In October 2020, I went on a sabbatical after working full-time for eight years straight. No more managers. No more renting my time to others. I just wanted to take one year off and work on my own stuff.

I’m a programmer at heart, but I did not touch a single line of code during the first three months of my sabbatical. Instead, I focused on my hobbies: woodworking, drawing, writing, and reading books. It was so liberating to be in control of my own time: no deadlines, no meetings, no roadmaps.

All this took a different turn in January 2021. Sahil Lavingia, the CEO of Gumroad, announced a cohort-based course entitled The Minimalist Entrepreneur. I was intrigued. Following him on Twitter for the past year taught me a lot about his way of building and running a business. I felt there’s a lot I can learn from him, so I enrolled. I got accepted, and in February, the course started.

This was the first cohort-based course I ever attended. Over a hundred people attended, and I felt like I don’t belong there. Impostor syndrome hit me hard. I was at my first bootstrapped company. No revenue. No customers. No audience. 

One week into the course, I realized I’m in a privileged position. The lesser you know, the more you can learn and grow from an experience like this one. And guess what?  On the second week, I closed my first sale ever on one of my apps. It wasn’t much, $6, but what an incredible feeling!

During week number three, Sahil shared with the cohort a little side-project he was working on. He wanted to apply the same learnings he was sharing with us to his own idea. It was a simple web app that generates links to share supplemental content on Clubhouse. He asked for everyone’s feedback. 

I immediately went into the browser. I opened up the developer console to check the source code. There was a piece of code that could’ve been simplified. I rewrote that part and sent it back to him. He appreciated the help and asked me if I can rewrite another small part of the app. A few minutes later, it was done.

I felt like I had an opportunity here. What if I could use this as a wildcard to get hired at Gumroad? They weren't hiring at the moment, but I knew from one of Sahil’s tweets that he hired a handful of people via cold reach. I had a shot back in August 2020 but did not get past the coding challenge. 

I already prepared a list of ten improvements and bugs that I noticed when I set up my Gumroad account. All I had to do was DM Sahil. He instantly replied if I’m willing to send him an email. I was thrilled! I had another shot. 

The next day, I started drafting my cold email. It took me a couple of rewrites, and a few days later, this was the final version I sent:

 

It worked! Four days later, at 2 am on my birthday, we hopped on a short call and discussed a bit about my background, the role, and the company. Close to the end of our conversation, I found out the next step: a coding challenge. I wondered if it’s the same as the one I previously got back in August, and he said yes. I was bumped. 

Coding challenges are my nemesis. I never passed one, so I kinda knew this was the end of it. But I did not surrender. I still wanted to give the best I could. The coding challenge consisted of three parts: a quiz, a frontend challenge, and a backend challenge. Previously, I only did the quiz and the backend challenge, so I knew this time I will go for all three. 

There was a time constraint — 10 hours for the entire coding challenge. I ended up building a quick Rails app to solve both the backend and the frontend challenge. It took me a bit longer than the suggested time, but it was all worth it. I passed! The first coding challenge that I managed to pass. But it wasn’t over yet. I had to go through a one-month trial, and only afterward would I know if I’m hired. My excitement was still through the roof. I had a chance to work for one month at Gumroad. At freakin’ Gumroad!

The first week into the trial, Gumroad raised $5M from its creators and close friends through a crowdfunding round via Republic. You weren’t supposed to be an accredited investor to participate in this round. Anybody could invest up to a $1k limited check size. You can imagine I became an investor too. I believe in the company’s future and want to be part of the creator economy’s future growth.

Three days after the crowdfunding started, Sahil DMs me on Slack, saying that my work has been awesome and they would love to keep working with me as long as I want to work with them. This was it! A dream come true. 

I’ll have to pinch myself every morning to believe that I can actually contribute to Gumroad’s journey and be part of it. I became a Gumroad creator in January. A few days into the trial, I became an angel investor at Gumroad, and now the circle was complete.

Hopefully, stories like mine, Daniel Vassallo’s, or Justin Mikolay’s will inspire future candidates. 

I feel like there’s no such thing as the best applicant. It’s mostly about luck, and I had a lot by taking the opportunity laid ahead of me. 

Develop a keen eye for opportunities and seize them. It could be one in a lifetime. This was probably my once-in-a-lifetime.