The Economics of Connection

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Hey honeys and hustlers,

I was listening to a podcast episode on Creator Science where Jay Clouse talked with the founder of Tropical MBA about how he uses events to grow his income and community. I've been wanting to talk about the economics of community building and monetizing relationships as a source of revenue – not only for creators, but also brands, businesses, and a lot of the retail and e-commerce businesses that we see placing a higher emphasis on community building using social media and events in 2025.

There are two types of communities that you can build: one is information-based and the other is connection-based. How much you charge for these communities really depends on the level of access that people get and that could be the access they have to you but that could also be the access they have to other members within the community. In a lot of the connection-based communities that I see, they charge a higher amount because assumingly the person who is hosting the community is a big enough name, to warrant that level of desire to connect with them.

The other half I see is communities like Hampton, which was started by the previous founder and writer of the Hustle newsletter who had a multi-million dollar exit. It's an elite community where the draw isn't necessarily just the founder of the community, but the other people that you'll be in rooms with, that you'll get to network with, work with, collaborate with, and just have within your network as a result. And those charge a huge premium.

My community, Please Hustle Responsibly, is largely information-based, and I'm trying to bridge that gap between information and connection without overextending myself as a creator. All communities start in one place, and they start with relationships. So let's talk about how I started, and probably how a lot of people listening to this are starting, and that's using social media to connect with other people.

Relationships don't just happen when you post something on social media. They happen in the comments and the DMs. One interesting stat that I heard in Jay Clouse's interview with Natasha Willis who helped Tori Dunlap of Her First 100k grow her Instagram and newsletter and revenue using automated DMs on Instagram was that one metric she looks at to see if someone is primed to work with them regardless of their follow account is how many comments they average per post.

According to Natasha:

And she's worked with accounts of 50,000 followers up to 45 million, which is a huge range. You can leverage your comment section to get into someone's DMs. Manychat for Instagram is probably the foundation that people are using to do this. I'm sure you've seen the posts that say, “Comment ‘grow’ and I'll send you a PDF on how to grow your own food at your house.” You comment “grow,” and five seconds later you get an automated DM with a link to download.

I don't use Instagram but I would love to see a Manychat for LinkedIn. Twitter has an auto-dm feature with Typefully. You can manually respond after the automated message begins the conversation and keep it going to add that touch of personalization, but depending on how big your audience is, they may not be feasible after a long amount of time. In the beginning, I do think it's important for not all of the process to be automated. There should be some level of personalization there. Using automation to start the conversation on LinkedIn has been really helpful at scale. The first message is typically automated, but the second message and following messages are always me personally responding to everyone who responds to me.

When you're posting, you should have a call to action of some kind that gets people to comment. You should also have a system for reaching out to people within your network that you're already connected with, no matter the platform, to follow up with them, and develop a deeper relationship with them. I personally try to have at least three call to actions that I rotate between on each post in the comment section. And to keep this simple for you, you could maybe choose one call to action per week that you're using in conjunction with what you're posting. So if you're trying to get more newsletter signups, your call to action could be related to getting people to sign up for your newsletter. But trying to get people to sign up for your newsletter, click your affiliate link, download your lead magnet, and listen to your podcast is a lot of different messages that you're sending people and it probably will get pretty confusing both for you and for them and harder to track what's working and what's not working.

So what does all this cost me besides the time that I'm using to create the posts that you see online? Budgeting for online communities really comes down to your time and your tech stack. Between beehiiv, Octopus CRM, Captivate, Obsidian, and Notion I spend probably around $500-$600 a year. I also use Canva for graphics, but I'm on a free plan there, so there's no extra cost. These costs are pretty straightforward and they only require me. If you're doing events for communities, that's a whole different beast. You have to budget differently for these and probably have help.

One of my connections on LinkedIn writes GenZTea and she wrote an incredible article about IRL communities. One thing that I really thought was interesting was the guy who runs Tropical MBA started his events by having members of his community volunteer to create and put on events all across the world.

He started off paying them just as a subcontractor as needed and then he reached a point where he just knew it was time to bring on a full-time person that was dedicated to running events for his community. He decided to amplify and elevate someone who is already in his community versus getting a dedicated events manager.

Tropical MBA has memberships ranging from $700/year to $5,500/year, which is a huge price tag. And then on top of that, the events are not free just because you're in the community, but you can only access them if you are in the community. So not only do you have to pay an annual membership, but you also have to pay anywhere from $1,000 to $3,500 per event. And he said they have up to five signature events a year. Jay Clouse’s memberships are in a similar range. I believe his smallest membership is just his courses, and that's about $700 per year. If you want entry into the Lab, which was originally capped at 200 people, is around $1,000 per year. And he may have a higher tier that gives more access to him. All of the events that he's done so far have just been tacked on to creator industry events that he was going to attend anyway, and where members of the lab are also likely to be. One of those was Create + Commerce, which is in Boise, Idaho. And that is Kit’s, formally Convertkit’s, annual email conference. They're community affinity events, not revenue-generating events.

For the business structure that Jay Clouse has around the Lab, that makes a lot of sense for him. If he's already getting people who are paying a thousand plus a year and he's generating. I think he said he's generated over $350,000 from the Lab. If he were to do more, that would likely stress him out. And he admitted as much, saying he would rather have time stress than money stress. There's also a third option, and I take a lot of inspiration from him. The person I'm referring to is Brett Dashevsky of Creator Economy NYC.

His business is built around brand-sponsored events that are recruiting events for his online community. So he does the opposite of Jay and Tropical MBA — he uses real-life events to create a community online. In his newsletter, he shares community perks which are affiliate links that people can click on to support him.

So there are a lot of different models here, and I want to try some IRL events. I would love to do a take on Sofar Sounds for live podcasting shows in secret venues, of course in North Carolina, but maybe in a city near you, and they will be capped at 15 to 20 people. Kept super small and intimate. I’ve also played around with a trivia night or game night. As someone who is pretty introverted and wants to create an environment where I can really feel comfortable connecting and talking with people, these feel most natural to me.

I care about my community having access to information and having connections to the right people. Creators who have physical products, digital products, or an e-commerce store may do really well appearing at other events occasionally rather than creating their own. There are great ways to build deeper relationships by attending and speaking at an already-established event.

Speaking at events is nerve-wracking, for me at least, but truly underrated for attracting like-minded folks to you. As an attendee, you also get to see what you like, what you don't like, what you want to implement for your events, and what you do differently at your events. One element that I think allows people like the guy from Tropical MBA to do so many high-ticket events is that he has help.

They do a lot of member-led events, and he also mentioned that he hired a speaker coach for members who were up on the hot seat for these in-person events.

All of that starts with a one-to-one connection.