Building silly little projects off the side of my desk
What if you hired a creator-in-residence?
I, like all you fellow gifted-kids-turned-laptop-workers, can’t imagine a life where I’m not creating new things. For a particular type of person, no degree of consumption, neither in quantity nor quality, can fill the gaping hole left by lack of creation.
It’s a compulsion.
I love riding the waves of our collective unconscious, speculating around what discourse might bubble up next, riffing on a concept to get ahead and around it, shitposting on Twitter to test different angles, moodboarding art directions and worldbuilding. In short, I, like many of you, was born, bred, or made in some other way with this delusion that I can, in a small way, disturb the universe.
I spent a decade cycling through anonymous pen names, building silly little projects off the side of my desk to scratch this itch where various full-time jobs couldn’t. The reality is that it was an integration problem, an inability for my “work-self” and “creative-self” to co-exist, both philosophically and pragmatically. But I’ve now had some space away from a full-time job for a while, and I’ve been wondering: What could an integrated role, or life, look like? Could a sensitive young man/woman scratch the itch for real creativity, while still fitting into the realities of being on someone’s payroll?
You might think that working in a broad content or social media role would accomplish this, and, with the right constraints, maybe it does. And maybe it doesn’t matter! We with the hubris to create things are not owed anything, certainly not a steady paycheck and an outlet for artistic dreams. But, just to humour the thought experiment, for a role like this to exist and actually make sense for all parties involved, I bet it would look something like a “creator-in-residence.”
It would be an employment relationship that prioritizes creating new IP and shares in its upside.
Prioritize New IP — Create an adjacent media property
The line between “employee” and “content creator”1 continues to blur. Eugene Healey has a fantastic video on employee-generated-content, but I don’t think that trend is really getting to the heart of what I’m talking about with the “creator-in-residence.” Companies like Starbucks and Ulta are smart to incentivize their employees to post content, but in this context, the act of creation is still rooted in the company’s products. The Starbucks creators talk about coffee, the Ulta creators talk about makeup. For a hopeful creative, a more interesting version of this job would be to abstract away from the product that your company sells, and towards the broader thesis statement or problem set it covers. Then, you give the creator-in-residence the freedom to create new IP within those constraints. Just to illustrate: if the Starbucks brand is more about community than coffee, what if their creator produced and starred in a short-form show about a group of laptop workers who hang out in a coffee shop?
One of the best examples of this is Macy Gilliam’s “Out There” show with Morning Brew, a standalone series that lives within the media company’s broader YouTube channel. She started working there in ~June 2023, but in April of this year, her agents at UTA2 negotiated her a new contract, in which Morning Brew continues to own the show IP, but gives her a cut of all show revenue and traffic to her own socials. “It’s a really safe way to be an entrepreneur…” in her own words.3
Pushing creator tendencies on your employees has long been a topic of contention in legacy media, but it’s finding a new foothold in tech.4 Ara Kharazian is fintech company Ramp’s “In-house Economist,” producing “public-facing economic research with first-party data.” He isn’t writing about Ramp and its slate of finance products. He’s using Ramp’s data to write about the things that will be enjoyed by those who might buy Ramp’s suite of finance products. Stripe just hired a Chief Economist. Anthropic had a recent job posting up for a policy writer. Opal spun off its own edutainment creator to talk about screen time.
A creator-in-residence is less about creating content about your company and more about building a media property around the mission of your company.
Share In The Upside — Compound their personal leverage
People start side hustles for the chance at unlimited upside, and they start them while they’re still employed for the downside protection. Startups have long known that equity compensation is one way to get employees to go “all-in” on their jobs — they’re meaningfully invested in the long-term success of a business, but they’ll still collect a paycheque as long as they stick around. A “creator-in-residence” role, then, might be another way to strike this balance that doesn’t rely on future equity liquidity.
The exact execution depends on the business model. For Macy Gilliam, it makes sense for Morning Brew to sell ads against her show and then cut her into the pie. Their entire business model is built around ads! For Ramp, though, it probably doesn’t make sense to sell ads5 against Ara’s newsletter, but maybe it makes sense to bonus him on attributable booked demos or something of that sort. On the other hand, it might not make sense for Morning Brew to let Macy own the IP to “Out There”, while it might make sense for Ramp and Ara to share ownership over the email list that he’s building (privacy laws permitting.)
This isn’t exactly the creator-in-residence model, but another proof point is Money With Katie. She was making something like $250K in topline revenue as an independent, but since her acquihire by Morning Brew in 2022 she has at least 4x’d her business. Practically speaking she still presents like an independent creator to her audience, separate IP and accounts and all, but she now has a shared backoffice with the rest of Morning Brew. They get to bundle her and her audience as a complementary ad product to their existing advertisers, and she gets to offload the operational work to focus on what she does best: create.
The key is to strike a happy medium where the business wins and the creator feels that every incremental unit of work is building their long-term personal leverage.
It is deeply satisfying to be an independent creative, but as I’ve become intimately familiar with over the last ~month since launching this newsletter, it is also grueling. If companies are looking to evolve into media empires, and creatives want to make good art and build their personal leverage, the creator-in-residence model feels like the rare opportunity where both are actually aligned.
Thanks for reading! I write about branded entertainment, exploring how brands and startups become media companies.
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That painful flattening of artistry.
Having a talent agent negotiate a contract with your current employment is fascinating in and of itself.
I guess there’s something to be said about “safe” and “entrepreneur” not belonging in the same sentence. But, if done right, this seems more similar to “derisking via venture capital” than “derisking entrepreneurship entirely.”
Growth stage tech companies are specifically well positioned to take a risk on this sort of experimental role. When someone like Suno raises $250M on $200M ARR with a headcount of <200, surely they have some room to spare on some creative experimentation. Ramp literally has a Head Of Creative Experimentation, which is something you’re far less likely to see from a bootstrapped DTC brand eking out 10% net margins.
It would be interesting if they “bought” ad space on his newsletter for Ramp ads, and then just paid him a standard CPM based on the size of his audience to incentivize him to keep growing.