Exit Planning Case Studies: Regret vs. Reward for Business Owners

In this ongoing series, we are profiling several Simon Quick clients to reveal some of the financial and estate planning challenges faced by wealthy families and how we have been able to help them meet these challenges.

All names and identifying details have been changed, but otherwise, the case studies reflect real-life families and situations.

One day, you will look back and reflect on your business’s story — its evolution while you were at the helm. Do you want to feel nostalgia and pride, or frustration and regret?

While it’s a redundant question with an obvious answer, in reality, the latter is an all-too-common outcome.

That’s because some business owners approach their exit with a deliberate exit strategy, while others step into it unprepared.

This article shares two real case studies that show both sides of the coin: one plagued by mistakes and disappointment, and another that showcases the payoff of thoughtful, holistic planning.

The Perils of Skipping the Exit Planning Process

Hindsight can be harsh.

Take the story of a brilliant healthcare software founder who built his company from the ground up. Business operations were as strong as ever. On paper, it was worth at least $50 million. But when the chance to sell finally came, he resisted nearly every best practice of business exit planning.

He declined to hire an investment banker to run a competitive process, balking at the fees. He dismissed the need for proactive tax planning. He relied on his longtime general attorney (not a seasoned M&A specialist) to negotiate the deal. And rather than engage a dedicated advisory team, he placed his trust in a buyer’s banker, who ultimately represented the acquirer’s interests.

At first, the outcome looked promising: $40 million in cash, plus 40% equity carry. But within a year, the promises unraveled.

The private equity firm cut costs aggressively, abandoned planned acquisitions, and failed to reward key employees as expected. The company’s culture fell apart. Clients noticed. The founder — frustrated, powerless, and tied to weak legal protections — walked away, effectively writing off his remaining 40% stake.

To make matters worse, he had moved too quickly to sign the letter of intent. Consumed by due diligence, he never circled back to pursue tax strategies that could have preserved millions.

Yes, he walked away wealthy. But seven years later, the wealth is overshadowed by lingering frustration and thoughts of what could have been.

The Payoff of Proactive Planning

While many exits end in profound regret, that’s generally because the business owners weren’t truly prepared to exit — from either a personal, financial, or market readiness standpoint.¹

Fortunately, for those who do prepare, the outcome is a much different story.

A married couple who owned a successful manufacturing company were at a crossroads. They weren’t sure if they should sell or keep the business. Their concern was twofold: they didn’t know the company’s true value, and they feared they couldn’t replace the income that supported their lofty lifestyle, which they had grown accustomed to.

Rather than guessing, they engaged Simon Quick to help. First came clarity: an assessment provided a realistic range for the company’s valuation and attractiveness . Next came alignment: a deep dive into their personal goals revealed they could meet a lifetime of needs and still plan for their family’s future, all while designing a purposeful charitable legacy.

With this confidence, they moved forward.

The process was meticulous. We hired an advisor to conduct a sell-side quality of earnings review. We then exhaustively interviewed a slate of investment bankers who specialized in their industry, ultimately helping to choose the right fit. We then sat alongside our clients throughout the M&A process, while suitors were identified, vetted, and the right partner was ultimately chosen.

Meanwhile, advanced tax strategies were built into the plan: meaningful deductions in the year of the sale, deferrals into the future, and charitable structures that aligned with their values.

The result exceeded expectations. The company sold for more than anticipated, to an acquirer that proved to be a strong cultural and strategic match. Their agreement protected the family’s interests and set them up for a second “bite of the apple” when the company one day sells again. Most importantly, their wealth plan accounted for lifestyle, discretionary, family, and philanthropic goals with purpose and grace.

This was not only a lucrative sale but also a smooth business transition, that carried all the hallmarks of a truly successful exit.

Exit Planning Defines the Ending

Both case studies started with successful businesses. The difference was not the companies themselves — it was the planning.

In the first story, a founder relied on shortcuts and skipped professional guidance. The outcome was wealth, yes — but also frustration, missed opportunities, and lasting regret.

In the second, a couple embraced a structured exit planning strategy, engaged the right professional advisors, and aligned every decision with their personal goals. The result was a higher-than-expected sale price, a protective agreement, and a secure legacy for their family members.

The lesson for business owners is clear: you may only exit once. Don’t leave it to chance.

At Simon Quick, we help owners navigate this once-in-a-lifetime transition with clarity and confidence. As your dedicated exit planner and deal quarterback, we coordinate the advisory and “deal” teams, bring rigor to valuation and tax strategies, and align your exit goals with the legacy you want to leave behind.

Your business transition may be the final chapter of a story you’ve been writing for decades. Make sure it ends with pride — not regret.

Ready to start building your roadmap? One conversation today can change your life.

1. 2023 National State of Owner Readiness Report