Bootstrapping With A Paycheck to YCombinator and $10M Series A: Ryan Chan, CEO of UpKeep (Part 2)

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. I loved not only working as a process engineer that I spent four years in college learning about but also expanding my horizons and learning how to program and code.

Sramana Mitra: What happened after you had this prototype ready? What did you do with it?

Ryan Chan: It wasn’t like I built this thing and millions of people came. It was actually a very long process. I think that’s a misconception that a lot of people have. I was working on this app for about three to six months while I was working full time as a process engineer.

It wasn’t ready for anyone to purchase. So I just released it on to the app store for free. Again this was a project for me. I just wanted to do it because it was fun.

When my girlfriend at that time – my wife now – got into UCLA medical school, I had to make a decision. Are we going to try to do long distance? Am I going to quit my job and move down to Los Angeles with her?

I made the decision to quit my job and move down to Los Angeles. This also gave me an opportunity to continue building out UpKeep. But I was still the worst programmer in the world, but I got very lucky when I moved to Los Angeles. A group called DTS hired me as an iOS developer. I basically got paid to learn how to code. I’m so fortunate that they gave me this opportunity. While my wife was going through med school, I was working and learning how to continue this career and passion of mine for building mobile applications.

While I was working at DTS, I just continued building UpKeep on weeknights and weekends. I honed my craft as an iOS developer, and I just continued to iterate on the UpKeep product.

Sramana Mitra: If you look at calendar years, what time frame are we talking about? When did you join this company? To be an IOS programmer while all this Upkeep development is going in parallel, what years are we talking about?

Ryan Chan: I graduated in 2013. I had left my first job after a little over a year. So this is now 2014. I got a job as an iOS developer and was working on UpKeep on the side for about two years. Now that takes us to about 2016.

Some time in 2016, about three years ago, I met one of my friends. He was another very successful entrepreneur. He said, “Ryan, how is UpKeep doing?” I was like, “Actually, pretty cool. It’s pretty fun. It’s a completely free product. We have a couple of thousand users using our free product.” He was like, “Ryan, that’s crazy. That’s insane. That’s amazing.”

If you imagine where I was and where I came from, this was over a very long period of time. So there’s never a period where I shipped this product and then millions of people came the next day. It was really this idea that I was building and iterating on the product every single day.

It first started out with one person who downloaded it. My mom. The next day, I was able to get my wife to download it. Then the next day, my brother grudgingly downloaded it. It was this very steady and slow growth for me and for us.

I think what happened was, after two years of working on this with slow and steady growth, there’s never a moment where, “Oh my God! This is going viral!” I realized its success when my friend said, “Turn around. Look at what you’ve done.” Then that made me realize how far we had come.

This segment is part 2 in the series : Bootstrapping With A Paycheck to YCombinator and $10M Series A: Ryan Chan, CEO of UpKeep
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