MySpace Is a Reality Check

Nobody warns you that one of the hardest parts of building a company is deciding what kind of person you want to become while you're building it. It doesn't happen in one dramatic villain speech. It happens in a hundred perfectly reasonable decisions.

Like most founders, I can tell you what makes The Merriment different. I have frameworks I'm proud of, ideas I believe in, and a point of view about communication and AI. For a long time, I thought my job was to have the right answers. Now I spend considerably more time thinking about the kind of creator I want to become while pursuing the things I believe in.

Then a LinkedIn notification interrupted me.

Okay, I'm about to do that thing where I pause the movie to explain the backstory. Trust me - this context makes the next scene a lot more interesting. In case you missed the latest wave of internet nostalgia, here's the short version. In a recent documentary about MySpace, filmmaker Tommy Avallone interviewed current owners Tim and Chris Vanderhook about their plans to bring the platform back as an algorithm-free alternative to modern social media. 

Like a lot of people, I found the idea fascinating and couldn’t help wondering what that might look like. My inner monologue gladly took it from there. 

Fast forward a few days, Tim Vanderhook accepted my LinkedIn connection request. The notification lasted about five seconds. Afterward, I laughed. Apparently, that was all my brain needed to start writing scenarios involving myself even though reality hadn't agreed to anything yet.

First impressions almost always begin with overthinking. Once they do, our minds become very talented at filling in information we couldn’t possibly know. 

Let’s name a few.

"Tim accepted your connection request" is an invitation to begin rehearsing every possible future conversation. I should message him. I should spend forty-five minutes thinking about messaging him, which is clearly a completely different activity. 

Then like a floodgate, the irrational questions commence. 

If I message him immediately, does that seem eager? If I wait too long, does that seem disinterested? And is there a mathematically perfect amount of time to wait that communicates confidence without accidentally suggesting I disappeared into the woods? 

Once you’ve decided you’re probably going to send a message, attention shifts to all the tiny details that somehow feel capable of ruining everything.

A few examples might include: Wondering whether sending it at 8:03 a.m. feels ambitious and 8:07 a.m. somehow feels desperate. Reading it one last time and wondering if you sound like a completely different person than the one who wrote the first draft. Deleting an exclamation point because it suddenly feels too enthusiastic. Debating whether "Hi, Tim" is too casual while "Hello, Mr. Vanderhook" somehow sounds like you're emailing your high school principal. And, somewhere near the end, wondering whether you're demonstrating confidence...or auditioning for a true-crime documentary.

Buried underneath the lunacy is the realization that first impressions have a funny way of making twelve words feel responsible for twelve years of your character. Which is slightly unfair because by the time anyone reads your first message (or worse, no one ever does), they have no idea they're reading version seventeen or how much thought went into twelve words.

It's remarkable how much interpretation happens before there's anything to interpret. And somewhere between version twelve and version thirteen, another thought quietly interrupted all the others.

My first instinct wasn't about Tim. It was about me.

The uncomfortable part wasn't imagining what his success might mean for me. It was deciding whether that moment of honesty would change what I did next. 

I stopped writing. Then I sat with discomfort. Not because I'd decided not to reach out. Because I knew I wasn't ready to. The draft wasn't the problem. My relationship to the draft was. I wasn't trying to understand Tim yet. I was still trying to position myself. Those aren't the same thing. And no one is interested in pretending they are.

And this is where things get complicated when you're building something of your own. When you are part of what you're selling, where is the line between introducing yourself and selling yourself?

Consultants, authors, speakers, founders, coaches - none of us can completely separate ourselves from what we offer. Our judgment, perspective, experience, and personality are part of the value. It's difficult to leave yourself out of the sales pitch when, inconveniently, you keep showing up as part of the product.

The goal isn't to pretend we don't have an agenda. The goal is to make sure our agenda isn't the only thing in the room. And even deeper, my discomfort felt strangely familiar. I'd been here before - another time when I was so focused on an opportunity that I hadn't stopped to understand what I was hoping to become part of. 

I don't think these feelings are limited to founders, either. My father watches Survivor, and somewhere around the third episode, he stops watching people survive on an island and starts developing his own survival strategy. What he'd build. Who he'd trust. Which alliance he'd join. At that point, it feels reasonable to keep the phone nearby in case the producers call.

Human beings have a tendency to insert themselves into stories they haven't actually been invited into. I experienced this more than two decades ago when I wrote an open letter to Shane Snow after applying for a job at Contently. 

At the time, I didn't know nearly as much about the company as I thought I did. I knew enough to want the opportunity, but not enough to understand it. Youth is wonderfully efficient that way. Sometimes confidence arrives several years before context.

The application invited candidates to share their story. I couldn't figure out how my résumé was supposed to tell mine, so I wrote an open letter instead. It was unconventional. It worked. Shane responded. We talked. Naturally, I took this as confirmation that I was a visionary rather than someone who had an idea, tried it, and was fortunate enough to receive a gracious and curious response. For years, I told myself it was a classic case of fortune favoring the bold.

Ironically, the original open letter included one of Shane's favorite Richard Ayoade quotes about preparing to eat your own words. More than twenty years later, it turns out I was the one setting the table.

Over the years, I read Shane's books, followed his writing, and listened to him talk about storytelling and the company he'd helped create. The more I learned, the more I understood what I'd missed the first time around. Great storytelling wasn't simply about getting someone's attention. It was about earning it.

I had gotten Shane's attention. I hadn't yet taken the time to understand what Contently was building.

Twenty-something me had an open letter. Forty-something me had seventeen drafts of a LinkedIn message. Growth is not always linear. Of course, for all I know, the other side of this story was nothing more than someone clicking “Accept” on LinkedIn. Meanwhile, one completely ordinary interaction gave me enough material for an existential inquiry into the human condition.

So rather than pretend I understand the Vanderhooks' vision from a documentary and a handful of things I've read online, I'll leave room for what I don't know. What they've shared publicly is enough to make the idea interesting. Beyond what’s been shared publicly, their story is theirs to tell.

And maybe that's a good reason not to rush to place ourselves inside it. Judging by the number of Reddit threads devoted to the subject, plenty of people are eager to know what's coming next. The internet has questions. Many of them. But curiosity isn't an invitation, and interest doesn't automatically create a role. Sometimes someone else's story gets to remain theirs until they decide who to invite into it.

Perhaps all that should be offered is a creator's blessing:

May every creator encounter people whose curiosity comes before strategy, whose questions seek understanding, and whose ambitions always leave room for human connection.

For those of us still becoming the creators we hope to be, may we remember to offer the same.