This post was originally posted here. I sometimes struggle to figure out the best way to convey something that is important to me to others. That may come as a shock to many of you because of all the articles and blogs I write, and the speaking gigs I have, and the fact that I’m in the business of recommending things to millions of people — but it’s true. For much of 2014 and 2015, I banged my head against a plane window flying back and forth between Austin and Silicon Valley
I’m focused on solving a problem I’m passionate about and delivering venture sized returns for my investors without a VC firm, but it wasn’t always that way. The photo below is from early 2014 when things were much different, especially my dependency on the idea of what VCs represent. Looking back, I can genuinely say that I was always jealous when I read about these massive venture-backed rounds for competitors like Sosh ($10m+ raised from VCs), YPlan ($35m+ raised from VCs), Foursquare ($230m+ raised from VCs) and countless others, not
A lot of founders and VCs give advice to startup founders after they’ve become millionaires and notched some wins, which certainly produces some helpful tips but also loads of success bias. On the other hand, some of the best advice I’ve gotten is from fellow entrepreneurs in the earliest stages of their startups, just like me. I can’t consider myself successful yet, but I can say I have some experiences worth sharing with other entrepreneurs. One of the most frequent things I get asked is “how did you raise the