When Is the Best Time to Sell Your Business?

Rethinking the "Timing" Conversation

Most owners quietly carry the same question in the back of their minds:

“When is the right time to sell?”

You hear stories about people “nailing the timing” - selling right before a downturn, or at the peak of some industry cycle. You also hear, just as often, about owners who waited too long and ended up selling under pressure: health issues, burnout, or declining numbers.

Here is the uncomfortable truth:

The “best time” to sell your business has far less to do with calling the top of the market and far more to do with the shape of your business and your life when you actually go to market.

If you’re trying to think about timing in a serious, grown-up way, here are a few principles to focus on.

1. Company Performance Usually Matters More Than Market Timing

Yes, interest rates, election cycles, and industry sentiment all influence valuation. But for most lower-middle-market and mid-market businesses, buyers are looking at something much more basic:

• Are revenue and profits growing, or at least stable?

• Does the business look resilient across cycles?

• Can a buyer see a clear path to maintaining or improving performance?

  
  

Buyers pay the most when they believe two things:

1. The earnings they see are real and repeatable.

2. The future looks at least as good as the past.

A company with:

• Steady or growing revenue

• Solid margins

• A track record of surviving “normal” bumps in the road will almost always command a stronger multiple than a company whose numbers are flat or declining.. even if the macro environment is “better” for the second one.

Think of it this way:

• A strong business in an average market often sells better than

• A weak or declining business in a great market.

  
  

When buyers see consistent performance, they don’t just see profit; they see competence - teams, systems, and processes that are likely to keep working once the current owner steps away.

2. The Best Exits Happen When Your Numbers and Your Life Are Moving in the Right Direction

Timing isn’t just about the business. It is also about you.

The strongest exits we see tend to share a pattern:

• The business is on an upswing or at least stable.

• The owner is choosing to sell from a position of strength, not because they have to.

• There is a clear plan for “what’s next” after the sale.

  
  

On the other hand, some of the weakest deals happen when:

• Health issues force a quick sale.

• Burnout has already bled into the numbers.

• A spouse, partner, or life event pushes the owner into a corner.

  
  

Buyers can feel when an owner is pressed to sell. That pressure often shows up as:

• Sloppy financials (“We’ve been too busy to clean this up.”)

• Deferred maintenance or underinvestment

• Key people on edge because they sense something changing

  
  

All of this erodes negotiating leverage.

A much better position is:

• “The business is healthy.”

• “I’m not being forced to sell.. I’m choosing to explore options.”

• “I have enough runway to walk away from a bad deal.”

  
  

That combination.. strong company performance plus a proactive, not reactive, decision - is where owners typically see the cleanest processes and strongest outcomes.

3. The Less the Business Needs You, the More It’s Worth

One of the biggest drivers of valuation (and buyer confidence) has nothing to do with macro conditions at all:

How dependent is the business on you?

Buyers will ask, directly or indirectly:

• Who really holds the key customer relationships?

• Who makes the important decisions?

• Who solves the biggest problems when things go wrong?

  
  

If the honest answer is always “me,” you do not own a fully transferable business.. you own a demanding job with staff attached.

The ideal time to sell is when you can reasonably say:

• “Day-to-day operations run without me.”

• “We have a second layer of leadership that actually leads.”

• “Key processes are documented and followed.”

• “Customers and vendors trust the company, not just me personally.”

  
  

Why does this matter for timing?

Because the process of reducing owner dependency takes time:

• Hiring or promoting a second-in-command.

• Gradually shifting decision-making.

• Moving key relationships from “founder-centric” to “team-based.”

• Documenting processes that have lived only in your head for years.

  
  

You don’t want to be doing all of this while you are trying to sell. The best time to start is 1-3 years before a potential exit.

When a buyer sees a business that doesn’t crumble if you take a two-week vacation, they are far more comfortable paying a premium multiple. In many cases, this “transferability” premium is worth far more than whatever you might gain by guessing the perfect moment in the economic cycle.

4. Yes, Macro Timing Matters - But Mostly at the Margins

This is not to say market conditions are irrelevant. They are not.

Things that can move multiples up or down include:

• Interest rates (higher rates can compress valuations in some sectors).

• Election cycles and regulatory uncertainty.

• Industry-specific cycles (construction, energy, healthcare reimbursement, etc.).

• Availability of debt and “dry powder” in private equity.

  
  

However, here’s the nuance:

• For a strong, well-run business, these factors usually influence how many buyers show up and how aggressive they are on price and structure.. not whether the business is sellable at all.

• For a weak or heavily owner-dependent business, these same factors can turn a marginal deal into no deal at all.

  
  

So, yes, it makes sense to be aware of:

• How buyers are behaving in your industry today.

• Whether financing is tightening or loosening.

• Where we are in your sector’s typical demand cycle.

  
  

But those macro elements are best treated as refinements to timing - “Do we go to market this quarter or next?”.. not as the primary driver of when you start exit planning.

5. What “Good Timing” Actually Looks Like in Practice

If you put this all together, “good timing” tends to look like this:

• Your financials show 3+ years of clean, reasonably stable or growing performance.

• You’ve partially or fully reduced owner dependency.. there’s a real second layer of leadership.

• You’re not exhausted to the point of checking out; you have the energy to participate in a serious sale process.

• Your personal life is at a point where a liquidity event would unlock options, not just plug a hole.

• The market and your industry are at least neutral-to-favorable.. not in outright crisis.

  
  

You will never have a perfect moment where:

• Your numbers are at an all-time peak

• Your stress is at an all-time low

• The economy is perfectly calm

• And all buyers are paying irrationally high prices

  
  

That’s not how real life works.

What you are looking for is a window where:

• The business looks good.

• Your personal timing makes sense.

• The external environment is “good enough,” not catastrophic.

  
  

Owners who recognize that window and act intentionally usually fare better than those who wait for something that feels perfect and then find themselves forced to sell two or three years later under much worse conditions.

Where an M&A Advisor Fits In

You do not need to decide, today, “I am selling in 12 months.”

What you can do, right now, is get clarity on:

• How your business would look through an M&A lens today.

• What buyers would likely focus on - performance trends, risk areas, transferability.

• What changes over the next 12-36 months would materially improve your valuation and terms.

• Whether the gap between “where you are now” and “where you’d like to be at exit” is mostly about numbers, structure, or timing.

  
  

A seasoned M&A advisor can help you:

• Translate your current financials and operations into how buyers actually think.

• Identify specific actions (not generic advice) that would make your business more attractive.

• Give you a realistic sense of valuation range and likely buyer types.

• Map out a timing strategy that respects both your business performance and your personal goals.

  
  

You don’t have to commit to selling, and you certainly don’t have to commit to a specific date, to have that conversation.

In fact, the owners who get the best timing usually start talking to an advisor before they are ready - when they are still in a position to make changes that move the needle.

If you’d like to pressure-test whether now, 12 months from now, or three years from now is the right window for you.. and see what would most improve your position in the meantime - it is worth having that discussion sooner rather than later.