Upsolve Wins $50K from Robin Hood…and the “Midterm” Update

Now that I’m about half way complete with my semester off from school, I thought I’d take a moment to reflect on my experience. Today’s also a good day to reflect because Upsolve just got admitted to Blue Ridge Labs’ Catalyst Program, which comes with a $50K prize.

As summer came to an end, and I decided to keep going with Upsolve, I wrote in August that “I’ve never been more content.” My friends often say that I get excited about what I’m doing too easily. There’s some truth in that. Not too much truth, though.

From June through August, working on Upsolve never felt like a grind because everything I did, I did for the first time. For most of those three months, I felt like I learned something new each day. First, I discovered that people couldn’t file bankruptcy on their own. Then, I learned the regulatory hurdles a legal tech product would face. Each new problem presented a unique, seemingly manageable challenge.

Today, I have a much less rosy picture of the task I’ve laid out for myself and a much better understanding of the grunt work it takes to start something. About 10 percent of the last two months have been sexy and glamorous — the puff piece media article, being called “miracle workers” by the people we’ve helped, the fancy 59th floor law firm lunch.

The other 90 percent? It’s hustle I’d hesitate to wish upon anyone. It’s cold phone call after cold email, trying to get community based organizations to help us get the word out. It’s reading and re-reading and re-re-reading the 60+ pages of bankruptcy forms, trying to include each question in our product. It’s iterating the survey our users complete to fill out their forms…34 times (and counting). It’s copying (a lot of copying) the tax returns from our users, which we need to physically mail to the court. This fall, I realized that automating bankruptcy is 5–10x than I thought it was going to be.

I should also mention that it’s a lonely experience. I’m surprised that despite how many people live in New York City, working on an idea you’re passionate about can make you feel like there’s nobody else around. Without my co-founder Jonathan and the friends at school I know I’ll return to in the near future, I’m sure my mental health would have been sub-optimal. This experience has helped me value the importance of a support network and healthy personal life. As one of my mentors says, “If you’re not winning in your personal, professional, and social lives, you’re not winning.”

Here’s the picture that keeps me going through the daily grind. It’s everybody we’ve helped file for bankruptcy so far. 20 new friends I’ve made in NYC over the last few months.

Our First 20 Users

I hope to see this list grow. And you can bet that Jonathan and I will keep grinding to make sure that it does.