The Viral Gen Z App backed by Jeff Bezos, Marc Benioff & Dara Khosrowshahi

Dylan Diamond, CEO of Saturn

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

I’m so excited to finally share our conversation with Dylan Diamond, Co-Founder & CEO of Saturn. Saturn is a viral Gen Z calendar app that's raised $68M, scaled to millions users, reached 18,000 schools, and hit #1 in the App Store ..after first starting out as a high school project.

What’s so special for me about this conversation is that Dylan & I went to High School together! We both grew up in Westport CT, and went to Staples High School. A school previously known for it’s theater program and football team, but now it’s printingggg out soon-to-be tech unicorns like Saturn, Whop, and more. I recently interviewed them all in a legendary, packed, 500-person room at a Startup Westport event in November (more below).

However, this story takes me back to 2019 I was reintroduced to what was once called iStaples, after graduating college. Around that time, Saturn had just been founded and backed by Silicon Valley heavy weights. Denali Tietjen, now Director of Product, invited me to their SoHo office to help with new user onboarding (a funny story shared in the pod). I had gotten to know Denali well during college before she joined her portfolio company, Saturn. At the time, she was still investing at General Catalyst and running Rough Draft Ventures with Peter Boyce II (I founded a company at NYU & got close to the team there). Fast forward to today & Saturn is a rocket ship.

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Highlights

• Taking on an $80 Billion Dollar Market with Gen Z

• Raising from Bezos, Benioff & Dara Khosrowshahi

• Reaching #1 in the App Store

• Going Viral in Lenny’s Newsletter

• Working with Viral App Advisor: Nikita Bier

• Building  the First New Ad Unit in Consumer in Years

• Playing the Long Game

• Surprising lessons from growing a viral app → friends are stronger than celebrities

  "We even had Bieber tweet out the product once and the retention was not strong."

Going Viral

Co-Founded by CEO Dylan Diamond and COO/CSO Max Baron, Saturn has raised a total of $68 million to date. With investors including some of the top funds and high profile Founders in Silicon Valley: General Catalyst, Coatue, Insight, 01 Advisors (Dick Costolo & Adam Bain), Jeff Bezos, Marc Benioff (CEO & co-founder of Salesforce), Dara Khosrowshahi (CEO of Uber), NEO, Sound Ventures, Elad Gil, Dylan Field (CEO & co-founder of Figma), Inspired Capital, and more.

What began as a simple solution, called iStaples, to improve & share class scheduling at Staples High School evolved into a venture-backed viral GenZ calendar app called Saturn. The product has matured into a daily-use calendar that boasts impressive retention metrics (shared below), leveraging both organic, word-of-mouth growth & data-driven product development to build a resource that highly resonates with finicky Gen Z behaviors.

Its advanced AI integration automates processes such as image-based schedule uploads and real-time crowdsourced updates, while a conversational interface transforms the calendar into a proactive planner for personalized event recommendations. Saturn is designed to meet the unique needs of high school students, and has grown to be adaptable enough to remain their calendar of choice through college and beyond. More recently, Saturn debuted a new, innovative, embedded advertising model with huge brands like Nike and Uber, that delivers contextual, engaging content directly within the calendar interface.

Key product development milestones include:

• Early Adoption: The original schedule-sharing project rapidly transitioned into a calendar platform. Initial word-of-mouth growth led to penetration rates rising from 30% to as high as 80–90% in certain high schools

• Broad User Base: Saturn now serves millions of users across 18,000 schools nationwide.

• App Store Performance: During the summer back-to-school season, Saturn has achieved the ranking of #2 in the App Store, and #1 in the Productivity category.

Timestamps

01:43 - Raising From Bezos, Benioff, Dara & More.

03:06 - From School Project to VC-Backed Company

05:09 - User Retention and Growth Strategies

16:56 - Adapting to Gen Z Trends

19:50 - AI Integration and Future Plans

22:41 - Advertising Model and Monetization

28:16 - Expanding Saturn Beyond High School

33:58 - Fundraising

36:54 - Gen Z Secrets: Insights and Future Trends

We go deep into..

User Engagement & Retention Metrics, Technical Evolution & AI Integration, Monetization Strategy & Innovative Ad Units, Long-Term Strategy & Market Expansion, Team Composition & Business Operations, Fundraising..

Sold-Out 500 Person Room

Last November, I had the opportunity to moderate a panel back in my hometown of Westport, CT along with other Staples High School alumnus for Startup Westport. Founders included Dylan Diamond CEO of Saturn, Jack Sharkey CTO of Whop, as well as Josh Karol CTO & Max Hammer CEO of CrowdVolt.

Collectively the group has raised well over $100M+ backed by some of the largest names in Silicon Valley.. including Jeff Bezos, Elad Gil, Dara Khosrowshahi, Coatue, Thiel, Chainsmokers, Insight, 01 Advisors, General Catalyst, YC, and more.. watch the full panel here.

User Engagement and Retention Metrics

A central pillar of Saturn’s strategy is a focus on long-term user retention rather than just rapid acquisition:

• Daily Engagement: The core metric—daily activity among monthly active users—is consistently around 50%.

• D30 Retention: Metrics show that new users enjoy D30 retention rates well above 30%, while existing users maintain rates near 70%. In many cases, over 90% of new users return annually.

• Seasonal Acquisition: At its peak, particularly during the back-to-school season, Saturn is acquiring over 100,000 new users per day. On average, each user invites four to five friends, fueling organic growth.