The $20 Million Dollar Man: How Rodney's Stubbornness Cost Him a Fortune
Not every story ends at the closing table. This one is a cautionary true story every business owner needs to read.
Rodney built a successful company.
Over nearly three decades, he grew a home services business from a single truck and a prayer into a multi-million dollar operation with a loyal crew, a strong reputation, and customers who asked for him by name. He survived recessions, labor shortages, and a global pandemic. He outworked every competitor in his market. He did it the hard way, and the way he knew how.
By any honest measure, Rodney had built something worth being proud of. Something worth real money.
The problem wasn't his business. The problem was Rodney.
The Number
A few years ago, Rodney decided it was time to sell. He was tired of the business and wanted to venture off and do other things. His wife had been patient long enough. He'd earned the right to sell, cash out, and finally take that trip to Portugal they'd been talking about for fifteen years.
So Rodney did what a lot of confident, self-made business owners do. He started fielding calls from buyers directly and talking to a few brokers along the way. And he had his number.
$20 million and out the door within 30 days. Not a penny less or a day more.
To Rodney, it wasn't arrogance, it was his conviction. He'd bled for this business. He knew what it meant to him, what it had cost him, what it had taken from his family on holidays and weekends and sick days.
Rodney had heard a few multiples tossed around from other businesses that were sold. He wanted his share and he felt like his business was worth a premium.
The calls started coming in. Buyers were interested, serious buyers, too. Private equity-backed platforms. Regional strategic acquirers. Operators looking to expand. His business was exactly the kind of asset the market wanted. And then, one by one, they went quiet.
What Rodney Didn't Know
Here's what Rodney didn't understand: Rodney's $20 million demand wasn't just a high number. It was a signal. He brought it up in every conversation and made it clear he needed $20 Million and wanted to leave within 30 days. That told every sophisticated buyer in the market exactly what kind of deal process this was going to be.
By most reasonable market measures, Rodney's business was worth $15 - $18 million.
That's not a bad number. That's a life-changing number. That's Portugal every year for the rest of your life. That's never setting an alarm again. That's your kids' futures, secured. But $15 to $18 million wasn't $20 million. And Rodney made it clear on those calls he wouldn't budge.
So the best buyers, the ones with real capital, well defined internal processes, and track records of treating sellers fairly, quietly moved on. They didn't argue. They didn't counter. They didn't send a strongly worded email. They just stopped calling. Because they didn't have to chase anyone. They had a pipeline full of sellers who were ready to become multi millionaries.
What was left was a shrinking pool of tire-kickers and buyers who couldn't close a deal this size even if they wanted to.
The Brokers He Burned
Rodney did talk to brokers. Several of them, in fact.
He just refused to pay their fee. He listened to their pitches, ignored their process, and decided each time that he could do it himself and keep the commission in his own pocket. But a few of those brokers genuinely believed they could find a solution and kept working on it anyway, hoping to bridge the gap between Rodney and a qualified buyer.
They brought him some of their best people. Serious, well funded, motivated buyers who had closed deals like this before and were prepared to move quickly for the right business.
Then Rodney started moving the target.
In one conversation he'd tell a buyer there was another offer on the table at $20 million, so they'd need to hurry up and decide. They would probably need to be at $21M or $22M. On the next call, the number had quietly crept higher. The story kept changing. The urgency felt forced and manufactured. And the buyers, who had done hundreds of deals between them, recognized exactly what was happening.
One by one, the brokers stopped returning his calls too.
It wasn't just the price. It was the trust. When a seller tells a buyer there's a competing offer that doesn't exist or that offer is pushing the value beyond reason, or the initial terms shift, then any momentum or trust that was building dies. And the seller's reputation follows them. The brokers who went out on a limb for Rodney, vouching for him to their networks, found themselves embarrassed. They moved on and never came back.
In the end, Rodney didn't just fail to sell his business. He managed to burn the very relationships with the best M&A advisors in the industry. The few advisors in this industry that may have been able to get him his number had he just trusted them to manage the process and do it the right way.
The Transition Problem
The price wasn't even the biggest issue.
Rodney also made it crystal clear that he had no intention of staying with the business after the sale. He wanted out. Sign the papers on Friday, gone within 30 days at most.
To Rodney, that felt like freedom and he didn't understand why he should be expected to stay longer. To every buyer, it looked like a red flag the size of a billboard. Think about it from the buyer's perspective. They're about to wire $15M, $17M, maybe $20 million for a business built almost entirely around one man's relationships, reputation, and institutional knowledge. The employees trust Rodney. The customers call Rodney's cell phone. The key vendors know Rodney. And Rodney wants to disappear with his $20M? A deal this size doesn't just turn over within 30 days.
That's not a business acquisition. That's a huge gamble.
Buyers aren't just buying revenue. They're buying confidence that the revenue will still be there in 12 months. A seller who commits to a 1 or 2 year transition, staying on in a leadership or advisory role, introducing the new ownership team, reassuring key customers and employees, dramatically reduces the buyer's risk. And reduced risk means a higher price and a faster close.
Rodney refused. And in doing so, he didn't just lose a few hundred thousand dollars in negotiating leverage. He lost the whole deal, over and over again.
Where Rodney Is Today
Rodney is still working. He's still putting in 40-hour weeks. Still managing employees, managing HR, watching his competitors evolve. Still waiting for that one perfect buyer to show up and hand him $20 million, with no negotiation required.
That buyer isn't coming. Not in the way Rodney expects.
What makes it even harder to swallow is this: had Rodney taken a little less or been more negotiable on the transition period and closed the deal a few years ago, he would have had his time back. And for a man who spent more than two decades sacrificing weekends, holidays, and sleep, time is worth more than any gap between $15 million and $20 million. The money he left on the table is trivial compared to the years he's still spending behind a desk.
And here's the other thing nobody tells you. That $15 to $18 million, invested wisely and working quietly on his behalf, would very likely be worth more than $20 million. Instead, every dollar he has is still locked inside a business he can't sell, exposed to every risk that comes with owning and operating a company in an industry that never stops demanding more. He still makes a good living. But he could be making a good living without carrying the weight of payroll, liability, equipment failures, and employee turnover every day.
Meanwhile, the market has changed considerably The buyers who were once willing to pay the highest multiples a few years ago and who maybe would have paid close to his $20 Million are paying far less today. Multiples have contracted across the home services and contractor industries. What commanded a premium valuation then is being scrutinized much harder now. The window that was wide open when Rodney first started talking to buyers has been narrowing ever since to more normal historical numbers. The free capital that flowed after covid is long gone.
The painful truth is this: Rodney already had his number. It just wasn't the number he'd decided on. A realistic valuation, a trustworthy process, and a willingness to stay for 18 -24 months post-close could have put $15M to $18 million in his pocket, and with the right advisor maybe more. He should be in Portugal right now.
Instead, he chose the illusion of control. And he got neither the exit he demanded nor his retirement.
The Lessons Rodney will eventually learn the hard way (So you don't have to)
1. Your number has to match the market. What your business means to you emotionally is real, but it's not a valuation method. Buyers pay multiples of earnings, not multiples of sacrifice or rumors of what other companies may have sold for.
2. Refusing to transition is refusing to sell. A seller who demands to walk out the door immediately after closing is a risk, not a reward. Commit to a reasonable transition and watch your offers improve dramatically.
3. Trust is everything in a deal process. The moment a buyer or advisor feels misled, the deal is over. Credibility, once lost, is nearly impossible to recover.
4. The best buyers have options. They don't chase difficult sellers. Sellers who are difficult to work with are just passed on. They move on, quietly, politely, permanently. But when they're gone, they're gone for good.
5. Time is the one thing no exit can give back. Every year you wait is a year you're not living the next chapter, and in today's market, waiting may mean a lower number too.
Is Your Business the Next Rodney Story, or a Success Story?
At NorthBase, we've seen both. We know what separates the sellers who walk away with life-changing outcomes from the ones who are still waiting years later.
Jason Hoff is the Founder and Managing Partner of NorthBase.
NorthBase is a Merger & Acquisition firm that specializes in representing home service and contractor business owners across the country, including HVAC, plumbing, pest control, landscaping, garage door, roofing, and general contracting businesses.