Millennial Masters

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The Exit Files 🚪 When growth takes over

PART ONE • The pain before the payout

Daniel Ionescu's avatar
Daniel Ionescu
Sep 25, 2026
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I’ve spoken to enough Millennial Masters who’ve sold their businesses to know how much getting to an exit takes out of you.

Ask them what the years around the sale felt like and you’ll hear about exhaustion, or going back to work with millions already in the bank.

🚪The Exit Files series follows the experiences of ten founders, from hypergrowth, through to the sale and into life after.

First, the years spent building towards a payout nobody could guarantee, and what they really cost. 👇🏻

The exit’s in sight, but there’s still a business to run. Illustration: Flow/MM

The sale is still years away

Luke Tobin was winning work faster than his agency could look after it. Digital Ethos was doubling in size each year, heading towards almost 100 people in five years. He was trying to hire enough people and put systems in place to deliver the work he’d already sold.

“Honestly, it was always a bit unstable.”

Every new client creates work that somebody has to deliver, and hiring someone to do it takes time. When the business doubles again, whatever worked last year is already stretched.

He eventually sold the business for a reported £8 million. Knowing that makes the pressure easier to justify in hindsight. He had to keep running the business without knowing whether the sale would go through. The strain can start years before you negotiate a sale.


Keeping up is hard work

Matt Watson lived it at VinSolutions, which made software for car dealerships. During the financial crisis, dealers were looking for ways to cut costs and sell cars online. That created demand for his business at a time when others were struggling.

“We were growing way faster than we could even keep up.”

VinSolutions reached $30 million in annual revenue without outside investment. But it didn’t have enough servers or support people. Matt could see how a cash injection would help the team hire ahead of demand. Eventually, profits grew enough that they no longer needed outside investment.

Revenue makes a company look further along than it may feel when you’re running it. A customer can sign today and need help tomorrow. Recruiting and training someone to provide that help takes longer. Until then, you and your existing team take the hit.

Luke’s agency and Matt’s software company were different businesses, yet both had customers arriving faster than they could serve them. Keeping up was exhausting, and every new sale added more work to an already stretched team.

Getting bigger doesn’t guarantee this will ease. More demand puts more pressure on your team while customers still expect everything on time.

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