I was a cofounder of a fashion and consumer startup, it was sort of like a focused Pinterest. We had a very enthusiastic user base before taking on SV money, but unfortunately never grew much beyond that.

I was the engineer (and briefly CTO), and the foremost thing on my mind was marketing and promotion. I was constantly told that word-of-mouth and natural virality was how things worked in the Web 2.0 era, so put it out of my mind and focused on the technical stuff.

I eventually got fired (justly so; I was good enough to get a personal project off the ground, but not FAANG material at the time), and watched as they squeezed out a redesign and an app and eventually sold out as an acquihire. (I’m told that means it’s “not a failed startup” but sure doesn’t feel like it.)

If I had it all to do again, as soon as it was apparent that I had reached the limits of what I could do as an engineer, I would have flipped to being the hype man for the product. Someone should have been hitting the pavement every day making connections at GQ, Supreme, HypeBeast, etc. My partners say we crumpled because we couldn’t build another round of funding; I say we couldn’t get the funding because of dumb naive belief in word-of-mouth.

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coda: after that, I returned to another side project, a visual RSS reader for graphic designers and artists. Same problem, no plan to promote the damn thing.