This week, I hosted my first virtual summit. It was called the Membership Summit—and it was all about building a membership in 2026. You either got a lot of emails from me about it or somehow missed them. In either case, sorry!
It was amazing. We had nearly 4,000 people register, ~2,000 show up live at some point, and an overall wonderful experience. On Friday, I hosted a group Q&A just for folks who purchased a VIP ticket and ended up talking for three hours to get through everyone's questions.
One of the most surprising parts of the Summit, though, was the audience's response to a short story I told about how I've always struggled to fit in. Frankly, it's a big reason why I developed a knack for community building.
I wrote about this a few months back on my personal Substack, but thought I'd republish it here this week in light of the response I received.
'Tweener: The identity I never wanted
Every spring of my teenage years, I was measured and fit for new football equipment. They measured my height, my weight, the width of my shoulders, and even the circumference of my head.
“Hmm…” said the czar of pads and helmets as he measured my skull. “You’re a ‘tweener.”
This was the ruling every year. We were never quite sure whether I belonged in a medium or a large helmet—I was stuck in between. If we chose medium, I would deal with headaches from the pressure. If we moved up to large, it was a little too loose, which looked funny (a terrible way to look in high school), and lost some of its protective benefits.
I remember this seemingly innocuous comment, decades later, because it has described so much of my life.
***
My best friend growing up had a brother a year older than we were. For a few years, I found myself hanging out with his brother and his friends more than the kids my age—we just seemed to understand each other better. I’m hesitant to call it maturity (we certainly weren’t very mature), but hanging out with the older kids just felt more comfortable. Maybe it was growing up with two older sisters (one four years older, another eight years older), but I never quite felt like I fit in with my classmates. The close friends I did make were ‘tweeners of their own right, spending time in just about every social circle but really only belonging in our own.
This followed me to college, where I quickly discovered an undergraduate student club focused on entrepreneurship. I was a freshman, and the club was full of juniors and seniors who were all-in on tech (this was the period of Facebook, Uber, Airbnb, etc.) It was so cool just to be around them. They had big business ideas, and they were DOING them—in college!
Shortly after graduation, several of them moved to the West Coast (San Francisco and Seattle) to immerse themselves in startups. Many of them are now post-economic (i.e., they made enough to retire). I stayed involved in the club as I got older and they had graduated (I eventually led it as president), but I couldn’t recreate that magic. What’s more, I never quite felt like I was on their level to begin with.
In every season of my life, I’ve always been a 'tweener. I was virtually always the youngest person in the room, which came with equal parts exhilaration and isolation. I felt like I had somehow snuck into a space I didn’t belong in. I was always excited, but also a bit terrified that someone would ask, “How old are you?” When I’d answer, they’d always make the same face—a look that was equal parts shame and disbelief. Disbelief because I present as older, and shame because they believed it. I’ve maintained a beard since my early 20s in hopes of staving off the question entirely.
I’ve never outgrown this. Even today, I identify with the perspective of parents and people 5-10 years older than me. The audience analytics across all my content channels show my audience is typically 5-15 years older than me. My wife and I moved to a neighborhood where we seem to be the youngest couple.
I started my content business in 2017, which was both years ahead of most creators today but years behind the class of bloggers like Pat Flynn, Mark Manson, Tim Urban, or Maria Popova. In recent years, a new class of creators has blown the doors off on YouTube, Instagram, and TikTok, while I still find my way there. Somehow, I was both late to blogging and podcasting, and too slow to take social media more seriously.
One constant throughout all this time has been my ability to build community. Whether it was leading clubs, organizing in-person events like Startup Weekend, or online communities like SPI Pro and The Lab, I’ve always had a knack for creating space for people.
Maybe it’s because I’ve spent so much time feeling out of place that I really want to create a space where I feel at home.
My friend David Spinks shared this post, which I felt a little too personally:
The painful irony for community builders, though, is that when you play such a crucial role in the formation and moderation of a space, the community itself treats you a little differently. Not badly, but actually with a certain amount of respect and esteem reserved only for the leader(s) of that space. It’s kind, it’s flattering, but ultimately it actually creates distance between you and the rest of the community, which feeds into the same pattern of loneliness and isolation as before. So, by creating a space where you feel you belong, you actually create conditions in which just fitting in is more difficult.
I share all this because I’ve been thinking about friendship a lot lately.
When my wife and I were planning our wedding, one of the first decisions was how many guests to invite. Once family is accounted for, the question comes down to friends—and that forces some uncomfortable clarity.
What is a friend? Depending on how you define it, I may have two thousand friends—or maybe I just have two. As I’ve gotten older, I’ve realized that while my outer ring of friends has expanded, my inner circle seems to have gotten much smaller.
Now that we have a daughter and are growing our family, I’m noticing that my “village” is actually pretty small. Our neighbors are friendly, but none of them are friends. Their kids are several years older than ours, or they’re empty nesters.
By spending a decade striving, I deprioritized many friendships. Of course, I’m friendly with many of the people I’ve met over the years, but I haven’t made many new lifelong friends. Worse, I lost touch with some of my oldest friends—and you can’t make new, old friends.
So, after a decade of helping people become better creators, I find myself, as a creator, pulled to explore how to become a better person. Instead of connecting with an audience, I want to better connect with myself and the people around me. Maybe this identity of being a “tweener” isn’t something I need to hold onto. Maybe through different actions and priorities, I can actually feel comfortable belonging.
Speaking of building community, I do believe I have a knack for it. And in July, I'm putting that talent to use to help YOU do the same.
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.
By the Sendoff call on August 3, you've built (or fixed) the base of a membership with:
a Promise clear enough that someone knows in three sentences whether it's for them
a launch plan for your situation
a strategy for retention and renewal
You'll walk away with real, paying members. Just like Marissa:
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.
