Six Months as a Dropout

What I've learned about life and startups in six months as a full time founder and college dropout

Today marks six months since what would have been the start of my junior year at Columbia. I made the decision to leave school to work full time on in July, but it wasn’t entirely real until September, when all my friends returned to school for a new semester. As they set their class schedules, I found myself alone in New York City with no schedule or structure—just a blank slate.

I struggled for the first few months with this unshakable feeling of both physical and creative isolation. My two original co-founders drifted away early on. It was disheartening, even though I knew it would happen. When something went wrong, it would weigh on me for days, even weeks. I found myself intensely preoccupied with my motivation and energy levels, concerned that I wasn’t working hard enough. I went from having thousands of peers in my immediate vicinity to virtually zero. Unfunded, twenty-year-old, dropout founders are not especially numerous. It’s hard to grasp just how influential and stabilizing your peer group is until it’s all but empty.

I spent the better part of the fall “putting out fires”—hurriedly fixing bugs at the eleventh hour and hacking in just about any feature a customer was willing to pay for. It made for a wholly underwhelming customer experience. It didn’t help that I was in well over my head as a developer. I had been capable of shipping a working prototype, but lacked the skillset to structure, stabilize, and grow a complex, mission-critical application.

By December, I’d convinced myself that something needed to change. I started to doubt (mistakenly, I now realize), whether event fundraising was a large enough opportunity to sustain me. I’ve written before about the dangers of seeking external validation, and yet it started to tug at me. I began to mentally explore how I could reposition the still-immature product into an investable business. That’s, after all, what tech entrepreneurs do, right? They create a product, build excitement, and then seek the hundreds of thousands of dollars they need to ensure that the roller coaster never loses steam? That, I managed to convince myself, was what I wanted too.

For December and January, I increased my ambition, reimagining the product as an in-website plugin that would employ the same user interface that had performed so successfully at events. I stopped looking for new customers for the prototype, focusing entirely on a heavily optimized infrastructure for which I had no committed buyers lined up. While I can now reflect with conviction that this was the absolute wrong decision, it was the most fortunate mistake I’ve ever made.

Within weeks, the stifling feelings of inadequacy that had plagued me began to lift. Both my output and mood rose in lockstep. I wrote concise, well-tested code for the new product and triaged problems quickly. I began contributing to open source projects and could call myself a developer without triggering symptoms of impostor syndrome. Working on the wrong product was a relatively minor misstep. The change of pace forced me to think seriously for the first time about what I wanted from the business, rather than what the business needed from me. I began to acknowledge that I needed have an identity outside of the company, both for my own sanity and for the business to succeed.

I’ve released numerous open source projects in the last month. I started working with Firebase as their NYC evangelist and lead Javascript workshops around the city a few times a month. I’ve started devouring books, something I’ve never done. I figured out in high school that the difference between reading the assigned material and spending a frenzied hour with a study guide just before exams was nearly nonexistent, at least as far as grades were concerned. I very well may have managed to read fewer than one hundred pages a year for school and maybe another five hundred for pleasure. By my count, I’ve read more than four thousand pages since January, spanning scientific tomes to spy thrillers to David Sedaris. I’m exploring new genres of music too. It all feels incredibly fluid—never repetitive or forced. It feels like what college was supposed to be.

Re-engineering my lifestyle and habits prompted me to scrutinize my business and reflect on what I truly wanted it to be. I’ve discovered that, at least for the present, I’m not interested in the desperate sprint to the next funding milestone that so often characterizes startups. When asked where I want to be in a year, my response is now a confident: “I want to run a fundraising software business with revenue of $100,000 per full time employee.” It’s still brazenly ambitious, to be sure. But I’m careful to make no assumptions about investments, number of customers, or number of employees. I’m starting from what I want for myself and letting my personal development and well-being dictate everything else.

In practice, this means that I’m re-devoting myself to the original product and undertaking a ground-up rewrite. I now have the ability as a programmer, designer, and product-thinker to do this the right way in a tiny fraction of the time it would have taken me previously. I’m building a product that I’m proud to sell to a market (nonprofits) that truly deserves it. I don’t regret spending nearly two months on a product that is mostly shelved while taking in no revenue. Discovering my own identity was priceless.

Even in a few short months, devoting attention to my own development has substantially de-risked my choice to forgo a college degree. I’ve forged connections with founders whose own skills, experiences, and companies I deeply admire. I know not only what I want to do, but precisely who I would want to work and learn with if for some reason my own founder journey were to come to an end. It’s deeply calming to be regularly reminded that, no matter what happens, I will always be able to feed, clothe, and house myself comfortably.

This knowledge is incredibly precious in a world where so few people feel confident in their employability and fewer still are content with the jobs they do have. There is nothing so important as finding fulfilling work. Having the confidence that I’m building the right skill set gives me the energy to pursue the necessary risks to grow a company.

What we fear doing most is usually what we most need to do. —Tim Ferriss

It takes a thick skin to build and sell a product. It requires a willingness to take countless rejections in stride. In hindsight, I was foolish to believe that I could confront these challenges on my own, especially coupled with a shortage of skill and experience. But had I not dove in headfirst well before I was ready, I would not be where I am today. I would still be a listless student with a passing interest in software. I know I’m fighting a long, slow, uphill battle—but I’m now certain I hold the right cards. These past six months were the prologue. I’m now ready to begin the first chapter.