My first company was called Accolade, which focused on online SAT prep, but we were rejected by Y Combinator because my co-founder and I were part-time and had other commitments.

We decided to build a product we wished we had in Carrot 6, which led us to create Spradley, a company we applied to Y Combinator with in Winter 2010.

In our second venture, Carrot 6, we improved the time from our first line of code to our first paying customer from infinity to six months, but realized our growth pace wasn't sufficient for a large, impactful company.

The first project I built in college was called CourseMatch, which helped students see what classes their peers were taking, but I lost it when my laptop fried.

My early ventures were more about enjoying what I was doing with friends rather than analyzing market opportunities; we built websites around our passions, like soccer and technology.

We initially planned to build a chat app for gaming, but we thought we could bootstrap it through a game. When the game failed, we realized we could launch the chat app directly instead.

I found a significant number of users asking for parenting advice, which I had never considered before, and it led me to create educational games with my kids using Claude.

My first startup aimed to solve the problem I faced as a backpacker by creating a mobile app to book hostels and bed-and-breakfasts.

My co-founder Andy and I wanted to skip traditional jobs after college and dive straight into our startup, which we applied for with an idea similar to mint.com for businesses.