The Right Time To Sell?

Exit Strategy  ·  Business Sale

When Is The Right Time To Sell Your Business?

Eric Gilboord  ·  CEO, WarrenBDC  ·  Business Sale Coach

You built this company with your own hands. You showed up before everyone else, stayed late, made the hard calls, hired the wrong people, hired the right ones, survived recessions, a pandemic, and a supply chain that seemed personally out to get you. You did all of that.

And somewhere in the back of your mind, for longer than you want to admit, you've been thinking about the exit.

Maybe you've casually researched it. Talked to a friend who sold. Picked up a book. Googled "how much is my business worth" at midnight and then closed the browser before anyone could see. Then you went back to running the company because selling was never really serious — you still had too much to do.

Here's the truth: the best time to start preparing to sell is before you're ready to go.

Most Gen X business owners are sitting on their most valuable asset and don't fully realize it. In Canada alone, there are an estimated 550,000 Boomer and Gen X business owners expected to exit in the next decade. That's a lot of businesses hitting the market at the same time. The owners who get top dollar will be the ones who prepared. The ones who didn't? They'll either leave money on the table or struggle to find a buyer at all.

The Signals That It Might Be Time

There's no single moment when a light goes on and says sell now. It's usually a collection of signals that build up over time. Here are the ones I see most often.

You're chasing a new idea.

You've got something new pulling at your attention — a different business, a passion project, a concept you can't stop thinking about. Trying to run two things at once rarely ends well. One of them suffers. Usually both.

Life has changed around you.

You're in your 50s or 60s. A parent needs care. Your spouse retired and is waiting for you to show up. The kids have no interest in taking over — and that's okay, even if it stings a little. The personal priorities that once fit neatly around your business schedule no longer do.

You've stopped having fun.

This one matters more than people admit. The energy that drove you to build this thing — the problem-solving, the momentum, the satisfaction of making something work — has faded. You look for reasons not to go in. You leave earlier than you used to. The business still runs, but you're not really there anymore. That's a signal.

The business has outgrown you — and that's a compliment.

You built a great management team. The company runs well without you in every meeting. Your people have it handled. That's actually the ideal time to sell — when a buyer can see the business functions independently of the founder.

Your industry is shifting.

Markets change. The things that made you successful for 20 years may not be what drives the next 10. If your sector is consolidating, shrinking, or being disrupted, getting out at the right time beats hanging on too long.

Someone came knocking.

You got an email or a call from someone claiming to have a buyer for your company. Most of these go nowhere. But it got you thinking — and that's worth paying attention to. What would you do if it were serious?

Retirement isn't hypothetical anymore.

When retirement shifts from "someday" to "soon," the math changes. Over 82% of business owners expect the sale of their company to fund retirement. That's not a backup plan — that's the plan. Which means the business has to be ready when you are.

What's Holding Most Owners Back

Less than 10% of business owners have a formal exit or succession plan in place. That number still surprises me, even after years in this business.

The reasons vary. Some owners don't want to think about it — the business is their identity and the exit feels like an ending. Some think they can figure it out when the time comes. Some have convinced themselves the company isn't worth as much as it could be, so why bother.

Here's what I know: the owners who prepare get dramatically better outcomes than the ones who don't.

This Is Where AI Changes the Game

Here's something that wasn't true five years ago: you now have access to tools that can meaningfully increase the value of your business before you sell — without adding headcount or taking on risk.

AI isn't just for tech companies. It's for the business you're running right now.

Think about what buyers actually look for: strong systems, predictable revenue, a business that doesn't depend entirely on the owner, clear documentation, and growth potential. AI can help you build all of that.

→Document your processes — the ones that live in your head or in a single employee's head. Turn tribal knowledge into operational systems a buyer can see and trust.

→Analyze your customer data — which customers are most profitable, which relationships are at risk, where the real revenue growth is hiding.

→Sharpen your financials — identify cost inefficiencies, clean up reporting, build the kind of clear picture that makes due diligence easier and faster.

→Automate repetitive tasks — so the business looks leaner and runs more predictably without you.

A business that runs on documented systems, with clean data and repeatable processes, is worth more than one that runs on the owner's relationships and institutional memory. Buyers pay a premium for businesses that don't require them to depend on the seller staying around.

You don't need to be a tech person to use these tools. You need a plan and the right support to implement it.

The Bottom Line

Is it time to sell? Only you know the answer. But if you're asking the question — even quietly — that's usually a sign it's time to start getting serious about the answer.

The process takes longer than most owners expect. It's more complicated and more expensive in time and energy than you think going in. The owners who do well are the ones who start preparing early, get the right advisors in their corner, and use every available tool — including AI — to maximize what they've built.

You spent decades building something valuable. Don't leave the last chapter to chance.

The Bottom Line

It took hard work and smart decisions to build your business. Selling it is no different.

80% of businesses listed for sale will not sell.

The ones that do didn't get lucky — they prepared.
Find out where you stand right now.

Go to syb4m.com → Free resources to help you prepare your exit

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Quick Answers

When should you sell?

When you're emotionally ready to move on and no longer willing to invest in growing the value of the business. But ideally, you've prepared well before that moment arrives.

How do you know when to close instead of sell?

Have an honest conversation with your accountant and a business advisor. If the business can't run profitably, closing is the responsible move. If it can — sell it, don't close it.

How do I find out what my business is worth?

Start with a conversation with your accountant, a business broker, or an M&A advisor. For a larger or more complex business, hire a licensed business valuator for a formal assessment.

What's the right way to close a business if it comes to that?

Be responsible and honest — with yourself first, then with your employees, suppliers, and customers. How you finish matters.

What are the real reasons businesses close?

When they can no longer operate profitably and there's no realistic path to change that. If the business still has value, the right move is to sell it, not shut it down.

© Eric Gilboord  ·  WarrenBDC  ·  syb4m.com