One of the most common questions founders ask is: When is the right time to sell my business? Should you go to market now — or wait one more year? Can you time the market? Will just one more milestone make a meaningful difference?
In this episode of The Founder’s Journey to Exit, Evergreen M&A Advisor Hannah Huke is joined by Dr. Azza Kennedy, Managing Director, and Robert Radlich, Founder and Partner at Evergreen, to unpack the reality behind timing an exit — and why waiting too long is one of the most costly mistakes founders make.
You can listen to the full episode on Apple Podcasts, Spotify, or Buzzsprout.
As Dr. Azza explains, founders rarely delay selling for irrational reasons. Most are deeply invested in their businesses and believe that one more good year will change everything.
“We say, let me just grow revenue a little more, fix this one thing, or hit that next milestone,” Azza shares. But while founders wait, markets shift, valuations cool, and energy begins to fade. The irony is that many founders don’t realize the best time to sell isn’t when they’re tired — it’s when the business is performing exceptionally well.
Robert sees this pattern repeatedly. Founders are growing fast, optimistic, and focused on expansion — opening another location, hiring another provider, or checking off one more goal. But when those plans stall or the market changes, the opportunity window quietly closes. “Follow up a year later,” Robert explains, “they didn’t do those one or two things, now the business is declining, it’s worth less, and the market has shifted.”
This is why Evergreen emphasizes a simple but powerful truth: the best time to sell your business is when buyers want to buy it. Strong inbound interest is a signal — even if you aren’t ready to transact yet. Exploring offers doesn’t mean you have to sell, but ignoring market demand can mean missing it entirely.
Robert compares this to how professional buyers operate. Before they even close an acquisition, they’re already thinking about their exit. They stay in constant communication with investment bankers, positioning the business years in advance. Founders, he says, should be thinking the same way. You don’t need to be ready to sell to start preparing intelligently.
Readiness, as Azza explains, comes down to three critical dimensions: financial, emotional, and strategic.
Financially, founders need clarity. What number actually changes your life? Emotionally, are you still energized — or running on fumes? And strategically, can the business operate without you? Buyers pay a premium for stability, momentum, and transferability. When the business is strong, founders have leverage: the ability to choose the right buyer, negotiate better terms, and retain equity.
That equity component — often called the “second bite of the apple” — can be one of the most powerful wealth-building tools in a deal. Robert breaks this down simply. Beyond cash at close, deals may include earnouts, seller notes, and rolled equity. Rolled equity allows founders to retain ownership in the larger platform, meaning their upside continues as the business grows.
In many cases, that second bite can grow two, three, or even five times in value, sometimes exceeding the initial cash payout. But, as Azza emphasizes, this only works if the business still has gas in the tank. Selling from strength always beats selling from fatigue.
Not all equity, however, is created equal. Robert cautions that structures vary widely — common equity, preferred equity, and different return profiles can dramatically change outcomes. This is where the right advisors matter most. Running a competitive process ensures founders don’t just get an offer — they get the right structure aligned with their long-term goals.
Finally, the episode addresses a reality many founders overlook: most exits don’t mean walking away immediately. Buyers often want founders to stay on for a transition period — sometimes two to five years — especially in provider-based businesses where relationships and leadership continuity are critical. Understanding this timeline upfront is essential to choosing the right moment and the right partner.
The key takeaway is clear: timing an exit isn’t about guessing the market — it’s about awareness, preparation, and momentum. Founders don’t need to sell tomorrow to benefit from understanding where they stand today.
Get in Touch
If you’re wondering whether now is the right time to sell — or simply want clarity on your business’s value and readiness — Evergreen can help you evaluate your options with confidence. Contact Senior M&A Advisor, Hannah Huke, at hannah@evergreenforfounders.com or 617.470.3462.