Derek Sivers started the now page movement; seemed like a good idea to me! Last updated May, 2018.
I joined the core team at Pioneer Square Labs in early May, 2018.
PSL is a “startup studio” and a venture capital fund. It has quickly become a central focal point for interesting activity in the Seattle startup community.
My job at PSL is to vet the technology and go-to-market strategies of a large number of potential new startups — perhaps a hundred over the course of a year. Sometimes the startup ideas are generated in-house through a process best described as creative chaos; sometimes they come from entrepreneurs who join the PSL community as residents. Vetting sometimes requires a deep survey of the technology landscape in a particular market segment; other times, it requires architecting and implementing entirely new software systems.
My path to PSL was unexpected. After departing StackPath, the company that acquired my bootstrapped startup Cloak (now re-branded as encrypt.me), I began working on a number of potential new “indie” projects. I quickly realized that a few of those projects shared a common technology core.
At the same time — and in a happy coincidence — I reconnected with a friend who happened to also be an entrepreneur in residence at Pioneer Square Labs. He was incubating a potentially very interesting business there; it didn’t take long to discover that it too had similar technology characteristics. I suggested that we work together, and the next six months became legend… sort of.
The business we attempted to build ultimately didn’t pan out, but all’s well that ends well: along the way, I got to know the PSL community. To my surprise, they turned around and offered me a full time job. To some of my friends’ surprise, I accepted. But it was actually an easy choice: the PSL community is uniformly lovely, talented, and ethically aware. I was having a ton of fun hanging out with them. Who wants that to end?
Raising a family
This is my other full-time job. Ellie is absurdly fun.