Most founders who come to us have been thinking about selling for longer than they’ll admit.
Not obsessing. Not planning. Just carrying the question quietly — usually somewhere between the fourth quarter budget review and the drive home on a Friday when nothing went right. At some point, this has to end. The thought arrives and then gets filed away, because there’s still too much to do and it still doesn’t feel like the right time.
The problem is that “the right time” is a feeling, not a market condition. And that feeling, left unchecked, will cost you.
The peak trap
The most common version of this goes: I’ll sell when the business is at its best. Revenue is climbing. Margins are clean. The team is solid. That’s when you go to market — when you can command the best number.
The logic is intuitive. It’s also how founders end up waiting too long.
Here’s the thing about peak performance: by the time you’re certain you’re at the peak, you’re probably past it. Markets shift. Key customers consolidate. Industries that looked stable for a decade suddenly aren’t. The window that looked wide open closes faster than anyone expects, and the founder who was waiting for the “right moment” is now explaining to buyers why last year’s EBITDA was higher than this year’s — which is exactly the conversation you never want to have in a deal process.
The buyers who pay the best multiples aren’t buying your past. They’re buying your trajectory. And trajectory is a story that gets harder to tell once the trend line starts to flatten.
The readiness trap
The second version goes: I’m not ready yet. And this one is trickier, because it’s not wrong — it’s just incomplete.
There’s a version of readiness that’s real and important: the business needs to be transferable, financials need to be clean, key-person dependency needs to be addressed. Those things take time and they’re worth doing. A business that falls apart without the founder in the room is worth meaningfully less than one that doesn’t.
But there’s another version of readiness that’s really just resistance in disguise. Waiting until every operational issue is resolved. Until the right manager is hired. Until the next growth phase proves itself out. That version of readiness is a horizon that keeps moving — and founders who chase it often sell later, under more pressure, with fewer options.
The question isn’t whether you’re ready. The question is whether you’ll be more ready in three years than you are today — and whether the market will still look the same when you get there.
What timing actually means
The founders who get the best outcomes aren’t the ones who timed the market perfectly. They’re the ones who started the conversation early enough to have options — to prepare, to address what compresses value before a buyer sees it, to choose a buyer instead of accepting whoever showed up.
The best time to sell is somewhere between when you first seriously started thinking about it and before you actually need to. That window is wider than most founders realize. And narrower than they’d like.
The worst version of this story is the founder who waited for the feeling of readiness, watched the window close, and sold from a position of weakness. The best version ran a process on their terms.
If you’re carrying the question — even quietly — that’s enough reason to understand what you’re working with. What the business looks like to a buyer today. What’s driving value and what’s discounting it. These are answerable questions. And the answers change everything.
Ready to understand what your business is worth? Schedule a conversation
Richmond Partners is an M&A advisory firm working with founder-led and family-owned businesses.
This article is for informational purposes only and does not constitute financial, legal, or investment advice.
