This is part two of 🚪 The Exit Files, my three-part Millennial Masters series following ten founders through the years around a business sale.

In part one I explored the pressure of building towards a payout nobody could guarantee.

This time, I’m looking at the months or years of work that can follow a sale, and how the deal shapes the handover. 👇🏻

The sale goes through, and the founder’s diary is still full. *Illustration: Flow/MM*

An hour after the money landed

The money arrived in Luke Tobin’s account on a Monday afternoon. About an hour later, he had a big presentation with the team. They didn’t know he’d sold Digital Ethos, and he couldn’t tell them yet.

The sale took about fourteen or fifteen months. Luke spent so long thinking about the figure that seeing it land in his account felt strange and anticlimactic. He still had a meeting to get through.

You can complete a sale and spend the next two years working in the business. The deal determines how much money you still have to earn and when you can leave.

The Millennial Masters I spoke to agreed to very different terms. Their experiences show why it’s worth looking closely at the job you’ll have after the sale, including who gets to make decisions about the business you built.

Another two years on the job

Thibault Louis-Lucas, known as Tibo, and his co-founder sold Tweet Hunter and Taplio in a deal that could reach $10 million. He expected to start building something new almost immediately, but buyers wanted him to commit another two years.

“Something that we didn’t anticipate is that all the buyers out there were asking us to stay two years in business with the acquisition.”

Staying meant spending two more years growing businesses he no longer owned, with much of his payment depending on how well he did.

The buyer paid $2 million upfront, with up to $8 million more tied to revenue milestones over the following two years. A headline price can include money you’ll only receive if the business keeps growing.

Tibo knew the buyer’s founder from school. The team was relatively small, and he felt they understood how he liked to work. In our conversation, he credited the freedom to keep building independently with helping the arrangement run smoothly.

They hit five of the six revenue milestones, so the total sale amount came to $8 million. The teams stayed quite separate, though, and Tibo thought closer collaboration could have helped them grow further. The independence he wanted also limited how much they worked together.

You’ll be working with the buyer while pursuing those targets. How much control you keep over the work deserves as much attention as how long you agree to stay.

The Exit Files 🚪 When selling means staying

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