Sell in Good Times, Not Bad: Why Timing Matters More Than You Think
When it comes to selling a business, most owners know that valuation matters. What fewer consider is that timing the sale during a high point in your business lifecycle isn’t just about the price you get—it’s about the quality of the transition, the confidence of the buyer, and the legacy you leave behind.
If you're a business owner who has built something real, something meaningful, then the decision to sell isn't just about numbers. It’s about people, pride, and purpose. And that’s exactly why you should consider selling during a period of strength, not struggle.
Let’s unpack why selling in the good times is one of the smartest, most strategic decisions a business owner can make.
1. You Have Negotiating Power When You're Thriving
Buyers, especially sophisticated ones, look for patterns of strength. When your business is growing, profitable, and well-run, you have options:
You can attract multiple interested buyers.
You can negotiate better terms, not just price.
You can set expectations for how the transition will work.
Selling from a position of strength means you're choosing your exit, not reacting to circumstances. When the winds are at your back, you control the narrative—and the terms.
Contrast that with a downturn scenario: when revenue is flat or declining, key staff are jumping ship, and you're mentally burned out. That’s when buyers get picky, cautious, and opportunistic. And that’s when your negotiating leverage is gone.
2. Buyers Want Momentum
Momentum is contagious. A business with solid revenue trends, strong customer retention, and a confident team is infinitely more attractive than a business in survival mode. Why?
Because buyers aren't just buying your numbers. They're buying your trajectory.
If you wait until the wheels are coming off, the buyer isn't buying growth. They're buying a turnaround. And most buyers, especially individual operators or search fund acquirers, don’t want to inherit a crisis. They want a business with clear upside, not something they need to rebuild from the ground up.
Selling when the business is in a good place tells buyers, "This company works. Your job is to keep it moving."
3. It Gives You Time to Plan the Right Exit
Too many exits happen under pressure: a health scare, burnout, a family issue, or a sudden drop in revenue. But the best exits are intentional. They take time.
When you're still enjoying the work, when your books are clean, and when your team is stable, that's the perfect time to start planning:
You can clean up any loose ends (contracts, compliance, tax planning).
You can work with advisors to structure the deal the right way.
You can help select and train your successor.
That level of thoughtfulness isn’t just good for you. It reassures buyers and creates continuity for your employees and customers. Planning from a place of stability increases the odds of a successful handoff—and a legacy you can be proud of.
4. Your Energy and Enthusiasm Still Show
Buyers can tell when an owner has checked out.
If you're coming into meetings with low energy, expressing frustration about the business, or talking about how "tired" you are, that's a red flag. It says, "This business needs saving."
But if you're still energized—because the business is humming and you enjoy your role—buyers get excited. They see:
An owner who cares about a good handoff
A team that's still being led well
A culture that's intact and motivated
In other words, they see opportunity, not risk.
Selling before you're burned out helps buyers feel more confident. And it helps you present your business in the best possible light.
5. You Get to Be Strategic, Not Desperate
The right time to sell is before you need to.
Desperation leads to rushed decisions, poor deal structures, and limited buyer pools. Worse, it invites buyers who want to take advantage of the situation—not partner in your legacy.
When you're strategic, you can:
Choose between multiple offers
Time the deal around your personal goals
Wait for the right cultural fit, not just the highest bidder
That means you can say "no" to the wrong deal without worrying that it's your only shot.
6. It Creates the Best Experience for Your Team
A strong exit should feel like a milestone—not a surprise.
If your team is in a good place, a planned transition gives them clarity and confidence. You can communicate:
Why you chose to sell
What the buyer brings to the table
How their roles are protected or will grow
When you sell from a position of strength, your employees feel secure, not expendable. And that makes all the difference in how the new owner is received.
If instead you're selling to "get out of a mess," it creates anxiety and turnover—the exact things that kill post-sale momentum.
7. You Maximize Your Legacy
Most business owners don’t start with the goal of building something to sell. You build because you care about your work, your people, and your customers.
But when it comes time to pass the baton, your legacy matters. It’s not just about what you built—it’s about how you passed it on.
Selling in a good season means:
You chose someone who aligned with your values
You ensured the business could thrive after you
You exited on your terms, with pride
And that’s how people remember you. That’s how your name stays on the wall.
8. You Unlock More Options for Life After the Sale
If you sell in a slump, your focus is often on damage control. You might not have the time, money, or energy to move confidently into the next phase of life.
But selling in the good times opens doors:
You have the financial flexibility to retire, consult, or start something new
You feel emotionally resolved about your decision
You leave on a high note, with fewer regrets
That peace of mind is priceless. It makes the next chapter a clean slate, not a recovery mission.
Final Thought: Good Times Don't Last Forever
Markets shift. Customers move on. Health changes. Leadership transitions are inevitable.
You may love what you do today. But if you're within five years of considering a sale, the time to start the conversation is now—while you still have the wind at your back.
Buyers are out there. Capital is available. And businesses with strong fundamentals are in demand.
Selling in good times isn’t about "cashing out." It's about choosing the moment that serves everyone—you, your team, and the business you worked so hard to build.
So if things are going well, don’t wait for them to go south. That’s not when your business deserves to be handed off.
Sell while you're proud. Sell while you're strong. That’s when you know it's right.
