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Thinking in Systems, Not Tactics
Growth challenges rarely come from a single decision. They come from the systems beneath them. Here we share perspectives on infrastructure, AI, operating models, and leadership, focused on helping teams scale with clarity, accountability, and intention.


12. The Frog Is Already in the Pan. Is Anyone Watching the Stove?
I had a really engaging conversation this week with a digital marketing leader at a Fortune 100 financial services company. Smart, thoughtful, and wrestling with something I am hearing more and more. The AI problem is real. But not in the way most people think. His frustration was not with the tools. It was much bigger than that. What LLM are we actually using? There was an internal mandate but he knew not everyone was following it. What is the end goal of our AI investment?

Sean
Mar 232 min read


11 . Stop Pitching Like a Mechanic: How to Triple Your Account Size with AI + HI
Building a $5-$10 million agency is a grind. Most small shops get stuck in a "month-to-month" loop because they pitch like mechanics instead of consultants. They tell a prospect their account is broken and promise to fix it. Lately, I have been out talking to people who say they want AI + HI (Human Intelligence). But when I press them on it, they aren't 100% sure what that actually looks like in practice. I want to share a real-world example of that intersection: the lifeline

Sean
Mar 143 min read


10. AI Won’t Fix a Broken House (And Other Lessons from a Cranky Week)
I’ll be honest: I’m feeling a little cranky this week. I’ve been out in the market talking to agencies of all shapes and sizes. I’ve seen the full spectrum: the small shop desperate for an AI miracle, the mid-sized firm drowning in "change fatigue" and organizational trauma, and the boutique looking for a Head of Media who is "hands-on" for an executive-level role. Everyone is looking for a silver bullet. Usually, they think that silver bullet is finding an SVP of Data Entry.

Sean
Mar 103 min read


9. Can We Use AI for Good? (Or Are We Just Putting the Treadmill on a Faster Setting?)
I saw Crime 101 over the weekend. For a gritty LA crime movie, it’s surprisingly obsessed with mental wellness. Characters played by Chris Hemsworth, Halle Berry, and Mark Ruffalo meticulously monitor their sleep, drink green smoothies, listen to wellness podcasts and hit yoga classes. But here’s the rub: they’re doing all this just to survive toxic professional environments. Berry’s character is attacked for her age, Ruffalo is forced to lie to keep the peace, and Hemsworth

Sean
Mar 22 min read


8. I’ve been doing a lot of jigsaw puzzles lately.
It’s the first time I’ve picked one up since the peak of the COVID lockdowns. There is something incredibly therapeutic about it. Sorting the chaos, finding the edge pieces, building the frame. It quiets the immediate noise and it allows the mind to start to wander. Lately, my mind has been wandering to the job market. I’ve been doing a lot of networking and outreach over the last few weeks, reading through endless job descriptions and agency manifestos. Almost every single o

Sean
Feb 233 min read


7. 17 Shows, 35 Years, and the Value of the "Old Pro"
I saw Nine Inch Nails on Wednesday night in DC. It was my 17th time seeing Trent Reznor live. My first time was at Lollapalooza in 1991. It was daytime, the stage was stripped down, and he was just a guy with a keyboard and a LOT of angst playing songs from Pretty Hate Machine . Tickets were $27.50 for the whole festival. Fast forward 35 years: he is 60 and has created a stage show that is a mind-blowing feat of lighting and engineering, and the ticket prices have hit $150 fo

Sean
Feb 233 min read


6. Got the Time? Why Strategic Capacity may be the Only Metric That Matters
I have a song stuck in my head. If you’re a fan of high-speed Joe Jackson or maybe the Anthrax cover, you know the feeling of "Got the Time." It is that frantic, caffeine-fueled pulse of a day that starts with a ringing phone and ends with a pile of letters you never got "just right." No such thing as tomorrow, only one, two, three, go. In the agency world, we live in that "tick-tick-tickin'" rhythm. We are running so fast just to keep up with the Slack pings and reporting de

Sean
Feb 103 min read


5. Stop Guessing and Start Scaling: A Roadmap for the Modern Agency
I love a good puzzle. Whether it was keeping the engines humming in a Navy machine room or managing a $35M agency P&L, I have always been fascinated by what happens "under the hood." Lately, I’ve been talking a lot about the "hamster wheel" and the "monkeys and bananas" problem. These are the invisible frictions that keep great teams stuck in a cycle of reactive firefighting. But how do we actually help agencies and businesses move past the friction? How do we build an archit

Sean
Feb 43 min read


4. A Surprised Client is Rarely a Happy Client
When my daughter was four, she was obsessed with a show called BeatBugs. It’s a cartoon where bugs go on adventures and sing Beatles songs. One day, they did "A Day in the Life," and she was floored. She looked at me like she’d just discovered fire. I just shrugged and said, "The classics are the classics for a reason, kid." Years ago, back when I was a management trainer for a bank in Colorado, a boss handed me two “classics” that I still lean on today. One was the Performan

Sean
Feb 23 min read


3. Do you have a "Monkeys and Bananas" Problem?
When I started as the Head of Client Services at Jellyfish, the President and Founder, Rob Pierre, flew in from London for a new-hire induction. About five minutes in, he started a story I hadn’t heard in ages, but one I’d lived through many many times in my head. "Five monkeys are in a room," he began, "with a ladder leading to bananas..." I couldn't help it. I laughed out loud. Rob shot me a look of pure, British disapproval and kept right on going with the tale. The Allego

Sean
Feb 24 min read


2. Strategic Partnerships that Work
In my last post, I talked about the "hamster wheel"—that invisible friction that keeps agency teams spinning their wheels without actually moving the needle on margin. If we agree that growth happens when we clear the deck for our talent, we have to look at who is actually doing the clearing. Historically, when an agency hit a wall, they had two choices: hire a full-time, high-priced executive or bring in a consultant. One is a massive overhead bet; the other is often a dirty

Sean
Jan 213 min read


1. Why Are We Doing This?
I love agency life . Plain and simple. It scratches two very specific itches for me: I love solving puzzles, and I’m an unrepentant people pleaser. Over the last 20 years, I’ve seen it all, from massive holding companies to tiny boutiques. If I’m being honest, I’m rooting for the small guys. These shops are usually started by entrepreneurs who have one massive advantage: they actually know how to inspire talent. They just need a little nudge to get over the top. Lately, ever

Sean
Jan 193 min read
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