One hundred episodes. I did the math, which I should not have done, because now I know that if you listened to this whole show back to back, no breaks and no snacks, you would be in that chair for about 36 hours.
I did not plan on 100 of these. I am notoriously extra about planning, with spreadsheets and color codes and a document about the documents, and a hundred was in none of them. What kept it going was you replying.
So this one is a thank you and a Q&A, because the community founder questions landing in my inbox every week are a better use of a round number than a clip show of my own greatest hits. Here’s what a hundred of these taught me, then the answers to the ones I get asked most.
What Did 100 Episodes Teach Me?
That the only reason the early ones got better is that I kept making them. Not the gear, not the course I bought. Volume and time.
I listened back to a few this week, which I don’t recommend as a Tuesday activity. They were rough. I can hear myself reading, trying to sound like a person who has a podcast instead of a person just talking to you.
I say that because a lot of you are at episode six of your own thing right now. Six posts, six emails, six members, reading the tea leaves of a sample size of nothing. Six is not a verdict, and the version you’re making now is not the version people will find you for. Mine wasn’t.
Two other things worth handing over:
- The format was never the problem, the room was. I tried this show as video on YouTube and nobody watched it there, so I went back to audio only and made the channel about tutorials instead, because that’s what people wanted from me there. Right thing, wrong place, and 5,200 subscribers later it’s still growing.
- You’re not short on ideas, you’re looking in the wrong place. When I had nothing, I read what people were asking in the Circle customer community that week and built an episode out of it. Once my own community got bigger, I pulled from in there instead.
Then there are the five you listened to the most, counted down fifth to first:
- Fifth: Why Self-Care Doesn’t Work for Founders
- Fourth: What Your Community Actually Needs on Day One
- Third: The Pre-Launch Validation Nobody Does (But Should)
- Second: Your First 10 Members Matter More Than Your First 100
- First, by a mile: The Lowdown on Free, Paid, and Hybrid Communities
Not one of those is a hack. Four of the five are about the boring structural decisions you make before a single person walks through the door, which is the exact thing I’m forever trying to talk people into caring about. So you’re all secretly structure people. I knew it.
How Do You Write a Circle Onboarding Email for Every Kind of New Member?
You don’t. Circle already branches it correctly for whoever is standing there, and that is not something you can hand-build in an email no matter how many times you rewrite it.
This came in as a voice note from someone trying to cover a brand new member, a member who already has a Circle account from another community, and an SSO member in one email. It’s maddening to write, which is the clue that it isn’t a copywriting problem.
When somebody buys through a paywall, Circle sends a post-purchase email if you have it turned on, and you write that in the Post Purchase tab inside your paywall settings. New and existing members both get it, and if onboarding is set up in your community settings, new members get those too. Then the link sorts people: an address with no Circle account lands on a join page to set a name and password, and one that already has an account gets sent to log in with the password they have. On SSO there’s no invitation email at all, since they sign in with your credentials and Circle creates the member record on first login.
So turn on the email Circle gives you, write it in your own voice, and get out of the way. Spend the energy where people actually get lost:
- Check your Invited tab. The account isn’t active until someone finishes the profile step. People buy, click through, start the sign-up and quit before the profile, and then sit in invited on your Manage Audience page. They paid you and they aren’t in there yet. That’s the list that matters.
- Walk the whole thing yourself. On Gmail or Google Workspace, use plus addressing: your own address with a plus sign and any word before the @. Circle reads it as a brand new person and everything still lands in your inbox. Make yourself a 100 percent off coupon, buy your own membership with that address, and go through it. Then do it again with an address that already has a Circle account.
Twenty minutes of that will tell you more than I can.
How Do You Turn a Following Into a Paying Community?
You don’t turn one into the other. A following is a pile of separate relationships between each of those people and you. A community is a web of relationships between those people and each other, and you build that second thing on purpose, from nothing.
Putting a paywall in the middle of an audience doesn’t convert it, which is good news: the size of your following is not what decides whether this works.
The joining, consuming, and quietly evaporating happens when the first thing you hand somebody is content. Walk a new member into a library and they’ll treat it like a library: take what they came for, leave, and feel fine about it.
So the first ask cannot be consume. It has to be say something, and then have somebody who is not you answer them. You being warm doesn’t count, that’s your job and they expect it. Another member reading what they wrote and going “oh, same” is the part that lands.
Make the first prompt answerable in one line
“Tell us your story” is a term paper. People open that box, feel tired, and close it. Ask something a person can answer while standing in the kitchen with one hand free.
Go smaller than feels right
Nobody wants to introduce themselves to a crowd they can’t see the edges of. Run things in a smaller room: cohorts, groups that start on the same day and move through together. Fifteen people who arrived at once will build something 1,500 people in an open feed never will.
Build the first week before anything else
Not the whole curriculum, not 12 spaces. The first seven days. What they see, what you ask them to do, who says hello, and what happens if they do nothing at all. Almost every membership I get into has a gorgeous library and no first week, and the first week is where somebody quietly decides whether they belong in there.
Should You Run a Free Community Alongside a Paid One?
Only if it’s a funnel. That’s the whole test. Either the free community does a job for the paid one, or it exists for its own sake because you decided that’s reason enough. Both are legitimate. The middle is not, and it’s where almost all of them live: sort of marketing, sort of a product, sort of a hobby, quietly eating your Thursdays.
When it works as a funnel it’s some of the best traffic I have. People come in free, get a feel for how I run a room, and the ones who want the real thing go get it. The part people get squeamish about is what makes it work: free members don’t get much interaction. They can see the plays and get a sense of who’s in there, but they can’t participate the way members participate, because that’s what members are paying for. That isn’t cold, it’s clear.
The mistake I watch founders make over and over is building a free community so good and so active that nobody has a reason left to pay for anything, then being baffled about conversion. Your content is not your product. Access to each other is your product. Give them enough to want in and not enough to have it.
If yours is the other kind, the one you run because you want it to exist, give it a budget of hours like anything else you volunteer for and stop measuring it against revenue. It was never built to make any. Still deciding which one you have? Start with the free, paid, and hybrid breakdown.
Why Is Your Community Quiet?
Usually because you’ve been posting things that are impossible to answer. Before you panic about engagement, check whether the room is quiet or just silent, because those are different.
Look at who logged in this week and how many people read the post. In most small communities I get into, the reading is happening and the replying is not, and the founder decided the whole thing was failing on reply count alone.
Then look at what you’ve been posting. Nine times out of ten it’s announcements, resources, and long reflections that are frankly complete. There’s nothing left to add. What is a person supposed to say to that? Ask something a human can answer in one line. That’s the entire bar. If it’s still quiet after that, it isn’t an engagement problem. There’s no reason to come back on a particular day, which is a design problem.
What I’d Tell You 100 Episodes In
I used to think the hard part was building the thing. It’s not. Building it is fine, and there are a hundred episodes here to help you do it. The hard part is staying interested after it works. You get it running, it’s steady, it pays you, and then on some ordinary day you’re sitting there thinking is this it, wondering whether to blow it up and start something new. That urge is almost never strategy. It’s boredom wearing a business plan.
I changed my mind about size too. I spent a couple of years making everything bigger, and the business got heavier while I got worse at my actual job, which is paying attention to people. So now I make things smaller on purpose. Fewer offers, fewer rooms, more attention in each one.
If planning next year is on your list, that’s what we’re doing inside Launchpad 2027, November 9 to 12, 12:00 PM to 3:00 PM ET each day. An hour of teaching, a break with something interactive in it, then an hour in breakout rooms where everyone works on the same thing at once. Most goal planning stops at a revenue number. We set the community goals next to the business ones: retention, participation, how many members you want to know by name, what you’re going to stop running, who you’re going to let lead something. The planner is included and you fill it in live with us. Free inside coCreator Society, or $297 on its own.
If I get to pick what I’m known for at the end of all this, it isn’t the biggest launch or the cleverest funnel. I want to be the person who taught you how to hold the people who walk into your space, because that’s the actual job. Everything else is logistics. Somebody trusted you enough to come inside, and whether they stay has almost nothing to do with your tech stack and almost everything to do with whether they felt held once they got there.
A hundred of these, saying that in slightly different outfits. Thank you for being here for them.
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Listen: Your First 10 Members Matter More Than Your First 100. Your number two episode of all time, and the case for being small on purpose.
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