Myth Busting: What Founders Get Wrong About Selling Their Business
Selling a business is often framed as a transaction. For founders, it is more often a question of legacy, timing, and trust.
It is a decision about people, customers, identity, and the future of something that likely took years or decades to build. That is why many of the biggest mistakes founders make are framing mistakes. They start from the wrong assumptions about what a sale means, what buyers value, and what happens after closing.
Look Beyond the price
Founders often assume the winning offer is the one with the biggest number attached to it. In practice, price is only one part of the decision.
Time horizon, cultural fit, operating philosophy, and post-close plans can matter just as much, especially when the founder still cares deeply about employees, customers, and the long-term future of the business.
Des O'Mahony of Bookassist captured this well. Some offers were financially attractive, but he did not feel confident about what would happen to the company. What ultimately mattered was finding a structure that allowed the business to continue, the team to stay, and the next chapter to feel aligned with what he had built. In his words, the Vertus option "solved my issues" because it combined de-risking with continuity. (Vertus Group, Bookassist | The Acquisition Process, 2024).
The real question is not just, "What is the price?" It is, "What exactly is being bought, and what happens to it after I sign?"
Selling does not always mean stepping away
Another common misconception is that a sale automatically means the founder leaves the business.
That can happen, but it is far from universal. In the right structure, a founder can stay involved in the parts of the business that matter most to them, while gaining support, stability, and a stronger operating foundation.
This is why the type of buyer matters so much. Founders and operators consistently point to continuity, autonomy, and room to grow as deciding factors. When CAST joined Vertus, the company explicitly framed the move as continuity with acceleration, not replacement. When Bookassist sold, the founder emphasized that he could continue pursuing the strategy and next steps he cared about. (Vertus Group, Vertus Group Acquires CAST, 2025; Vertus Group, Bookassist | The Acquisition Process, 2024).
For some founders, the right sale is not an exit. It is a transition into a different kind of role, one that allows them to focus their time and energy on the parts of the business they are most passionate about.
Timing Is often misunderstood
Founders sometimes wait until burnout, stagnation, or operational pressure to force the conversation of selling. This is not the highest-leverage point. The stronger moment is often quieter: when the business is healthy, the team is capable, and the founder still has the space to think strategically about what comes next. (Vertus Group, The Quiet Moment — Knowing When You Are Ready to Sell, 2026).
Founder transitions are often more complex than traditional leadership changes, and growth eventually requires founders to hand off more decisions and build leaders around them. (Groysberg et al., Leading After the Founder, 2026).
In other words, the company remaining overdependent on founder stamina is not a sign of commitment. More often, it is a sign that the transition started too late.
Buyers look beyond growth and EBITA
Revenue and profitability matter. But serious buyers, especially in software, typically look deeper.
They look at recurring revenue quality, customer stickiness, operating maturity, and the resilience of the business model. They want to understand not just how the company has performed, but how durable that performance is likely to be.
Leadership depth matters too. McKinsey points out that the leadership required at startup and scale-up stages is different, and that founder vision cannot remain the only force guiding a growing company. As businesses mature, buyers want evidence that the company can continue to perform without every important decision flowing through a single founder. (McKinsey, Scaling up: How founder CEOs and teams can go beyond aspiration to ascent, 2022).
This is where many founders underestimate what buyers are really evaluating. They are not simply buying historical performance. They are buying the probability of durable future performance.
Closing is not the finish line
Closing is the moment when a buyer's operating model is tested in practice.
This matters for those founders focused on preserving what they have built. Buyers create value through what happens next: how they support leadership, preserve momentum, communicate through change, and provide a framework for growth. If that model is weak, the business can lose ground quickly. If it is strong, the transition can reinforce the decision to sell in the first place.
This is exactly why founders should diligence the buyer as seriously as the buyer diligences them.
Buyers are not built the same way
Some buyers ultimately optimize for a later exit. Others optimize long-term stewardship. That difference shapes far more than ownership structure. It affects hiring confidence, product investment, customer trust, and the degree to which the business can keep building rather than defend against short-term financial pressure.
Vertus' Hold Forever model is compelling for precisely this reason. It is not presented as a slogan, but as an operating commitment. It shapes how acquired businesses are supported, how decisions are made, and how continuity is preserved.
Jason Pearsall, founder of Club Caddie, put it plainly: “I sleep at night now.” That line reflects something many founders are ultimately looking for: confidence in what comes next. (Vertus Group, How Vertus Group Helped Club Caddie Grow).
Framing the future
Founders do not get selling wrong because they are careless. They get it wrong because they reduce a deeply strategic decision to a narrow financial one.
A different lens is this: a sale is not just about taking value off the table. It is about choosing the environment in which the business will continue to create value.
For founder-led software companies, the right outcome is not always the best multiple. It is the right next chapter, with the right structure, the right incentives, and the right home.
Read More
Vertus Group. (2026, February 6). Founder perspectives. Vertus Group.
Vertus Group. (2026, February 25). What it means to “hold forever.” Vertus Group.
Vertus Group. (2026, March 18). Handing over the keys: Knowing when your business is ready for its next chapter. Vertus Group.
Vertus Group. (2024, February 29). How Vertus Group helped Club Caddie grow. Vertus Group.
Hellauer, S., Kos, S., Vermoote, J., Werner, S. S., & Wright, B. J. (2026, January-February). Leading after the founder. Harvard Business Review.
Austin, J. B. (2019, August 12). How scale changes a manager’s responsibilities. Harvard Business School Working Knowledge.
Jules, C., Kshirsagar, A., & George, K. L. (2022, November 9). Scaling up: How founder CEOs and teams can go beyond aspiration to ascent. McKinsey & Company.
Kordestani, K., Kaetzler, R., Bernauer, T., Dutta, A., & Krenz, L. (2026, February 13). Unlocking merger value through operating model design. McKinsey & Company.
Kordestani, K., Van Oostende, M., Sherman, E., Moore, H., & Kuritsky, N. (2026, February 13). Excellence in M&A communications: From preannouncement to postclose. McKinsey & Company.
Hagedorn, C., Liu, A., Naharro, J., & Van Ingelgem, K. (2023, December 1). When a transaction forges a transformation. McKinsey & Company.
