Rolling my own community | #328

Metcalfe’s law says that community value increases with the number of edges, or relationships. But deeper research has shown that many edges are not very valuable in most communities, with a small number of people and interactions creating most of the value. There’s a 90-9-1 law of the internet: 90% of people are lurkers, 9% are editors, and 1% are creators. Most paid communities re-create these ratios because a lot of the “community” is basically a paywalled feed that copies social media. The game if you are “building” a community then, is just to scale to as many people as possible.

This never appealed to me. I’ve always been more of a creator socialist, excited when the group around me thrives, and not just a select few super-participators. I also have always sense that there must be a better way to architect digital communities in ways that make it easier for the members to connect with each other, especially in ways that don’t even require them to participate publicly. And for the first time, I think the possibilities to do this in fun ways are better than ever.

I’ll share what I’m doing but first, let’s backtrack a second.

Community 1.0

I started a community using the Circle platform in 2023 after dozens of people kept asking me if there was a place where they could find other people on pathless paths. I looked at other options like memberful, mighty networks, and Podia, but chose Circle because the costs were relatively low and I could host my courses there too.

But from the beginning, I struggled to be energized about it. Circle was solid but it didn’t quite do what I wanted it to do. This is no fault of Circles. It exists in a broader VC-funded ecosystem of a “creator economy” that needs to serve customers while increasing revenues, and eventually, profits. Over time, all of the incentives and narratives have coalesced around creator businesses, helping single creators make a lot of money and build businesses.

But building a creator empire has never been the most interesting thing to me. I don’t want to be a billion dollar creator. Hell, nor do I want to be a million dollar creator. I simply want to create, connect with others, explore ideas, and hopefully keep funding my ability to do it all. The reason I wanted to setup a community is because people wanted it.

Alas, Circle has to build a business and pay employees and return investor money. And importantly, it can’t focus on people like me who don’t think about scaling their business and maximizing monetization all the time. And so at the end of last year, as I was mostly breaking even on the community, I attempted to go in and change some of the email workflows and take advantage of some new AI features. I was hit with aggressive upsells.

This was incredibly frustrating. I felt like I already wasn’t doing a good job with my community and that if I wanted to be able to build the things I wanted to, I would first need to pay a lot more money to Circle. Luckily with the improvement in agentic coding tools, I knew I might be able to roll my own platform, something I wrote about a couple of weeks ago in my rewilding the stack essay.

So that’s exactly what I’ve done. And the core of the new platform is all built around one simple idea:

The Goal:

Every single action someone takes should help to increase the odds that they meet someone else on a similar path or increase the amount of courage they have to keep going on their path.

In other words, the group doesn’t need many more people to increase the value of the community, it only needs more varieties of possible edges between community members.

Edge #1: Easy ways to plant flags (literally)

Many of the people in the pathless community travel for events, host online events, and want to meet people IRL in various places around the world. I wanted to make that easier.

Step one was getting people to tag where they are in the world (the boat are those marked nomadic).

And/or share travel plans and events:

Step two, once we have this information is doing a few things:

• Having a high value weekly email with relevant notifications (more below)

• Investing in targeted local IRL events and hopefully building up bigger capacity for a larger event next year

Over the past few years there have been many random meetups that have happened around the world, something with me knowing and sometimes without me knowing. The feedback from people is that they usually want to meet more people. I love hearing about these connections and so I wanted to try to make more of them happen.

Edge #2: Curiosity Conversations

My community has always featured people sharing “curiosity conversation” links, or open call links where people can connect without an agenda. But until now, it was one-off posts lost to ephemeral feeds in WhatsApp and Circle.

Now I have a dedicated page and so far 14 people are open to chatting:

Every week, people get a highlight of who added a link and what they might want to talk about.

Edge #3: Slow posting social optimized for conversation

I don’t mind posting in public in 2026 but for many people, it is not a good experience and not something that I wanted to do. Inspired by Craig Mod’s local social media called “the good place,” I wanted to create my own mini social feed, and so I have spun up something called Field Notes.

There are two rules:

1. You can post once a week, but it has to be minimum 300 characters

2. You are allowed to reply infinite times

So far its been pretty good. People seem to like it. The goal is really to have a place where people can share deeper ideas and thoughts and have nuanced conversations without worrying about the blowback of wider social media.

Serendipity Emails: The thing tying it all together. a high-value weekly digest

Email really is the killer app and using AI tools, you can create something that’s pretty magical. I now have a workflow that:

• Captures all relevant new information, links, calls, locations, and new members and shares that each week

• Creates a draft I can review and add personalized information and an intro

• Ships it with automatic login links that are easy to use

The goal here is to create something that triggers people’s curiosity and has them saying “ooh I want to open this.”

Sample digest

👋 Newly Activated Members

• Maya is in Lisbon, Portugal; former strategy consultant now testing whether “portfolio career” can mean writing, teaching, and wandering around looking at cats

📍 Location Updates

🇯🇵 Japan

• Dev is in Kyoto and is willing to host anyone over the next year

✈️ Travel & IRL

• Sam is in New York from July 8-12 and would love to meet anyone working on Web 1.0 startups

💬 Community Invitations

• Nina is hosting a tiny async experiment called “No Meetings Week,” where participants attempt to reclaim their calendar and then write emotional reflections about email.

☕ New Curiosity Conversations

• Marco, a product designer in Berlin, added a curiosity-call link for conversations about independent work, career pivots, and learning French

  • Book a conversation

🧰 Member Creations Worth Sharing

• Priya launched a website that helps people decide how to set rates as a freelancer

  • Open the project

📝 Field Notes

• Jordan wrote “I thought quitting would fix everything, but then I was still myself,” a Field Note about freedom and structure

  • Read Field Notes

🔗 Other Links From WhatsApp

• Link 1

• Link 2

It’s not going to be AI summaries, it’s literally just going to be what people are doing, what they are sharing, and who they might want to connect with.

Finally, flexible payments

I’m never quite sure how to charge for things. I personally love one-time payments but they are also not great for sustainability.

So I decided to just offer two models: Annual or one-time. I suspect many will choose one-time payments and that’s fine. The good thing is that I now have a platform that is cheap to run (total costs are about $5/month now) and even easier to maintain, so I don’t need it to be a big financial business like I felt it needed to be when on Circle.

Future thoughts on “community”

As you can tell, I’m very excited about all of this. The things I can do that weren’t possible twelve months ago are borderline magical for someone like me who’s been hacking away online for decades.

If community 1.0 on the internet has mostly been about monetizing attention to the creators benefit, I hope that this is part of a community 2.0 movement where value can spread to the entire group much more easily. In the past that required A LOT of energy from the creator, like what Jay Clouse has built with The Lab. But with AI tools, you can spin up all sorts of things that are delightful for users and participants that never made sense financially for any company to build or offer.

And beyond that kind of value I am thinking a lot about financial value too. What does it look like to build and share squad wealth? How do we maximize the digital GDP of the broader pathless community and not just my own pocket? What are the opportunities that we are not yet thinking about that tools like Stripe + agentic coding tools unlock?

I’ve always been motivated by bringing others along, rooting for them, and then trying to connect and support as many people as possible. Most of this kind of effort is not valuable in an economic sense. But at least now I can build my own platform around this and align my energy such that the odds of stumbling into a financially viable part of my business are much higher.

And I think that’s pretty cool.

Check out the community here