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.
The 5 Things Buyers Look at First (That Most Owners Aren't Thinking About)
Most business owners think valuation is about revenue. Get the top line high enough, and the rest will follow.
Buyers think about it differently.
When a serious buyer — whether that's a private equity firm, a strategic acquirer, or an internal successor — evaluates a business, revenue is almost never what they look at first. It's table stakes. What they're actually trying to answer is a different question entirely: can this business perform without the person selling it?
Here's what they look at to find out.
1. Owner dependence
This is the first thing any experienced buyer is looking for, and it's the one most owners underestimate.
If you are the primary relationship with your top clients, the closer on every major deal, and the person your team comes to when anything unusual happens — a buyer sees that as risk, not value. They're not buying a business. They're buying a job. And they'll either walk away or discount the price significantly to account for the transition risk.
The question to ask yourself honestly: if you disappeared from the business tomorrow, what would stop working within 30 days? 90 days? A year?
The answer tells you exactly where to focus before you're ever in a room with a buyer.
2. Revenue quality
Not all revenue is created equal. Buyers assign very different multiples to different types of revenue, and most owners haven't thought carefully about which bucket theirs falls into.
Recurring, contracted revenue — subscriptions, retainers, long-term service agreements — commands a premium because it's predictable. A buyer can model it. Project-based or relationship-dependent revenue is harder to underwrite, especially if it's concentrated in a handful of clients.
A few things buyers flag immediately: one client representing more than 15-20% of revenue, revenue that requires the owner to close or service personally, and any contracts that contain change-of-control clauses that could let clients walk at the point of sale.
If your revenue story has any of these wrinkles, the time to address them is before a buyer finds them in diligence.
3. The leadership team
Buyers are not looking for a talented founder. They're looking for a team that can execute without one.
That means a leadership bench that has clear roles, documented accountabilities, and a track record of making good decisions independently. It means someone other than the owner who can have the hard conversations with clients, manage performance issues on the team, and keep the business moving during a transition period.
If you're the only true leader in the building, that's the work. Not because it makes you more sellable — but because it makes your business more resilient right now, regardless of what you decide to do with it later.
4. Clean, clear financials
This one sounds obvious, but the number of businesses that hit diligence with messy books is staggering.
Buyers want to see at least three years of clean financial statements. They want to understand the story behind the numbers — what drove a strong year, what caused a dip, what's recurring versus one-time. They want to see that the owner's personal expenses aren't running through the business in ways that will take a forensic accountant to untangle.
More than the numbers themselves, buyers are reading the financials for trustworthiness. If the books are hard to follow, it signals that other parts of the business might be too.
5. Documented processes
Can someone other than you explain how the business works?
This is the operational version of the owner dependence question, and it shows up everywhere in diligence: how do you acquire customers, how do you onboard them, how do you deliver your core service, how do you handle exceptions when something goes wrong?
Businesses with documented, repeatable processes are easier to underwrite, easier to transition, and easier to scale — which means buyers can pay more for them because they're taking on less risk.
The goal isn't a 200-page operations manual. It's enough documentation that a capable person walking in on Day One could understand what good looks like and start running toward it.
“A buyer isn’t buying your past. They’re buying their future — and they need to see that future clearly before they’ll pay full price for it.”
What this means for you right now
None of these five things are things you fix in the six months before a sale. They're things you build over years — which is exactly why the owners who get the best outcomes are the ones who started thinking about them long before they needed to.
A buyer isn't buying your past. They're buying their future — and they need to see that future clearly before they'll pay full price for it.
If you want to know where your business stands against these five factors, our Exit Readiness Assessment gives you an honest picture of where you are and what to focus on first. Most owners come out of it with a clearer sense of their business than they've had in years.
Ripples Edge Advisors is an exit readiness and growth advisory firm based in Chicago. We work with small and mid-sized business owners who want to build something transferable — whether they sell it, pass it on, or simply run it better. Learn more at ripplesedgeadvisors.com.
What Playing a Team Sport Taught Me About Building a Business That Runs Without You
I played volleyball for most of my life. Club, college, and well into my adult years — the kind of sport where you are acutely aware, at all times, of where everyone else on the court is and what they need from you.
What I didn't realize until much later was how much that experience was shaping the way I approach business. Not just mine — my clients' too.
Because here's the thing about athlete entrepreneurs: we are, almost universally, both the best and the worst clients to work with when it comes to building a business that runs without us. The very instincts that made us good at our sport — the competitiveness, the work ethic, the "I'll just do it myself if I want it done right" reflex — become the ceiling we keep bumping into as founders.
The "I'll cover it" instinct
In volleyball, there's a version of a play where the ball is heading somewhere that's technically someone else's responsibility, but you read it faster, you're closer, you know you can get there — so you call it and take the ball.
It's the right call in that moment. You make the play. You get the point.
In business, that same instinct looks like this: a client email comes in at 7pm and you answer it before your account manager even sees it. A proposal needs to go out and it's faster to just write it yourself than to explain what you want. A new hire is struggling and instead of coaching them through it, you step in and handle their work.
Every single one of those is you calling "I got it" on a ball that wasn't yours.
And every time you do it, you're training your team that you'll cover for them — and training yourself that the business can't run without you in the game.
“The best coaches I ever played for didn’t win by doing everything themselves. They won by building a team that could execute the system without them calling every play.”
What great coaches actually do
The best coaches I ever played for didn't win by doing everything themselves. They won by building a team that could execute the system without them calling every play.
They spent practice creating muscle memory — running the same rotations until they were automatic, building trust between players so that in a pressure moment, nobody had to think about who was supposed to be where. The system ran. And when it ran, the coach could see the whole court.
That's the job of a founder who wants to build something transferable.
Not to be the best player on the floor. To build the system, develop the players, and eventually trust the team enough to run without you on the bench.
That transition — from player to coach to owner of the whole program — is the hardest identity shift in business. Especially for athletes, because we are wired to compete, to perform, to be in it. Stepping back feels like losing. It isn't. It's the whole point.
The identity underneath the business
Here's where it gets personal, and I'll say it plainly because I've seen it in too many clients to pretend it's rare:
A lot of athlete entrepreneurs have wrapped their identity around being the best person in the room. The most capable. The one who gets things done. It's what drove you on the court, and it's probably a big part of why your business exists in the first place.
But that identity — "I am the one who makes this work" — is exactly what keeps a business from becoming transferable. Because a business that needs you to be the best person in the room is a business that stops when you do.
The founders we've worked with who make the leap — who build something that genuinely runs without them — almost always describe a moment of recognition that sounds something like: I don't need to be the MVP here. I need to be the general manager.
Different job. Harder job, in some ways. But the one that actually builds something lasting.
Three athlete instincts to retrain
If you played competitive sports, you probably recognize these in yourself:
The "I'll just do it" reflex. You're faster, you're better at it, and delegating takes more time than doing. True in the short term. Devastating over time. Every time you take the ball that wasn't yours, you slow down the development of the player who should have had it.
Performing under pressure personally rather than building systems for it. Athletes are trained to rise in a crisis. Founders who rely on that instinct build businesses that lurch from fire to fire — and call it culture. Real resilience is a business that handles pressure without requiring heroics from the owner.
Measuring success by personal output. How many emails did you send, calls did you take, proposals did you write? That's an athlete's scorecard. A founder's scorecard looks different: how much did the team accomplish, how many decisions got made without you, how much of the business ran on its own?
What the shift actually looks like
It's not a personality transplant. It's a set of deliberate choices, made consistently over time.
It looks like building a sales process that someone else can run, and resisting the urge to jump in when they're still learning it. It looks like documenting how you do things — not because it's exciting, but because it's the only way to transfer what lives in your head. It looks like hiring people who are genuinely excellent at things you're not, and getting out of their way.
And eventually, it looks like a business that surprises you with what it can do without you. That's the moment. That's what we're building toward.
We work with a lot of athlete entrepreneurs at Ripples Edge — founders who are wired to compete and need a partner who gets that, while also being honest with them about the instincts worth retraining. If that sounds like you, let's talk.
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 an anthropologist by training — which means she spent a career studying how people work before helping founders build businesses that do.
Exit Planning for Small Business Owners Who Aren't Thinking About Selling Yet
Here's something we hear in almost every first conversation with a new client:
"I'm not really thinking about selling. Is this still relevant for me?"
Yes. Probably more than anything else you could be doing for your business right now.
Exit planning has a branding problem. The word "exit" implies a door you're walking toward — and if that door feels far away, the whole conversation can feel premature. Something for future you to worry about. We get it. But that framing is exactly what costs business owners time, money, and options when the moment actually arrives.
So let's reframe it. Because the owners who benefit most from exit readiness work aren't the ones with an offer on the table. They're the ones who started three years before that.
What exit planning actually is (and isn't)
Exit planning is not about getting ready to sell. It's about building a business that gives you options — so that when the time comes, whether that's in two years or twelve, you're choosing your next chapter rather than scrambling to catch up.
Think of it this way: exit readiness is just good business strategy with a longer horizon. The same things that make a business attractive to a future buyer — consistent revenue, a strong leadership team, documented processes, reduced owner dependence — are the same things that make a business easier, more profitable, and more enjoyable to run right now.
You're not building toward an exit. You're building a business that doesn't need you in every room for it to function. That's valuable whether or not you ever sell.
The myth that's costing owners millions
We worked with a founder who received a $10M offer from a private equity firm. On the surface, it looked solid. But when we ran him through our Exit Readiness Assessment, it became clear pretty quickly that the business couldn't run without him. The sales process lived in his head. The leadership team was green. Profit margins had room to grow.
He made the decision to wait — and to work on the business instead.
Eighteen months later, the same buyer came back. Their new offer was $15M.
The work he did wasn't "exit prep" in the traditional sense. He hired a sales lead, trained his leadership team, tightened the margins. He built a business that someone else could step into on Day One and actually run. That's what transferred value looks like — and it added $5 million to the outcome.
The myth is that exit planning is something you do when you're ready to sell. The reality is that by the time you're ready to sell, it's almost always too late to do the work that moves the number.
““Exit planning is not about getting ready to sell. It’s about building a business that gives you options.””
Three signs you need exit readiness work — even if selling is the last thing on your mind
1. You are the business.
If you stepped away for 30 days — no email, no calls, no "quick questions" — what would break first? If the honest answer is "everything," that's not a business problem. That's an owner dependence problem, and it directly affects what your business is worth to anyone other than you.
2. You don't have a clear picture of what you want next.
A lot of founders know exactly what they want their business to look like. Far fewer have thought through what they want their life to look like when the business is no longer the center of it. That's not a soft question — it's a strategic one. The kind of buyer you choose, the timeline you work toward, the terms you're willing to accept: all of it flows from knowing what you actually want on the other side.
3. Your growth feels founder-dependent.
When revenue goes up because you had a great quarter of selling, that's not scalable growth — that's hustle. Transferable value comes from systems, processes, and a team that can generate results consistently without you carrying the load. If your best growth lever is still you, there's work to do.
What "exit ready" actually looks like
An exit-ready business isn't a business that's for sale. It's a business that has options.
It has a leadership team that can run the day-to-day. It has recurring, reliable revenue that doesn't depend on any single relationship. It has clean financials that tell a clear story. And it has an owner who has thought through what they want — not just for the business, but for themselves.
That last part matters more than most people expect. We've sat with founders who had every financial metric in order and still almost walked away from a deal they would have regretted — because they hadn't asked themselves the harder questions about legacy, team, and what "done" actually means to them.
Exit readiness is emotional before it's strategic. The strategy is the easy part.
Where to start
If any of this is landing, the first step isn't a big one. It's just an honest conversation about where you are and what you want.
Our Exit Readiness Assessment is designed exactly for this moment — for the owner who isn't ready to sell but knows there's work worth doing. It gives you a clear picture of where your business stands, where the gaps are, and what to focus on first.
You don't have to be planning an exit to start building a business that's ready for one.
Ripples Edge Advisors is an exit readiness and growth advisory firm. We work with small and mid-sized business owners who want to build something transferable — whether they sell it, pass it on, or simply run it better. Learn more at ripplesedgeadvisors.com.