When Joel Pilger invited me onto The Fabulist podcast alongside Dustin Devlin and Winston Macdonald from Vagrants, I knew it would be a conversation about creative business. I didn’t expect it to feel like a therapy session for founders.
All of us went in expecting to talk about production, from how studios evolve, how the Boston scene has changed, and how we all fit into this gray space between “agency” and “studio.” But somewhere in the middle of the conversation, I found myself realizing just how much Pennant’s story has been shaped by that in-between.
From Intrapreneur to Founder
Joel asked me how Pennant started, and I had to rewind a bit. Before founding the company, I spent over a decade inside a marketing and PR agency. It wasn’t the glamorous ad agency kind, but the kind where you wear every hat imaginable. I was the first creative hire there. I built the video department, led business development for the group, managed clients, and handled budgets.
At the time, I didn’t think of myself as an entrepreneur. But as Mitch Munson once put it, I was an intrapreneur: running a business inside someone else’s business. When Dustin (whom I’d met years earlier through a mutual friend) asked me what kind of revenue I was managing, it hit me. I was essentially running a production company already, just not my own.
That realization, mixed with a few late-night margarita conversations together, was the spark.
Why Pennant Exists
Joel asked a question that stuck with me: “Why not just do all this under Vagrants?”
It’s a fair question. On paper, it might have made sense to fold my work into their brand. But Pennant needed to be its own thing, its own voice, its own model. I wasn’t trying to build “another production company.” I wanted to build a company that solved a different problem entirely.
Most studios chase projects and are built to execute once the brief arrives. But I saw an opportunity to help clients long before that in what marketers call the messy middle of the buyer’s journey. The awareness ads and Super Bowl spots get all the glory, but what happens after that? How does a brand build trust across months of decision-making? Especially when it comes to B2B brands.
That’s where Pennant lives: the mid-funnel. The consideration phase. The space where attention turns into trust, and trust turns into belief.
We’ve built our company around a framework we call the Video Marketing Trifecta™:
- Differentiation – why you exist (the anthem)
- Demonstration – how you solve problems (the explainer)
- Validation – proof you’re worth believing in (the customer endorsement)
It’s not sexy language, but it’s not meant to be. It’s a strategy disguised as storytelling.
The Beauty of the “Messy Middle”
During the podcast, Joel compared my model to the old-school studio mentality, focused solely on “top-of-funnel” awareness work. I laughed because that used to be the holy grail: the big-budget spot, the cinematic 30 seconds that made everyone stop and stare.
But the reality is that kind of work doesn’t always build relationships. It may get you noticed, sure, but not remembered.
What drives me now is helping brands stay relevant after that first impression. Mid-funnel storytelling is quieter but more enduring. It’s about clarity, consistency, and trust, not virality. Resonance over reach.
In a way, it’s about holding both sympathy and empathy at once—sympathy for the client navigating internal pressures, and empathy for the audience whose decisions we’re trying to make easier. That balance is what I love about this kind of work.
Sister Companies, Shared DNA
When Joel described Pennant and Vagrants as “sister companies,” it made me pause. We’ve had discussions about that phrase before, but hearing it from someone else embodied precisely what it feels like to work alongside Vagrants.
We share the same DNA: a belief in challenging norms, in designing better ways to work, in growing the next generation of studios that don’t see each other as competition.
At first, Vagrants brought me in to catch the overflow. Usually, it was the smaller, less glamorous jobs. But what we all discovered, very quickly, was that Pennant wasn’t a side project. It was a new chapter.
Now, our teams flow between both worlds. Editors from Vagrants cut our work; our Pennant motion designers bring ideas to theirs. We learn from each other constantly. It’s the kind of ecosystem that proves “rising tides raise all ships” isn’t just a slogan — it’s a business model.
Redefining Creative Success
Recording The Fabulist reminded me how different this all feels compared to when I started my career. Back then, success meant landing the next big client or campaign. Now, with craft being the table stakes, success means clarity — knowing what we do, who we serve, and why it matters.
Pennant was never about building more work. It was about building a better understanding and giving marketers something they could actually use, not just admire.
When Joel asked what makes this new era different, I said it comes down to intention. Studios like ours aren’t just chasing cool projects anymore. We’re chasing sustainability, purpose, and longevity. To quote Joel, “Running a studio is the most interesting project.”
The creative industry is evolving fast, and we’re all figuring it out in real time. But if there’s one thing this conversation made me sure of, it’s that the future belongs to studios willing to rethink their place in the funnel and in the ecosystem.
We don’t need to be the loudest voices in the room. We just need to tell the right stories, at the right time, for the right people.
That’s how we’re raising the banner at Pennant.
