Chapter 5 of 15 · Retention and Engagement
1 The bottom line
Retention rises when users need other people, so build small circles, two-way loops and a community inside the product. Close ties give people a reason to return that no single-player feature can.
2 Key takeaways
- Make the product need other people, not just the user. Once two sides depend on each other, neither drops off easily.

Sam Chaudhary, ClassDojo17:30: the teacher-only tool reached about 12,000 teachers by demo day but leaked users, and sticky retention came only after parents and kids joined.
- Connect people to a few close ties first. Value sits in close relationships, not in friend count.

Bangaly Kaba, Instagram1:17:20: retention doubled over a year and a half after sign-up put real friends ahead of celebrities.
- Build loops where one person's action needs a reply, and measure the replies. Back-and-forth between people drives return visits.

Mark Pincus, Zynga46:10: going from zero to one round trip with a friend gave an 80% chance of seeing the player the next month.
- Put other people inside the first days of the experience. Validation and feeling not alone keep new users coming back.

Nancy Anderson, Natal48:27: of users who join the community, 31% return on day two and 14% on day three.
- Grow a community slowly, starting with your most vocal fans. Small, active groups beat big, quiet ones.

Camille Ricketts, Notion38:29: the 2019 ambassador program began with 20 people and grew into a worldwide network with about 30 in-person events a month.
as soon as you have a multiplayer product, it becomes harder for either side to drop off
Sam Chaudhary, ClassDojo
2.1 Check that your product fits a social design
Before you build features, test whether your product creates something people share and a real network.
- Test whether your core mechanic creates network value, not just satisfaction.

Casey Winters, SuperMe16:40
- Instant AI profiles worked well, but he called them fulfillment, not a network product.
- He then built search across profiles to add the network part.
- The profiles took about 10 minutes to create, got shared on LinkedIn, and surprised people with how representative the answers were.
- Invest in community only if users create something they want to share.

Camille Ricketts, Notion20:45
- It fits freemium products with an atomic unit of sharing that shows something about the user, such as Notion templates and workspaces.
- Figma and Canva work the same way. Products with long sales cycles or high prices that need many touchpoints should not make community their top investment.
- Pick the community type with a two by two.

Camille Ricketts, Notion34:00
- Plot your company as pre or post product-market fit, and enterprise or consumer.
- Pre-PMF enterprise suits customer advisory boards. Post-PMF enterprise suits champions and consultants, as Salesforce built. Post-PMF consumer suits ambassadors and influencers.
- Avoid pure anonymity.

Sarah Tavel, Pinterest25:00
- Pseudo-anonymity, as on Twitter or Reddit, still builds a persistent identity with accruing benefits and mounting loss.
- Pure anonymity, as in Secret, has neither, so users can leave and return months later with no difference in experience.
- Founders keep trying it because the early growth is fun.
- Read your support tickets for social demand.

Ajay Mehta, Tolan35:15
- Users already ask whether friends' Tolans can chat and introduce their Tolan to people nearby, so the team plans to let Tolans interact.
- Support gets a couple of these tickets every day.
2.2 Make it multiplayer and keep circles small
Add the people around the user, and aim for a few close ties rather than a big network.
- Add accounts for the people around your user.

Sam Chaudhary, ClassDojo17:30
- ClassDojo added accounts for parents and kids, with shared photos, videos and messages.

Yoav Sharon, Simply15:44, added a family plan, then multi-profile with up to five profiles across apps, because someone in the household is always engaging.- Simply's multi-app, multi-profile accounts have by far the strongest retention in any cohort.
Naomi Ionita, Evernote7:05: Evernote was philosophically anti-social, which capped its growth, and you can't retrofit collaboration.
- Steer users to the shared use, not the solo use.

Rachel Hepworth, Notion27:46
- People could use Notion alone inside a company, but that was less valuable for them and for Notion.
- Show the collaborative value and the full feature set, such as databases, not just a docs replacement.
- Aim for circles of three to four people.

Giordano Contestabile, Life36034:03
- Circles of that size convert and retain significantly better than smaller or larger ones.
- Larger circles are friend groups or extended family, who are less motivated to pay for safety.
- Smaller ones are couples or families whose kids left for college, a big churn reason.
- A paying circle averages about four people, and one subscription benefits about 12% of monthly users.
- Connect new users to real friends before showing celebrities.

Bangaly Kaba, Instagram1:17:20
- Instagram retention flattened, then dipped again at 7 to 9 months, because users followed celebrities, posted months later and got no response from friends.
- The fix prioritized human-to-human connections at sign-up and kept celebrity recommendations for people who already had a graph.
- He had to argue this to the founders with data.

Evan Spiegel, Snap4:50: Snapchat beat much bigger networks by connecting people to a best friend, a partner or a spouse.
2.3 Build loops that need a reply
Design actions that pull the other person back, then measure the back-and-forth.
- Hide the partner's answer until the user answers too.

An (Anup), Flame16:16
- The lock creates a missing-out effect that pushes you to answer.
- When your partner answers, it pulls them back too, so the loop feeds itself.
- This was one of the mechanics behind the climb to 50% day-30 retention.
- Make players owe each other.
Tom Hammond and Steve P. Young, TheoremReach3:51
- In Clash of Clans and Clash Royale, members donate cards or troops and join clan wars so everyone gets a reward.
- Players who do not pull their weight feel guilt toward clan mates, and that adds long-term retention.
Joel Julkunen, GameRefinery8:34: once a guild system exists, it is much easier to add co-op modes, team competitions and live events on top of it.
Joel Julkunen, GameRefinery9:45: almost all top match 3 games now have co-op events where players team up with random players or guild members.
Ravi Mehta, Tinder15:16: Tinder U ran a swipe-off where colleges compete for swipes.
- Find one social loop metric and build product work to raise it.

Mark Pincus, Zynga46:10
- Zynga counted Active Social Network, the round trips a player had with a friend, such as a turn and a turn back or a gift and a gift back.
- At four round trips, there was an 80% chance of seeing the player 22 of the next 30 days.
- Do not let a leaderboard auto-approve top scorers.

Ron Schneidermann, AllTrails9:57
- Points for trails, edits, reviews and photos lifted user-generated content at first.
- Users above a threshold had edits auto-approved, so people competed hard for the board.
- Some uploaded 600 to 800 photos from a camera shooting every 10 seconds, and fake trails appeared. Quality fell and the team had to rethink the system.
2.4 Put other people inside the product
Show other users at the moment of use, and give each newcomer a human and a group.
- Show encouraging feedback from other users inside the core experience.

Headspace
- Headspace showed positive thoughts from other users during meditation sessions.
- Measure trial survival, meaning how many free trial users stay active, not only conversion at the end.
- The test produced a 3% increase in the survival rate of free trial users.
- Give users small cohorts of people like them.

Greg Stewart, Ladder35:25
- Users join coach-led teams with in-app group chats, where people on the same persona and workout talk daily.
- Ladder added platform-wide topic chats (supplements, equipment, music) and geo chat rooms for major metros.
- The top unexpected benefit in surveys is making friends in real life, and members have started meeting up.
- Get new users in touch with a real person early.

Nancy Anderson, Natal48:27
- A real person DMs each new user to welcome them.
- Expert coaches answer questions all day in the in-app community, free for anyone.
- She thinks the lift comes from validation and feeling not alone, not from the feature itself.
- Host the community where users already spend their day.

Camille Ricketts, Notion46:20
- Notion uses Slack so it is not another destination to visit, and a notification badge is a strong nudge.

Elena Verna, Lovable49:46: Lovable runs on Discord with community managers and an ambassador program, and has hundreds of thousands of members.
2.5 Solve the cold start
A social feature is empty without people, so bring density before day one.
- Build a waitlist before launching a social app.

Jay, Nomad Table46:42
- Without critical mass on day one, the app is a revolving door. He built a waitlist of about 12 to 15K people and recommends Andrew Chen's book The Cold Start Problem.
- The app works with just two people in a place, so it worked even with people spread worldwide.
- About 6K people got the app on day one, and hotspots like Barcelona had around 20.
- Seed the scarce side of a two-sided app first.
Steve P. Young and a guest app growth consultant, App Masters0:58
- In a dating app, the guest says there must be at least 10 to 20% women to attract the men.
- With one or two users there is not much value in a dating app.
- Seed a feed with your creators and favor new content.

George, Wrestle AI38:10
- Wrestle AI added a TikTok-style feed so users have a reason to return between matches.
- A simple point-based algorithm heavily favors new content, since a paid app has few posts.
- Every sponsored creator also posts in the feed, which solves the cold start.
2.6 Run the fan community
Start with the people already talking, reward them with access, and keep the group small enough to talk.
- Start with your top 10 to 100 power users.

Rachel Hepworth, Notion20:06
- Notion gathered the people already talking about the product, running events and making courses, into a Slack group.
- Later it added a campus leaders program for students and a Champions program for super users inside companies.
- Community was Notion's first marketing hire after the head of marketing.
- Reward members with access, attention and a path to income.

Camille Ricketts, Notion39:15
- Notion offered feature previews with product team feedback, Q&As with founders, subsidized events, and put community creations front and center on social.

Camille Ricketts, Notion22:50, also nurtured paths such as selling templates, consulting and making courses, because income tied to the product makes people evangelize it.- In mid-2021 one creator made about $35,000 in 4 months selling a single template.

Claire Butler, Figma1:17:40: Figma gives champions speaking slots at its events and promotes them on social.
Zoelle Egner, Airtable48:50: Airtable gave champions items like branded AirPods, a couple hundred dollars each, judged totally worth it.
- Add people slowly and activate the ones you have.

Camille Ricketts, Notion43:16
- Notion ran a light application and admitted roughly 20 ambassadors a month, so members had time to welcome newcomers.
- If 20% of members are active, aim for 50% rather than adding more people

Rachel Hepworth, Notion30:29. - A community of 5,000 ambassadors sounds good on a website, but the conversation is very muted.
- Listen to members before you design the program.

Camille Ricketts, Notion26:57
- Notion's head of community spent a huge amount of time in one-on-one and small group calls asking why people were there and what would make it better.
- Monthly community highlights in all-hands and Slack keep the company close to who it builds for.
2.7 Where they disagree
| Life360 (safety) | Simply (content) | |
|---|---|---|
| Ideal group | 3–4 people | Up to 5 profiles |
| Why they pay | Safety of loved ones | Shared learning at home |
| Who's in it | Couples, close family | Whole household |
| Retention logic | Tight ties convert best | Someone is always engaging |
Sources split on network size, on when to measure, and on where the community should live.
- Small close circles versus a bigger network.

Evan Spiegel, Snap4:50, says it was not about having the most friends but about close friends.- One guest says each new user should make the app more valuable to existing users, and calls the network effect the best retention driver for most apps
Steve P. Young and a guest, App Masters2:11. - Size may depend on the job. Life360's three to four person sweet spot comes from a safety product where couples and families pay.
- Measure early or protect enthusiasm first.
- Zynga picked a social metric and built product work around it

Mark Pincus, Zynga46:10. 
Camille Ricketts, Notion19:41, says not to cut off a spreading community because ROI is not yet provable.- Notion did not measure community concretely until the year before she left, since it already saw organic scale in geographic expansion and in survey answers on how users found Notion.
- Zynga picked a social metric and built product work around it
- Community inside the app or in a tool people already use.
- Ladder and Natal run chats and coach access inside the app

Greg Stewart, Ladder35:25. - Notion chose Slack so it would not be another destination, and Lovable chose Discord

Camille Ricketts, Notion46:20. - In-app suits cohorts of people like the user. An outside tool suits fans and champions who talk about the product.
- Ladder and Natal run chats and coach access inside the app
Sources
- Social validation: Headspace's A/B test ·
abtest.design - Meet the ex-wrestler making $41k/mo with AI apps ·
Superwall - Edward Tian on Building GPTZero, Scaling to $30M+ ARR, and the Superhuman Acquisition ·
Subversive - How ClassDojo Built Network Effects to Reach 95% of US K-8 Schools ·
Subversive - How Simply Finally Cracked Facebook Ads with Web Funnels – Yoav Sharon, Simply ·
Sub Club - The hidden pattern behind successful products | Mark Pincus (FarmVille, Words with Friends, & more) ·
Lenny's Podcast - How Removing the Free Trial Grew Monthly Subs 2000% – Nancy Anderson, Natal ·
Sub Club - Protecting Freemium at 100M Users AND Driving $500M Revenue – Giordano Contestabile, Life360 ·
Sub Club - How to win when software is not a moat | Evan Spiegel (Snapchat CEO) ·
Lenny's Podcast - How SuperMe is Building the Professional Network for the AI Era ·
Subversive - Copy This UGC Strategy, It'll Make Your App Go Viral ·
Superwall - Full App Growth Guide 2026 - How to Make Viral Content to Get Users & Make Your App Retentive ·
Superwall - The new AI growth playbook for 2026 | How Lovable hit $200M ARR in one year ·
Lenny's Podcast - How Runna’s Laser Focus Led to Its Successful Acquisition by Strava ·
Subversive - How Tolan Built a Viral AI Companion ·
Subversive - How Notion’s Community Helped it Win in AI ·
Subversive - How Ladder Nailed Product/Channel Fit on TikTok and Meta to Grow 2,000% ·
Subversive - How AllTrails Crossed the Chasm to 1M+ Subscribers ·
Subversive - How Tinder's Monetization Strategy Propelled it to $1B+ in Revenue ·
Subversive - 2 Secret Retention & Monetization Strategies (Stolen From 7-Figure Apps) #retentionstrategies ·
App Masters - Unorthodox frameworks for growing your product, career, and impact | Bangaly Kaba (YT, IG, FB) ·
Lenny's Podcast - The hierarchy of engagement | Sarah Tavel (Benchmark, Greylock, Pinterest) ·
Lenny's Podcast - An inside look at Figma’s unique GTM motion | Claire Butler (first GTM hire) ·
Lenny's Podcast - How the Gaming Ecosystem is Approaching Growth in 2023 ·
App Masters - How to achieve hypergrowth in your business and career | Carilu Dietrich (Atlassian) ·
Lenny's Podcast - Early Stage Strategies to Drive App Subscriptions ·
App Masters - Lessons from Airtable’s unconventional growth strategy | Zoelle Egner ·
Lenny's Podcast - How to price your product | Naomi Ionita (Menlo Ventures) ·
Lenny's Podcast - An inside look at how Figma builds product | Yuhki Yamashita (CPO of Figma) ·
Lenny's Podcast - How Notion leveraged community to build a $10B business | Camille Ricketts ·
Lenny's Podcast - This Budgeting App Makes $400K a Month ·
App Masters - 5 Ways to Increase Mobile Game Revenue ·
App Masters - Hottest Monetization Trends for Mobile Games ·
App Masters - Influencer Marketing: How to Decide Who is a Good or Bad Influencer ·
App Masters - Success Report: July 2016 (Another Apple Feature) ·
App Masters
Part of Retention and Engagement in the growth library.