Taking on an $80 Billion Dollar Market with Gen Z | Dylan Diamond

Dylan Diamond is the Co-Founder & CEO of Saturn, a viral Gen Z calendar app that's raised $68M after starting as a high school project. In this conversation, Dylan shares his journey of attracting major investors like Jeff Bezos and Mark Benioff, scaling the app to millions of users, and maintaining high retention rates across 18,000 schools. We also get insights into Gen Z behavior, the role of AI in app development, and building a sustainable product. This episode also explores the unique ad model Saturn has created, its long-term vision, and the challenges of maintaining growth and user engagement. I've teamed up with Passes to grant us access to a pro podcast studio in LA, exclusive early releases, audience Q&A, & BTS content. Sign up for Passes for more Sourcery content! https://www.passes.com/mollysoshea Molly on X: https://x.com/MollySOShea Follow Sourcery for the latest updates! https://www.sourcery.vc/ TIMESTAMPS: 00:00 - Introduction 00:43 - Reconnecting in Westport 01:43 - Raising From Bezos, Benioff, Dara & More. 03:06 - From School Project to VC-Backed Company 05:09 - User Retention and Growth Strategies 12:29 - Onboarding and Ambassador Programs 16:56 - Adapting to Gen Z Trends 19:50 - AI Integration and Future Plans 22:41 - Advertising Model and Monetization 25:28 - Building and Maintaining a Consumer Product 28:16 - Expanding Saturn Beyond High School 31:47 - Recruiting and Team Composition 33:58 - Capital Raising and Investor Relations 36:54 - Gen Z Insights and Future Trends #podcast #investing #technology #venturecapital #entrepreneur #startup #siliconvalley

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Molly O'Shea?

  We have General Catalyst, Kotu, Insight, O1 Advisors, Jeff Bezos, Marc Benioff. Dylan, how did you land all of these great investors?

• 0:10Speaker 01

  During the summer months, we reached number two on the entire App Store, number one in productivity.

• 0:15Molly O'Shea?

  Calendars are extremely sticky products.

• 0:17Speaker 01

  Yes.

• 0:18Molly O'Shea?

  I think I look at my calendar more than I look at my text messages.

• 0:21Speaker 01

  The high school market is very important to us because it's the first touch point with the user and we want to build a relationship with them for the rest of their lives. But then you must retain the user.

• 0:30Molly O'Shea?

  Please tell me all of your Gen Z insights. What do they want? What's coming next?

• 0:39Molly O'Shea?

  Dylan Diamond, it's a pleasure to have you.

• 0:41Speaker 01

  Molly O'Shea, thank you for having me.

• 0:43Molly O'Shea?

  Last time I saw you, we were in front of a packed audience of 500 people in this incredible small town.

• 0:50Speaker 01

  Westport Library.

• 0:51Molly O'Shea?

  Called Westport, Connecticut.

• 0:53Speaker 01

  Yeah. Wouldn't trade it for the world. The fame of Westport, Connecticut. No, that was a fun event. You did a great job and I thought the crowd really liked it.

• 1:03Molly O'Shea?

  Thank you. I think you did a great job as well.

• 1:05Speaker 01

  Thank you.

• 1:06Molly O'Shea?

  Very fun crowd. Interesting, interesting times.

• 1:11Speaker 01

  Well, what's cool was being there was all these kids, it was like the eighth generation of, what was it called? Ice Staples, but Saturn at that school. So it was cool to actually meet all the users where it all got started.

• 1:21Molly O'Shea?

  Do you visit schools often? Like, do you go and meet?

• 1:25Speaker 01

  It was easier when I was 19. Now, I feel like they're like, why is this adult in the school? But we do visits like, you know, a couple of times a quarter, like user research visits and stuff. I have not been back to Westport though since 21, so it was really fun to be back.

• 1:39Molly O'Shea?

  Yeah, it's nice.

• 1:40Speaker 01

  Yeah.

• 1:40Molly O'Shea?

  It's refreshing.

• 1:41Speaker 01

  Yeah.

• 1:41Molly O'Shea?

  Well, you are a big deal. You've raised over $68 million in funding by very large names in Silicon Valley. I'm going to name them out. Okay. We have General Catalyst, Kotu, Insight, O1 Advisors, Jeff Bezos, Marc Benioff, Dara, Neo, Elad Gil, Dylan Field, and Inspired Capital, and I'm sure there's more. So Dylan, how did you land all of these great investors?

• 2:12Speaker 01

  I think they're all builders. You look at everyone from Bezos to Benioff to O1 Advisors, which was the Twitter management team. You have Dick and Adam and David Fisher. They were at the helm of some of the most transformational companies ever, and specifically in consumer. They teach us everything. So whether it was GC to Snapchat, Series B, meeting O1, these people are builders. And in a world where a lot of venture capitalists haven't operated in the field as much, we learn everything from the go-to-market strategy to building out the first new ad unit in years, which we'll talk about. These advisors, these investors,

• 2:55Speaker 01

  have all been there and done that. And we're super grateful to work with some of the best and learn from them all the time.

• 3:01Molly O'Shea?

  We talked about this a little bit. We both grew up in Westport. We went to Staples High School. The company came out of Staples High School. So can you just talk about the transition from a Staples High School app, project, small thing, to now a full-fledged, VT-backed company?

• 3:19Speaker 01

  Yeah, so at Staples, you probably, I built a bunch of apps. I built an app to let kids better check their grades because the school's website wouldn't really work on your phone. Was using it just as a tool for myself. People over the shoulder would see it. They asked for the product. That continued to grow. And then kids from other schools wanted that. And it became the number one grossing app in the education store at the time. Built an app for Tesla, ended up working there just as a tool for myself. And then the product that is called Saturn today started off as iStaples. And it was a website where you would upload your schedule, type in your classmates, and see is your best friend, is your crush, who's in your class, who are you going to be stuck with

• 4:01Speaker 01

  for eight months of the school year. And that was all word of mouth spread. And you remember posting your schedule on Facebook and being able to like and comment if you have classes with people, doing it then on your story, and then later on iStaples. And that was a product that started as a schedule sharing. So it was used in the peaks of the semester. And then Staples is scheduled. As are most high school schedules incredibly complicated. So I took that schedule sharing product. I had the graph of and database of everyone's schedule and made it a calendar. So it could be used on a daily basis. And that spread word of mouth around my junior year. And then, you know, it spread from around, you know, thirty percent to fifty percent to eighty to ninety percent of all the students using the product every day, even after I left.

• 4:46Speaker 01

  And it was all word of mouth and just building tools for myself and then friends and classmates.

• 4:51Molly O'Shea?

  Calendars are extremely sticky products.

• 4:53Speaker 01

  Yes.

• 4:55Molly O'Shea?

  I think I look at my calendar more than I look at my text messages. Just to put some numbers against it, like maybe how many users have you had in total? Or how do you measure the kind of success?

• 5:08Speaker 01

  Yeah.

• 5:08Molly O'Shea?

  Like daily.

• 5:09Speaker 01

  So we've always been a retention based business. And I think the reason my co-founder Max partnered up with me was he saw the early Google Analytics data back in like twenty nineteen from Staples and saw that step function increase in Dow daily active users over the enrollment. And saw that even after I graduated, the engaged percentage of the student body continued to increase. So we look at a lot of things. We have, you know, our Dow now, the stickiness daily active, the percentage of monthlies that are active every day is over fifty percent. Our D thirty retention of brand new users is well over thirty percent with seventy percent for existing. Ninety percent of new users return every single year. So that's why, you know, freshmen use it as sophomores and kind of grow up with the product.

• 5:56Speaker 01

  You know, we have millions of users at eighteen thousand schools right now, but retention is always what we focused on. I think a lot of other products in the space may have focused just on user acquisition numbers. And we probably grow more slowly than some would like. It's not been an overnight journey. We've been at this for five and a half years, but during the summer months, you know, we reach number two on the entire App Store, number one in productivity, ahead of some great tools like Chat GPT and others, TikTok. Just because, you know, we focus on the K factor, we focus on the user acquisition, but then you must retain the user. I think that, you know, just acquiring users is not really building a sustaining product.

• 6:36Molly O'Shea?

  Love what you're hearing on Sorcery VC? Unlock even more with passes. You'll find exclusive bonus content from this podcast, deep dives, behind the scene insights and extra resources tailored for founders, investors and startup enthusiasts. Head to passes.com to access everything you need to take your knowledge to the next level. How does this stack rank against other calendar apps?

• 7:00Speaker 01

  Well, I think with the high school demo, they're not really using other calendar apps. Their solution are pieces of paper, notes, reminders, their parents telling them what to do. But in terms of, you know, consumer social, A16 quotes it as anything above 25% in the D30 is like best in class. We're well north of that. And I think calendar apps don't grow virally. They're enterprise tools that your companies give you, or they're single player products that you use as kind of a notes app, but you don't really use it socially. So we look at consumer social metrics more than calendar apps. That said, we have the viral growth, but we also have the retention. So you're correct that whether it's a calendar or a calculator app, you're probably going to use it a lot, but it might not grow virally.

• 7:45Speaker 01

  You gotta kind of blend the two to both have viral acquisition, but the stickiness that you need to endure. And there have been a lot of social products since we've started the company that have grown much faster, but then, you know, they have the reverse K factor where your friend tells you to use it, you use it, your friend stops using it and then you stop using it. And with Saturn, it's a great calendar for you. It gets even better when your friends join. But if your friends stop using it, your usage is the same.

• 8:11Molly O'Shea?

  How do you deal with the cyclical nature of school seasons? You know?

• 8:17Speaker 01

  I mean, it's tough. Like we are, it requires a lot of effort and focus to prepare for the back to school season. We're acquiring over 100,000 new users per day during that time period. And the average user invites between four and five friends to the platform, propelling the growth. They're sharing their schedule on different platforms, which is all organic led growth.

• 8:37Speaker 01

  You know, you could have a company that's more spread out growth, like month over month. Saturn is a little untraditional in that it is, the growth is really confined to the back to school window compared to the rest of the year, but the retention is the same. So if you look at it on a yearly basis, you know, it all kind of nuts out.

• 8:54Molly O'Shea?

  I want to go deep into this part because you mentioned it a couple of times, but the viral factor

• 8:59Speaker 01

  Yeah.

• 8:59Molly O'Shea?

  of the product itself.

• 9:00Speaker 01

  Of course.

• 9:01Molly O'Shea?

  Last year, you were featured as a collaborative piece in Lenny's newsletter. He has almost a million subscribers.

• 9:08Speaker 01

  Lenny's amazing.

• 9:08Molly O'Shea?

  The most popular newsletter ever.

• 9:10Speaker 01

  Yeah.

• 9:11Molly O'Shea?

  Um, could you just break down what builds that consumer product for you guys? Like, what, what is the recipe there?

• 9:18Speaker 01

  Yeah. Um, so for the first couple of years of the product, we didn't even ask the user for their contact book. We had no invite flows. It was all word of mouth. That was slower, but it allowed us to focus on the downstream retention and the core jobs to be done in the product. I think a lot of times people will build a viral flow, but they won't think about retention. And then you will see that reverse K factor effect. Users won't actually engage with the product and you could acquire users more by either if daily active users equals acquisition minus churn. Increasing your retention reduces churn, but acquiring more users without reducing churn

• 10:03Speaker 01

  is not, I think, a recipe for success. It's users will invite people to products without knowing what they do. We've seen time and time again, products reach the top of the app store for one or two days and then completely die off. There is a playbook to that. Um, we took a pretty hand to hand approach with building out the products early. In the newsletter piece, we talked about how we would white label each product. So if at Staples, it was called I Staples. Weston was I Weston. Greenwich was I Greenwich. And the app felt really homemade. It was easy to spread word of mouth. It was branded in the app store for your specific school and that drove us to getting 50 plus percent penetration, sometimes within 48 hours, often within the first week at those couple dozen schools.

• 10:44Speaker 01

  And that was before any of the playbook growth hacks that you might think of today. As we've hit more scale, uh, we've been able to, you know, do the usual growth work with, you know, contact book and invitations. But really the value prop has to be communicated to the user, which is, hey, share your schedule with your friends. See who's in your class, set your calendar up in minutes. And that's, um, that's, I think, what we've perfected over the years. But it's an evolving science and, you know, as Apple updates their OS, things change and you gotta stay ahead.

• 11:15Molly O'Shea?

  Have you ever incentivized with money? Like, how do you think about gamifying it?

• 11:20Speaker 01

  Well, it's more about what's the value prop for the user? All the referrals that have been monetarily incentivized have failed. So saying invite your friend for $5, no. And we even had Bieber tweet out the product once and you know, the retention is not strong. I think if your best friend tells you to use something, you're much more likely to use it than if a celebrity tells you to use it.

• 11:40Molly O'Shea?

  I know that onboarding was a hard process for you in the beginning.

• 11:44Speaker 01

  Very.

• 11:44Molly O'Shea?

  Getting people.

• 11:45Speaker 01

  You know of all people.

• 11:46Molly O'Shea?

  I know of all people.

• 11:47Speaker 01

  Thank you again.

• 11:50Molly O'Shea?

  Back in the day, um, I, I'm friends with Denali on your team.

• 11:56Speaker 01

  Denali is phenomenal.

• 11:57Molly O'Shea?

  Love, loved Denali.

• 11:58Speaker 01

  Five years later, she's leading product and she's crushing it. So.

• 12:01Molly O'Shea?

  Good.

• 12:02Speaker 01

  We are so lucky to have.

• 12:03Molly O'Shea?

  Shout out to Denali. But I, yeah, I got close to Rough Draft Ventures and in college and she worked for General Catalyst and yada, yada, yada. Next thing I know, I'm in your office helping out with your lead gen strategy and I'm cold DMing.

• 12:18Speaker 01

  Yeah.

• 12:19Molly O'Shea?

  High school students, um, for Saturn. And I got completely burnt down. They are.

• 12:28Speaker 01

  We've all been there. I know. I look back at my former high school self and I wonder, I'm like, I hope I wasn't that bad.

• 12:33Molly O'Shea?

  Like, wow, they, they are something. If you need your ego checked.

• 12:37Speaker 01

  Talk to a high schooler.

• 12:38Molly O'Shea?

  Yeah, talk to a high schooler. Maybe don't DM them. That's.

• 12:40Speaker 01

  Do not DM them.

• 12:41Molly O'Shea?

  Be weird. Um, but let's, let's.

• 12:49Molly O'Shea?

  Let's talk about the onboarding flow now. So what was the process of working that out?

• 12:54Speaker 01

  So we started off with my cousin who went to Weston High School and he gave us his friend who was our first ambassador and actually intern for Saturn for many years. And we would then use her to go to a boy at Greenwich and a kid at Darien and sort of all word of mouth, no paid, no incentives, just, hey, we need to launch the product. And often when we would encounter a new school, we would need to work with that ambassador to build the schedule infrastructure for that school. It was not done over the air. We were hard coding apps. So the ambassador felt like a product builder. They were enlisted on the team, working with us for a couple of weeks to get the school off the ground. You know, flash forward, kind of, uh, you know, five and a half years, we've, you know, it's all done with AI over the air. We don't need ambassadors.

• 13:38Speaker 01

  But you know, at the time, when, when you were here, we were focused on, okay, Saturn is not established as a brand. How do we convince a kid to? Uh, one, want to work with an app called Saturn that they cannot use and download yet. They're on a waitlist and give us all this data. I realize in hindsight how that may have been a lot of asks for the user. And, you know, you were phenomenal with everyone else who had to, you have to kind of do the unscalable to ultimately make breakthroughs. And working with ambassadors at the time was a multi-step process. They would churn, we'd recruit them all early in the summer. You hit Labor Day, they're all gone, right? They'd be in a spreadsheet and then you'd go to message them to launch the school. It would all be gone. We started with manual ambassadors.

• 14:23Speaker 01

  We've then evolved to having a waitlist product where people could fill out a form. They would log into Saturn and if their school wasn't online yet, they would fill out a form, give us the bell schedule, other things we needed to launch the school. And then later on, we made the decision, hey, why don't we just launch all 18,000 public high schools in the country and have the users come to us? And even if in year one, the school doesn't get to 50%, it might in year two, three, four, that's what our data shows. So we actually reduced the high-touch component of launching a school by working with a high schooler. Instead, we are demand-led now where we did the waitlist and then now every school's online. So schools can just grow on their own through our invitation hooks and through people just discovering the product.

• 15:09Molly O'Shea?

  I feel like that's very hard though, because as a startup, you have so much pressure to grow super, super fast.

• 15:15Speaker 01

  You do, I mean, we made bad product decisions, I think, early on when either investors wanted shorter-term growth. COVID was a huge hurdle for us because our user base went to zero overnight. We had to adapt, we built a web app that worked on Chromebooks and, um, you know, that was great. It got like an hour of usage a day, but then we pivoted back to kind of the mobile strategy after COVID.

• 15:37Speaker 01

  But yeah, you. One of our board members says, "Our growth is fast and steady. It's not overnight domination, but ultimately it endures. It prevails." And I think that, you know, we now have six, seven years of cohort data that shows that schools grow significantly year on year. As an anecdote, the first 50 schools when they launched, 7% of all the high schoolers who were enrolled at all those 50 schools were active weekly. Now it's 60%. So schools grow year on year. Saturn becomes a fixture at the campuses, but you just gotta have patience. And a lot of investors didn't have that patience and we're grateful for the ones that do.

• 16:16Molly O'Shea?

  What was your thinking being in the founder's seat, like shifting over to a long-term mindset? Like, I can't imagine that.

• 16:22Speaker 01

  It was not a decision that we said, "Let's shift to a long-term mindset." It was more, it just happened. And you gotta persevere to see it happen. But I remember, we were seeding all these schools in like 2021, 22, and they were getting maybe a couple dozen installs. And we were frustrated, but then the following year, back to school, those schools would go from 30 Dow to 1,200, all because you had people on the campus who kickstarted the seed, who were then able to penetrate the school.

• 16:52Molly O'Shea?

  Hey, it's Molly. If you enjoy our interviews, check out our newsletter, sorcery.vc, where we deliver a one-time-a-week top deals and tech headlines report and go deeper on our conversations. Subscribe to Sorcery today. And don't forget to subscribe to the podcast on YouTube, Spotify, Apple, or wherever you listen. The link is in the description to sign up. Shifting to like the Gen Z perspective on this, how has Gen Z trends affected the growth of virality, or at least the adoption of the company itself? I'm sure other products have popped up, but how do you stay relevant with it?

• 17:31Speaker 01

  It's affected the marketing strategy. When we were in high school, TikTok wasn't a thing.

• 17:36Speaker 01

  And I'm cognizant that You know, I built the app with no design team, no UXR team. I would just build for myself. Now trends are a little bit different as you think about the needs of other people. I'll talk about AI in a little bit of just how we've been able to make the calendar a lot more approachable to people who otherwise were put off by archaic traditional interfaces. I think also the, with Gen Z, they're super smart and they have really high standards for products. So if you think about all the products that will be on a young person's home screen, their dock even, the bar is really high. So we're, you know, use 10 plus times a day. We need to compete on that side. And whether it's mobile design, performance, the size of the app, a lot of kids have older phones.

• 18:22Speaker 01

  They're not, they don't have strong cell service. The product needs to work offline. You need to adapt for all these things so that the product can work, whether you have low, high bandwidth, new phone, old phone. And kids are very twitchy. Their attention span is quite short. I think that's also what separates Saturn from traditional calendar and products.

• 18:44Molly O'Shea?

  Have you had to implement new features or any features because of those behavioral aspects?

• 18:51Speaker 01

  We built an Apple Watch app, a live activity. We've, we've done a lot of work around trying to predict when the user will open Saturn and notify them in advance. Even though as an investor, you might see that hurts like number of sessions. We don't really care because it spreads word of mouth. If you're putting content on the user's lock screen for them. The onboarding flow, they used to be eight minutes. We cut that in half and then cut that in half again with AI. Just like take a picture of your schedule, upload it much faster than typing things in. So they're, you know, there are always changes.

• 19:25Molly O'Shea?

  Well, like what are like the social aspects between friends and like that?

• 19:28Speaker 01

  Oh, I mean, you want to make it something that people will invite their friends to. So whether that's posting to their Snap story, then doing that on Instagram, then, you know, iMessage is sort of taken off even more so. You want to make it that you drop your Saturn link in, you get all your friends on the product. You want to be careful of privacy. I think a lot of people are. More privacy conscious, so being in control of who you're sharing your calendar with. We've had to do a lot of work on verifying that you are an actual student in that high school.

• 19:56Molly O'Shea?

  Yeah.

• 19:56Speaker 01

  For a lot of the social effects, like browsing your friends' schedules and calendars and your classmates. We used to only work with, you know, schools that used a school email. Now we work with schools that don't. So you need to always adapt and make sure that it's still really fun, but also a secure environment.

• 20:13Molly O'Shea?

  Going into the AI element of it.

• 20:16Speaker 01

  Yeah.

• 20:16Molly O'Shea?

  So where are you at now with AI implementation within the app?

• 20:20Speaker 01

  So we've done two things with AI. We've been using it already for years and obviously in the last like 18 months. In the last week, it's every week, it's crazy, but it's accelerated our school launching process and really reduced OpEx. So if you think about every school website has all these calendars out there. And we're the only ones crazy enough to want to structure that data. But now you can agentially crawl all the sites, get the data, always keep it up to date. We built crowdsourcing tools in the product. So if it's a snow day, an early dismissal, you can just snap a picture of the schedule, take a screenshot. Boom, it's in your schedule. If enough people do it, it propagates to the whole school. Kind of like how Waze, if someone reports an accident or a police officer, after a couple of people do it, it'll appear on the map for everyone else.

• 21:02Speaker 01

  And we used to have agents overseas that would do it. Now the agents are AI. So it's obviously lower latency, higher retention and kind of lower OpEx. And then in the product, what's really cool is you can talk to your calendar now. So your calendar will give you a summary of your day. You can talk to it through, you know, voice and text. And I think that type of interface is approachable to young people because they do their homework on ChatGPT. They're the fastest adopters of LLM. They're the most receptive to it. Outside of all software engineers, young people are adopting the technology at the fastest clip. And I think it enables you to take a generation of people that otherwise would not be a calendar user because you think about traditional calendars. You open them for the first time, they're empty. You need to learn what recurring events are, structuring your day in minutes.

• 21:46Speaker 01

  And if you're not taught that in an enterprise setting, it's really hard. So you use notes. You don't structure. You use reminders. You scribble things down. Your parents tell you what to do. And if the calendar can kind of gently prompt you for that information, you don't need to structure it, it'll structure it for you. So we're building with our team, a lot of new modalities and, you know, tools in the app to help you stay organized and input data into a calendar that are not those kind of, I joke, it's a global entry application to create an event. There are so many fields, it takes too long. And it's, you know, I don't think the, the voice control on a lot of products is good enough. And high school kids want to just talk like they talk to a friend.

• 22:22Molly O'Shea?

  Right. How do you work with schools?

• 22:24Speaker 01

  So we're all bottoms up, all, you know, word of mouth. School's a part of your day, but it's not your whole day. High school is the first chapter of your, you know, journey. And we want to stick with you through college and beyond. Today, we are millions of people's first calendar, but our ambition is to be your last. And we don't, you know, we have a harmonious relationship with schools, but we don't need to work with them. And our business model is built right now, or doing advertising with some top brands. And I think, um, you know, we, we don't really need to work with the school for that.

• 22:54Molly O'Shea?

  All right. So they're not one of your customers?

• 22:56Speaker 01

  No, we work with, you know, Nike, Uber, huge brands.

• 23:01Molly O'Shea?

  So let's talk about that. So let's get into the ad model component, because this is new, this is newer.

• 23:06Speaker 01

  Yeah. So it's really exciting. And, uh, you know, we, we've built the first new ad unit in consumering years. I think since stories are really, what Snap did to the camera, which was amazing with the geo-filter, uh, we're doing to the calendar and actually making it a ripe canvas. Monetization is a stakeholder in that, but I think UGC and recommendations and making the calendar rich is the vision. And you care about so many things that are on the dimension of time that have events, whether it's, um, you know, a new movie coming out. Whether it's a basketball game with the NBA, brands can play into that. And it's not just ads. Ads are a component to it. But I think that in the future, everyone will have a Saturn. You'll have an Instagram for your photos.

• 23:49Speaker 01

  You'll have an X to speak your voice to your customers. And you'll have a Saturn to communicate all your events. And if that content can be rich, engaging, live in people's calendars where they already are, we think that's really beneficial. And we've been fortunate to work with great partners who feel that young people shouldn't be scrolling all day, that the form of advertising that is dominant right now is not necessarily highest converting, most engaging. Even though there are more eyeballs there, our ad unit, we are confident is higher performing, is more engaging, can actually get people doing things in the real world with others.

• 24:20Molly O'Shea?

  What does the placement look like inside the app?

• 24:22Speaker 01

  It's really cool. You're scrolling in your calendar and you get a video feed of, it's a video of what's going on. So it could be a movie, it could be an ad, like Nike ran their Super Bowl ad to millions of young people on Saturn yesterday.

• 24:38Molly O'Shea?

  Oh, my God.

• 24:39Speaker 01

  Which is really cool and is their first Super Bowl ad in years. The team there is phenomenal. But you can have a CTA, do RSVP, see which friends are kind of going. Even if it's not a real event, it's still fun to create a conversation.

• 24:53Molly O'Shea?

  Right.

• 24:53Speaker 01

  Unlike other ad platforms where if you and I each pull out our Instagrams, we're going to see different ads and we expect that. If you're in a high school, college setting and you're all having lunch together, it's really cool to all see the same ad together and have a conversation about that topic. So brands want to create conversation among their customers and kind of be part of the culture. And we have video, it could be static, you can link to a different page. But the engagement's really good. I think Nike did the thing yesterday, they were offering free t-shirts. And I think it was like within a couple of minutes, they ran out of free shirts because the click through was so high on the ad. So we're just getting started with it. And again, everything that a brand wants to offer usually has a time component to it. Could be in-store event, movie, whatever. And the calendar is the best way to do that.

• 25:39Molly O'Shea?

  Is that viewed as like a higher premium kind of ad because it's so hyper-specific?

• 25:43Speaker 01

  Yeah, you could target. The entire nation, you could target a given school.

• 25:48Molly O'Shea?

  Yeah.

• 25:48Speaker 01

  Uh, you could target, you know, all the, uh, people who, you know, are on the football team. Like you could target it in really interesting ways because you have the calendar data.

• 25:57Molly O'Shea?

  We talked about this like a little bit before, but I just want to zoom out. How hard is it to build, monetize and maintain a zero to one consumer product?

• 26:07Speaker 01

  Yeah.

• 26:07Molly O'Shea?

  A lot of these take off like a rocket ship and then they plateau or they go down and they fade away. And we'd ever see them again.

• 26:14Speaker 01

  Or they can't monetize.

• 26:15Molly O'Shea?

  Or they can't monetize.

• 26:16Speaker 01

  I would say we have the best team for our stage in consumer, uh, you know, consumer productivity, consumer social, consumer AI. Uh, we hired the team out of Snapchat that built, uh, a lot of their AR product, the guy who ran AR, the guy who built the augmented reality, uh, ad unit. And building an ad unit, uh, has all these regulations and standards I did not know about. So I'm really grateful to their expertise to learn how to properly do it. My co-founder, I think is the best salesman ever. He's worked, you know, top, top brands, every, you know, top brand these young people love is in our pipeline. And that took, you know, it was like a zero to kind of six month journey from no ad product to now running the Nike Super Bowl ad and doing Uber ads and many more to come.

• 27:01Speaker 01

  Um, but it is a different process. You have to have more redundancies, metrics, measurement, engagement. Um, you know, I say the rest of the company is a little more on the move, fast break things mindset. The ads you gotta be, you gotta report correctly. You gotta have redundancies. But then I think, you know, for the rest of the consumer product, monetization, certainly something the VC market pushed us towards in terms of, you need to be measured on your fundamentals, your unit economics. That's ARPU, that's thinking about the LTV of the user. These are things that when we raised previously and looking at a lot of those apps you were referencing, um, they may not have been as important then, but I think now they are. And it is a good forcing function to make sure you're actually building a business, not just a product.

• 27:47Molly O'Shea?

  I always find it really in like fun and kind of. I don't know, devious to to take bets on consumer apps that grow and rise. Obviously, Nikita Beer is super good at building these viral apps over and over again. But you never know how to maintain.

• 28:04Speaker 01

  I mean, Nikita is a good friend and an advisor. We've worked with him a ton over the years. I think the magic was, how do you put a growth flow on an already really retentive product? With, you know, Dow Mao, 55% D30 retention for new users in the high 30s, existing high 70s. Like, that's ripe for a growth product. But a lot of times, people are just like, look, let's build a growth product and then throw a million darts at the wall and see what works. We were fortunate to be in the reverse position.

• 28:36Molly O'Shea?

  As we think about where you started in high school, how are you thinking about expanding Saturn?

• 28:43Speaker 01

  Like, I mean, we're in 18,000 schools. Those schools continue to grow year on year. The high school market is very important to us because it's the first touch point with the user. And we want to build a relationship with them for the rest of their lives. So rather than pick a different tool, they start calendaring with Saturn when they're 13. And we want them, we want to build the personal calendar for the rest of their lives. So in college, there's no purpose-built calendar. When you graduate college, you of course will enter the workforce and use enterprise tools. We think those can be complementary to the graph that Saturn is best, you know, fit to to serve, which is friends, family, the people closest to you. I joke, it's the people in the apple share sheet, everyone who you care about, whether they go to your college or not.

• 29:24Speaker 01

  And it's probably a stronger tie graph than it is in high school, where you care about your 30 classmates in each room. You probably care about, I don't know, maybe five to eight people. It's like your Find My Friends list. We think that's that list for your calendar. And we are, our competitive advantage is we always build the edge case, extra mild tools that no one else would think to support. So in high school, it's your complicated schedule that you think only your school has and you think no one else can explain. Kids struggle to explain it to their parents. Everyone who goes to a high school relates to this and they have different schedules. When you get to college, your routine is so different each day. You don't have those productivity habits and, you know.

• 30:06Speaker 01

  The enterprise calendar apps that we use are best fit for work. You can't just type in a friend's name in the calendar and see what they're up to. And it's more cumbersome. And then in the real world is the same thing. So we are very excited to keep building on that track and always just build for the needs of the user. So it's not really a college product. It's more, hey, what are your needs from 18 to 22? What are your needs from 22 to 28 and beyond? And we have the incumbency in high school and we'll continue building as we graduate our users.

• 30:34Molly O'Shea?

  Just, I want to ask for a selfish question, but like, how does the app change? Like, once you exit high school, does it look different? Does it feel different?

• 30:42Speaker 01

  So in high school, it has your school's logo, your school's colors. And there's a directory that has everyone in the school. We often find people wanting to look up other people's schedules and understand their classmates more. But when you get to college, you don't care about the 200 person lecture hall. You care more about, hey, what are my friends up to? Whether they're on the campus, whether they're across the country and I want to know when they're free to FaceTime. Your parents might want to know your schedule, friends from, you know, across town at different schools. So the graph is stronger, it's not weaker. And also, there are a lot of apps trying to do this. I don't think it's a winning strategy beyond to endure with the user beyond school, which is dominate, you know, parties in Greek life.

• 31:24Speaker 01

  Because sure, you might get the acquisition from that entity, but that entity won't stay with you beyond school. That's why we see a lot of messaging apps that might work only in college, don't last beyond college. And it's really important for us to build the behavior of using Saturn as your calendar, regardless of if it's an event for school, regardless of if you're sharing your calendar with someone who's at that school or not. And I think that that will hopefully set the user up to keep Saturn with them. The UI is a little less school centric. School soon will not be required. And unlike high school, you can use the product between communities.

• 32:00Molly O'Shea?

  Wow. So we went pretty deep into the product itself. I want to shift over to the business, building the business of Saturn. How did you initially recruit your team and what is the composition look?

• 32:11Speaker 01

  So Max, uh, Max, my co-founder, he recruited me over LinkedIn. I was working at Tesla, was their youngest software engineer, and he was doing a lot of marketing work as the youngest managing director at Havas, a global ad agency. And we were like, hey, we're both not in Greek life, you know, let's team up, let's build something together. He was much more data savvy than I was. He saw the early retention metrics, down, out, penetration, all that from Staples and was like, wow, why don't we bring this to a different school? So technically, I was the first recruit in my own company with him, but um, you know, that's sort of, uh, you know, how things work and, uh, you know, he's phenomenal. So then Denali was our third hire. She was

• 32:54Speaker 01

  on the deal that we were doing at GC and, uh, was excited by the company and joined forces, uh, now leads a ton of product. And then we hired friends early on from Penn and kind of the tech community. Uh, and then, you know, the company is mostly in New York. Uh, we have some Snap folks on the West Coast and I think, uh, the, you know, the age is sort of, I used to be kind of in line with everyone. Now I'm definitely on the younger side of the team. Um, that's okay. We've been able to hire really great people. As I said, BP product, led a lot of product at Snap, um, had a monetization, built the zero to one ad unit at Snap and AR. And then we've done, you know, hiring great engineering talent

• 33:34Speaker 01

  from top companies. So I learned a lot from them. Uh, but I also think, given now I am not the high school user, it's important to, you know, keep people around the office who are high school, college age to help you build the product.

• 33:47Molly O'Shea?

  How do you get that product feedback?

• 33:50Speaker 01

  We have a great user researcher. We go on the ground. We do events. We do a lot of user research through the app. We're fortunate to have an engaged audience and brands want to pay for the same sort of insights product that we use ourselves to understand what's working and what's not. I think we have a great data science team and we probably, you know, early on I did data science at Tesla. We, we took a really data centric approach to the product, which was probably premature for the stage we were at at the time, but it really helped us growth.

• 34:17Molly O'Shea?

  Shifting into the capital raising, you have raised a quite substantial amount of money for the company. How did you work with investors to get them comfortable with the cyclical nature of this type of company?

• 34:32Speaker 01

  I think a lot of investors self-selected out who weren't. And, you know, one of my closest mentors is this prolific investor operator, Hadi Partovi. And he wrote me an email, I remember, in 2021, when you had the crypto craze and you had all these kind of consumer social products that you named. And everyone was saying, grow faster, do what they're doing, ignore high school. And he said, build the high school infrastructure for every calendar in the country. Build the calendar infrastructure for every high school in the country. And just keep that as your north star. And, you know, don't worry about anything else until you do that. Don't worry about the seasonality. Your metrics are, you know, very, very strong. And just have that confidence. And

• 35:16Speaker 01

  I was very grateful for that advice because it was a time when a lot of investors maybe didn't have that patience and wanted us to use those shorter term growth tactics over retention, which we refused to do. So they've been, you know, all the investors on the cap table have taken that bet. And it has been a longer term strategy. But if you look at the year to year data, it definitely was worth it.

• 35:39Molly O'Shea?

  What were the biggest challenges that you've had to overcome as a founder building this out?

• 35:45Speaker 01

  Well, look, you have all the eye candy. You have all these products that early on were growing faster, would reach, you know, before we were top of the app store, all the time, the, you would see these products that were doing that. And investors would, you know, text you those links and want you to build that stuff. You know, I remember NFTs in the high school classroom was one of the more outrageous ones. But I don't know, you've just got to stay focused. I think keeping a team around you that believes in that vision and then focus, learning what not to build. We had different features. We had a bulletin board. We had likes. We had comments. We had all these things that were not really integral to what Saturn wants to be, which is the personal calendar.

• 36:22Speaker 01

  So we've jettisoned those and have instead reduced surface area in the app, increased focus and really want to build, you know, deep, uh, single player and multiplayer calendar to build. And now with AI that allows us to open the aperture of users who are want a calendar, who otherwise wouldn't think to calendar. And the other thing that I think separates us from a lot of those other products that may have not lasted is the single player utilities, the emphasis on utility, which might not be sexy, but it does retain and you need that retention in order to then build the viral, which is more the cherry on top.

• 36:54Molly O'Shea?

  Okay. We have to end on a spicy note. So please tell me all of your Gen Z insights. What do they want? What's coming next?

• 37:04Speaker 01

  Well, I think we've seen, we've seen they want companionship and a productivity partner that AI is already providing them. And I think that with the calendar, they don't know they want a calendar. They use notes. They use reminders. Their time in their head is unstructured. Yet you can now structure it with AI. And if you can get more inventory, more calendar data from them, you can then be a better assistant, a better buddy with them and help them succeed academically in their personal lives. You know, suggest content for them to do. It is a little bit of the antidote to the TikTok problem, which is just you leave high school and you scroll.

• 37:44Speaker 01

  When we were in high school, you know, I did cross country, I did ski team, I did other things and then I'd be coding until 3am. There are a lot of kids that do that, but I also think that, you know, you have this social media, which is even, I don't even like to call Saturn social media. I think that's why our ad product is appealing to brands because it is the antithesis to that.

• 38:06Speaker 01

  But I think if, you know, same way you have a proactive parent that helps you stay on track of your calendar can also do that. It'll just learn more, have more serendipity, more fun, more imagination. Um, so that's why, why I'm really inspired by what we're building. Uh, and then, you know, I think they're, they also want to build access to education is easier. Like I did, you know, I did college and I did the Teal Fellowship and things. And you don't need to always go through these. Um, I, I found that I was learning more in the, you know, in Tesla factory than. In an engineering classroom at Penn and now people can have that knowledge like personalized to them with AI. I think learning is going to change in a big way. And you know, it just,

• 38:49Speaker 01

  it's all about the context that it has on you. So the cool thing about Saturn is we form that relationship when you turn 13 and we can grow up with the user. So it's something that's always changing.

• 38:59Molly O'Shea?

  Will we be adding a marketplace for DIY courses?

• 39:04Speaker 01

  I think everything will have a Saturn. So if you have a course and you have events to that course, you can integrate and people can follow your Saturn in their calendar. You know, you can do NBA games in your calendar. You know, when the White Lotus comes out next week, that'll be in your calendar. So yeah, sure.

• 39:23Molly O'Shea?

  Okay. Well, Dylan, it was a pleasure to have you on.

• 39:26Speaker 01

  Always a pleasure, Molly.

• 39:27Molly O'Shea?

  Great to catch up.

• 39:28Speaker 01

  So great to catch up.

• 39:29Molly O'Shea?

  And learn more. I'm excited for this next year.

• 39:31Speaker 01

  Yeah, me too. Thank you.