The Story Behind My Investment In EaseCentral

If you’re from Minnesota and you’ve met me, you’ve likely heard me share this refrain: “I love people from Minnesota; they are among the nicest people I’ve met.”

@courtstarr is in that class. Many of you know him, of course. I am lucky to have made friends with him as I first moved to the Valley, and what stuck out about those early hangouts and conversations is that Courtney actually listened to what everyone else was saying. He’d remember. And, he looked for hidden talents in everyone rather than trying to judge people and concepts too quickly. Along the way, we’ve both introduced good people we know to each other, though I am in further debt to Courtney for making me meet Mitchell of Hashicorp early, a company that became one of my earliest investments.

As he was winding down his tenure at Kiip, a company he co-founded, he brought up a topic that we touched on in our TechCrunchTV episode years ago: An incarnation of a previous company he founded in the insurance space was relevant again given changes to healthcare laws. We had a few conversations about this and as Courtney zeroed in on his own conviction to lunge forward with this as his next entrepreneurial adventure, I of course told him, like Anand with Trusted, to count me as the first check.

Over the next month or so, Courtney dusted off his fundraising skills, reactivated his networks, and had longer discussions (not pitches) with a set of familiar investors. I knew early on that his model would evolve with the feedback, but I didn’t worry myself about these details too much because I know Courtney to be a stickler for doing things the right way and that as a repeat founder he wouldn’t sign up for such an endeavor without attaining conviction for himself.

Making a small investment decision in EaseCentral, the new company, was also a learning process. I got to see how a friend turns into an operator, rallies support, calls on his network, and negotiates. Turns out, he’s not only a good Minnesotan, but a good dealmaker, too. I also learned more about the insurance broker market, the changes in the laws coming up, and how the public markets view brokerages versus software service models. There will be some very interesting TBDs here, for sure.

All in all, this particular investing episode reminded me of a line by Mike Maples in my TechCrunchTV discussion with him. Of the venture business, Maples remarked: “…this is a people-flow business and not a deal-flow business. I’ve always had this leap of faith that if you just spend all your time with smart awesome people, that the dots will forward connect. The deals will reveal themselves, and somehow you’ll get into some good ones.“