I have sold four companies. A radio station, a property technology business, a healthcare software company and a managed services firm. On paper they have nothing in common. In practice the same six lessons decided how each one ended, and I wish someone had told me all six before I started the first.
1. The exit is decided in the first year, not the last
Every business I sold well was built, from the start, to run without me. Every one I struggled to sell was built around me. Buyers are not paying for your talent. They are paying for a machine that produces cash whether or not you turn up on Monday. That machine has documented processes, a management layer below the founder, customers who have contracts with the company rather than relationships with you, and numbers a stranger can audit in a week.
You cannot bolt that on in the six months before a sale. Acquirers see through it, and the price reflects what they see. So the question to ask in year one is simple: if I disappeared for three months, what would break? Then fix those things, one at a time, until the honest answer is nothing important.
2. Revenue quality beats revenue size
My proptech business was not the largest in its category when a US acquirer bought it. It had something more valuable than size: recurring revenue, low churn, a pricing model buyers understood, and a customer base that no single account dominated. The radio station taught me the opposite lesson the hard way. Advertising revenue came in lumps, depended on a handful of relationships, and had to be resold every month. The same dollar of revenue was worth a fraction of the software dollar because a buyer could not count on it.
If you take one number into every board meeting, make it net revenue retention. If existing customers pay you more this year than last, you have a business that compounds. If they pay you less, you are on a treadmill, and acquirers price treadmills accordingly.
3. Capital efficiency is a multiple in its own right
Two of my four exits were from businesses that had raised little or no outside capital. That changed the maths completely. When you own most of the company, a modest exit is life changing. When you have raised three rounds, a good exit can leave the founder with less than a senior employee's share scheme. I have watched founders celebrate an acquisition announcement and then quietly discover that the preference stack took most of it.
This is the thesis of my book and of Groove, and it came from these exits. Grow on revenue for as long as you can. Raise when a specific use of capital will return multiples, not because a round is available. Every dollar you do not raise is a dollar of the exit you keep.
4. Healthcare taught me that trust is the product
Selling software to doctors and clinics was the slowest sales cycle I have worked in and the most loyal customer base I have had. Clinicians do not switch systems lightly. Once they trust you with patient records and billing, you have a customer for a decade, and that durability showed up directly in the valuation. The lesson generalises. In any regulated or high stakes industry, the hard part is earning the right to be there. Once you are in, the moat is real, and buyers will pay for moats.
It also taught me patience with sales. We nearly killed that business twice by pushing growth faster than the market would move. The business was never the problem. Our expectations were.
5. Managed services showed me the limits of people businesses
My services business was profitable from early on and grew every year. It was also the hardest to value, because the asset was people, and people can leave. The buyer paid a fair multiple, but a fraction of what a software business with the same profit would command, because they were buying the next three years of effort rather than an annuity.
I do not regret building it. It funded other ventures and taught me how to run operations tightly. But I learned to be honest about what kind of business I was in. A services business should be run for cash and lifestyle, or it should be converted into something with recurring product revenue. Trying to sell it as if it were software is how founders end up disappointed in the data room.
6. The deal is not done until the money clears, and sometimes not then
Every sale I have done had at least one moment where it nearly fell over. Diligence findings, a buyer's board getting cold feet, a key staff member resigning mid process, a market wobble. The founders who get through those moments are the ones who prepared the data room a year early, kept running the business as if no sale was happening, and had a second option they were willing to take.
And read the earnout clauses as carefully as the headline price. An earnout is a bet on how the acquirer will run your business after you no longer control it. [I have had direct experience of how differently a buyer and a seller can read the same clause.] Get specialist advice, define every metric precisely, and assume the people who agreed the deal will not be the people who administer it.
What I would tell myself at the start
Build to sell from the first day, even if you never intend to. Choose revenue that compounds. Keep the equity. Pick industries where trust creates a moat. Be honest about what your business is worth and why. And treat the last mile of a deal as the most dangerous part of the journey.
Four exits later, those six lessons are what I bring to every founder Groove backs. None of them are complicated. All of them are hard to do when you are in the middle of it, which is exactly why having someone on the other end of the phone who has done it before is worth more than another cheque.