Sramana Mitra: Kevin was also doing YCombinator? Ryan Chan: I was part of the YCombinator class of winter ’17. Sramana Mitra: But you didn’t hire him through YCombinator. You hired him and brought him into your YCombinator membership. Ryan Chan: Right. We went through YCombinator. It was an amazing experience. I got introduced to this
Sramana Mitra: What did you learn as you went through the customer base, started getting to know the customer base, understanding the customer base, and understanding who’s converting from free to premium? What did you learn in terms of who were the ones that were really important for the business from a segment point of
Sramana Mitra: What did you do when that aha moment came? Ryan Chan: I hadn’t talked to this friend of mine in almost three years. He said, “Ryan, I will give you a little bit of money if you quit your job today and start working on Upkeep.” I did. I quit my job working
Sramana Mitra: So you started building. Did you still have your day job? Was this on the side? Ryan Chan: This was a hobby on the side. I did this from 6PM to 10 PM, three times a week. I love learning things. I love building. For me, it was fun. I loved doing this.
If you haven’t already, please study our Bootstrapping Course and Investor Introductions page. Ryan took a hobby project that he bootstrapped with a paycheck and managed to get into YCombinator. From there, he raised a $10M Series A from a top-tier Silicon Valley firm, Emergence Capital. Excellent execution thus far. Sramana Mitra: Let’s start from the very beginning of