Founders are problem solvers. It is in their DNA. When something needs to get done, the instinct is to figure it out, move fast, and handle it personally. That instinct is usually what built the business in the first place. But when it comes time to sell, that same instinct can cost you everything.

Krystyn Harrison learned this firsthand. She had built Prosper, a digital coaching platform with 30,000 users across the world and an impressive client roster that included RBC and Lululemon. The business was real. The technology was strong. The mission - democratizing access to coaching - resonated. But the competitive landscape shifted when a U.S. competitor raised $150 million, and Krystyn found herself facing a decision that many founders eventually confront: the options are narrowing, cash is constrained, and a sale becomes the most viable path forward.

So she did what founders do. She ran the process herself. She picked up the phone and called 75 corporate development leaders looking for a strategic buyer. She found interest. She found alignment. She had a seven-figure letter of intent on the table - a deal that would have been life-changing. And then it fell apart in eight weeks.

Without competitive tension - without another bidder in the room - the buyer had no urgency. Krystyn had no leverage. And with cash constrained and no backup offer, the negotiating position eroded quickly. She ultimately found a home for the platform, the brand, and her team. Her investors and board were satisfied. But the outcome was a fraction of what had been on the table just weeks earlier.

When I heard Krystyn tell this story on ‘The Cash Rich Exit Podcast’, it landed hard because I see versions of it. Founders who are brilliant operators, who have built something genuinely valuable, and who assume that the same skill set that grew the business will translate to selling it. It rarely does.

Here is why. Running a business and selling a business are fundamentally different disciplines. When you are operating, you are optimizing for performance - revenue, margin, team, product, customer satisfaction. When you are selling, you are optimizing for perception, positioning, and leverage. You need multiple interested parties at the table at the same time. You need a process that creates urgency without desperation. You need someone whose full-time job is managing the buyer's experience - fielding questions, protecting information, controlling the timeline - while you continue to run the business as if nothing has changed. Because if performance dips during the sale process, the buyer notices. And if the buyer is the only one at the table, they have every incentive to slow things down and wait for your position to weaken.

That is competitive tension, and it is the single most important dynamic in any sale process. Without it, you are not negotiating. You are hoping.

Matt Harrison, Krystyn's co-founder at Horizon Advisors and a veteran of M&A transactions, reinforced this from the buyer's side. He described the management meetings that happen during a sale process - three-hour sessions where the founder presents to potential buyers. There are things you want the founder to say and things you absolutely do not. Boasting that you are the best salesperson in your company is one of them. It tells the buyer that the business depends on you, and that the moment you leave, the revenue engine is at risk. That is more of a risk and less of a selling point.

Matt also pointed out that the most common reason owners came to market during his M&A career was not because they had a plan. It was because life forced their hand - a health crisis, a divorce, a death. In those scenarios, the lack of preparation compounded the pressure. Financials had small errors that eroded trust. Tax planning that should have started two years earlier had not been done. Due diligence became a 60-hour-a-week second job on top of running the business. And all of it was happening under emotional duress.

This is the pattern I want every founder reading this to internalize. The sale of your business will be one of the most consequential financial events of your life. It will determine whether you walk away with the resources to fund your next chapter or whether you leave meaningful value on the table. And the outcome will be shaped not by how good your business is, but by how well the process is managed.

That does not mean you hand the keys over and disappear. You are still the person who knows the business best. You are still the one presenting in management meetings, answering due diligence questions, and maintaining relationships with your team and your customers through the transition. But the architecture of the deal - the positioning, the competitive dynamics, the timing, the negotiation strategy - should be managed by someone whose only job is to get you the best possible outcome.

Krystyn's other lesson is equally important and far less discussed. After the deal closed, she had an empty calendar. No plan. No structure. No identity beyond the company she had just sold. She described it as a dark period - an unwinding of self from the business that nobody had prepared her for. She eventually found her footing, journaled the entire journey, catalogued every mistake and every win, and used all of it to build what came next. But that transition did not have to be so disorienting. It could have been planned for, just like the transaction itself.

So here is what I would say to any founder who is beginning to think about a sale, whether that is six months away or six years away. First, do not assume the skills that built your business are the skills that will sell it. They are different muscles, and the cost of learning that lesson in real time is measured in seven figures. Second, start the preparation now - clean financials, tax planning, reducing founder dependency, building the systems that make your business look like an asset rather than a job. And third, think about what comes after. The deal is not the finish line. It is a doorway. And you want to know what is on the other side before you walk through it.

If you are wondering whether your business is ready for a sale - or whether you are - book a one-on-one Wealth Gap Analysis with me. We will look at what your business needs to be worth, what it is worth today, and what the gap looks like between where you are and where you want to land. Reach out on LinkedIn - Colleen O’Connell-Campbell - or email me.

TTFN (ta ta for now),

Colleen O'Connell-Campbell

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