Founder exit regret is more common than most people assume: according to the Exit Planning Institute, between 50% and 75% of founders and business owners experience regret after leaving their businesses. PwC research cited by the Institute puts the figure even more starkly, finding that 75% of business owners profoundly regret selling their company within just one year of the transaction completing. Which leaves an obvious question: if so many founders feel this way, what are they getting wrong before they sign on the dotted line?
Anthony Villis, director and cofounder of wealth management company First Wealth, argues that the root cause is rarely the exit itself. It is the absence of a coherent plan, both for the business transaction and for personal life afterwards.
The emotions behind founder exit regret
Building and running a company generates a complex emotional landscape. There is the pride of ownership, the identity that comes with being a founder, and a deep bond with the business and the people in it. Those feelings do not simply vanish on completion day. On one hand, a successful exit can feel like a reward for years of sacrifice, long hours and risk. On the other, the question of “what if?” can linger, and quickly curdle into regret if life after the sale does not match expectations.
The motivations for selling vary widely. Emotional factors, including burnout, a desire for more time with family, or a wish to pursue something new, were the primary driver for 56% of founders, while 44% cite personal wellbeing and family considerations. Then there are the more urgent, unplanned triggers. Harford Financial Group describes these as the five D’s of exit planning: Death, Disability, Divorce, Distress, and Disagreement. When one of these forces a founder’s hand, the likelihood of a carefully structured exit falls sharply, and regret tends to follow.
Yet even founders who exit on their own terms often find themselves unprepared. Nearly half (48%) of owners have no exit strategy in place at all, and 13% say they had not even considered the need for one.
Matching the exit route to personal goals
Part of the problem is that founders sometimes fix on a post-exit vision, sitting on a beach, travelling, working part-time, without checking whether the exit they are planning can actually fund it. The range of options available is wider than many realise, and each comes with different implications for how much money a founder walks away with, how quickly, and on what terms.
An initial public offering (IPO) suits larger businesses with governance already in place, but brings significant regulatory scrutiny. A management buy-out (MBO) preserves continuity and can reward senior staff, but requires buyers to access sufficient capital. A private equity sale typically means a PE firm takes a majority stake with the intention of growing the business before its own exit, with founders often retaining a smaller equity share in the meantime. Employee ownership trusts (EOTs), where a trust buys a controlling stake on behalf of qualifying employees, are growing in use in the UK, partly because of favourable tax treatment and partly as a way of protecting company culture. Trade sales, mergers, and family succession each carry their own distinct trade-offs, with family succession perhaps the most emotionally complex of all, requiring honest assessments of capability and fairness across generations.
Villis illustrates the stakes with a case study. A founder who had built a consultancy over more than 30 years faced a choice between an external sale, which risked the culture and put long-standing staff at risk of restructuring, and an MBO. The MBO made sense as an exit strategy. What the founder lacked was the personal plan: clarity on what they actually wanted, how much they needed, and whether the MBO structure could deliver it. Only by building the personal financial plan alongside the exit strategy, working with appropriate advisers, did the picture come together. The result was a founder who exited financially secure, confident about retirement, and assured that the team, including family members remaining in the business, was aligned and well-positioned to move forward.
The lesson Villis draws is straightforward. An exit strategy and a personal plan are not the same thing, but they have to work together. Without both, a founder can end up technically exiting on schedule while being tied to the business through a strict earn-out period, working as hard as ever with less autonomy, and no closer to the goals that motivated the sale in the first place.
Nearly half of founders have no exit plan at all. For those approaching the question now, that is the starting point worth addressing first.
