This is part four of 🚪 The Exit Files, my Millennial Masters series following founders through the years around a business sale.
Part one looked at the pressure of building towards a sale. Part two followed the work that continues after the deal. Part three explored how founders adjusted as the businesses they sold changed around them and after they finally left.
Several founders went back to building after selling. In this final instalment, I wanted to know what they chose next and whether the experience changed how they approached their next business. 👇🏻
The sales call she never wanted to make
Melissa Kwan found herself doing live demos for eWebinar, a product she built so customers could see it working and sign up without talking to anyone. The subscription cost around $100 a month. The calls took her back to the job she decided not to create again.
She sold Spacio, her real estate technology business, after nearly a decade of building companies in that industry. By then she knew what she wanted from the next one. She wanted a small remote team and a product she could sell online without spending her days at conferences or on calls.
eWebinar was meant to fit that life. When growth slowed, Melissa reached for something she knew she could do: sell. She spent months on calls with potential customers, even though the price of the product couldn’t support that kind of sales process. “I was getting on these calls to prove to myself that I could be productive,” she told me.
Melissa initially blamed the slowdown on her burnout. She later realised eWebinar’s marketing mainly reached businesses already convinced they needed automated webinars. She was reworking it to reach companies still satisfied with live webinars. Months of sales calls hadn’t solved that problem.
Trying to prove the next idea wrong
Nick Telson and his co-founder spent seven years building DesignMyNight before selling it for over £25 million. They stayed for another two years. When they began working on Trumpet, they wanted to keep building businesses without repeating the pace that took so much of their twenties.
They kept each idea under a project name while they took several possibilities to potential customers. They spent a month or two on each, looking for the reason it wouldn’t work. Nick would send a one-page outline and ask what people already used and why the proposed product might fail.
A fintech idea got good feedback. Nick and his co-founder still had to ask, “Are we the right people to run a fintech business?” Neither felt passionate enough about it to go ahead. Trumpet, a product for digital selling, passed both tests: customers saw a use for it, and the founders wanted the job that came with it.
They also invited Rory, a third co-founder, to be CEO. He could lead the team and be the face of the company while Nick and his original co-founder focused on the parts they wanted to own. Nick said they knew they didn’t have to work themselves to the bone this time.