Yet for many business leaders exiting, especially founders and family owners, the celebration fades fast. According to the Exit Planning Institute's State of Owner Readiness research, 75% of business owners who successfully sell their companies experience profound regret within one year of the exit. Not mild disappointment. Not nostalgia. Profound regret.
This is not about the price they negotiated. It is not about letting go. It is about watching the company they built slowly unravel under new ownership: key people leave, culture erodes, and the mission that once defined the business fades into the background. The transaction that was supposed to secure their future has instead placed their life's work in the wrong hands and liquidated its meaning. This is seller's remorse.
How Auctions Destroy Legacy
Founders spend decades building revenue generated from a distinctive way of operating: how problems are solved, employees are treated, clients are served. That culture is the true engine of competitive advantage.
Yet in a price-driven process typical of the standard M&A playbook, the buyer is chosen for their wallet, not their stewardship. M&A advisors, compensated as a percentage of the final transaction price, orchestrate a sale process as a competitive auction centered on financial value. Price becomes the dominant selection criterion.
Even when sellers articulate concerns about legacy, employee welfare, or strategic continuity at the outset, these priorities are progressively marginalized by the transactional machinery. The due diligence covers financial, legal, commercial and technical documentation but rarely captures the informal networks of trust, the unwritten decision-making norms, or the cultural practices that actually generate the company's performance.
The process exploits a natural ambivalence: the pull between financial maximization and the desire to see the company thrive in capable hands. The allure of a record valuation provides the expectation of an exciting personal future and the social validation, while the auction's urgency and structure make non-financial criteria operationally invisible.
The result is a systematic gap between intention and outcome. Sellers may start with broader aspirations, but by closing they often end up selecting the highest bidder, regardless of cultural or strategic fit. This gap is not accidental, but structural in the standard M&A playbook.
When the buyer is misaligned, when their management style, values, or methods clash with the internal equilibrium, the fallout is swift. PwC's "Creating Value Beyond the Deal" research shows that in deals where significant value was destroyed, 82% of companies lost more than 10% of key employees in the first year. Talent exodus takes institutional knowledge, client relationships, and operational know-how out the door. What remains is a hollowed shell that may carry the same name but no longer delivers the same results.
The Poisoned Check
For sellers who stay on during transition (often contractually or out of moral obligation), this is excruciating. They become powerless witnesses to decisions that contradict everything they built: cost cuts that slice through muscle, cultural impositions that demotivate teams, strategic shifts that abandon the original mission.
The regret deepens with recognition of complicity: they prioritized the size of the check over the quality of the handover. They allowed the validation of a high price to override instincts about fit and continuity.
What sellers receive in most deals can be described as a "poisoned check": immediate liquidity that comes laced with the delayed certainty of having commodified something alive.
The Reputational and Legacy Cost
The pain extends beyond personal anguish. In professional networks and industry communities, how a leader exits matters. Selling "to the highest bidder" without clear discernment can be perceived as sacrificing integrity for expediency. This creates a discontinuity: the image of long-term thinking, loyalty, and purpose that took years to build is suddenly at odds with the observed behavior.
Most profoundly, legacy, the lasting imprint the leader hoped to leave, is erased. Legacy cannot be quantified, benchmarked, or compared in a price matrix, so it vanishes in the shadow of financial competition. The transaction becomes the sale of a financial asset, not the transmission of a mission.
Clayton Christensen's distinction between 'Reinvent My Business Model' and 'Leverage My Business Model' acquisitions captures this precisely. Sellers have built something worthy of reinvention, continuation, and evolution. Buyers, focused on recouping a price too high through immediate synergies, approach it as leverage: a resource to be extracted, rationalized, and absorbed. The very uniqueness that commanded the premium becomes the first casualty of integration.
Defining Success: Exit vs Succession
Seller's remorse is avoidable. But avoiding it requires rejecting the standard M&A playbook from the start.
When the process treats the company as a pure financial asset, it creates the structural conditions for remorse before the sale and purchase agreement is executed. If legacy, employee welfare, and continuity are genuine priorities, they must be made operational, not aspirational add-ons. This means for the responsible M&A advisor structuring a process that makes intangible value visible and defensible, and for the responsible Seller accepting that the right steward may not offer the highest number.
Above all, it requires reframing the definition of success. In the standard M&A playbook, success is the size of the check at closing. In a succession M&A playbook, success is the health and trajectory of the enterprise five years later.
The choice facing every business leader contemplating a sale is deceptively simple: Are you executing an exit, or are you stewarding a succession? An exit extracts maximum value today, regardless of tomorrow. A succession ensures that what you built continues to thrive, guided by hands you deliberately chose.
One delivers a check. The other produces a legacy.
The difference is the difference between a transaction you'll celebrate long after it is completed, and one you'll spend the rest of your life regretting.
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Amine Laouedj Managing Director, Glenshore
I advise responsible business leaders who wish to ensure their company ends up in the right hands and continues to flourish after their exit. If these perspectives resonate with your thoughts, I welcome a conversation. Please connect or message me on LinkedIn.
Glenshore is a boutique investment bank with the Succession M&A Playbook, a disciplined approach to align financial outcomes with long-term mission and legacy preservation. Learn more at glenshore.com.