Why I left a Unicorn to join the world of VC
Ten years ago, I got a call from David Blake, offering me a job at Degreed. To sell me on working for a startup, he asked me to imagine what the future could look like if Degreed were successful.
I am pleased to report that I failed to dream big enough at that moment - because Degreed surpassed my every expectation. Degreed, and all I met through working there changed my life.
When I took that call from David, I was early in my career and completely naive to the world of venture-backed startups. Yet “the best way to learn is by doing,” and nothing presents opportunities to get work done like a fledgling company. Each day at Degreed taught me something, and I’ll forever be indebted to David Blake, Eric Sharp, Chris McCarthy, and Nate Kimmons for carving out a space where I could grow through failure and victory.
Each success at Degreed was hard fought. Yet through that grind, we eventually found product market fit, then we landed our first customer, and then hit $1MM ARR, then $10MM ARR, then $50MM ARR, and on and on she grew.
I joined Degreed as a front-end developer when it was not much more than an idea, and I left as President and CXO of a global company worth over $1.4b. I was there for every step as we scaled from an idea to a unicorn, and in that decade, I absolutely fell in love with SaaS.
As I neared ten years at Degreed I was compelled to find a way to take those lessons and amplify their impact beyond myself. As fate would have it, my friend and mentor Curt Roberts sent me a text on a day I was pondering what my next ten years could look like.
That text catalyzed conversations about the goals I had for my career, and over many a pancake breakfast, the potential of a career pivot into Venture Capital started to come into focus.
I’ve spent over three years getting to know the Kickstart team, and they continually impress me. Each of the General Partners and the expanded team operates with authenticity and principle, and they have done the work to create an incredible space for each other, the founders they back, and their LPs. Their passion for investing in the Mountain West is infectious, and as I came to know their vision for the future, I knew I had found my team.
As I transition to my role as General Partner, I’m confident my fifteen years of operating experience will give me a unique perspective as an investor—one that allows me to not only spot talented entrepreneurs from all backgrounds but also to serve as a mentor, fostering innovation through every stage of the company’s growth.
This newsletter will be where I house my thoughts and lessons learned along the way. Onward!