I'm a programmer by trade... I founded DreamHost in 1996 while at HMC.edu, bootstrapped it to $40M in revenues, and in 2013 sold my stake to strike off on my own. In 2012 I put $250K into bitcoin that I'm still holding long term. In 2014 a DreamHost spin-off Inktank sold to Redhat for $190M. I created Bitcoin Builder over a weekend in February 2014, and two weeks later it was (briefly) the largest bitcoin exchange in the world.
I started investing in YC startups randomly in 2010 when I stumbled across chart.io because it was something I had developed internally at DH. I then tried to invest in twilio but they were full. I first attended demo day in S13 after selling my DH shares, and invested in Lob, SpoonRocket, Easypost, and Buttercoin. I missed demo day in W14 but still invested in Rickshaw and Zinc. I invested in Doblet and Shift Payments from S14. I've also invested in a few non-YC bitcoin-related companies such as maicoin, coinhako, and pylon (boost S14).
Overall, I'm looking for (likely almost 100% YC) startups with a product I would use (or an idea I've had myself), that already have some traction, where the founders are smart and nice, in an area I have some experience with (software/cloud/bitcoin/consumer). As "conservative" as possible, for an angel!