Q&A: How did you come up with the idea for myYearbook?
📬 Question from a reader: How did you come up with the idea for myYearbook?
(Every month, I answer a recent reader question. If you would like me to answer yours, shoot me a message on Substack or respond to this email!)
Let me take you back to the beginning—before venture capital, before acquisitions, before the public company. myYearbook all started in 2005 with a yearbook and an annoying photo.
My brother Dave and I were flipping through a normal high school yearbook. We were still newish to the school—Montgomery High School in Skillman, NJ. I was in 10th grade and had moved to the school district the year before. Coming from a class of 50 kids to a school of 400 per grade was intimidating. Dave, a junior, was already more comfortable, but we were still finding our footing.
We were looking for a picture of a girl in Dave’s class when he pointed out that the photo didn’t look like her anymore. I agreed, said mine was bad too, and we started riffing. Why are yearbook photos so terrible? Why couldn’t we update our photos? High school was core to our lives, and the yearbook wasn’t capturing it. We thought: yearbooks should be living documents. They should be online.
We told our older brother Geoff, who had recently read about Facebook in a Harvard alum magazine. At the time, Facebook was only in a few colleges. Geoff saw an opportunity: we could build something like that for high schools.
We didn’t build “Facebook for high school,” but we did create something meaningful. A place for people to find where they belonged. A way to meet friends, even spouses. A way to end loneliness. That was the magic of myYearbook.
We had no idea what we were doing back then, but we had nothing to lose. The worst case was that it failed, and then what? We’d still live at home, be in school, and have health insurance. And maybe we’d have a cool story to write about in our college essays. Our fallback jobs were at the local grocery store or Friendly’s. When there’s no downside, the choice is obvious: try.
We wanted to make it easy for people to meet others at their school. The idea was simple: a profile to share your interests, see who shared your classes, and message someone new.
We had a vision, but we needed a product. We were not developers, so we hired a firm on eLance (now Upwork) based in Mumbai. Because of the time difference, we’d work with them late into the night—until 2 or 3 a.m.—then wake up for 7:30 a.m. homeroom at our high school. I don’t remember feeling tired. I was too energized. Every day brought more progress. We'd note bugs and send them off just as their day started. It was like shift work across time zones.
We launched at our high school first, Montgomery High School. It was the school we knew and the students we could reach.
To build buzz, we made shirts. But not boring ones. We knew we couldn’t just slap “Meet new people in your school” on the back. So we went with lines like:
“myYearbook launches. Old people afraid.” – New York Times
“Who are your friends’ friends and are they hot?”
We wore them every day, gave them to friends, and even made tracksuits for the gym. Within two days, the halls were buzzing.
We also built an email list from every class group, project, and friend-of-a-friend we could find and started emailing them all. I blogged on Xanga and turned my profile into a giant myYearbook billboard. The idea was to be everywhere.
And it worked. People started coming up to us at lunch or around the track to say they’d joined. One classmate called it the “best procrastination tool ever.” We got real-time feedback on what worked and what didn’t. It felt like everyone was building it with us. It didn’t feel like our site—it felt like Montgomery’s.
In that first week, we hit 400 users.
It was buggy. It was beta. But it was working.
And we were just getting started.
Lessons from This Phase
1. Start with the problem in front of you.
The spark for myYearbook came from flipping through a yearbook and being annoyed. Ideas frequently come from lived frustration. Take note when something bugs you. How could you improve it?
2. You don’t need to be technical to start.
None of us were developers. We used eLance to find the help we needed. You can learn and outsource as you go, and perhaps vibe code.
3. Launch where you are.
We focused on one school—ours—which gave us density, direct feedback, and real usage. You don’t need to launch big; you need to launch somewhere.
Thanks for reading!
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