Ryan Chan of Upkeep on The Solo Road to Building His Team

Asnapshot — Upkeep simplifies the workflow process for maintenance teams. They have recently raised $2.7 million in seed funding from Battery Ventures, Bain Capital Partners, Y Combinator, and other investors. Ryan founded Upkeep in 2015 and bootstrapped his way into YC’s 2017 winter batch. Upkeep now has over 40,000 users, is cash flow positive, has over $400,000 in ARR, is growing 20% month over month, and 95% of those customers have come in organically! Learn more on how Upkeep is killing it at onupkeep.com.

See the full interview here

Q. Why did you make the jump?

A. The reason why I quit my job as a chemical engineer, learned how to code, and took the leap into software was because of the problems I faced as a chemical engineer. I was working at this manufacturing plant and all of the maintenance guys out in the field were using pencils and paper when they had a smart phone in their pocket! Everyone was writing notes on paper, then coming back to their desktop, and proceeded to retype everything back into their computers. That’s when I said, “I am going to build something for technicians out in the field to avoid this double and triple entry process.” However, here’s the kicker: the actual triggering point as to why I quit my job in Santa Barbara, moved down to L.A., and started focusing on Upkeep was because my girlfriend got into med school at UCLA! I took a night class on coding in Santa Barbara, which enabled me to get a job as an iOS developer in L.A., and then I spent weekends and nights with this great guy I outsourced from India to build Upkeep.

Q. What brings your team together?

A. The one thing that we can all rally behind is eating good food. If you bring your lunch [to work], you’ll get made fun of. We’ll pressure you to go out and eat with us. We’re in Westwood [California], and there is so much good food around, but sadly the place that we go most often is freaking Chipotle!

Q. How do you hire the first few?

A. For us, it was really important to make sure that we clicked, and making sure that there was team chemistry. The way that we knew that for almost everyone was that we’ve worked with them before. You can do that at this early stage, but as you grow and scale, it’s obviously not going to be possible to have worked with everyone that you hire. We just hired our seventh employee, who hasn’t worked with any of us. In that instance, the entire team spent about 5 seconds making up their minds; it was 100% yes all around and everyone just knew that he was our guy. Since then, he has been doing a phenomenal job for us. We will never sacrifice hiring someone who doesn’t have the three core values that we live by: do they have humility, do they absolutely love to learn, and do they have pure grit?

Q. How do you prevent your team from losing focus?

A. If you keep people close to the problem that they are solving and if you keep people close to the actual customer then, shit, I don’t need to do anything. The team can see the frustration in our customers’ eyes and they can see the frustration in people’s day-to-day lives. If you separate [the team] from the voice of the customer, then it’s really easy to forget why you’re doing something, why you’re building Upkeep, and why you’re trying to help technicians. Even the developers are in our support system; they will go through our support tickets line by line and understand, “Oh crap- this is actually preventing people from doing their jobs.”

Q. Do you have a favorite story about Upkeep?

A. Everyone always asked me, “how big is your team? Who are your biggest customers?” I couldn’t answer, “there is only one of us, and my headquarters is my mom’s garage”. I wanted to make my company feel and seem bigger than it actually was. So, I basically put my girlfriend’s name on the website, I put my brother on the website, and I actually put my brother’s girlfriend on the website. I called them customer support, sales, and implementation manager. I would answer support tickets as my brother and I would write articles as my girlfriend.

Q. Any more advice for entrepreneurs building their founding team?

A. Surround yourself with people that you would like to hang out with on a day-to-day basis. Every single person that we have brought on, I feel like they’re the type of person that I would like to spend the weekend with. If you have someone you want to hang out with, then they will be someone you want to train, someone who you want to develop, and someone who you will want to lead your next team. When you create this awesome culture, it makes people want to have a higher output; at least that’s what I hope!

Q. What not to do?

A. Don’t sacrifice the previous plan; don’t sacrifice the idea that every single person that you bring on is going to be someone you want to hang out with, going to be someone you want to see succeed, and someone that you want to be on this journey with for the next five to ten years.

This interview with Ryan Chan, Founder & CEO of Upkeep, a maintenance management software company, was conducted and condensed by me. Every so often, I’ll ask the startup founder(s) about the specifics behind team chemistry, leadership, and what it looks like to have a successful startup molecule. See the full interview here.

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