When Is the Best Time to Sell Your Business?
By Ryan Kuhn, founder of Kuhn Capital, an M&A advisor to mid-market technology companies.
Selling a business successfully requires weighing personal circumstances against market conditions, then adjusting as both shift. The following short quiz highlights the most important considerations when deciding whether now is the right time or, if not, how to exit optimally anyway.
When & How Exits Happen
Factors driving exits range from internal considerations, like the “desire to retire,” health, and family and management needs, to external factors such as competition and shifting technology trends.
Exit Drivers
Deciding when to sell a business is a deeply personal choice. For some owners, no matter how strong the evidence for selling is, the idea feels impossible. So they wait, and, as a result, over one-third of those who go to market are, at the end of the day, compelled to do so.
The data backs this up (see chart below): while 63% of exits are voluntary (led by retirement at 27% and new opportunities at 20%), a striking 37% of owners find themselves dealing with sudden shocks like health crises (12%) or partnership disputes (10%).
The Exit Readiness Questionnaire
To get a better fix on your exit horizon, print this page, grab a pen, and circle your answers. The more your responses lean in one direction, the clearer the signal whether to sell now or wait. If your results lean toward selling, speak with a trustworthy M&A advisor before investing time and money in next steps. Based on that feedback, you may still find you’re a bit early.
1You want to exploit a fleeting market opportunity but don’t have the resources.
YESNO
2You’ve been thinking more about selling the company to fund a better lifestyle or new opportunities.
YESNO
3You’re bringing less energy or passion to your work than before.
YESNO
4External threats (tech changes, competitors, regulations) are complicating life.
YESNO
5M&A valuation multiples and deal closings in your industry are up.
YESNO
6You’re uncomfortable having so much of your wealth tied up in the business.
YESNO
7You’d like to transfer wealth to family members in a tax-efficient way. (FYI, the lifetime estate and gift tax exemption threshold is $15 million per individual as of 2026. Using this exemption to gift your business’ equity or place it in trust will freeze value, removing future appreciation from your taxable estate. Talk to a planner.)
YESNO
8Demand for your products or services is cyclical, seasonal, faddish or susceptible to tech trends.
YESNO
9You’re concerned about your health or relations with co-owners.
YESNO
10You’re unhappy with the direction of current economic, political, or social trends.
YESNO
11Your company’s revenue exceeds $10 million.
YESNO
12You no longer feel the need to prove anything.
YESNO
13You have no clear successor in sight, and you’re over 60.
YESNO
14You’ve received an unsolicited purchase offer. (Warning: Accepting an unsolicited bid without running a competitive process typically leaves 20% to 30% of your business’ true value on the table.)
YESNO
15Your products or services could fill a strategic gap in a larger competitor’s lineup.
YESNO
16Your IP may be worth more in someone else’s hands than yours.
YESNO
17The Russell 2000 index has materially appreciated over the past 12 months. (Small-cap public valuations tend to pull private company multiples along with them.)
YESNO
18You’ve found another entrepreneurial opportunity that you’d like to pursue.
YESNO
19Your company is at or near peak financial performance, with no clear path to materially better numbers.
YESNO
20You could complete various value-enhancing initiatives (e.g., key hires, new products, an updated sales management system) before beginning the company sale process.
YESNO
21Sales have been flat or declining, and you don’t have a clear plan to reverse that within a year.
YESNO
22Your industry’s M&A cycle is in a down phase and you lack the time or resources to wait it out.
YESNO
23You’d find a recession lasting as long as five years difficult to weather, whether for reasons of age, health, or patience.
YESNO
24You have no remaining value-adding projects you both want to complete and could finish in a reasonable time. (For a list of such projects, see Quick Ways to Increase Value Before Sale and Bigger Projects That Increase Value More.)
YESNO
Answer the questions above and your score appears here. More Yes answers indicate a stronger sell signal.
Last Thoughts
There are many reasons to delay: not knowing what you’d do next; believing no
one else can run the business as well as you; like being your own boss; thinking you first need to grow the business more; or believing you can handle the challenges without outside help.
All of these perspectives can be valid. But entrepreneurs wired to push through adversity can sometimes miss the benefits new ownership unlocks. That may be simply because they haven’t seen enough examples of successful exits. Or they’re narrowly focused on the next business objective.
Since, at the end of the day, nearly four out of ten owners must sell, waiting until you are emotionally “ready” may be a gamble. The best insurance policy is to build a sale-ready business before you decide the time is right. To many business owners’ surprise, the best time to sell may be when they’re saying, “not yet.”
Kuhn Capital’s principals have advised on more than 80 mid-market technology transactions worth over $3 billion. For suggestions on preparing your company for a safe, successful sale, contact us at (650) 353-3353 or by email. Also see our M&A Resource Hub, which carries dozens of articles on growing and preparing a mid-market tech company for sale.
Revised 10/2/26 © 2026 Kuhn Capital, Inc. All Rights Reserved
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Posted by:
Ryan Kuhn
10/04/2026
Ryan Kuhn is the founder of Kuhn Capital, an M&A advisor to mid-market technology companies.
