Bullets dodged

July 31, 2018

Back in 2011, I co-founded a startup called Wishery. It did OK—thousands of customers who loved it—but not enough top-of-funnel volume (signups) to be a viable venture business. We sold it to Zenbox in 2012 and moved on.

I was looking for jobs. A guy I'll call Steve (not his real name) asked me to be CTO of his payments company. It was pretty obvious there was no chance of success; he was competing directly with credit card companies without any "unfair advantage". The company had gone through AngelPad (same class as Wishery) and received investment from a bunch of famous people: Mark Cuban, Tim Draper. With a good salary, a great title, and "name brand" investors, It wasn't easy walking away from that opportunity. Nonetheless, I trusted my own assessment, and stayed away.

A few years later, that company is nothing but a bug on a windshield.

I was approached again recently by a guy who wanted to disrupt healthcare. He had a lot of good ideas, great resume, but no real strategic direction or even a sketch of a viable business. I decided to pass on that one, too.

Everybody loves entrepreneurs and startups but a lot of stuff has no chance of working. I'm perhaps too conservative, as some silly cab company called Uber kept trying to recruit me around 2011-2012. Still, I'm pretty proud of all the bullets I've dodged—all the times I've said no—standing back, watching from a safe distance as the fireworks go off, and things unravel. Investors lose capital, sure, but that pales in comparison to the stress, and outright loss—of time, earning potential, and career advancement—of the grunts on the ground.