Helping a business owner sell their company is a significant accomplishment. But helping them look back years later and say, "I'd do it all over again," is something entirely different.
The difference isn't simply achieving the highest value. It's helping owners avoid the three regrets that surface again and again after a business sale.
Advisors who can guide clients through these challenges create an experience that builds trust, referrals, and lasting relationships.
One of the most common regrets business owners express is accepting the first unsolicited offer that comes their way. At first glance, it can feel like a dream scenario. A buyer makes an attractive offer, sparing the owner the perceived hassle of taking the company to market.
Unfortunately, that's often where the problems begin. An unsolicited offer may feel like a shortcut, but it's also the point where many owners unknowingly give away their negotiating leverage. If your client is considering one, the single most important piece of advice is this: Don't let them sign a letter of intent (LOI) before they've explored other options.
The moment they sign an LOI, the buyer gains exclusivity. From that point forward, the buyer largely controls the process. Even if they opened with an attractive number, they can use due diligence and quality-of-earnings findings to renegotiate the price, extend the timeline, or change the terms. At that stage, the seller's only real leverage is the ability to walk away.
Creating competition changes the conversation. Consider one recent example. A business owner had spent months negotiating with a single buyer, eventually reaching a $10 million offer. Nearly half of that value, however, was tied to an earn-out, and the buyer insisted there was no room to go higher.
At the recommendation of the owner's financial advisor, Cornerstone completed a Real Market Analysis (RMA). The valuation confirmed the buyer's headline number wasn't unreasonable, but it also revealed something more important: A company of this size and profile would typically command 75% to 90% cash at close—far more than the roughly 50% cash component in the unsolicited offer.
Knowing they could likely receive substantially more cash at closing, the owner decided it was worth engaging an investment bank and running a competitive process.
They weren't sure how to respond to the buyer, so we suggested a simple message: "We really like your firm and think you could be a great fit. But we only get one chance to do this right, so we're having Cornerstone run a process. They'll be in touch shortly."
Minutes after that email went out, the phone rang. The buyer's first words: "What's it gonna take for you not to sign with Cornerstone?” Suddenly, that $10 million ceiling didn’t look quite so firm.
We ran our Assurance 360™ process, brought in roughly ten offers, and closed at $14 million. That's 40% more, with about $9 million in cash at close, nearly twice what was originally on the table.
Because their financial advisor encouraged them to test the market rather than accept the first offer, the owner walked away with something far more valuable than a higher purchase price. They were confident they hadn't left money on the table. And they were able to choose the buyer who was the best overall fit, not simply the first one to knock on the door.
The lesson is that business owners deserve to know what the market is truly willing to pay before making one of the biggest financial decisions of their lives. For advisors, helping clients resist the temptation of the unsolicited offer can be one of the most valuable conversations they ever have.
The second regret: Owners don't think about what a successful deal actually looks like until they're already in it, with emotions running high.
When that happens, almost everyone defaults to money. It's the first thing people ask: “What multiple of EBITDA did you get?"
So owners chase the highest number. Then, weeks or months later, they discover that the culture is a poor fit, that key employees have been let go, or that the new owner's vision clashes with theirs. Or maybe they agreed to stay three years when they really wanted out in six months.
The fix is simple. Have your client complete a short deal-priorities assessment while they're calm and thinking clearly, long before any offer is on the table. (Download our Deal Priorities Worksheet.)
As sellers get closer to closing, their thinking tends to become more emotional, and life-changing decisions shouldn't be made under that kind of pressure. Taking time up front to rank what matters most lets them reflect on what really counts.
There's no right or wrong answer. The hard part is that every deal point matters, and your client has to decide which ones matter most. Some owners will gladly take the second- or even third-highest offer, because the other terms matter more to them than price alone.
The third reason owners end up with seller's remorse is that they don't know what they'll do after the sale.
In our national study, 65% of owners said they're deeply emotionally tied to their business. And more than 30% said they don't even know what they'd do without it.
Author Bo Burlingham highlighted this challenge in Finish Big, describing how many entrepreneurs struggled after a sale, not because they lacked wealth, but because they lacked purpose. Owners who spend decades serving customers, leading employees, and solving problems often find retirement very different from what they imagined.
That's why exit planning should include conversations that extend beyond valuation and taxes.
Simple exercises can help owners begin envisioning the next chapter before they reach the closing table. Building a meaningful bucket list, for example, encourages them to think beyond "I'll play more golf" and instead consider experiences, relationships, travel, philanthropy, or new ventures they genuinely want to pursue.
Another powerful exercise asks owners to reflect on how they hope to be remembered by their family, employees, community, and friends. Those conversations often reshape priorities and help owners recognize that their legacy extends well beyond the business itself. (Download our “Bucket List Beyond the Business” exercise.)
Owners who have a clear vision for what's next approach the sale with a very different mindset than those who are simply focused on leaving what they've built behind.
Help your business-owner clients through these three pivot points:
Do that, and you take them from a plain transaction—they sold, they got some money, and they're full of what ifs—to what we call a Legacy Level Deal™. They went out on top. They finished on their terms. And they're genuinely excited about the future and their life ahead.