The Importance of Side Projects

This post originally appeared on Teddy Citrin’s Medium blog.

Life is filled with peaks and troughs. A low point at work combined with a low point personally, can make you feel pretty hopeless. I was in one of these ‘combination’ low points 2 years ago.

I had just found out some devastating family news, and I was in limbo at work. I was transitioning between teams at eBay, and was unsure whether or not I would stick it out. I was going into work without any excitement, and I felt like I had little control over my future. The good thing about times like these however, is your mind is free to wander. I started keeping a running list of ideas that I could invest some time into during this period of flux.

After a few weeks of jotting ideas down, I finally landed on a concept that I felt really excited about. I could tell this one was different because the other ideas I had wouldn’t get further than a days worth of thought. I couldn’t stop thinking about this one for a week. I began to mock up what the app (in this case) would look and feel like. Prototyping tools are powerful enough nowadays that without any programming chops anyone can easily create a simple UI/UX of an App or website. I used proto.io and UXPin. The experience of moving from concept to something tangible was an incredibly freeing feeling. Even getting to this stage and no further would be a rewarding experience.

The next step was gathering enough courage to pitch the idea to someone who could help build it. I chose to share the idea with my good friend Max Shaw. He is open minded, yet challenging and highly opinionated. I also knew he was always tinkering with things on the side. I’ve known Max forever, but when it came time to actually pitching him, I was surprisingly nervous. Even though the idea was nothing more than a slightly interactive drawing, it was a very vulnerable feeling to put something out there that you actually spent time on.

Max and I were on different coasts at this point, I was in SF and Max was in NYC, so we did this late night over google hangouts. It turns out that he also had an idea that he wanted to share with me. Dueling pitches. I went first. My idea was to create an anonymous messaging board for colleges on mobile. At Wesleyan, CollegeACB.com was huge, and the founder Peter Frank, who was a classmate of mine, had recently sold the property. While most people cringe at anonymous anything, on CollegeACB.com I loved the freedom it gave people to speak their mind. Outsiders dismissed the site as solely a bullying engine, however I found it extremely useful for vetting professors and classes; and the chronologically ordered anonymous banter was highly entertaining. Max liked the idea.

Next Max shared his idea. He wanted to build a group picture messaging app that would automatically take a selfie when you pressed send. We have a large group of high school friends that communicate regularly on group messaging apps, but he realized that we never saw anyone’s faces. I liked the idea.

Since Max knew how to program and had already started building the app we decided to go with that idea first. Oh the leverage that comes with actually being able to build something…We agreed that I would help with design, additional features, prioritization, and any other task that didn’t involve coding. We named the app SeeMe.

We started from that conversation, and I immediately noticed a change in my demeanor and outlook. I was now able to expend mental energy on something with a real and visible output. Since Max and I were remote we became Slack power users, trading back and forth ideas throughout the day. A month later a beta version was ready and our friends began piling on. A couple months after that we were approved by the App Store Gods. Max’s thesis had turned out correct, and groups of friends across the country were trading hundreds of messages a day on SeeMe.

Time flew by and before I knew it I had moved over to a new Product Manager role at eBay based in NYC. While things were moving slower because we had serious full-time jobs, we kept executing and improving the experience. We hired a developer named Mark Koslow, who was a CS student at Duke who wanted to learn more about iOS in his free time. We had a friend of ours, Annalora Von Pentz, a great designer from Wesleyan, help make the experience more delightful. We finally launched on Product Hunt and got great reception and feedback. We even got a cease and desist letter from another large company with a similar name, which was a huge validation point!

Fast forward to September 2015 and it is clear that SeeMe is not the next Snapchat nor will we leave our jobs to pursue it full-time. Our numbers have flat-lined and we rarely update the app anymore. Our core users still say they get a lot of joy out of the app so we keep the lights on. While this didn’t turn out to be huge idea , it far exceeded what I thought would come from a mere thought exercise during some tough times. In the process of building SeeMe we not only learned a ton, but we genuinely had a blast doing it.

In a world of over-analyzing takeaways and life lessons I will only leave you with one. Build things, especially in times of uncertainty and self-doubt. A lot of joy and learning will come from it.

Teddy Citrin

Associate • New York, NY

Based in the New York office, Teddy’s responsibilities include evaluating investment opportunities, sourcing new deals, and working with existing portfolio companies.

Prior to joining Greycroft, Teddy was a Product Manager at eBay. Teddy was responsible for the product strategy, day-to-day execution, and a/b testing for the eBay homepage across all devices. Prior to the homepage, Teddy worked on eBay’s Geographic Expansion Team, launching and growing eBay in Russia, China, Brazil, and Mexico.

Teddy holds a B.A. from Wesleyan University in Political Science. He was also a 4 year starter on the Wesleyan Men’s Varsity Lacrosse Team. Teddy is a member of the Shining Hope For Communities (SHOFCO) leadership board, a non-profit organization that combats gender inequality and extreme poverty in urban slums in Kenya.

It’s Never Over Till It’s Over