Feb 21, 2025 · 39m · sourcery
Taking on an $80 Billion Dollar Market with Gen Z | Dylan Diamond · Sourcery with Molly O'Shea
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Host Molly O'Shea interviews Saturn co-founder Dylan Diamond on building a dominant Gen Z calendar app backed by $68 million in venture funding. Diamond discusses Saturn's viral growth mechanics, automated AI schedule processing, time-based ad model, and plans for lifelong utility expansion.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Molly holds 17.4% of the talking time here. How this is scored →
Molly as informed peer 3.4 Guest teaching 3.3 Guest disagreement 0.4 Molly pushing back 0.6
speaking balance: gold is Molly, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 35:50 Dismissing investor-driven hype and short-term trends
Dylan openly derides distractions pushed by investors, calling out ridiculous suggestions like putting NFTs into high school classrooms.
Hardest push from Molly ▶ 15:09 Pressing on startup growth pressures versus patient roadmapsMolly challenges Dylan on how difficult it is to maintain a slow, multi-year school seeding strategy under intense venture capital pressure to show rapid growth.
Biggest teaching moment ▶ 7:00 Explaining why traditional calendar metrics do not applyDylan educates Molly on why single-player calendar benchmarks fail to capture Saturn's consumer social dynamics and a16z viral retention standards.
Molly holds their own ▶ 12:03 Recounting first-hand lead gen grind for SaturnMolly demonstrates deep insider knowledge by sharing her personal experience cold-outreaching to high schoolers on Saturn's behalf through Rough Draft Ventures.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Molly as informed peer | Guest teaching | Guest disagreement | Molly pushing back | Why |
|---|---|---|---|---|---|---|
| Attracting Builder-Investors to Consumer Tech | 4 | 2 | 0 | 1 | Molly establishes their shared Westport roots and lists Saturn's high-profile backers. Dylan explains the value of builder-investors and shares baseline retention metrics without any tension. | |
| Sponsor Segment: Monetizing Fan Communities on Passes | 3 | 5 | 1 | 1 | Dylan reframes Molly's question comparing Saturn to other calendar tools by explaining that high schoolers do not use calendars and that Saturn must be judged against consumer social retention benchmarks rather than utility apps. | |
| High School Growth Mechanics and Onboarding Challenges | 5 | 2 | 0 | 1 | Molly demonstrates first-hand operational context by recounting her time doing cold outreach to high schoolers for Saturn while at Rough Draft Ventures. Dylan details the evolution from manual school ambassadors to automated AI onboarding. | |
| Mid-roll Promo: Sourcery Newsletter and Podcast Community | 3 | 3 | 0 | 0 | Molly inquires about Gen Z behavior and app features. Dylan describes adapting to short attention spans, older device constraints, and privacy-preserving friend networks. | |
| Integrating AI and Redefining Calendar Interfaces | 2 | 4 | 0 | 1 | Dylan walks through how AI agentic crawling parses unstructured school calendars and how conversational interfaces lower the friction of creating calendar entries. | |
| Pioneering Time-Based Advertising for Major Brands | 4 | 3 | 0 | 1 | Molly probes into monetization risks and cites consumer growth expert Nikita Bier. Dylan details their time-based ad unit, Snap executive hires, and campaign results like Nike's Super Bowl placement. | |
| Expanding Lifelong Utility Beyond High School | 3 | 4 | 1 | 0 | Dylan explains Saturn's strategy for retaining users through college and adulthood, contrasting their close-friend graph with fleeting Greek-life or party apps. | |
| Building the Team, Investor Alignment, and Filtering Hype | 3 | 3 | 1 | 0 | Dylan recounts resisting investor pressure during market hypes, specifically rejecting suggestions to integrate NFTs into high school classrooms in favor of steady execution. |
Statements from this episode (22)
O'Shea: Saturn raised over $68M in funding from top Valley investors
“You raised over sixty eight million dollars in funding by very large names in Silicon Valley.”
O'Shea lists Bezos, Benioff, Coatue, and GC as Saturn investors
“We have General Catalyst, KOTU, Insight, O-One Advisors, Jeff Bezos, Mark Benioff, Dara, Neo, Elad Gill, Dylan Field, and Inspired Capital, and I'm sure there's more.”
Diamond: Saturn maintains over 50% DAU/MAU stickiness and 90% annual retention
“We have, you know, our DAO now, the stickiness daily active, the percent of monthlies that are active every day is over 50%. Our D-thirty retention of brand new users is well over 30% with 70% for existing, 90% of new users return every single year.”
Diamond: Saturn hits #2 in App Store during summer, beating TikTok
“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 ChatGPT and others, TikTok”
Diamond: Saturn acquires over 100,000 users daily during back-to-school
“We're acquiring over a 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.”
Diamond: White-labeled apps drove 50%+ school penetration in early days
“And that drove us to getting 50 plus percent penetration, sometimes within 48 hours, often within the first week at those couple dozen schools.”
Diamond: All monetarily incentivized referrals at Saturn have failed
“All the referrals that have been monetarily incentivized have failed.”
Diamond: Justin Bieber tweeting about Saturn yielded weak user retention
“And we even had Bieber tweet out the product once, and you know, the retention is not strong.”
Diamond: Saturn launched across all 18,000 US public high schools
“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?”
Dylan Diamond: Saturn's user base dropped to zero overnight during COVID
“COVID was a huge hurdle for us because our user base went to zero overnight.”
Dylan Diamond: Saturn's first 50 schools grew from 7% to 60% weekly active users
“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, seven percent of all the high schoolers who were enrolled at all those 50 schools were active weekly. N…”
Diamond: Saturn cut onboarding from eight minutes to two using AI
“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.”
Diamond: Saturn replaced overseas manual data agents with AI agents
“And we used to have agents overseas that would do it. Now the agents are AI.”
Diamond: Young people adopt LLMs faster than any group except engineers
“Outside of all software engineers, young people are adopting the technology at the fastest clip”
Diamond: Saturn serves as the first calendar for millions of people
“Today, we are millions of people's first calendar, but our ambition is to be your last.”
Diamond: Saturn built the first new consumer ad unit in years
“We, we've built the first new ad unit in consumer in years. I think since stories are really what Snap did to the camera, which was amazing with the geo filter we're doing to the calendar and actually making it a ripe canvas.”
Diamond: Nike ran its Super Bowl ad to millions on Saturn
“Nike ran their Super Bowl ad to millions of young people on Saturn yesterday.”
Diamond: Greek life and party apps fail to retain users after college
“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, because sure you might get the acquisition from that entity, but that entity won't stay with you beyond School. That's why w…”
Diamond: Products need single-player utility retention before adding viral features
“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 o…”