Why I sold Northline (and almost didn't)

The email came on a Tuesday, which felt wrong somehow — offers like that should arrive on a Friday, when you have the weekend to sit with them. Instead I had four days before my next customer call to decide whether I even wanted to think about selling.

Northline had crossed 40,000 users the month before, almost entirely through word of mouth from service businesses telling other service businesses. Growth was steady, not explosive, and that steadiness is exactly what made the offer tempting: I could see the next three years clearly, and they looked like more of the same good, un-exciting work.

What tipped it wasn't the number. It was realizing I'd stopped opening the roadmap doc. I was maintaining a good business instead of building one, and I hadn't noticed the shift until someone else pointed at it with a term sheet.

I still think about the version of this where I said no. It's not a wrong answer, just a different one. If you're facing a similar call, the only advice I'd actually stand behind is: notice whether you're excited to open your own roadmap. Everything else is negotiable.