The Third Leap

You’ve started a business and sold it. Now comes the truly terrifying bit: freedom.

Launching a business is an act of optimism. Consultants may tell you that robust planning mitigates risk. Well, up to a point. At some stage, you stop analysing spreadsheets and start signing cheques. This is Leap One: into the void.

Leap Two is selling your firm. The due diligence will be thorough. Lawyers will earn their keep. Your buyer will nod solemnly and talk about alignment, vision and values. Your advisers will nod too, slightly faster, at £450 an hour. And still you’ll go to bed wondering if you’ve just handed your life’s work to the wrong people.

Leap Three arrives after the earn-out, when your handcuffs turn from gold to brass. You could retire, of course—become one of those people who emails friends photos of sunsets captioned “My office today”. But if that sounds like a punishment, not a perk, you’ll be itching to do something. Anything. This is where things get interesting.

Not least because you may find your options constrained. If your sale agreement was drafted with anything approaching competence, you won’t be setting up a rival firm across the road with “New” awkwardly glued to the name. Other restrictions may apply: clients you can’t poach, sectors you must avoid, and a non-disparagement clause which means you can’t even say what you really thought of the internal comms team.

So what now?

There are, broadly, two types of post-exit founder. The first is the cliff-jumper, thrilled by the breeze of uncertainty.

My mate Alex Challoner is one. He built and sold a respected public affairs firm, Cavendish, which was so good the acquirer eventually took its name. Then, after a period of integration and respectability, he leapt again—this time with no plan, no pitch deck, no cash-flow forecast. Just a reputation, a phone book and the rare confidence that comes from knowing people actually want what you do. As it turns out, they did. Clients showed up. Work followed. So did revenue.

The other sort of founder prefers steering wheels to parachutes. People like me. We enjoy control (or at least the illusion of it).

After my own exit, I took up coaching PR firm founders (still do). But I also spotted a delicious gap in the professional services market: business development. Or rather, the total absence of it. Lawyers, accountants and consultants—clever people all—were often spectacularly inept at selling themselves.

So I started advising them. It went well, mostly. I even found actuaries to be a lively and receptive bunch. (Who knew?) Lawyers, on the other hand, were harder work. Many operated in eat-what-you-kill cultures, yet became oddly offended when someone tried to teach them how to hunt.

Eventually, I tired of billing stress as a service. Just then, the Institute and Faculty of Actuaries asked me to deliver a talk—on how to shorten board papers. I did. Unbeknownst to me, a chief actuary from one of the world’s biggest firms was in the audience. He liked what he heard. A contract followed, and with it, an entire line of business advising global giants how to write less and say more. No one saw that coming—least of all me.

So, what to conclude?

If you had the grit to start a business, and the stamina to scale it, then you almost certainly have what it takes to leap again. Just don’t expect the landing zone to look like the PowerPoint slide.

Some will plan. Others will leap. Both routes can work. The only wrong move is to freeze—clutching a payout, terrified of doing anything that might blemish a perfectly good ending.

Yes, it’s a leap of faith. But if you’ve made it this far, you’re probably quite good at those.