- 56 minutes 51 seconds#313: How 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.
My guest this week is Tom Ross, the founder of Learn.Community, where he helps community builders design learning experiences that actually stick. His clients have reached millions of people and generated tens of millions of dollars in revenue. Tom has been building online communities for 20 years, and he's been a member of The Lab since 2022.
In this episode, we talk about:
- Why an application process might be the most underused retention lever in the membership world
- The “bacon medicine” framework for making your membership both sellable and sticky long-term
- Tom’s “delight, direct, connect” onboarding philosophy — and what almost every community gets wrong
- How he rebuilt his course into learning pathways, drove completion from 20% to 50%, and turned a siloed module into the main engine of community engagement
By the end of this episode, you will understand exactly why most membership churn is decided before someone joins, and what to actually do about it.
Full transcript and show notes
***
TIMESTAMPS
(00:00) “People inherently don’t know what they don’t know”
(00:29) Tom's background: 20 years building communities, what we're covering
(04:06) Most retention problems start before someone joins — the targeting failure
(07:51) Application process as the biggest membership lever — and how to handle rejections kindly
(10:09) Closing doors creates demand: one client’s launch sold out in 4 minutes
(14:43) The “bacon medicine” approach to membership positioning
(24:28) Tom’s “delight, direct, connect” onboarding framework
(29:01) Responsive vs. linear onboarding — why static sequences break
(33:01) Learning pathways: reinventing the traditional course
(36:47) AI agents, deep worksheets, and vibe-coded SaaS tools inside the pathways
(40:02) Turning off course comments and routing engagement back into the community
(50:49) Real results: completion up from 20% to 50%, churn down, engagement way up
***
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#260: Detailed Breakdown: Our First Offline Event (And What We’ll Do Differently Next Time)
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28 July 2026, 7:00 am - 1 hour 1 minute#312: Everything We Learned From Our Second In-Person Event — The Good, The Bad, and The Full Economics
This week, my wife Mallory joins me for only her second podcast appearance ever to break down everything from The Lab Offline Powered by Circle — our second annual 2-day in-person retreat for Lab members, hosted June 8–9 at Hotel Renegade in Boise, Idaho. Mallory planned essentially everything: seating charts, venue contracts, menus, swag, run of show. She's been at it for roughly 6 months.
In this episode, we talk about:
- The full economics of running a community retreat (we lost $8,300, which is actually an improvement)
- How we took breakfast from a 4.8 to an 8.1 rating — and what we'd cut to reduce costs next year
- What ranked #1 for attendees 2 years running, and why trivia (our favorite activity) came in 7th
- Whether we'll keep doing this in Boise — and what Columbus, Toronto, and doing 2 events per year might look like
By the end of this episode, you will have a clear picture of what it actually costs to run a high-quality community event, what's worth paying for, and what we'd do differently.
Full transcript and show notes
***
TIMESTAMPS
(00:00) Cold open: people were moved, tears were shed
(00:53) The Lab Offline explained: 2-day member retreat, goals, and agenda
(06:44) Initial impressions: a reunion feeling, smoother logistics, zero fires
(13:08) Attendee feedback numbers: 9.3/10 overall, 91% returning, 34% said underpriced
(18:46) Event economics: $30,459 revenue, $38,800 costs, $8,300 loss
(23:05) Top cost drivers: hotel catering, travel, venue rental, dinners
(26:52) Planning challenges: acoustics, dietary restrictions, every decision is a trade-off
(36:52) What to keep: assigned seating, Kat's Immunity to Change workshop, Fighting Off the Sleepies
(42:04) What to improve: more mastermind sessions, less solo writing, better acoustics
(47:49) Open question: should the event stay paired with Craft and Commerce?
(53:49) The case for Columbus, 2 events per year, and an international option
***
RECOMMENDED NEXT EPISODE
#260: Detailed Breakdown: Our First Offline Event (And What We’ll Do Differently Next Time)
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- 🚀 Get CreatorHQ (creator operating system)
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21 July 2026, 7:00 am - 55 minutes 42 seconds#311: How 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.
I have been building community in some form since 2012. I ran Startup Weekend events in Columbus, led online Mastermind groups, consulted on the launch of SPI Pro, and spent 2021 leading the community team at Smart Passive Income before going back out on my own. In early 2022, I launched what became the Lab, a membership for creators earning at least $10,000 per month in non-service revenue or with 10,000 followers on a single platform. The Lab now has around 340 members across three tiers and is still standing after years of waves of communities coming and going.
In this episode, we talk about:
- Why scarcity and urgency drive signups but can crater your retention a year later
- The two onboarding "secrets" I kept quiet for a while
- The mastermind paradox
- How to think about scaling a community without accidentally eroding the culture you've built
- What I would tell anyone thinking about launching a membership before they write a single line of copy
By the end of this episode, you will have a clearer picture of how a membership actually works over years, not just at launch.
- The Lab Membership
- The Lab Membership Teardown (free)
- Circle (community platform)
- Kit Craft and Commerce Conference
- Chenell Basilio on Creator Science
Full transcript and show notes
***
TIMESTAMPS
(00:00) Introduction and episode context
(02:08) How Jay started the Lab (from Startup Weekend to SPI Pro to Creative Companion Club)
(09:37) The scarcity play: record revenue month followed by record churn
(10:38) What actually works as a marketing lever for a community
(13:46) Why Jay runs applications and has a 90% conversion rate for accepted members
(16:30) The design philosophy: reduce effort, increase impact
(24:19) Mid-boarding: the missing piece between onboarding and renewal
(35:13) Jay's onboarding framework and the two secrets he's been keeping
(40:46) Why offline events matter for retention (not necessarily growth)
(47:00) How to think about scaling community without destroying culture
(49:19) Who shouldn't launch a membership (and what to figure out first)
***
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- Creator Science Newsletter
- Get CreatorHQ (creator operating system)
- Join The Lab (private membership community)
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14 July 2026, 12:55 pm - 48 minutes 46 seconds#310: Brad Hoos — What 50,000 influencer campaigns tell us about what brands really care about
Brad Hoos is the CEO of Outloud Group, one of the top influencer marketing agencies in the United States. His clients include AG1, Chomps, KitchenAid, and Whirlpool, and he’s managed campaigns across tens of thousands of creator partnerships. Jay found Brad while researching for his book proposal on trust, trying to track down the agency behind AG1’s dominance in podcast advertising.
In this episode, we talk about:
- Why the creators who say no the most often are actually the most valuable to brands
- The difference between brand voice and brand advocacy, and why getting this wrong kills campaigns
- What Outloud learned running AG1’s campaigns across tens of thousands of creators
- The data across 50,000 campaigns showing no meaningful correlation between CPM and performance
By the end of this episode, you will think differently about how brands choose creators and how creators should position themselves for long-term partnership success.
Full transcript and show notes
***
TIMESTAMPS
(00:00) Introduction
(01:10) What brands actually want when they hire an agency
(06:20) The two things brands need to understand before a campaign starts
(07:09) Brand voice vs. brand advocacy: why the difference matters
(10:18) How trust changes what brands allow creators to do
(15:48) What running AG1’s campaigns taught Brad about influencer marketing
(20:39) How creators can position themselves to attract brand deals
(22:52) Why entertaining your audience beats being the “perfect” brand advocate
(27:24) Why the creators who say no most often perform best
(39:10) The data: no meaningful correlation between CPM and creator performance
(42:47) What Brad believes is true but can’t yet prove with data
(44:09) If you could only pick two platforms right now
***
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#179: Justin Moore – A step-by-step strategy to get anyone sponsored, regardless of audience size
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7 July 2026, 7:00 am - 13 minutes 2 secondsI 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.
Here's what you'll get:
- 4 weeks live. 10 sessions taught by me (July 3 to August 3).
- Kickoff call (Friday July 3) and Sendoff call (Monday August 3).
- Recordings of every session.
- A Circle space for homework, questions, and cohort chat.
- A year of Lab Basic (member directory, questions answered, frameworks).
That last bullet is a big deal. Because after these four weeks are over, a year inside our Basic Membership (which typically costs $699/yr on its own) gives you monthly office hours with me for a year. So after the cohort, you aren't totally on your own again; you still have our community by your side.
I won't run this again in 2026. The timing just doesn't work with our next baby on the way—so I'll be going all out on THIS cohort. By the way, it’s going to be a hell of a lot of fun.
Here's the full cohort page to learn more. We have more than 30 students enrolled already, and enrollment closes Wednesday, July 1 at 11:59pm ET.
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28 June 2026, 12:44 pm - 56 minutes 15 seconds#295: Community Building Trends for 2026 with Becky Pierson Davidson [Greatest Hits]
I brought back Becky Pierson Davidson to compare notes on where community is headed — and we found a few areas of disagreement. Becky works with 6, 7, and 8-figure businesses helping them build memberships and courses through design thinking and customer research, and she's seeing a major shift right now: course businesses are slowing down, and the smart ones are pivoting to membership models. The difference? Shared learning experiences are replacing self-paced education. Community is what people stay for.
We dig into the real mechanics: how to set expectations that don't feel like a bait-and-switch, why meaningful engagement isn't what most people think it is, the mastermind paradox (increases retention, decreases forum activity), and why in-person events might be the most important retention lever you're not using. Becky's hot take for 2026: content drops are dying. People don't need more stuff — they need connection and programming that moves them forward.
- Affinity Collective
- Build with Becky podcast
- Episode 197: Building Raving Fans (with Becky & Chanel)
- Circle (community platform)
- TightKnit (Slack archive plugin)
- Dreamers and Doers
Full transcript and show notes
***
TIMESTAMPS
(02:35) Defining community as a product, not a growth engine
(04:09) Why community is rising as a business model in 2026
(06:02) The reality of transitioning from courses to memberships
(08:01) Finding the right community design for your appetite
(10:02) How to avoid the bait-and-switch with member expectations
(13:06) Value perception vs. value experience
(13:57) The smallest viable promise for your sales page
(16:44) Where we disagree: transformation vs. community of practice
(21:14) Forum design: why fewer spaces wins
(23:17) Solving the engagement problem (what meaningful engagement actually is)
(25:50) How the best members actually use your community
(29:46) The mastermind paradox: retention up, forum participation down
(32:09) In-person experiences and the graduation weekend model
(36:39) The economics of offline events
(39:35) 2026 Hot Take: Content drops are dying
(43:07) Retention rethink: Did I get my money's worth vs. Will I next year?
(46:04) Why connection drives retention more than results
(48:23) Tool stack: Circle 9 times out of 10
(51:14) The future: personalization in community software
***
RECOMMENDED NEXT EPISODE
→ Episode 197: Building Raving Fans
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25 June 2026, 7:00 am - 53 minutes 51 seconds#309: A 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.
Before Circle, he was the third hire at Teachable, where he helped build the infrastructure for the creator economy before the term even existed. He spent four years as a tech blogger, writing about startups five to ten times a day, and was one of the first people to ever cover YouTube—back when it was a dating platform!
- The one thing Sid says separates successful communities from the rest
- Circle Eclipse: what it is (AI partner + connective tissue + Discover marketplace) and why 80 of 100 engineers have been on it for 4 months
- The “course as wrong abstraction” insight: why Sid saw self-paced courses heading toward terminal decline as early as 2018
By the end of this episode, you will understand why the most successful community businesses aren’t built around content — they’re built around a specific transformation.
Join the waitlist for early access to Circle AI
Full transcript and show notes
***
TIMESTAMPS
(00:00) Introduction
(01:44) Teachable origin story: the “I don’t want to play Tinder with you” email that started it all
(06:18) Tech blogger at Mashable — and the story of being first to write about YouTube
(09:15) ~280 employees, $30M raised — the scale of Circle today
(12:52) Why self-paced courses are in terminal decline (the leading indicators Sid saw in 2018)
(17:16) The “course as the wrong abstraction” moment — community as the right container
(22:00) Circle Eclipse: the three major updates launching
(24:00) The connective tissue opportunity: one plus one must equal ten
(33:19) Admin dashboard evolution — where Circle AI lives for returning users
(35:30) The morning brief: five recommended next steps, then you’re good for the day
(38:50) The biggest bet in Circle’s history: 80 engineers, 4 months, Spain offsite
(40:00) Member-side AI agents and where they’re heading
(43:24) Discover: from supply-side listing directory to the first real marketplace for transformations
(48:00) The promise: Discover will never market inside your community — ever
(51:55) Sid’s #1 recommendation: define your transformation
***
RECOMMENDED NEXT EPISODE
#295: Community Building Trends for 2026 with Becky Pierson Davidson
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17 June 2026, 7:00 am - 58 minutes 55 seconds#308: Live Podcast Audit: Jeremy Enns Diagnoses What’s Holding Creator Science Back
Every few years, someone asks you the question you've been avoiding. For me, this was it: does your show actually have a premise, or does it just require people to already know and like you?
Jeremy Enns is the founder of Podcast Marketing Academy, where his primary product is podcast audits. He has spent years analyzing what separates shows that grow from shows that stall, and he runs Podcast Marketing Academy to help hosts fix both. He has been a member of The Lab since the early days.
In this episode, we talk about:
- Why podcast problems are almost always brand and product problems in disguise
- The difference between a show that requires you to already be known vs. one that earns listeners on its own merits
- What "killer concepts" are — and why a sharper premise makes episodes easier to produce, not harder
- The case for featuring Lab members as guests, and why it could be the highest-converting version of Creator Science
By the end of this episode, you will have a new framework for auditing any creative project — including your own — and asking whether it's designed to grow or just to persist.
Full transcript and show notes
***
TIMESTAMPS
(00:00) Cold open: what a "killer concept" actually is
(02:20) How this episode came to be: Jeremy's years of quiet notes on Creator Science
(04:04) What Jay actually wants from this conversation
(09:36) Where podcasting fits in the funnel — why it's the Lab's best front door
(13:23) "If you were starting today": the co-host question
(22:14) Does Creator Science have a premise? Jeremy's honest take
(26:11) The container model: Song Exploder vs. Reply All
(31:09) The density problem: why 80% of episodes aren't relevant to most listeners
(34:49) The missing IP: Jay's philosophy exists in his head, not on paper
(38:31) Why featuring Lab members could be the highest-converting version of the show
(44:51) A three-part lens: discovery, trust, monetization
(53:28) Jeremy's prescription: what the ideal Creator Science show looks like
***
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#273: How to create a scrappy industry report that elevates your brand | Jeremy Enns
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9 June 2026, 7:00 am - 50 minutes 5 seconds#307: Richard van der Blom — The state of LinkedIn in 2026 (based on data from 1.3 million posts)
Richard van der Blom published his first LinkedIn algorithm report years ago as a curiosity project. This year, he and his team analyzed 1.3 million posts from 50,000 creators — and the headline number is hard to ignore: reach is down 60% for active creators over the last two years. Even harder to stomach: 80% of the comments Richard receives in the first five minutes of any post are written by AI.
Richard is the author of the annual LinkedIn Algorithm Insights report — the most data-backed independent study of the platform I've found. He's also been targeted by LinkedIn's legal team, banned from the platform, and watched the third-party tools he relied on get shut down one by one. He keeps publishing anyway.
In this episode, we talk about:
- Why reach is down 60% for active creators — and why LinkedIn says that's intentional
- What "topic fingerprinting" is and how to use it to re-teach the algorithm who you are
- How your comments now shape your interest graph, not just your human visibility
- Why LinkedIn newsletters are outperforming regular posts on reach, engagement, and conversion
By the end of this episode, you will understand exactly what changed in the LinkedIn algorithm, why the old playbook is working against you, and the specific moves to make in 2026.
Full transcript and show notes
***
TIMESTAMPS
(00:00) Introduction
(02:36) Richard's one-word description of LinkedIn in 2026: "turbulent"
(07:38) The shift from relationship graph to interest-based graph — the biggest change in 10 years
(11:36) Topic fingerprinting: how to re-teach the algorithm who you are
(14:47) Why commenting on the wrong posts actively hurts your reach
(16:41) Richard's 25-30 minute daily commenting system, broken down
(25:17) The free bookmark search trick for building curated feeds
(31:41) Newsletters vs. standalone articles — the numbers are not close
(35:16) LinkedIn newsletter analytics: click-by-link tracking is now live
(39:37) Optimal posting frequency: down from 5-6x to 2-4x per week
(41:18) Why text-only posts require exceptional copywriting to work
(43:20) What the top LinkedIn creators know that everyone else misses
(45:29) Richard's prediction: LinkedIn is at a crossroads
***
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#188: Richard van der Blom – How the man behind the LinkedIn Algorithm Report uses LinkedIn.
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2 June 2026, 7:00 am - 1 hour 10 minutes#306: What 16 Years Behind YouTube's Biggest Channels Taught Josh Mattingly About Hiring And The Current State of YouTube
Josh is the founder of Upright Media, an operating partner for content creators handling operations, consulting, recruiting, and post-production. His clients include some of YouTube's biggest channels — Erak, Smosh, Emma Chamberlain, Dude Perfect, Matthew Beam, and Chris Williamson. He runs 11 full-time staff and about 40 contractors worldwide. He describes himself as a creator without a channel. This conversation also took a turn into what YouTube actually rewards right now, why "companionship content" is quietly eating the internet, and the concept of the "shitty flow state" — that experience where you put down your phone 35 minutes after opening Instagram and can't name a single thing you saw.
- Upright Media
- Brad Stulberg — The Way of Excellence
- Monday.com (project management tool Josh uses)
- Topper Guild (YouTube channel)
- Speeed (James Pumphrey + Jesse Wood)
Full transcript and show notes
***
TIMESTAMPS
(00:00) Josh's opening: don't lose sight of the big goals that motivate your team
(00:26) Who Josh Mattingly is and what Upright Media does
(08:16) Excitement vs. panic — how much of working 80 hours a week is actually anxiety
(12:49) Why most creators hire from panic — and how Josh reframes it around a goal
(22:35) Build the team around what you're doing well, not where you think you're going
(24:36) The positioning exercise: what is your channel, actually — and why it drives every hire
(20:36) Speeed channel case study: lean team, clear mission, "GQ for this generation"
(27:02) What YouTube is biased toward right now: real connection over spectacle
(30:02) The content spectrum: entertainment → education → companionship content
(40:01) The "shitty flow state" — why most of what we consume doesn't satisfy
(55:52) Hiring mistake: moving too fast — interview 10 more after you find "the one"
(56:56) Building a hiring committee as a solopreneur using peers and friends
***
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#175: Angus Parker – Ali Abdaal’s right-hand man shares a YouTuber’s guide to hiring.
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26 May 2026, 7:00 am - 35 minutes 49 seconds#305: Big 3: Three Wins, Three Concerns, and Three Experiments for May
Every month inside the Lab, I do a full retrospective: wins, concerns, experiments, with all the numbers on the table. I've never felt comfortable putting the whole thing out publicly, but I do think the practice itself is worth sharing. So this episode is my lightweight version: three big wins from April, three things I'm genuinely worried about heading into May, and three experiments I'm kicking off. I'm also testing a new name for this format: the Big Three.
April was, by most measures, a really good month. A baby boy on the way, the biggest partnership deal I've ever signed, and a speaking slot at Press Publish LA. But sitting alongside all of that is a real anxiety: I'm watching my audience pull back, sales slowing, people tightening up. And I'm rebuilding a lot of the business simultaneously, too. This episode is me thinking out loud about all of it.
- The Lab — Creator Science membership community
- Circle — community platform powering the Lab
- Press Publish LA — Colin & Samir's creator event, late May
- Build a Beloved Membership — Jay's membership course (cohort coming July)
Full transcript and show notes
***
TIMESTAMPS
(00:14) Introducing the lightweight retro format ("the Big Three")
(01:38) Win #1: Baby boy on the way — and what it means for the next six months
(04:28) Win #2: Biggest partnership deal ever — Circle for the rest of the year
(06:03) Win #3: Speaking at Press Publish LA
(07:24) Concern #1: The oxygen mask moment — slowing sales and audience withdrawal
(09:47) "Give where it hurts" — the counter-intuitive move in uncertain times
(13:41) Concern #2: Rebuilding the business from the ground up
(18:56) Concern #3: Are we trying to do too much?
(19:25) Experiment #1: Building out the team (Ana, Ritzy, and Tubey in Slack)
(27:46) Experiment #2: The Membership Summit (June 23–26) + cohort in July
(30:41) Experiment #3: A new AI-forward product model, piloting inside the Lab first
***
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#291: 48 Hours With Clawdbot: How I’m Using It and Initial Reactions
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19 May 2026, 7:00 am - More Episodes? Get the App