Community & Memberships
Every essay
Shared Experiences (And Why You Should Invest In Them)
The opportunity hiding in plain sight for many content creators
4 min read→Jan 9, 2026Experiment: Cohort to Membership Sales
Does running a live cohort-based learning experience translate into membership sales?
4 min read→Apr 18, 2025Gumroad buys Small Bets – was it a good deal?
Analyzing the rare $4M community acquisition.
9 min read→Mar 15, 2025Pricing for Memberships
When I talk to creators who run memberships, I'm almost always shocked by their low retention rates. Most creators I speak to
3 min read→Dec 7, 2024Building Better Community Products
Why we need to let go of, "You get out of it what you put into it," and put ourselves back on the hook.
4 min read→Mar 26, 2024"When should you start a membership?"
This month marks the start of year three in my membership community, The Lab . Since launch, we've kept the community at 200
2 min read→Jul 23, 2023The magic of pricing tiers
It's probably safe to assume that you'd be happy if you were able to increase your revenue. But I find
4 min read→Sep 17, 2022Why (and how) I designed my community to stay small
I launched my membership community, The Lab, in March of this year. In just 6 months, it has: * gained 135 members * generated $96K * nearly
14 min read→Mar 18, 2022Introducing the Creative Companion Club
I'm coming up on five years since I started my creator journey. I started writing Creative Companion in January 2017 (though, by
5 min read→Mar 6, 2022Online community-building predictions 🔮
I organized my first local Startup Weekend event in 2012 – that puts me at a full decade now of community building. And since 2017,
6 min read→Episodes about Community & Memberships
How Tamara Grominsky Predictably Grows Her Membership Each Month
My guest is Tamara Grominsky, founder of PMM Camp — a private, application-only membership for senior product marketing leaders with 280+ members.
Listen or watch→Sep 15, 2026The $9/month membership earning more than $500k/year AND buying Smart Passive Income — Pt. 2 featuring Liz Wilcox
My guest is Liz Wilcox, the creator behind Email Marketing Membership — a $9/month newsletter template subscription she’s kept at the same price for six years, that now generates close to half a million dollars a year.
Listen or watch→Jul 28, 2026How Tom Ross Doubled His Community Engagement and Retention With Training Pathways
Closing the doors to a membership is supposed to hurt signups. But one of Tom's clients did exactly that — closed it, added an application, doubled the price, then reopened. His next launch sold out in 4 minutes. Same community. Same people. Just different mechanics.
Listen or watch→Jul 14, 2026How to Build a Successful Paid Community | Growth in Reverse
The highest month of membership revenue in Lab history was also the setup for the highest month of churn. One year later, February delivered both records.
Listen or watch→Jun 28, 2026I want to help you build a membership in July. (limited time opportunity)
For the first time ever, I'm teaching my most popular course, Build A Beloved Membership, live over four weeks. You'll learn the exact approach I've taken to building The Lab to a ~$500K/year membership.
Listen or watch→Jun 17, 2026A Deeper Look at Circle Eclipse with Circle CEO Sid Yadav
Sid Yadav is the CEO and co-founder of Circle, a community platform trusted by creators like Jay and thousands of others to build membership businesses. Today, Circle has ~280 employees and has raised around $30 million.
Listen or watch→Mar 3, 2026Community Building Trends for 2026 with Becky Pierson Davidson
I brought back Becky Pierson Davidson to compare notes on where community is headed — and we found a few areas of disagreement.
Listen or watch→Nov 30, 2025I helped a YouTuber design his membership
Meet Tommy. Tommy has a YouTube channel dedicated to helping Americans retire in France.
Listen or watch→Jul 22, 2025How I Built A Community-Driven Business ($500K/yr) | Niche Pursuits Crossover
Jared Bauman interviewed me on the Niche Pursuits podcast about how we built The Lab, our membership community, into a $400,000+ part of the business.
Listen or watch→Jan 28, 2025Valerie Feghali – Her FAST evolution from coach to creator with custom software
Valerie Feghali is a member of our membership community, The Lab. She impressed me immediately – and during my paternity leave, she hosted a workshop inside The Lab about how she’s used paid ads to grow her business.
Listen or watch→Jan 17, 2025OK I have some thoughts on AI (and its impact on creator-educators) [Voice Memo]
Why I'm prioritizing memberships more than ever
Listen or watch→Dec 17, 2024Dan Andrews – Secrets of building a 1300-member, international community (with in-person events)
Dan Andrews founded the Dynamite Circle and Dynamite Jobs and is now a repeat guest. Dan was first on the show in episode #32 in November 2020.
Listen or watch→Oct 29, 2024Ryan Hawk – Anatomy of a $12,500 membership earning $400,000+ per year
Ryan Hawk is a keynote speaker and the host of the Learning Leader Show. The show has been listened to by millions of people in more than 150 countries, and Forbes called it, “the most dynamic leadership podcast around.
Listen or watch→Jun 13, 2024How to build raving fans and real connection (feat. Chenell Basilio and Becky Davidson)
Last week, I spoke at ConvertKit's annual Craft and Commerce event in Boise, Idaho. It's one of my favorite events of the year, and this year may have been my favorite event ever.
Listen or watch→May 8, 2024I coached Ali Abdaal on building a membership.
Ali Abdaal was in the early stages of building his own membership community, so I coached him through it. This is that conversation, from Deep Dive with Ali Abdaal.
Listen or watch→Mar 7, 2023Maurizio Leo – the sourdough bread blogger who became an overnight success
How this baker was impacted by the sudden sourdough craze admist the global pandemic
Listen or watch→Feb 28, 2023How Brennan Dunn is Designing and Pricing His New Course Product
Brennan Dunn is a friend and a man of many skills and accomplishments – he’s a writer, marketer, developer, and even designer.
Listen or watch→Jan 24, 2023Mariah Coz – Selling high-ticket programs on evergreen (without sales calls)
Mariah Coz teaches coaches, course creators, and CEOs strategies for growing a course company that is sustainable, impactful, and evergreen.
Listen or watch→Dec 6, 2022Neville Medhora – Making millions with remarkable copywriting
Neville Medhora is the creator of Copywriting Course and SwipeFile.com
Listen or watch→Nov 29, 2022How to build a great community (my appearance on The Learning Culture Podcast)
Recently, I spoke with my friend Andrew Barry on The Learning Culture podcast, and we talked about all things community.
Listen or watch→Nov 15, 2022Kayse Morris – from government assistance to multimillion dollar membership
Kayse Morris is the creator of The CEO Teacher and has helped thousands of other teachers break through the classroom glass ceiling.
Listen or watch→Oct 18, 2022Pat Flynn and Matt Gartland – Courses, community, and the future of education
Pat and Matt lead Smart Passive Income, a trailblazer in the entrepreneurial space, developing state-of-the-art content, training, and resources to help you launch and grow your online business.
Listen or watch→Aug 30, 2022Jason Sew Hoy of Supercast – How and why to create a premium podcast subscription
Jason Sew Hoy is the cofounder and CEO of Supercast. He was previously COO & Chief Growth Officer at 99designs.
Listen or watch→Apr 12, 2022Jay-Talking about Memberships with Jay Acunzo
Over the last month, Jay Acunzo and I have both launched our own membership programs. And while we were in the thick of designing and launching those programs, we thought it would be a good idea to record a podcast about it.
Listen or watch→Mar 22, 2022Josh Hall – from freelance web design to professional creator earning $300K/year
Josh Hall is a YouTuber, course creator, and web design coach specializing in WordPress and Divi. Josh helps people build and scale 6-figure, work-from-home web design businesses.
Listen or watch→Nov 9, 2021Dru Riley – 45,000+ email subscribers in less than 2 years
Dru Riley is the creator of Trends.vc, which has more than 45,000 subscribers and 1,000 Pro members.
Listen or watch→Sep 28, 2021Bad Bunnies NFT – From idea to sold-out NFT project in less than 3 months
c4nopener is one of the creators of the Bad Bunnies NFT project. Bad Bunnies are 5,500 randomly generated, gamified NFTs, released from captivity to the Ethereum blockchain.
Listen or watch→Aug 3, 2021Gina Bianchini – Powering the business of community with Mighty Networks
Gina Bianchini is the founder and CEO of Mighty Networks. Mighty Networks helps creators bring their community, courses, memberships, and events together in one place under their brand.
Listen or watch→Jun 22, 2021Jay Clouse (interviewed by Ryan Hawk!) – Turning the tables for a crossover episode with The Learning Leader Show
Today is a special crossover episode. Last week, I interviewed the creator and host of The Learning Leader Show, Ryan Hawk.
Listen or watch→May 25, 2021Courtland Allen – Building (and selling!) a business creating community for Indie Hackers
Courtland Allen is the creator of Indie Hackers, the largest online community of startup founders. He created the site in August 2016 and it was acquired by Stripe in April 2017.
Listen or watch→Apr 27, 2021Corbett Barr – Why this pioneering digital creator is rebooting his entire online identity
Corbett Barr is the creator of Fizzle, a membership combining courses, podcasts, and community for creators.
Listen or watch→Mar 30, 2021Nick DenBoer aka Smearballs – From construction to early YouTube remixing, working on Conan, and selling NFTs
Nick DenBoer (also known as Smearballs) a director, animator, editor, music producer, remix artist and self-proclaimed "all around great guy."
Listen or watch→Mar 16, 2021Rosie Sherry – What community building really looks like (beyond the hype)
Rosie Sherry is the creator of Rosieland, a community and resource hub for community builders. She previously led community for Indie Hackers, a community of more than 140,000 independent makers.
Listen or watch→Mar 11, 2021BONUS: Building Community and Being Acquired (Indie Hackers)
In this bonus episode, I'm talking with Courtland Allen, the founder of Indie Hackers. As I’ve shared a couple times over the last few months, my accelerator and community Unreal Collective was acquired by Smart Passive Income in January of this year.
Listen or watch→Nov 10, 2020Dan Andrews – Helping location independent entrepreneurs build businesses and find community
Dan Andrews is the creator and host of the Tropical MBA podcast, a show for location independent entrepreneurs. The show has been downloaded millions of times since 2009.
Listen or watch→Oct 20, 2020Anne-Laure Le Cunff – From burnout to mindful productivity and quickly building an audience
Anne-Laure Le Cunff is an entrepreneur, an ex-Googler, and a neuroscience student. She’s the creator of Ness Labs and a Masters of Science in Applied Neuroscience candidate at King's College.
Listen or watch→Oct 6, 2020Bryce Conway – How a travel hacker evolved to become a content creator and affiliate marketer
Bryce Conway is the Founder of 10xTravel.com and Author of Takeoff: How to Travel the World for Next to Nothing and How to Fix Your Credit: Do it Once. Do it Right. Get on with Your Life.
Listen or watch→Aug 11, 2020Morgan Nield – Selling on Etsy, building a marketing strategy, Pinterest, and transitioning from physical to digital products
Morgan Nield helps Etsy sellers go from part-time hustle to full-time income.
Listen or watch→Jul 7, 2020Natalie Franke – Starting a photography business, competition, entrepreneurial loneliness, and the role of community
Natalie Franke is the Head of Community at HoneyBook and co-founder of the Rising Tide.
Listen or watch→