Landon Bennett reflects on the counterintuitive benefits of running a bootstrapped side business while maintaining a primary company.
Disclosure
Bennett: Bootstrapping derisks startup exits without requiring a massive winner
“We bootstrapped our businesses and, you know, kind of plan to do the same in the future. It just makes it for us, it really de-risked That whole process. Cause we know even if we don't have like a, you know, a huge winner, like we can still get something out o…”
Assertion Not checkable as stated
Userfeed generated 40 buyer inquiries and three acquisition offers in two weeks
“Probably 40, just like within the first like week or so, we had like 40 people reaching out, you know, requesting more information. I basically would, I spent a good amount of time kind of like weeding through those just to make sure that they were legit and, …”
Disclosure
Bennett: Userfeed generated cash flow for years and sold for six figures
“We had cashflow from it for multiple years and then we just sold it for six figures. Like that's a pretty good outcome for during that time, during that timeframe, our other business like grew, you know, hundreds of percent.”
Assertion Supported
Bennett: David Cummings Was the First Investor in Calendly
“He's like the starter of, like, he started, like, Pardot sales, technically, SalesLoft, Rigger. He's the first investor in Calendly. Like, you name the company, Terminus.”
Disclosure
Tope Awotona offered Bennett an early angel investment in Calendly
“Topa, I remember the day Topa was like, hey, you can invest in Calendly. It'll be the best investment you ever made. It was, yeah, it was I don't know how, like, if he was half serious or whatever, but at the time, they only had, like, I want to say it was lik…”