Focus: You've sold up and made millions, so what's next? Five founders tell all

The entrepreneur’s dream invariably goes like this: build a business, sell the business, use the pay-out to retire on a superyacht (the majority) or save the world (Bill Gates).

It almost never works out that way. Only half London’s start-ups actually survive their first three years; the remaining half, perhaps one or two will see a multi-million-pound exit.

But when they do, then what? “Retiring at 40 to do up your house and go on endless holidays sounds great — until you actually do it,” one multi-millionaire tech founder admits. He’s just back from a private bank’s wealth management dinner for those fresh from a big exit. “The bankers wanted to talk about ‘opportunities’ for parking our capital. But the founders only wanted to talk about their next big idea. Sitting around, planning your next holiday — it gets boring.”

Ready your bows for a chorus of the world’s smallest violins. But how does someone who has sold a start-up adjust from being the big boss through being wooed to waking up the morning after the sale with a huge pile and nothing to do?

Alex Depledge, Jules Coleman (Hassle.com)

The pair started cleaner-booking website Hassle.com in 2013. In 2015, they sold to Rocket Internet-backed Helpling for £27.5 million. In the run up to the sale, Depledge (far right) also had a baby: “I couldn’t get a minute of sleep, my hormones were all over the place. As part of the sale we had to stay on for six months, so we were expected to be best friends with everyone at the acquisition company — which was not the case. Our relationship was very fractious. I had to look after my team, and reassure them, while the acquisition team told me who they wanted to fire. Trying to save the staff who have been with me — and accommodate the people who have just given me a load of money — it was like being two people.”

When Depledge finally left, there wasn’t a chance to celebrate: “The first thing I did was get depression. I just couldn’t get out of bed, and with my 10-month-old baby, everything felt pretty bleak.” After a holiday to Silicon Valley that “mostly bummed us out” the duo set up 3D home design software firm, Resi.co.uk: “Despite saying we would never in a million years start a business again”.

Graham Hobson (Photobox)

The founder of photo and card-printing business Photobox sold it for “between £300 million and £400 million” to private equity in 2016. His final 5% stake earned him a £15 million-plus pay day.

“A large sum was transferred into my bank account but I’m not a yacht or Maserati or Rolex type of person. We never actually celebrated.”

After running out of money in his early days he’d got used to a lean existence but eventually sold to Expona and Electra. “I remember walking across Millennium Bridge on my way home that day, thinking, ‘I don’t know what to think’.”

Hobson made a list of 60 things he wanted to do that summer: “Travel to Iceland and Japan with my family, clear out the attic, become a qualified barrista, read books I’d wanted to read for ages, volunteer with homeless charities, do a half marathon.”

He got through 41 of the 60 in his first six months, then says he “realised how much I missed structured work”. He found start-up and tech consultancy work. “Now I’m full time again. I think I had imposter syndrome — that Photobox was a fluke, and I don’t deserve it. My ambition now is to do another growth-scaling company.”

Jamie Waller (JBW)

Waller grew up in the East End, left school with no qualifications and started a bailiffs business, JBW, in 2004. It had 170 staff and £40 million revenues when he pocketed £33 million by selling to Japan’s Outsourcing Inc last year.

After staying up all night sealing the deal, then phoning his biggest clients, Waller went to bed and got up again at noon. “My wife wanted to go out and celebrate — spa treatments in Knightsbridge then a fancy restaurant. Instead I drove us to Bethnal Green where I grew up and we had pie and mash.”

“I felt really strange. What was I going to do all day, every day?” Waller, who’d just had a baby girl, had planned to take a six-month break. But six days after banking his £33 million cheque, he was onto his next big thing; Hito, a fintech start-up that he went on to sell for £9 million; “after that deal went through, I took 11 days off before starting my investment business, Firestarters — because I didn’t want to be ‘rich and irrelevant’.” He did buy a £4 million yacht, though, “which I now spend three weeks of every month on working from the Med”.

Greg Marsh (Onefinestay)

Marsh sold Onefinestay, an upmarket Airbnb, to French hotel chain AccorHotels in April for £117 million. “When we finally closed the deal, I’d been ensconced in lawyers’ offices and awake for 48 consecutive hours. I was existing on adrenalin.” Having to be “monomaniacal” in his focus, abandoning friends and neglecting family, Marsh had “a sort of gap year” — teaching entrepreneurship at Harvard Business School, learning the piano, working on a government review and buying a house in Clerkenwell.

His “real extravagance”, he says, is not having to work — or, as he puts it, “having discretion about how I allocate my time”.

But he adds there “was a definite comedown” and he’s “trying hard to resist” building a new company: “The temperament and psychology of a founder who’s gone through the grunt work, misery and turmoil of building a business from nothing is unlikely to be fulfilled on a beach hut in Tahiti.

“In fact, if I were stuck there, I’d start to think about how to improve the Tahitian wifi and then end up starting up a wifi business. Success is like a bug — a neurotic pattern of hyper-achievement where the person can’t control their obsessive behaviour or stop working. You can’t just relax on a beach forever.”