What I learned watching 12 founders sell.

Dominic Monkhouse24 October 2026

Every office has a good pair of scissors. Everybody knows whose drawer they live in.

That person goes on holiday and the whole place is cutting cardboard with a Stanley knife. There’s a second pair in a cupboard somewhere. Blunt.

You’re that drawer. Not for scissors. For pricing, for the awkward client, for the hire nobody else will sign off.

Gerry Tombs wasn’t. 98% upfront,  and for the last 6 months he was doing nothing. I know how that sounds.

25 years from a garage to a 100 people across the UK and the States.  I coached him for 5 of them, and by the end he was so unnecessary the buyer paid almost all of it up front.  He made himself redundant and got 98% upfront for it, which is the only redundancy package I’ve ever been jealous of.

Your turn. Somebody offers to buy your business on Friday.  Good number, clean process. Then they ask whether you’d stay for 3 years.

Note the word STAY. You’d be an employee at your own company, with a boss and a performance review. At your company. If your answer isn’t an immediate no, you haven’t got a business to sell. You’ve got a job with your name above the door.

Buyers can smell it. Dogs smell fear and are nicer about it. I did the opposite of Gerry. 

At Rackspace every decision of any size sat in a queue with my name on it.  I thought that made me indispensable. I was in the way, and if I’m honest it felt lovely.

12 of the founders I’ve coached have now sold.  I was in the room before, during and after each one, which is where this week’s video came from.

In Partnership with CEOfriend

I ran my own company through an AI tool last week. It got my competitors completely wrong.

I gave it the obvious names. It gave me back a report full of companies I’d never compete with. That’s the problem with generic AI. 

It doesn’t know your market. It only knows the internet’s version of your market.

So I tried a different tool.  I gave it my real competitor list. The second pass gave me an angle on my market I genuinely hadn’t seen. 

That tool is CEOFriend – a strategic AI advisor built specifically for founders at the £1m to £20m mark. Not a chat interface. A team you can argue with.

The first month is free if you use my code STWTRIAL here

Four ways to take this further

1. Book a call. If growth is now making the company slower, heavier or more dependent on you, I can help you decide whether the constraint is people, strategy, execution, cash or your role as founder. No obligation, no pitch. You will know quickly whether this is the right kind of help.
2. Grab the book. F**k Plan B covers these principles in more depth, with the practical founder lessons behind customer obsession, honest communication, hiring, small teams and managers who coach.
3. Watch: 5 founder mistakes that kill growth. Five founder bottlenecks that quietly stop growth between 50 and 100 people, and how to clear them.
4. Subscribe to the newsletter. Get direct, practical thinking on scaling, founder bottlenecks, leadership rhythm and building a company that can run without you in every room.

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