The plan had always been to go for an A round in April. We had a solid idea (personal shopping!), enough cash to carry us through June, a great set of investors (seriously, some very nice and sharp people), and, to the degree to which you can depend on these kinds of things, a solid expectation of further funding – pending demonstration of traction.
And so, we built a great team, prioritized carefully, worked hard, and built a product we just couldn’t get people to use. So we looked at the funnel, identified where traffic was falling off, and optimized the hell out of each step. Get them past the home page. Get them to submit a request. Get them recommendations slowly, then quickly, then instantly. Take out the roadblocks. Stop requiring an account to get recommendations. Stop requiring an account to purchase. Make it easy to get to the checkout page. Make the checkout page easy to complete. Make it pretty. Make it fast. And still they didn’t buy.
It’s frustrating to have something that you love, that you yourself use, which you can’t convince other people to get into. Read this book, it’s great! Listen to this album, it’s amazing! Go to this restaurant, the food is unbelievable! Let us shop for you, it’s easy and free!
There was no final explosion, no drama, no walking into the office to discover we’d been locked out of our accounts. The CEO was transparent throughout the process, we all knew where we stood, and when it was finally time to shut things down, his priority was to help everyone find their next job. I’m sure he’s going through his own grieving process – he conceived of and built this company from scratch – but outwardly at least he’s put that aside for now to help everyone else. Truly, a master class in menschlichkeit.
Friends and family have asked how I’m doing, and while it’s true that my preferred resolution involved a pied-à-terre in Paris, I’ve had some time to get used to the idea that this wasn’t going to work out. Considering that my last startup took six years to die, on balance I’m grateful that this one failed fast instead of dragging on for years.
When I left TripAdvisor, I knew that working at a startup would be a great forcing function on personal growth. What I didn’t know was exactly what I’d learn. I’ve tried to write some of it down along the way – on hiring (here, and here), architecture (here, here, and here), analytics, and general impressions. A little embarrassingly, I think the biggest area of growth was in being
able forced to confront and throw off some technical prejudices, and embrace a radically different set of paradigms for web development.
As for what comes next, looking for a job is a stressful, interesting, time-consuming, frustrating, exciting process. It isn’t often that you get to decide how you’re going to spend the next couple years of your life, and it’s tempting to jump at an early offer, or to dismiss things too quickly. You’re simultaneously trying to optimize for growth, impact, happiness, pay, and credential, but it’s impossible to know if you’ve already seen the best option, if there’s hidden crazy behind the friendly smiles, or if something better’s out there.
Watch this space!