Reflecting on My Failure to Build a Billion-Dollar Company

How has a “failure” set you up for later success? “The hardest decisions to make in business are those that disappoint people you care about. One of the biggest mistakes I made in the early days of Behance was doing too many things. We had multiple products in market, multiple business lines, and our energy was divided across too many things. Final

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Because big businesses aren’t built on gimmicks. You can blitz your way through Sand Hill Road and spike up the App Store charts on gimmicks, but you can’t actually use them to replace Gmail, or Salesforce, or Instagram, or Instagram, or Instagram, or Instagram. Even seemingly instant successes can’t become lasting companies without putting in the ... See more

Sometimes the prize feels closer, other times farther away. Still other times it feels like we are drowning in aimlessness and exasperation. An identity crisis looms for any high achiever flirting with failure, and a calculation begins on the conflicting forces of sunk costs and lost time on the one hand, and reputational harm on the other. As entr... See more

Over time, I realized that the problem wasn’t Gumroad, the problem was me. I was still so focused on that elusive unicorn, I couldn’t see the thriving business humming along right in front of me. Gumroad was profitable, the right size for its market, and enabling more and more writers, coders, crafters, and other makers to achieve their dreams with... See more

When I was in grad school, the unstated assumption in most of what we were taught was that the sole point of a business (or any institution, really) was to grow. To grow, grow, grow, to as large a scale as possible. To build an empire, take over the world. My classmates — tycoons in waiting — lapped it up. “Lifestyle businesses”? Nah! Those were fo... See more