By playing, you agree to uListen's Terms and Privacy Policy and YouTube's Terms of Service.
My First MillionMFM #160: How to Build a Paid Community Making $20M a Year
Summaries, chapters, transcripts, and FAQs on this page are made by uListen, not YouTube.
Great conversations run long. Their best ideas don't have to.
uListen is free on iPhone, iPad, Android, Chrome, and Claude.
See howCHAPTERS
Jump to publisher timestampsChapter summaries
Cold open on verified police dispatch + studio banter
The episode opens mid-story with Sam describing the kind of detailed, verified information police dispatchers can immediately act on. The hosts then riff on appearance, voices, and inside jokes before pivoting toward the day’s main topic: paid communities.
- •Sam describes giving police a suspect description, crime description, and weapon detail in one call
- •Shaan and Sam joke about each other’s looks and how listeners mix up their voices
- •Sam tees up the plan to discuss paid communities and why they’re interesting right now
Tiger 21 breakdown: rich-person peer group economics and retention
Sam introduces Tiger 21 as a high-priced peer group for people with substantial investable assets, then breaks down the business math and meeting format. Shaan shares secondhand details from a friend in the group and discusses why a younger version could fit their audience.
- •Sam explains Tiger 21’s entry requirement, annual price, and member count, and estimates revenue from dues
- •Tiger 21 meetings include portfolio defenses, moderated discussions, and occasional speakers
- •Shaan describes the “who’s who” network vibe, including high-profile events
- •Sam mentions reported retention and private equity acquisition as signals it’s a real business
- •Shaan suggests a similar model for people with lower wealth thresholds and a younger demographic
Why paid communities can work (and when they don’t): speed, costs, churn, and scale limits
The hosts discuss why paid communities can be fast to launch, relatively cheap to run, and profitable—especially with an existing audience. They also outline the major pitfalls: churn risk and the fact that many communities get worse as they grow.
- •Shaan argues podcasts should consider business models beyond ads, citing his own audience-driven project
- •Sam lists benefits: quick growth (especially with an audience), low startup costs, lean teams, and profitability
- •They compare churn and retention dynamics between monthly and annual pricing models
- •Sam and Shaan explain why some communities don’t scale: exclusivity erodes and conversations get noisy
- •They contrast “close-knit” communities with content-driven communities where more members can help
Aventa case study: executive community monetized by sponsorships
Sam shares an example of a high-status professional community built around hard-to-reach executives. The core takeaway is that sponsors will pay large amounts to reach concentrated decision-makers, even when the community itself isn’t paid by members.
- •Sam describes Aventa as an invite/apply executive network with large membership
- •He explains the sponsorship-driven model: small curated sessions that attract high-paying sponsors
- •Sam cites a sale and profit figures to illustrate the value of executive attention
- •Shaan focuses on the “hard part”: recruiting credible executives into a new group
- •Shaan recounts how similar groups recruit via polished outreach that feels personalized but is sales-driven
Sole Savy and “cook groups”: paid Slack community for sneaker drops
Sam explains Sole Savy as a paid sneaker community that started as a Slack group and sells access to drop information and coordination. Shaan likes it as a business for an operator but questions whether it can become a venture-scale company due to scaling dynamics and member incentives.
- •Sam outlines the product: paid membership for insider drop info and coordination among sneaker buyers
- •He shares claimed metrics from their materials (membership, waitlist growth) and notes they raised capital
- •Shaan argues the model fights itself: more members can reduce members’ ability to benefit from the same info
- •They debate community platform choices, with Sam criticizing Slack as the foundation
- •Shaan frames it as an attractive lifestyle business rather than an obvious path to a very large outcome
What makes paid groups work: passion, ROI, clout, and non-googleable info
The hosts build a practical framework for choosing community topics and pricing power. They distinguish communities where members can make money from the membership, versus communities whose value comes from the status and scarcity of the people in the room.
- •Shaan says strong communities often pair high passion with a clear money-in/money-out payoff
- •Sam proposes a simple sizing lens: member upside (economic value) multiplied by number of potential members
- •Shaan contrasts “ROI communities” (like investing) with “clout communities” (hard-to-assemble executives)
- •Sam adds a key ingredient: the best groups share information that’s rare or embarrassing to discuss publicly
- •They brainstorm community opportunities including nurses, Google Sheets enthusiasts, and vetted senior engineers
Communities as a path to $10k/month + Shaan’s sponsor-funded Club LTV playbook
Shaan argues paid (or monetized) communities can be the fastest way for many listeners to build meaningful side income without building a massive company. He then explains how he quickly built a gated e-commerce operator group and monetized it through sponsorship instead of member dues.
- •Shaan claims a community can be a strong route to a side-hustle income target because members create value for each other
- •Sam notes his own experience: early-stage communities require heavy content and culture-building before they self-run
- •Shaan describes creating a gated e-commerce group with a revenue threshold as the entry filter
- •He explains the sponsor model: companies pay to reach a trusted group of qualified operators
- •Shaan outlines the operating format: monthly meeting, small breakout groups, and a recap of key insights shared afterward
Inertia: why people stay stuck and how to create forcing functions
Shaan introduces “inertia” as a concept that explains why people keep doing things they wouldn’t choose from scratch. Sam responds with tactics he uses to break inertia—creating irreversible commitments and starting with extremely small steps to build momentum.
- •Shaan describes inertia as doing something mainly because you’re already doing it, not because you’d choose it today
- •He shares tests for clarity: would you restart the project tomorrow, and would you choose the same partners again?
- •Sam says he combats inertia by “burning bridges” to remove retreat options and force focus
- •Sam also advocates tiny, immediate actions (e.g., making $1) to break patterns and start momentum
- •They discuss public commitments and “anti-charity” bets as psychological leverage to follow through
Producer feedback, audience polling, and launching a call-in hotline for Q&A
The conversation briefly shifts to feedback on the episode’s format and value, including the producer’s reaction. Shaan asks listeners to weigh in and proposes adding a hotline so the show can run Q&A-style bonus episodes driven by audience questions.
- •The producer says the community discussion felt less entertaining but potentially more valuable for the right listener
- •Shaan asks the audience to share feedback on whether they agree with the producer’s perspective
- •Shaan proposes a voicemail-style hotline so listeners can submit questions for future episodes
- •Sam agrees to a third episode format and notes Q&A requires little prep work from him
- •They outline the idea of selecting the best calls and responding on bonus episodes
Bonus interview: Deep Sentinel and “human-in-the-loop” security as a scalable service
The episode closes with a bonus interview featuring Dave Selinger of Deep Sentinel, sparked by Sam’s firsthand use of the product. Dave explains how combining cameras, AI filtering, and real guards enables verified intervention and faster police response, then explores expansion opportunities and why the model hits an underserved price band.
- •Sam describes Deep Sentinel as cameras monitored by real guards who can speak through two-way audio and escalate incidents
- •Dave explains the origin insight: cameras alone don’t stop crime, so he built a system to intervene in real time
- •Dave details scalability: AI filters events so one guard can cover many properties while staying engaged and alert
- •He explains escalation protocols (from gentle check-ins to sirens and immediate police contact) and why verified calls matter
- •Dave outlines adjacent opportunities (e.g., multi-tenant buildings, elderly check-ins, hotels, construction yards, car lots) and discusses ethics of avoiding government-run surveillance
Publisher timestamps
- 0:00Intro
- 2:08Tiger 21, a peer group doing 20m+ in revenue
- 18:13Sole Savy, a sneaker community that started on SlackRead this chapter
- 21:04What makes communities and paid groups workRead this chapter
- 24:03Community ideas you can start right nowRead this chapter
- 31:57Why communities are great and how Shaan built one quickly and profitably
- 39:59What is inertia and why it's stopping you
- 53:40The Dave Selinger of Deep Sentinel interview
- 1:12:40Dave applies the principles of Deep Sentinel for other sectorsRead this chapter
- 1:19:02Why Shaan and Sam might invest in Deep SentinelRead this chapter
