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!

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

***

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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:

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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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:

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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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.

Full transcript and show notes

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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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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.

Full transcript and show notes

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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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I’ve been a full-time creator for 8 years now and have earned $2,192,000 since 2022. I’ve spent a LOT of time and money experimenting with different ways to make money on the internet, so I’m going to rank them. The best and the worst.

I show you 15 different revenue streams and rate them from S to F based on their potential versus the effort required. By the very end of the video, you’ll know which ones are right for you. And at any point, if you agree or disagree, let me know in the comments.

⁠⁠⁠⁠⁠⁠⁠⁠Full transcript and show notes⁠⁠⁠⁠⁠⁠⁠⁠

***

TIMESTAMPS

(00:32) AdSense

(01:36) Sponsorship & Brand Deals

(03:30) Content Memberships

(04:30) Done-For-You Services

(05:27) Royalties

(06:28) 1-to-1 Coaching & Consulting

(07:38) Affiliates

(09:36) User Generated Content (UGC)

(10:17) Group Programs

(11:25) Digital Products

(12:56) Speaking

(14:27) Live Events

(15:53) Community Memberships

***

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Sam Vander Wielen is an attorney turned entrepreneur who built the go-to legal template shop for online businesses. Her flagship product, the Ultimate Bundle, a package of fill-in-the-blank contracts and video trainings, has generated over $8 million in lifetime revenue and now earns close to $2 million per year with essentially one full-time employee. She published her first book with Hachette in April 2025, and she runs everything through a single evergreen webinar funnel that quietly generates six figures a month between launches.

I met Sam at Craft and Commerce last year, and when I saw her post about 10,000+ webinar registrants and a $500,000 launch, I knew I had to talk to her. What blew me away wasn't the numbers; it was the simplicity. One product. One funnel. Two launches a year. Relentless customer research. She's the clearest example I've seen of someone who found the main thing and refused to let anything pull her off it.

Full transcript and show notes

***

TIMESTAMPS

(00:00) Jay introduces Sam and her $8M+ legal template business

(02:27) What the Ultimate Bundle actually is — and why it hasn't changed much since 2017

(03:47) The Olive Garden effect: how Sam thinks about community and lifetime customer support

(10:00) The $500K launch breakdown — what went right and why it wasn't an accident

(13:28) Sam's full launch strategy: the teaser period, invite period, and treating registration like concert tickets

(18:03) The on-webinar bonus that drove 128 purchases live — and why a book beat a $100 discount

(22:56) How Sam uses VideoAsk to boost show-up rates and make 11,000 registrants feel personally seen

(28:39) Voice of customer research: quarterly customer calls, AI transcript synthesis, and why Sam still reads the raw transcripts herself

(33:14) Why working less keeps making the business better — and what the 'entrepreneurial gap year' actually means

(36:04) What motivates Sam (honest answer: fear) — and what Jay relates to in that

(42:00) Why AI isn't a threat to Sam's business — and how she reframed the 'doubt language' from Google to Claude

***

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#292: Chenell Basilio — The state of email in 2026, growing your list without social media, and new predictions.

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Riley Brown posted the first TikTok video about ChatGPT the day it launched. It got 20 million views and took him from zero to 200K followers in less than two weeks. Since then, he's built an audience of 1.5 million across platforms, raised $9 million to co-found a vibe-coding startup in San Francisco, and developed a content system so systematic that a single viral video gets reposted across seven accounts every week for the rest of the year.

In this episode, Riley shares his philosophy for staying on the edge of any niche, why playing beats structure when it comes to content, how he runs a content operation with two overseas editing agencies and a separate thumbnail designer, and the Twitter strategy — posting viral videos across seven accounts — that tripled his company's revenue in two months. He also makes a strong case for educational screen-share YouTube videos as the single biggest content opportunity right now, and explains why using AI to write your scripts is, in his words, "suicide."

Full transcript and show notes

***

TIMESTAMPS

(00:00) How Riley's first ChatGPT TikTok got 20 million views

(04:56) First mover advantage:

(07:50) How Riley films his videos

(11:24) Why structure made his content worse

(13:06) Jay's honest moment

(21:33) The case for educational screen-share YouTube videos

(26:45) His content strategy

(30:43) The seven-account Twitter strategy that tripled revenue

(37:37) Gimmicks that actually boost retention

(41:00) Why AI writing your scripts is suicide in the long run

(42:37) The content farm future and how to survive it

(50:14) Platform rankings: where to start today

***

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#288: He gained 190K Instagram followers in 508 days…but wouldn’t do it again | Yoni Smolyar

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This episode is a little different. Michael Bungay Stanier, author of The Coaching Habit, with over a million copies sold, reached out and offered to do something I didn't expect: a live coaching session, recorded, here on the podcast. The topic: my delegation issue. Not the tactics (I know the tactics). Something deeper has its foot on the brake.

What unfolded was one of the most honest, vulnerable conversations I've had on this show. Michael walked me through the Immunity to Change framework, where we uncovered that I'm getting more out of the status quo than I realize. There are commitments I have to the way things are right now that I haven't even named. We named them. And then we ran small experiments to test whether the things I'm most afraid of would actually come true.

Full transcript and show notes

***

TIMESTAMPS

(00:00) The inner monologue: lack of courage

(00:22) Introducing Michael Bungay Stanier — and why this episode is different

(01:46) Michael's outreach: 'Your delegation issue is probably hard change, not easy change'

(03:24) The setup: Jay's wife is the only other 'full time employee'

(08:58) Easy change vs. hard change — and why more tactics won't solve hard change

(14:24) Defining the real challenge: more time on the business, not in it

(17:26) The embarrassing list: all the things Jay is doing (and not doing) contrary to his goal

(22:48) Flipping the script: what would you be worried about if you actually delegated?

(26:30) Competing commitments — the foot on the brake even while pumping the accelerator

(28:42) 'I'm committed to not let anybody else work in the business'

(34:15) The apocalypse: what if it all goes wrong? The deepest fear, named

(39:09) Reframe: it's not a lack of courage, it's a protective system

(40:15) Small experiments to test the fears, not just grit through them

(42:28) Experiment #1: Give Izzy more autonomy and outcome ownership

(45:10) Experiment #2: Lead sponsorship conversations, test revenue potential

(47:01) Experiment #3: Protect morning time for on-the-business thinking

(55:44) 'How fascinating' — shifting physical state to get out of anxiety

(59:35) The insight: running toward something vs. running away from something

***

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→ #82: Michael Bungay Stanier – How to Begin Setting a Worthy Goal

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Nir Eyal has spent his career studying why people don't do what they know they should. After writing Hooked and Indistractable, he kept getting a strange kind of call: readers who'd read the book, knew the steps, and still didn't do them. That puzzle led him down a six-year research path into the one variable missing from every motivation model: belief. In this conversation, Nir shares the science behind his new NYT bestseller Beyond Belief, and the framework that explains why knowing what to do is never enough.

We go deep on the Motivation Triangle (behavior + benefit + belief), the difference between limiting and liberating beliefs, and why positive thinking and visualization can actually make your goals harder to reach. Nir walks through the turnaround process live—we use my own imposter syndrome as the test case—and you'll hear him demonstrate, in real time, how quickly a belief that feels like a fact can dissolve when you examine it. If belief is the hidden ceiling on your performance as a creator, this episode is the blueprint for raising it.

Full transcript

***

TIMESTAMPS

(05:36) The Motivation Triangle

(07:22) Why information is a solved problem

(10:26) Beliefs vs. facts vs. faith

(15:48) Limiting beliefs vs. liberating beliefs

(21:46) The #1 reason people don't achieve goals

(22:59) Why the brain hates changing its mind

(31:31) Inquiry-Based Stress Reduction

(34:27) The turnaround: collecting a portfolio of perspectives

(42:24) Talking to Yourself In the Third Person

(47:24) The Circle of False Promise

(50:00) What athletes actually visualize

(53:51) 'Imposter syndrome' is not a real diagnosis

(56:10) Your labels become your limits

***

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→ #300: I Spent Three Days With A Dozen New York Times Bestselling Authors

→ #171: Nir Eyal – Writing books, persuasion vs. coercion, and how to be indistractable

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