When Is the Right Time to Sell?
When Is the Right Time to Sell?
Timing a business sale is one of the most personal and strategic decisions an owner can make, and while there’s no universal “perfect” moment, several clear signals can help you know when it’s time to start serious conversations.
First and foremost, you’ll typically attract the most interested buyers when both your company and the broader economy are healthy. Strong macro cycles tend to bring more capital into the market, and a business with consistent revenue growth, expanding margins, and high customer retention will command strong multiples. It may feel counterintuitive, but selling when your business is still on an upswing often yields far better value than waiting until growth levels off.
That said, not every buyer is just chasing market cycles. Many entrepreneurial buyers, particularly in the search fund space, are long-term operators, not short-term market timers. Firms like HSC are often active even in neutral or slightly down markets when the fundamentals of a business remain strong. Their focus is on long-term value creation, not financial engineering.
Of course, timing is always a balance: sell too early and you might leave money on the table; wait too long and potential buyers may question your growth runway. An earn‑out structure can offer a solution, letting you lock in a base price today while still benefiting from future upside if the business continues to thrive post-sale. When structured well, this can align incentives and ease the transition process.
But perhaps the most overlooked factor is the buyer themselves. Inboxes may be filled with inbound interest, but not all buyers are the same. Financial buyers often prioritize numbers; entrepreneurial buyers tend to emphasize culture, leadership, and legacy. The right buyer is often stepping in as a hands-on operator with a real desire to carry your business forward. Beyond market timing and performance metrics, a well-aligned successor can make all the difference. If you find a buyer or successor who truly understands and shares your company’s core values, feels passionately about preserving its culture, and has a credible plan to invest in your people, that partnership alone can justify accelerating your exit timeline. In other words, waiting for the “perfect” moment on paper can be less important than seizing the right opportunity in practice.
Ultimately, selling from a position of strength means watching for the alignment of three key signals: a healthy economy, proven and growing company performance, and the emergence of a buyer who “gets” your business. When these factors converge, you’ll maximize both your sale price and your confidence that the new owner will honor the legacy you’ve worked so hard to build. Thinking about timing your own exit? We’re always happy to talk through what to consider.
Key Takeaways
The best time to sell is often when your business is healthy, growing, and attracting attention.
Industry trends and a favorable market may indicate it’s worth exploring a sale, even if you weren’t actively considering it.
The right buyer matters more than perfect timing, and if you find someone who aligns with your values, it may be the right time even if the conditions aren’t “perfect” on paper.
