Five Years A Founder
Five years ago today, on January 10, 2017, I wrote the very first post on this blog announcing to the world what we’re building at Outseta. While our product strategy and team has remained quite consistent over the last five years, nearly everything else has changed—my personal life, my professional life, and my entrepreneurial experience look dramatically different than they did at the outset.
This post is a candid look back at the last five years—I hope it’s helpful to a younger version of myself that’s just starting out on their own founder journey.
I have always been entrepreneurial, but the reason I ultimately decided to devote 10+ years of my life to building Outseta can be summed up in two words: Dimitris and Dave.
I had worked with Dimitris for five years previously at Buildium, where we had a very successful start-up run. I knew him to be an excellent developer, but also someone I'm hugely philosophically aligned with. And I knew that Dimitris and several of my other colleagues had the utmost respect for Dave as a software engineer—they all talked about him glowingly.
In short, I saw a ridiculously talented development team—one that I was lucky to work with. I knew that whatever we built, it would be a world class product. A start-up always comes with lots of unknowns, but working with this team eliminated the challenges that permeate less experienced development teams. I think betting on the quality of the team was a sound decision...albeit an incomplete one.
