Gen Z-Focused Side Hustle Leads to $40M+ Investment


This Side Hustle Spotlight Q&A features Dylan Diamond, co-founder and CEO of Saturn. Diamond and his co-founder Max Baron launched Saturn, the calendar app “that supports the complexities of the high school day — even the most chaotic block schedules,” when they were students at the University of Pennsylvania in 2017.

Image Credit: Courtesy of Saturn. Dylan Diamond.

When did you start working on the side hustle that would become Saturn, and what inspired it?
In 2015, I built an app for my school that eventually became the foundation for Saturn. I was a junior at Staples High School in Connecticut at the time, and everyone was obsessed with finding out who was in their classes at the beginning of the year. I initially built a schedule-sharing web app where students could add their classes and find out their classmates.

It went viral at Staples — to the tune of 80% of the 1,800 students at the school using the app daily — and since everyone had added their classes, I realized it would be a quick improvement to make it a full-fledged calendar app that supported our insanely complicated rotation schedule. I called it iStaples, and it helped you manage your schedule and see what classes your friends were taking.

Three years after I built the first one for my school, my co-founder and I launched similar apps at several nearby schools and started working on Saturn.

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When did you decide to leave college to focus on Saturn full-time, and what motivated that decision?
It was less of an active “decision” than you’d think. My co-founder, Max Baron, and I met in 2017 while we were both sophomores at Penn. Max was also working full-time while being a full-time student, having built a consulting practice helping companies like Beats by Dre and T-Mobile develop their marketing strategies to reach young consumers. By the time we met, he had been recruited by Havas, a global marketing agency, to help lead their efforts with this demographic.

At the same time, iStaples continued to have very strong traction within Staples High School. Roughly 80% of the student body was still using the product daily. We decided to explore if the concept could scale. Three weeks after meeting, we launched another school using a white-labeled app to see if we’d have product-market fit at other schools. Half of this second school joined in three hours, and we considered that strong validation. Things quickly expanded to 17 schools, each with its own app, before we decided to consolidate to a single app, mainly so we could deliver features to users more quickly. We called it Saturn, named after the Roman god of time.

When we had 50 schools, we met investors in California for the first time, and General Catalyst led our Seed round. Almost immediately, we returned to Penn to pack up our apartment — we had moved in together by that time. There wasn’t much of a conversation. We both submitted to start a leave of absence and haven’t been back since.

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As a college student, you were also a Tesla employee. How did that work out?
During high school, I developed an Apple Watch and iOS application that effectively served as a remote control for the key functions of a Tesla — called Tesla Toolbox. It took off among Tesla owners, and the company reached out to me. They wound up hiring me, first as an intern and then as a full-time software engineer on the company’s Supercharger Analytics team.

I was based out of Philadelphia while studying at Penn but visited my team in San Francisco regularly. I was in a very demanding dual-degree program at Penn and made sacrifices to continue at Tesla, but I was learning more there than I was in the classroom, so it felt like the right trade-off.

What has Saturn’s fundraising journey looked like?
In 2019, we raised a $9 million seed round from General Catalyst and Coatue in two stages. In 2021, we raised a $35 million Series A from them and other investors, including Insight Partners, Bezos Expeditions, Marc Benioff, Dara Khosrowshahi, Inspired Capital, Sound Ventures, Dylan Field and others.

What were some of the biggest challenges you faced while building Saturn, and how did you navigate them?
Today, we support more than 19,000 schools, but it all started with an app I built for myself and my school that perfectly supported our calendar.

As we started launching more schools, we realized that having bespoke support for each school’s calendar would drive retention. It’s extremely difficult to deliver that experience to users when every school has a unique schedule, runs on rotations and changes constantly. This actually led us to double down on this strategy because we knew if we could solve it, we could preserve our retention as we scaled the number of schools we supported.

When you join the product today, you arrive in an app with every nuance of your calendar. That’s a magical experience for users and one of the ways that we’ve managed to build such a retentive experience for this hard-to-reach demographic.

Capturing that data at scale was challenging. Initially, we relied on our users telling us we needed to update the schedule. Today, that data is crowdsourced, which requires significant density in each school. Reaching that kind of density required years of patience, not just with our team but also with our investors.

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As you consider Saturn’s future, what are you most excited about?
We’ve built a calendar experience that we feel confident can change day-to-day for high schoolers. Not only does it make it easier for students to connect with their peers, make plans with friends and find events in their communities, but it also helps them manage hectic schedules and sets them up for academic and extracurricular success.

We’ve already transitioned from a utility app to a full-fledged social product and pride ourselves on being a social media app that saves time rather than serves as a time sink like the other products on the market.

What do you enjoy most about working on Saturn?
When I built the first app, it was to solve the problems that my friends and I faced every day. This past school year, millions of students used Saturn at more than 19,000 schools. Seeing how we have iterated to achieve that kind of resonance with students across the country is really satisfying. This is a product Gen Z clearly needs, and we are extremely passionate about giving them time back in their day instead of taking it from them with yet another feed.

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What’s your advice for others hoping to start successful side hustles or full-time businesses of their own?
Build products that tackle your own problems. Building products for user stories you deeply understand is much easier. Self-empathizing is so much easier than empathizing with others. Even when we started hiring, we focused on hiring talented young college students and recent grads who we thought would deeply understand the user base. Building for this demographic is already difficult as they have so many great products, and their expectations are calibrated by the performance of the now-mature offerings from Snap, TikTok, Instagram and others. We thought this proximity to the target user would give us a significant advantage.

This article is part of our ongoing Young Entrepreneur® series highlighting the stories, challenges and triumphs of being a young business owner.

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