"Should I sell now, or should I wait?" is one of the questions founders ask most often — and one of the most often framed the wrong way. Timing a sale is rarely about predicting the market. It is about whether waiting improves your options.
Key takeaways
- The right question is not "Will my company be worth more later?" but "Will waiting improve my negotiating position?"
- Waiting creates value when it is preparation. It destroys value when it is speculation — sometimes without the business changing at all.
- Founders cannot control the market. They can control the quality of the business, the team, the preparation and the sale process.
Timing the market — or timing your business?
One of the questions I am asked most often by founders is remarkably simple: "Should I sell my company now, or should I wait?"
It is also one of the hardest questions to answer. Not because the answer is unknown, but because it is usually framed in the wrong way.
Most people think the decision depends on valuation. Or on market conditions. Or on whether multiples might be higher next year.
In reality, timing a sale is rarely about predicting the market. It is about understanding whether waiting increases — or reduces — your strategic options.
The question behind the question
When founders ask whether they should wait, they are often asking something different. They are really asking: "Will my company be worth more in the future?"
Perhaps. Perhaps not.
The more useful question is: "Will waiting improve the quality of my future negotiating position?"
Those are not the same thing.
Internal factors vs external factors
The decision to sell sits at the intersection of two forces. Some are internal. Others are external.
Internal factors include:
- Growth potential
- Strength of the management team
- Customer concentration
- Scalability of the business
- Operational readiness
- Founder fatigue and motivation
External factors include:
- Market valuations
- Interest rates
- Availability of financing
- Industry consolidation
- Investor appetite
- Competitive dynamics
Good timing happens when both sets of factors align. Unfortunately, they rarely do.
When waiting creates value
Sometimes patience is exactly the right decision. I have advised founders to postpone a sale because the business simply was not ready.
Perhaps management was too dependent on the founder. Perhaps recurring revenue was still too low. Perhaps international expansion had only just begun.
In these situations, waiting was not speculation. It was preparation. And preparation often creates value. (The 14 questions to answer before you sell your company are a good place to start.)
When waiting destroys value: a lesson from 2007
But the opposite is equally true.
I remember one entrepreneur who had built an exceptional business. For several years, buyers became progressively more enthusiastic. Informal conversations suggested valuations moving from 7x EBITDA to 10x… then 12x.
Each year, the business continued to perform well. Each year, the founder decided to wait just a little longer.
Finally, in September 2007, he called us. "I think the time has come. Let's launch the process."
Unfortunately, the market had already changed. The financial crisis had begun. The valuations buyers had discussed only months earlier had disappeared.
The company had not lost value. The market had. Waiting had destroyed value without the business changing at all.
It was a lesson I have never forgotten.
Risk vs optionality
One concept I have come to appreciate over the years is optionality. Founders often think that delaying a sale preserves flexibility. Sometimes it does. Sometimes it quietly reduces it.
Every year that passes introduces new uncertainties:
- Markets change.
- Competition increases.
- Regulation evolves.
- Interest rates move.
- Technology advances.
- Personal priorities shift.
Waiting is not a neutral decision. It is an investment in an uncertain future.
The key question is therefore not "Can I wait?" It is: "Does waiting genuinely improve my options?"
Don't try to predict the market
Many entrepreneurs postpone a transaction because they believe valuations will improve. The problem is that markets are notoriously difficult to predict. Even professional investors struggle to time them consistently.
What founders can control is something far more valuable:
- The quality of the business.
- The quality of the management team.
- The quality of the preparation.
- The quality of the sale process.
Those variables are largely within management's control. The market is not. (On how a well-run process protects value, see Creating heat in the auction.)
A simple framework: four questions before deciding when to sell
Whenever I discuss timing with founders, I encourage them to think about four questions:
- Is the business ready?
- Am I personally ready?
- Is the market supportive?
- Will waiting increase my strategic options — or simply increase uncertainty?
None of these questions can predict the future. Together, they help frame a better decision.
A final thought
There is no perfect moment to sell a company. Only moments when the balance between opportunity and uncertainty becomes more favourable.
The founders who achieve the best outcomes are rarely those who perfectly time the market. They are the ones who prepare early, understand their options, and act before circumstances force the decision.
As the line often attributed to Seneca puts it: "Luck is what happens when preparation meets opportunity."
In M&A, opportunity rarely announces itself. The founders who are prepared are the ones most likely to recognise it when it arrives.
Frequently asked questions
When is the best time to sell a company?
When the business is ready (strong team, low dependence on the founder, solid recurring revenue), the founder is personally ready, and the market is supportive. Perfect timing rarely exists; the aim is a moment when opportunity outweighs uncertainty.
Should I wait for higher valuation multiples before selling?
Waiting for the market is speculation. Markets are hard to predict and can turn quickly — as in 2007, when offers at 10–12x EBITDA disappeared within months. Waiting makes sense when it is used to prepare the business, not to bet on multiples.
What factors decide the timing of a company sale?
Internal factors (growth potential, management strength, customer concentration, scalability, readiness, founder motivation) and external ones (valuations, interest rates, financing, consolidation, investor appetite, competition). Good timing is when both align.
How to prepare a company for sale and run the process is covered in the M&A Training Program and in my book Mergers & Acquisitions: Strategy, Execution, and Decision-Making.
First published in Inside Corporate Finance, my LinkedIn newsletter. Subscribe here.
