Upsolve: What I Learned in 2017 and our 2018 Goal

Morning of Jonathan’s Wedding!

2017 marks the first full year of Upsolve’s existence. And what a wonderful, challenging, fun year it has been. I thought I would take a chance to reflect on three things I learned, what we were able to accomplish this past year, and what we have our eyes set on in the year ahead.

The first thing I learned is that it is that being resource constrained is a wonderful thing. I used to complain about it, but now I love it. Being resource constrained creates an advantage because it leads you to be hyper focused on what you’re good at and what you need to do. For us, being resource constrained meant that we stuck to our Typeform MVP for 18 months, learning about our users and market rather than writing code from scratch, and waited the same amount of time to hire our first employee. Fred Wilson’s 306-word essay Resource Constraints helped me internalize this point this summer. My only qualification is that you must have baseline financial stability, while being resource constrained, or else you will be distracted by your financial uncertainty — like we were until this summer.

The second thing I learned is that there’s so much more to soft skills than being able to hold a conversation. I used to equate the two, but I realized this year that soft skills also entail so many other traits — like being able to give and receive frequent feedback, creating clarity around deadlines, and providing adequate guidance without being overbearing in direction. Similarly, I learned the importance of culture, and how you need to be just as deliberate about creating a positive culture as you are with choosing the right technical stack. Reading books like Radical Candor, Difficult Conversations, Getting to Yes, and High Output Management this year helped me grow in this area, and I recommend each of them. I intend to invest lots of time into pushing myself to grow further here in 2018.

Third, I learned that conviction is a huge competitive advantage, and I believe that as a founder you must avoid conditionals if you want to execute your vision. At the beginning of this year, I considered getting a job because I didn’t know whether Upsolve would be around at the end of 2017. Looking back, this lack of confidence only increased the likelihood that my fear would become a reality. I believe that startups can be a self-fulfilling prophecy, especially once you have found product market fit, and that you can will your dreams into existence. Using “ifs,” such as “if we’re around in 2019, we should expand to X market” is destructive. We’re building Upsolve to outlast us, which I know is at least a 10-year journey. Remembering this each day will make it more likely to come true.

When I wrote my 2016 “Year in Review” article, I had two big goals in mind for the year. One was to build a full fidelity version of our next product, moving away from the Typeform MVP that had served us so well serving New Yorkers in our early days. I’m proud to say that with the amazing, relentless work of Mary Gao, Vanessa Ting, and Jonathan Pyle, who spent years building the open source project we’re using and has a superhuman work ethic, we’re excited to be launching our new product in 11 states with 13 legal aid partners.

The second goal I had in mind was getting funded by the U.S. government through the Legal Services Corporation. In September, we were excited to announce a $160,000 grant in partnership with Philadelphia Legal Aid.

In 2018, our number one goal is to help 500 Americans get a fresh start with our product. This would be a 10x increase over our first 18 months of operation, which we consider our user research and product development phase. Making our user growth goal public is important to me because it compels us to accomplish it. To succeed, we hope to enter the three largest areas people need our help: Chicago, LA, and NYC, where we have paused operations to focus on our national expansion. All of our other goals around product improvements, fundraising, and revenue are secondary to this growth goal.

2018 also marks the year I graduate from college. Whenever I think about our work at Upsolve, I find myself grateful to have been so lucky to have found a cause that has been so fun, meaningful, and delightful to pursue. I love what we do, and I’m excited to continue when I graduate with no end in sight.

None of this would have been possible without the advisors, directors, and funders who took early bets on our potential. Their advice, introductions, and time have meant the world to us, and I hope this coming year gives me the same opportunity to support others.

Finally, I’m grateful for my co-founder Jonathan. I’ve learned so much from him and his commitment these past 18 months. It is one of the joys of my life to be able to work with him, and I’m excited that we’re just getting started.