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If you caught this chat live on Thursday, you know my chat with Sarah Elizabeth Hill didn’t bother with small talk. We dove straight into the deep end.
Sarah writes, produces, and runs Bobi Media. She took $400 and built it into an agency that works with Oscar winners, Deepak Chopra, and brands you see on billboards. On paper, it looks like she just levitated to the top of New York media. Spoiler: nobody floats in this city. You claw your way up, or you get chewed up.
But on Draw Me Anything, we don’t do glossy. We go straight for the mess under the sink. We talked about the invisible sacrifices—the stuff nobody puts on LinkedIn. The reality of trying to keep a business alive in a city that’ll eat you for breakfast if you blink.
Here are a few things we unpacked in the first half of the conversation…
The Reality of the Creator Grind
Turns out, creative brains are actually built for business… if you can keep the lights on, swallow your pride, and remember to actually send the invoice. We talked about those early days, stretching that initial $400 investment, and the sheer, unadulterated panic of realising you are the only safety net you have.
But that same tunnel vision required to build something out of nothing? It’ll burn you out faster than a …ugh. I’m too exhausted. I can’t think of a simile.
Sarah didn’t sugarcoat the human cost of the hustle. She talked about the time the grind nearly broke her completely:
“I was working so much I wasn’t leaving my desk... I hadn’t developed my habits and so was hospitalised, because I couldn’t get my brain to stop spinning.”
Building the “Infrastructure” of You
When your brain is your business, a breakdown isn’t just a personal crisis; it’s a corporate bankruptcy. We talked about the absolute necessity of building a team. And I don’t just mean hiring a virtual assistant. I mean building the infrastructure of you: Accountants. Therapists. The guy who tells you to stop staring at the screen and breathe. All of it.
Sarah made a brilliant point about treating your physical and mental health like non-negotiable client meetings. If you don’t carve out an hour to lift something heavy, walk around the block with the dog, or just stare at the ocean on a Friday afternoon, you’ll crash. The city doesn’t care. The algorithm doesn’t care. You have to work to live, not the other way around.
The “Hell Yeah or No” Rule
New York is an all-you-can-eat buffet of opportunities, which means the most dangerous thing you can do is say “yes” to everything. We dug into Derek Sivers’ famous rule: if it’s not a hell yeah, it’s a no.
“You have to protect your time like it’s the last glass of water in the desert. If you don’t aggressively filter what comes across your desk, you end up building someone else’s dream while yours slowly starves.”
The only way to keep your time from getting mugged by every shiny offer is to know your “Big Why.”
The Reframe, the Churn, and the AI Survival Guide
In the second half of the stream, we got into the stuff that actually keeps you up at night. The heavy hitters. The things we usually only talk about at the bar after the gig is over.
We cracked open the New York Churn- the endless, exhausting loop of people showing up, burning out, and getting spit back out to the suburbs. Sarah handed me a new way to look at the concept of “personal sacrifice” that completely rattled my brain. It made me rethink what it actually takes to stick around, keep your friends, and build a life here that doesn’t fall apart the second the rent goes up.
And then, we finally wrestled with the elephant in the room: Generative AI.
Sarah’s new book, Chat Sh!t Crazy, is all about using these tools to sharpen your sense of self, not erase it. Instead of complaining about the robots taking our jobs, we got into the weeds on how to use AI as a mirror for your own blind spots. We talked about how to survive the AI flood without losing your soul (or your rent money.)
To my free subscribers: If you want the whole thing -the raw, uncut hour- you’ve got to step inside the studio. The full replay is for the folks who keep the lights on and put dog food in Morris’ tummy.
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