I remember the moment it first hit me—this magic that a string of words, arranged just right, could make someone on the other side of the world do something. It felt like discovering a secret superpower. I’d watch internet marketers piece together persuasive copy, then see total strangers respond—clicking “Buy Now,” signing up for email lists, even handing over big sums of money. It was almost like they were casting spells, and the “spell” was simply a cluster of perfectly chosen words.
I became obsessed: how far could this power really stretch? I wanted to test the boundaries of what you could create—or control—with nothing but typed sentences.
Marketing reminded me of my earliest days learning to code. If you typed the right commands in the right order, the machine would do exactly what you asked. Pure logic, pure precision—a deeply satisfying sense of control. Marketing worked the same way, but with human beings on the other end. Write the right copy, hook into the right emotions, and people would respond—predictably, almost like code. But also not like code, because people are, you know… complicated.
The Skinny Jeans Trojan Horse
In 2006, I decided to put this “word magic” to the test in my small gym, where I had a few trainers on staff. I tried all the standard tools—Google ads, YouTube videos, landing pages, lead magnets. Some worked, some didn’t. But the real game-changer? A physical newsletter I mailed out monthly to all my clients—active and inactive. Sure, email was faster, but there was something special about a tangible piece of mail—personal, tactile, and almost impossible to ignore.
But let’s be honest: I wasn’t after practicality or efficiency. I wanted something memorable—something that didn’t just sell memberships but sparked conversations. A Trojan Horse stuffed with irreverent marketing genius—a stealthy way to weave myself into my clients’ lives without feeling pushy or salesy.
This wasn’t a gimmick; it was a purposefully designed tool: a conversation starter, a “you gotta check this out” moment that made it easier for people to talk about me.
I called it Skinny Jeans, and it was built on everything I’d learned from direct response marketing: purposeful stories, connection-creating testimonials, and clever persuasion techniques that made it feel personal. It wasn’t slick or glossy—it had a deliberately “homemade” quality. That was intentional. Honestly, it probably would’ve been faster and easier to use a polished, pre-built “newsletter” template. But making it ugly on purpose took more thought—and more time. I wanted it to feel like “WTF is this?”—approachable, maybe even a little rough around the edges. Like something you’d casually flip through at a friend’s kitchen table. The kind of thing that sticks with you precisely because it’s different.
How Skinny Jeans Worked Its Magic
One month, I ran a tongue-in-cheek testimonial from a returning client who swore the gym could’ve saved her marriage—and her career—if only she’d stayed. Instead, she left, but now she was back, remarried, and supposedly rich. We hammed it up, leaned into the absurdity, and it worked: within 45 days, 15–20% of our inactive clients rejoined.
People loved it. They’d bring Skinny Jeans to work, share it with friends, and use it to explain our weird, dark, loud, and fun facility in ways I never could. One client—a popular local dentist—left it on the coffee table in his waiting room every month, where patients flipped through it while waiting for their appointments. It sparked conversations, brought back lapsed clients, and generated referrals—all without me ever asking directly.
Hands down, Skinny Jeans was the best thing I ever did for my gym.
That newsletter taught me something fundamental: persuasion isn’t just transactional—it’s relational. Words don’t just sell; they create context, stories, and connection. It wasn’t about filling gym memberships; it was about building a shared language, fostering community, and proving that well-chosen words can do more than move people—they can bind them together.
Marketing as a Personal Identity Shaper
As I dove deeper into marketing, it wasn’t just the external results that fascinated me—it was the sense of self-agency it gave. It felt like learning a new language, one that made me think, “Wow, I can make things happen.” Instead of sitting around waiting for opportunities, I realized I could create them—with nothing more than a well-crafted message or campaign.
What surprised me most, though, was how marketing blurred the line between me and my brand. Especially as a solopreneur and public-facing figure, it became impossible to separate the two. My personal quirks, my humor, my worldview—all of it bled into my marketing.
At first, I tried to keep them separate: work identity in one box, personal identity in another. It felt “professional.” But the more I refined my marketing, the clearer it became: People don’t stick around for perfection. They stick around for personality—specific quirks, weirdness, and the way you see the world.
When I stopped treating marketing like a polished front and started letting the unpolished, human parts shine through, something clicked. It didn’t just feel better—it worked better. The same stuff I thought I needed to hide? That was what people connected with most. Turns out, showing the rough edges wasn’t a liability—it was the whole point.
Personal Growth Through Persuasion
Learning marketing tools—like persuading people to sign up or take action—came with an unexpected side effect: it reshaped how I interact with others.
Effective persuasion demands truly understanding the person you’re trying to influence. It means listening deeply, caring about their situation, and thinking critically about their needs. Even if you don’t fully feel it, showing you understand can be enough to build meaningful connection.
What I didn’t expect was how much marketing would sharpen my ability to understand people—not just in business, but everywhere. You can’t write compelling copy or craft effective campaigns without understanding your audience: what they want, what they fear, what they struggle with—even the hazy, unspoken beliefs they carry. If you can describe their problem better than they can, they implicitly assume you have the solution.
Marketing, oddly enough, became a kind of empathy training disguised as business. I started noticing emotional cues I’d missed before—not just in campaigns, but in conversations. Someone might say, “I just feel stuck,” and instead of launching straight into solutions, I’d ask, “What does stuck mean?” Seems obvious now—“No shit, Sherlock”—but honestly, that wasn’t natural to me. Maybe you’re more emotionally evolved or just a better person, but for me? That skill—listening for what’s unsaid—was a direct byproduct of studying marketing.
And because marketing provides measurable outcomes, it gave me a way to track how well I was connecting. If a campaign performed better this week than last, it often meant I’d sharpened my understanding of the audience. That’s the magic of marketing: it’s a skill you can refine, and the results make your progress impossible to ignore.
When Clients Resist ‘Salesy’ Marketing
A lot of clients I’ve worked with come to me because they need marketing help—selling a course, launching a program, or getting their ideas out into the world. But under the surface, there’s almost always this resistance. One client admitted, “I don’t want to feel like I’m tricking people.” Another told me outright, “Marketing makes me cringe—I don’t want to come off like a used car salesman.” It’s like they’re searching for some magical, frictionless way to sell without it feeling like selling.
What’s been the most rewarding for me is seeing how their perspective shifts as we work together. They start out hoping I’ll give them some kind of shortcut—a way to make marketing effortless, invisible. But what they often realize is that the best marketing doesn’t feel like selling at all, because it’s grounded in something real: their perspective, their stories, their connection to the people they want to help.
And when that clicks—when they see marketing not as manipulation but as a way to clarify and connect—it changes everything. They go from “I have to sell this” to “I get to share this.” That shift is huge.
You don’t need the perfect campaign or strategy to start. You just have to show up with something honest—an idea, a story, a stance—and let the work build from there.
Evolving the Craft: Beyond Control, Toward Real Impact
These days, I’m still amazed by how a few well-chosen words can make something happen—a purchase, a sign-up, or even a shift in how someone sees the world. But my relationship with marketing has evolved. Back when I first started, it felt like control: write the right words, get the result. And yes, control is still part of it—but now it’s layered with something else. Not just moving people, but aligning with them. Not just getting results, but making sure those results actually build something real—something that lasts.
Take Skinny Jeans, for example. It wasn’t just a quirky newsletter. It was a way to create real connection—to remind people that the gym wasn’t just a place to work out; it was a part of their lives. And the fact that it was physical, tangible, a little rough around the edges? That’s what made it stick. People didn’t just read it; they shared it. They talked about it. They brought it to work, left it on coffee tables, and used it to explain why they loved the gym in ways I never could.
I’m still fascinated by how marketing works—why it works—and the endless ways you can use it to create something meaningful. That initial awe I felt when I realized words could move people? It hasn’t faded. If anything, it’s sharper now. But these days, it’s paired with a deeper respect for the responsibility that comes with it—and a sharper focus on using it thoughtfully.
Not just as a lever to pull, but as a tool for sharper ideas, stronger relationships, and real clarity. And honestly, maybe it’s time to bring back a print newsletter. Something tactile, personal, and impossible to ignore—just like Skinny Jeans was. It might work even better now than it did in 2006.
If you’ve ever felt that instinctive cringe toward marketing—I get it. But there’s a way to do it that feels honest, even liberating. Maybe it’s a quirky newsletter, or maybe it’s something completely different. The point is, you don’t have to sacrifice your humanity—or your sense of fun—to grow your business.
Dude. This is fucking sick. I had substack read it to me while driving home — the guy did a really nice job! – and was feeling it the whole way through.
I don’t remember the exact context, but I do remember a couple years ago you said something like you weren’t sure what your magnum opus was going to be, but felt like you had one coming. My sense, for what it’s worth, is this arena could be it. Or at least, and probably of course, I really vibe with it.
I also feel like it’s something you’ve been doing and appealing to for a long time, if not just implicitly.
Such a good one, you should share an old copy of skinny jeans !!! I wanna read it! Ever since working with you, I made that shift from trying to curate the perfect emails to being more messy and showing personality - something I was resistant of- and it’s def changed a lot about how people respond to me and how I feel about my writing. Also, the selling part has been such a process, I loved hearing about the shift of the selling process because I feel like that is getting easier too since I’m curating more offers that make sense for me🤣. Also love the piece when you ask someone what stuck means - I feel like you’ve done that with me a few times and that has been super helpful.