Investment Thesis: Four Years Later

Four years ago I began a new journey. After a 15-year career as a participant in and co-founder of various businesses, I “switched sides” and became a full-time investor in early-stage software companies.

At the time, I published a series of posts that described how I was thinking about my work, and laid out in some detail the framework I intended to use when screening and evaluating new investments.

Every day since then, I have been humbled to learn all that I don’t know about being an effective venture investor, and how many miles I still have to travel on that journey.

But I have also had more fun — and touched more lives in (what I believe to be) a positive way — than in all my previous working years combined.

I have never been so hopelessly, happily hooked on anything, ever.

In the past four years as an investor I’ve:

Last week we hosted a portfolio review for our Founders Co-op investors. As I was putting together the deck for the meeting I realized just how much we’ve learned about running a fund, how much the world had changed around us in the past four years, and how our investment thesis has changed as a result.

It’s time for a refresh.

Over the next few weeks I’ll be revisiting the Investment Thesis topics I covered four years ago and talking about what still feels right, where I’ve made mistakes, and how my experiences of the past four years have shaped my ideas about the next four (and beyond).

Please join me + share your own stories and lessons learned so we can get better together.