Career choices, startup equity, variance, and lessons from founding, joining, and leaving startups.
At one point in my career, our company was hiring for role of a Head of Marketing. I got a strong referral from a friend, reached out, the match was great, and she passed the interview process with ease. And then we just... sat on it. The hiring manager said he wanted to consider three candidates and then pick the
Rationally valuing equity for startup employees
How I spent a year trying to start a startup -- and failed.
You might imagine all great startups started from a clear mission. Sometimes they were, but usually, that story is woven in hindsight to cover up the gnarly pivots of the early days. In PR-optimised founding stories, the narrative usually goes like this. Our visionary founders found an apparent $PROBLEM in the world; through hard work and over many different
As an employee, startup stock options are hard. I'm feeling pretty confident by now, but only because I've seen my friends get burned and been burned myself. What's so hard? 1. At one company, my option contract was to be signed "at a future date", not together with my employment contract. In
How do you end up with an outlier success? I guess the common advice would be to "leave your comfort zone". That's hard to do. In the comfort zone, everything makes sense. Things work. Clients are using the product. You might even be growing slightly. It would be stupid to mess with something that works, right?
There's an abrupt life transition almost everyone goes through: school to job. You might go from middle school to manual labour, or PhD to teacher. But regardless of details, a more gradual shift would be better. Most entry-level jobs could be apprenticeships that mix education and work. Why mix them? Trying to do a job well gives
Startups have high variance: the top few % reap most of the rewards. The same is true for artists of all kind, and to a lesser extent, software engineers: some Waymo engineers earn 100x the salary of the lowest-paid programmers. Risk is usually taken to be bad. But it might not be if you can influence the outcome. If you
“Founders at Work [https://www.goodreads.com/book/show/98233.Founders_at_Work]” is a unique book by Jessica Livingston, one of the founders of YCombinator. It contains un-narrated, almost unedited interviews with founders of successful startups like Paypal, Hotmail, Apple, and 27 others. I’m only through about 10% of the book, and it’s clearly one of
