Will Trowbridge didn’t know how to start an agency when he started Saylor. That turned out to be an advantage. While most founders came up through holding company ranks or split off with former colleagues, Trowbridge had something different: a decade in entertainment marketing and a growing conviction that social media was about to become everything.
From streaming comedy to startup chaos
The origin story starts with love letters. After leaving Netflix in 2021, where he’d run their comedy brand Netflix is a Joke, Trowbridge sent personal notes to everyone he knew at the company. Not because he was planning to start an agency—he didn’t know that yet—but because he sensed those relationships would matter.
“I had a feeling that that network and that community was going to be really important in the future,” Trowbridge explains. The month spent fielding job offers gave him clarity about what he’d miss from Netflix and how he approached work in general.
The obsession factor
Here’s what Trowbridge learned about himself: he likes to obsess over his work, and he expects that work to pay him back tenfold. If it doesn’t meet his obsessive level, he resents it. Simple math said he’d never feel that way unless he started something of his own.
His entertainment industry friends held the marketing budgets. He’d worked with plenty of agencies and production companies, so he knew what he liked and what frustrated him. That gave him confidence he could build “an agency that I would have wanted to work with, and that my ultimately, all my friends and colleagues would have trusted, inherently because they knew me.”
YouTube University and the misfit advantage
Saylor became a collection of people who wouldn’t have found each other otherwise. No shared college background or holding company pedigree. “This is like, truly the sailor employee base… from all walks of life. They’re all really at their core, like creative and obviously strategic. But they might, might have made TV before this, or they might have worked on, you know, more so project management, and now they’re working on accounts.”
While learning everything from accounting to tax compliance through YouTube videos, Trowbridge discovered that ignorance could be liberating. “Sometimes the best work comes from individuals and teams that actually are not burdened by a historical reference,” he notes about the creative services business.
Betting on social while others looked elsewhere
In 2021, Netflix understood social media’s investment requirements, but other entertainment studios were still figuring out ROI and achievable goals. Trowbridge saw the white space. “I don’t really see a lot of social agencies out there that get it. I understand that, and maybe I don’t need to understand how an agency works to build something… inherently progressive and also new in this space.”
His bet: social would win over time, and the people leading that charge would become the new leaders in marketing organizations. Get in early with them, build something specifically for their social-first minds, and you wouldn’t need someone else’s playbook.
The AI parallel
Saylor recently launched an AI-first creative studio, following the same logic Trowbridge used for social in 2021. While others debate or resist, he’s leaning in: “It’s important for the creative industry to understand… that AI is going to be a big part of what we do moving forward. It’s up to us to understand how it’s going to impact our lives and our creative work.”
Same philosophy as social media five years ago—invest early, get really good at it, don’t let it catch you blindfolded.
Cash flow and YouTube tutorials
The financial realities of independent agency life hit differently when you’re learning everything solo. “You are, like, moving personal money and freaking business money back and forth. You’re figuring it out. You’re like, oh my god, am I not gonna be able to pay my employees? What am I gonna say to them? Then you’re like, oh my god, I got paid in the last second here.”
But those scary moments that seemed world-ending in year one just become part of the rhythm. “You just get used to it, you know, and they don’t become scary anymore.”
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Contact: will@sayloragency.com
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