This Side Hustle Spotlight Q&A features Dylan Diamond, co-founder and CEO of the company Saturn. Diamond and his co-founder Max Baron launched Saturn, a calendar app that “handles the complexities of the high school day — even the most chaotic block schedules,” while they were students at the University of Pennsylvania in 2017.
Photo credit: Courtesy of Saturn. Dylan Diamond.
When did you begin working on the side project that became Saturn and what inspired it?
In 2015, I created an app for my school that eventually became the basis for Saturn. I used to be a student at Staples High School in Connecticut at the time, and at the starting of the yr everyone was obsessed with checking out who was in their class. Initially, I created a schedule-sharing web app where students could add their classes and find their classmates.
It gained huge popularity at Staples – as many as 80% of the school’s 1,800 students used the app every day – and as everyone added their classes, I noticed that a quick improvement can be to turn it into 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 folks were taking.
Three years after I built the first app for my school, my co-founder and I launched similar apps at several nearby schools and began working on Saturn.
When did you select to drop out of faculty to focus on Saturn full-time and what motivated that call?
This was a less energetic “decision” than it might sound. My co-founder Max Baron and I met in 2017 when we were each sophomores at Penn. Max also worked full-time as a full-time student after building a consulting practice helping firms like Beats by Dre and T-Mobile develop marketing strategies to reach young consumers. Before we met, he was recruited by Havas, a global marketing agency, to help lead its efforts in this demographic.
At the same time, iStaples continued to be extremely popular at Staples High School. About 80% of scholars continued to use the product every day. We decided to see if the concept might be scaled. Three weeks after the meeting, we launched one other school using a white-labeled app to see if we might have product market fit in other schools. Half of the other school joined inside three hours and we considered this a strong confirmation. The business quickly expanded to 17 schools, each with its own app, before we decided to consolidate into one app, mainly to give you the option to roll out features to users more quickly. We named it Saturn, after the Roman god of time.
When we had 50 schools, we first met with investors in California, and General Catalyst led our Seed round. We returned to Penn almost immediately to pack up our apartment – by then we were moving in together. There wasn’t much conversation. We each volunteered to take some day off and have not been back since.
As a student, you were also a Tesla worker. How did it work out?
In highschool, I created an app for Apple Watch and iOS that effectively served as a handheld remote control for key Tesla functions – it was called Tesla Toolbox. This resonated with Tesla owners, and the company contacted me. They ended up hiring me, first as an intern and then as a full-time software engineer on the company’s Supercharger Analytics team.
While at Penn, I lived in Philadelphia but recurrently visited my team in San Francisco. I used to be in a very demanding dual-degree program at Penn and made sacrifices to proceed working at Tesla, but I used to be learning more there than in the classroom, so it appeared like the right compromise.
What was Saturn’s fundraising journey 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 the biggest challenges you faced while building Saturn and how did you overcome them?
Today we support over 19,000 schools, but it began with an app I built for myself and my school that completely supported our calendar.
As we began launching more schools, we realized that individual support for each school’s calendar would increase student retention. It is extremely difficult to provide this user experience when each school has a unique schedule, rotates, and is always changing. This actually led us to double down on this strategy because we knew that if we could solve this problem, we could maintain retention as we increased the number of faculties we supported.
By joining the product today, you get an app with all of your calendar details. It’s a magical user experience and one of the ways we have been able to build such a lasting experience for this hard-to-reach demographic.
Collecting such data on a large scale has been a challenge. Initially, we relied on our users telling us we would have liked to update the schedule. Currently, this data is collected through crowdsourcing, which requires significant data density in each school. Achieving this density took years of patience, not only from our team, but also from our investors.
As you think about Saturn’s future, what are you most excited about?
We have created a calendar that we imagine can change from day to day for highschool students. Not only does it make it easier for students to connect with peers, plan with friends and find events in their communities, it also helps them manage busy 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 we’re proud to be the social media app that saves as an alternative of serving as a time waster like other products on the market.
What do you enjoy most about working on Saturn?
When I created my first app, my goal was to solve problems that my friends and I faced every day. Last school yr, thousands and thousands of scholars used Saturn software in greater than 19,000 schools. It is truly rewarding to see how we have achieved this resonance time and time again with students across the country. This is a product that Generation Z clearly needs and we are very passionate about giving them time to return to the past, moderately than receiving it through one other channel.
What is your advice for others looking to start a successful side hustle or their very own full-time business?
Create products that solve your individual problems. It’s much easier to build products based on user stories you deeply understand. Showing empathy is much easier than empathizing with others. Even when we began hiring, our focus was on hiring talented young students and recent graduates who we believed would thoroughly understand the user base. Building for this demographic is already difficult because they have so many great products and their expectations are calibrated based on the performance of already mature offerings from Snap, TikTok, Instagram and others. We thought that being close to the goal user would give us a significant advantage.
This article is a part of our ongoing Young Entrepreneur® series highlighting the stories, challenges and triumphs of being… young business owner.