Irrational Exuberance

Back when I was managing at Digg and Uber, I spent a lot of time delivering feedback to my management chain about issues in our organization. My intentions were good, but I alienated my management chain without accomplishing much. I also shared my concerns...

Pretty much every company I know is looking for a way to benefit from Large Language Models. Even if their executives don’t see much applicability, their investors likely do, so they’re staring at the blank page nervously trying to come up with an idea...

One of the most interesting questions I got after joining Calm in 2020 was whether Calm was a technology company. Most interestingly, this question wasn’t coming from friends or random strangers on the internet, it was coming from the engineers working...

At a recent offsite with Carta’s Navigators, we landed on an interesting topic: leadership roles sometimes mean that making progress on a professional initiative requires taking some personal risk.
This lesson was hammered into me a decade ago during my time at Uber, where I kicked off the Uber SRE group and architectured Uber’s self-service service provisioning strategy that defined Uber’s approach to software development (which spawned a thousand...