By Chris Spratling
For many entrepreneurs, selling their business is the culmination of years of hard work, ambition, and resilience. Yet, despite the significance of the transaction, the majority of business owners remain unprepared for their exit. In this article Chris Spratling, founder of Chalkhill Blue, explores how a lack of planning not only jeopardises the final sale value, but often leads to regret.
Most business owners believe they’ll sell one day.
Very few actually do.
That may sound blunt, but the data is unambiguous. Brokers and corporate finance houses estimate that only around 20% of businesses that go to market sell within a year, while as many as 65% never sell at all [1]. Even among those who do complete a transaction, the outcome is often disappointing: more than half of sellers are unhappy with the result, and around three-quarters regret the sale altogether, largely because of the price achieved [5].
This is not a marginal problem. It is a systemic one.
So why does this happen? Why do so many capable entrepreneurs – people who have built profitable, often impressive companies – fail to turn their life’s work into a successful exit?
After three decades working as a buyer, seller, and adviser, I’ve come to a simple conclusion: most businesses don’t sell because they were never built to be sold.
1. The myth of “I’ll sort the exit later”
One of the most damaging assumptions in entrepreneurship is the belief that an exit is something you think about at the end. In reality, selling a business successfully is the result of years of deliberate preparation. Yet research shows that fewer than half of business owners who expect to sell have any form of exit plan in place [3]. Gallup research similarly indicates that a significant proportion of owners have no exit plan at all or are uncertain about their future intentions [2].
This lack of planning has consequences. Selling a business is not a transaction you can improvise. It requires structure, evidence, governance, and a narrative that makes sense to a buyer who does not share your emotional attachment.
Owners who delay planning often end up doing one of three things: accepting a poor offer, pulling out of a deal mid-process, or discovering, too late, that their business simply isn’t attractive to buyers.
2. Overconfidence is not a strategy
Another common reason businesses fail to sell is unrealistic valuation expectations.
Forbes has repeatedly reported that more than half of small and medium-sized business owners have never formally valued their business [4]. Instead, owners rely on hearsay, competitor rumours, or crude valuation multiples lifted from online articles. The result is predictable: a yawning gap between what the owner wants and what the market is prepared to pay.
Buyers do not value effort, longevity, or sacrifice. They value future, transferable cash flows and manageable risk.
In practice, most sellers have no clear idea what post-tax income they actually need after a sale, nor how that figure relates to the real value of their business [7]. That disconnect alone derails countless exits.
3. Founder dependence kills deals
Many entrepreneurs are the beating heart of their business – and that’s precisely the problem.
A company that relies heavily on its founder for sales, relationships, decision-making, or technical delivery is not an asset; it is a job with overheads. Buyers know this, and they price accordingly.
Across multiple transactions, the same issues appear again and again: excessive reliance on the owner, dependence on a small number of customers, and weak second-tier management [7]. When a buyer asks, “What happens if you leave on day one?” and the honest answer is “It falls apart,” the deal is already dead.
4. Growth without scalability is not attractive
Many owners assume that steady growth is enough to attract buyers. It isn’t.
Buyers are not paying for your past performance; they are paying for credible, scalable future growth. Businesses that appear healthy on the surface often fail to attract interest once buyers discover that growth has plateaued or is entirely owner-driven [7].
Growing at 10% may feel impressive – until a buyer discovers that competitors are growing at 20%.
Without documented processes, repeatable sales engines, recurring revenues, and protected intellectual property, growth becomes fragile. Fragile growth does not command premium valuations.
5. The market doesn’t care about your timing
Owners also underestimate how much external conditions influence outcomes. Market cycles, sector sentiment, regulatory shifts, and technological disruption all shape buyer appetite. During the Covid-19 pandemic, for example, hospitality businesses struggled to sell, while IT and remote-services companies surged in value [8].
Too many owners decide to sell based on personal fatigue rather than market readiness. Unfortunately, the market does not adjust itself to your burnout.
6. Selling is a process, not an event
Perhaps the hardest truth is this: selling well takes time.
A well-planned exit often takes two to three years from decision to completion [7]. That time is spent improving governance, strengthening management, de-risking revenues, cleaning up financials, and aligning the business with buyer expectations.
Those who rush rarely win. Those who prepare almost always do better.
The uncomfortable conclusion
Most businesses don’t fail to sell because of bad luck. They fail because owners confuse optimism with strategy, leave planning too late, mistake emotional value for market value, and build businesses around people rather than systems.
The harsh truth is that a successful exit is engineered, not hoped for.
For owners prepared to confront that reality early enough, the odds change dramatically. For everyone else, the statistics speak for themselves.
About the Author
Chris Spratling is the Managing Director and Founder of Chalkhill Blue Limited and the author of The Exit Roadmap: The Insider’s Guide to Selling Your Business Profitably. He advises UK business owners on scaling, exit planning, and leadership transformation.
References
1. BizBuySell. BizBuySell Insight Report. BizBuySell, various editions.
2. Gallup. U.S. Small Business Owner Survey. Gallup, latest available edition.
3. Wilson, T. (2018). 48% of Business Owners Who Want to Sell Have No Exit Strategy. Brooks Holdings.
4. Forbes.
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De Pau, L. (2024). When Should You Decide to Sell Your Business?
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Hannon, K. (2018). How Entrepreneurs Should Prepare to Sell a Business.
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