The Story Behind My Fourth Investment, HashiCorp

On November 13 of 2012, before I started any of this investing stuff, a friend asked if he could intro me to one of his colleagues. He was making a small announcement and asked if I could help. Since I am not a reporter, I gave the kid some advice and moved on. A few days later, I decided to Google him a bit more and realized — hold on — this kid is no kid, he’s a machine.

Once his news settled, I met up with him in San Francisco. Over the course of the next few months, we would meet periodically. To be perfectly honest, I only had a loose idea of what he created, but I was absolutely sure of one thing — he was very smart on the left brain and right brain. In multiple meetings, he was both technically sound, organized, and personable — he listened, but said “no” when he disagreed. He carried himself much older than his age would suggest.

I tried to dig deeper into what he was building, but I could only get so far as larger themes. He’d authored one of the most popular open source frameworks used in machine virtualization — as a teenager. He maintained the project on the side and built a global community naturally around it. Eventually, after working for two years for a friend of mine (who made this great introduction for me), he was ready to focus full-time on his main love.

The framework he built is called Vagrant. The company he started to build a product and service around it is called “HashiCorp,” a sort of eponymous nod to his name: Mitchell Hashimoto. The idea behind Vagrant and other open source projects in this family is that it makes the act of creating development environments a bit easier. I knew this was a pain point from researching the “B2D” space (where the comments were very revealing), as well as helping my friends at Nitrous.IO. In just less than an year, Mitchell has grown his team carefully with only the very best from the open source community, been invited to speak on Vagrant all over the world (I haven’t seen him in months), and is on a mission to slowly build a lasting, durable company. The authenticity of his motivation is pure.

I knew very quickly that I wanted to be a part of whatever company Mitchell was going to build. And here, I go back to my interview with Mike Maples for wisdom around investing. Not only was it Mitchell who was gracious to invite me to participate (he doesn’t need me), I recall this quote from Maples:

In the early days, I decided 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.

Mitchell is a good one, and I was introduced to him by another good one. Maples, yet again, is right.