the one clients call when something goes wrong, still the person who stays late to fix what the team couldn't — that's not a business. That's a job with overhead.
Athlete entrepreneurs don't fail because they lack drive. They hit ceilings because they trust their own effort more than their systems — and eventually, effort runs out.
The identity piece nobody talks about
There's something underneath the operational pattern that's worth naming directly.
For most people who competed seriously, sport was where they learned who they were. It was the context in which they discovered they were capable, resilient, and exceptional. The locker room, the late practices, the pressure moments — those experiences formed them.
When that athlete becomes a founder, a lot of that identity transfers to the business. "I am the one who makes this work" becomes as true in the office as it was on the court. And the business becomes, in some ways, the new arena.
Which is beautiful, until it isn't.
Because a business that needs you to be the best person in the room is a business that can't grow past the size of your personal capacity. And at some point — whether through an exit, a health issue, a life change, or simply the desire for a different kind of freedom — you will need the business to run without you.
That transition is harder for athlete entrepreneurs than almost any other founder type. Not because they lack the intelligence or the skill. But because stepping back from being the star player requires a different kind of identity — one that isn't built in a season.
What we've learned about coaching them well
The founders who make the leap — who build something genuinely transferable and do it in a way they're proud of — share a few things in common.
They respond to honesty delivered with respect. Athlete entrepreneurs have been coached. They know what it feels like to have someone tell them the hard truth without softening it into irrelevance. They don't need to be handled. They need to be told clearly what the gap is and given a specific play to run.
They compete against their past selves once you give them the right scorecard. The problem isn't that they don't want to improve — it's that the metrics they're running on are the wrong ones. Shift the scorecard from personal output to organizational capacity, and athlete founders often outrun every expectation.
They need someone who can tell the difference between the instincts worth keeping and the ones worth retraining. Not all competitive drive is a liability. The relentlessness, the resilience, the willingness to do the work nobody else wants to do — those are assets. The "I'll just do it myself" reflex, the resistance to delegating before someone has proven themselves perfect — those are costs. Knowing which is which is the job.
Why they're worth it
We'll be direct: athlete entrepreneurs are our people. Not because they're easy. But because when the work lands, it really lands.
There's a particular kind of conversation we've had more than once with a founder who played at a high level — the moment they realize that building something that runs without them isn't a retreat from competition. It's the hardest game they've ever played. And they're built for hard games.
That's when the work gets interesting.
If you're a founder who competed and finds yourself recognizing any of this, let's have a conversation. We built a practice specifically to work with business owners at this intersection — and we know how to work with the competitive wiring, not against it.
Kimberly Wasney is the co-founder of Ripples Edge Advisors, an exit readiness and growth advisory firm based in Chicago. She is a former competitive volleyball player and has spent her career helping founders build businesses that are worth what they've put into them.
