This letter is part of our fourth edition of Creator Mag. To read the rest of the magazine, click here.

I spent the whole day in my head / Do a little spring cleanin’ / I’m always too busy dreamin’ – Mac Miller, “Good News”

In late May, I received a text I’ve been thinking about ever since.

You should write a book one day, my dad wrote. A Michael Lewis style romp through the creator economy.

One of the things they don’t tell you about when it comes to creative pursuits – or any venture as a solopreneur, really – is the sheer amount of decisions one has to make on a day-to-day basis. Those decisions can make the endeavor exhilarating yet exhausting, freeing yet lonely. It’s less about whether or not you’re making the right decisions every day – it’s more about making each decision with confidence in the plan and conviction to see it through.

My dad is often the first person whose opinion I seek when I have a big decision to make. I’ve called him a lot over the course of the last year to keep him updated and get his perspective on the pressing topic of the month. While he doesn’t have any experience in the media and entertainment industry, he worked in the corporate world for a long time, learning about business and, therefore, people. It also doesn’t hurt that he cares about me a lot, and I know everything he says has my best interests at heart.

The text in May came after I met an entrepreneur who is well-respected in the creator space. This entrepreneur showed up to our Zoom fifteen minutes late, upon which he proceeded to rapid-fire tell me everything I could be doing better with Creator Mag. And while he gave me some solid feedback, I tend to remember that call for a different reason. Because during the couple moments where he paused to let me speak, let’s just say he started vigorously digging for gold, all while his camera was still on.

I called my dad afterwards, and we laughed off this bizarre encounter over the phone before catching up on the important stuff. But ever since then, I’ve been keeping track of some of the strange moments and idiosyncrasies I’ve observed in this fascinating, fast-paced thing we call the creator economy.

Let’s just say that in one year building the magazine, I’ve collected enough stories to write that novel, and then some.

Whether those stories ever see the light of day is a conversation for another time. Nevertheless, even though it’s easy to get weighed down on the day-to-day, questions creeping in with every additional decision, I have to remind myself that this collection of experiences is worth more than any future book royalties could ever be.

In a recent episode of Colin and Samir, author Ryan Holiday shared his belief that “writers should live interesting lives.” He wasn’t stating that writers should approach their occupation through an elitist, holier-than-thou lens; on the contrary, he thinks most scribes could afford to venture out more frequently in a direct effort to improve their craft. The only way to gain new perspectives and insights worth writing about, Holiday says, is to push one’s boundaries past their office walls.

While I don’t believe I’m anywhere close to reaching “interesting life” levels, I’d like to think that the time I’ve spent with all sorts of creators – and the in-between moments within the greater community – have helped me strengthen Creator Mag’s editorial slant.

Besides, there’s only so much perspective to be gained when trapped inside one’s walls – or head.

I’ve been listening to a lot of Mac Miller lately.

Given how many times I’ve played his music as I write, I might as well owe the late rapper a royalty check from our sales.

The reason I connect with Mac and his music so much might be because of the birthday, January 19th, that we share. The more realistic explanation is the themes he aimed to explore through his creative work, along with his natural disposition. Friends and family described Mac as someone who couldn’t stop thinking all of the time, constantly agonizing over every small detail and sinking deeper into his process. The rapper was thrust into the limelight at 18, and though the outside world deemed him to be a thorough (albeit messy) success story all the way up until his unfortunate passing just eight years later, he often found it hard to see what they saw.

Mac wasn’t one to give many interviews, as he preferred to express his thoughts and feelings through his music and leave the rest up to interpretation. His last two albums, Swimming and Circles, explored how he felt stuck in life, and the process of learning how to move on from his problems in order to improve himself as a person. The albums join to form a continuous loop, as the former starts right where the latter ends, showcasing the constant state of reinvention we go through as we move forward in life.

A text conversation with my dad from May

When making all of those pesky decisions within a creative venture, after a months-long sprint, we oftentimes have to go right back to the drawing board. For a product – media – that’s so inherently outwards-facing, it can be difficult to explain our progress to outsiders (and even close ones) when it seems like we’re stagnating, reverting back to our original state. Even worse, we don’t want to appear as if we’re acting erratically as we rebrand, redefining and refining our creative output.

The boring version is quite simple. A lot of building the thing – whatever that thing is – consists of testing a hypothesis with the information we have, then iterating from there. Still, stop me if you’ve ever heard the words “iteration” and “sexy” in the same sentence.

Maybe I’ve been way too stuck in my head because I’ve been publishing Creator Mag for almost a year now, and with that fundamentally arbitrary anniversary comes all sorts of preconceived notions regarding what registers as meaningful progress. The truth is, I took a swing last fall, with the crazy-bordering-on-irrational belief required to launch any sort of early-stage venture. And when the doubt starts to seep in at a more frequent clip, it’s hard to not let it overcome pretty much everything, regardless of what the rational voice has to say about all of the tangible small wins we’ve experienced.

In the creative world, sometimes, the only way we know how to flush all of those swirling thoughts out of our head is through our art. For Mac, that was his music. For me, it’s my writing.

More specifically, my aim since the beginning has been to use these letters as a space to share the human side of making this damn thing, the vulnerabilities and insecurities that are just as much an ingredient as the dedication and irrational belief. It’d be easy to wield this space as a tool, a mirage, telling you – the reader – how this is going to be the next hundred-million-dollar media startup, and read off a list of all the names who have come into our orbit in the last year.

But that’d be doing all of us a disservice. We’re not here purely to profit off the names and likenesses of creators we collaborate with. There’s more to our mission than that.

After publishing Mag.3, I sent out a feedback form to readers, asking questions about the thing’s quality and value as they perceived it.

For any startup, asking for this type of constructive criticism requires putting the ego in check in an effort to improve our underlying product. And I’m glad I did, because one suggestion has guided a lot of my thinking towards our next phase:

I think you have to consider what "meta creator" media companies in the space can / should be doing better, and go after that…it will need to be about more than just these "drops" from time to time, but actually starting to consider how people want to interact with the stories behind the stories.

It makes sense. Humans connect with other humans. Audiences nowadays expect to form a connection with not just the story, but the storyteller themselves. That’s why vlogs have evolved over the years into an incredibly popular and intimate vehicle to launch creator careers across industries.

Plus, the stories I’ve chosen to tell up until this point have been serving two purposes: to explore the contemporary human condition, while also sharing unique roadmaps in creative entrepreneurship. We’re contextualizing internet-centric societal trends through the lens of the curators and tastemakers of the moment, charting the rise of niche media businesses – now being built with a democratized slate of tools – and the individuals who innovated through the power of their voice.

In less abstract terms, as creator careers become the New American Dream, I believe it’s important that we not lose sight of the real people behind all of the numbers and hype as we discuss these new-age businesses, both those in front of the camera as well as the small armies they’ve raised. With Dylan Lemay, ten years of scooping ice cream showed how no one’s truly an overnight success; mix in a defined niche and first-person film style, and you’ve got one hell of a sundae. With Cleo Abram, her experience at an established media company taught her world-class production skills, instilling confidence in an independent venture that was supported by interactive audiences from the jump. And with Steezy Kane, meeting viewers where they’re at – pranks – offered him a springboard for a career in Hollywood, as he grew up in front of a community that will now follow him wherever he goes.

Behind-the-scenes of our shoot with Anthony Potero (Photo by NGL)

Still, at a certain point, I do question how to approach the conclusions with each story. How much more is there to say about different creators’ journeys? How many more insights are there to glean? How can we evolve from the well-worn clichés of entrepreneurs working hard and pulling themselves up by the bootstraps to deliver authentic commentary, commentary that can lead to meaningful dialogue about our rapidly-digitizing world?

That’s where I keep coming back to me, and us. It’s the meta thing – if people want to invest in the storytellers just as much as the story itself (if not more), shouldn’t we take you along for the bumpy ride in building a damn magazine, getting a peek into the “interesting” life Holiday talks about? Shouldn’t we do a better job of showing you those vulnerabilities and insecurities so you can feel like you’re a part of our journey when the small wins and irrational beliefs pay off in a big way? Isn’t that what the creator revolution is all about?

The balance that’s then necessary to strike is between prioritizing trust with the creators we cover (a focus since the onset) and inserting ourselves into the world we’re crafting (a delicate feat without coming off as clout-chasers). It’s easier said than done; after all, this whole thing was founded off the hypothesis that creators deserve to be taken seriously, and we therefore don’t want to push our subject out of the spotlight we’ve set up.

Nonetheless, iterating on that original hypothesis is, again, necessary. A re-evaluation of our approach to video is the first thing on the docket, figuring out how to engage audiences that might not be ready to move all the way down the funnel and consume our longform writing. Along with that, a hard look at our distribution is in order, especially if we keep our drops quarterly to ensure quality yet also want to engage folks in between seasons. Events and activations are a route that brands have shown interest in collaborating on; figuring out how to enhance our stories through physical spaces is a daunting hurdle I can’t wait to tackle.

Per usual, I’m getting ahead of myself. Directly in front of us, this season features a collection of stories and essays that aim to tackle the circular nature of creative pursuits, finding beauty within the process of swimming. The first cover, a self-taught musician who didn’t find his true calling until he was in his thirties, yet he grew and sold an award-winning podcast to one of the world’s biggest streamers – all while raising a family. The second, a sketch comic born out of 2010s meme culture, taking several sharp pivots with his million-subscriber YouTube channel – only to publicly delete it and start anew.

Past this season, there will be time to refine our output, and redefine what it means to run a creator-centric magazine. With those decisions will come a whole new slew of problems to solve. Who knows — maybe I’ll be allocating more time to Premiere Pro and After Effects than Google Docs; video editing was my first love, and I have a strong feeling that you’ll soon see some vlogs emerge from the past several seasons.

And if the thing that comes out of all of this – the flights and train rides and photo shoots and trips to USPS and hours and hours of interviews, all of which I could’ve just mailed in at any moment yet chose to undertake in pursuit of something more – amounts to nothing more than a Michael Lewis romp through the creator economy, then so be it.

At least I’ll be certain it was worth the swim.

Coverage from Creator Mag.4 is coming soon! You can join us for the drop by signing up below.

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