How I Started My First Agency

And grew it to $5m

By the time I started thinking about starting an agency, I’d already lived a whole career inside other people’s institutions, beginning in the late 80s as an intern and ending, for a while, at the C-suite of a premium network.

I’d been Chief Creative Officer at a global media brand. I’d made big bets with other people’s money. I’d defended creative in meetings where creative was treated as a liability. I’d watched creative excellence get quietly negotiated down when the spreadsheet started talking.

In 2013, I started circling the idea the way people do when they’re not ready to admit they’re serious. I was watching the industry keep asking for more output, faster turnarounds, and tighter budgets, while still expecting the work to feel expensive. I also knew myself well enough to know I didn’t want to spend the rest of my career only approving other people’s ideas.

The lease that made the stakes physical

By 2015, I signed a lease for the agency’s office in New York City in the shadow of the Empire State Building.

It was a beautiful decision and a stupid one.

The rent was real. The fear was real. And for the first time in my life, my ideas weren’t something I defended inside a corporation. They were something I had to sell, deliver, and protect with my own name on the invoice.

When you commit to overhead, you lose the luxury of abstraction. Every week becomes a referendum. Not on your talent. On your ability to translate creativity into revenue without poisoning the work in the process.

The first job that proved the thing could breathe

My first paying client came from a former colleague who was the head of creative at a sports network. We’d known each other for over twenty years. We were peers. He had never known me as a vendor.

There was no pitch process, no negotiation theater. He knew I was starting my own shop and came to me with a real problem: a campaign for a sports talk show.

We produced a live-action shoot with the host, a Super Bowl Champion Quarterback on the street in front of Madison Square Garden. Permits, weather, time pressure, adoring fans clamoring for autographs while I am trying to film, the whole thing. Then we built out a run of polished spots through post-production.

I priced it well under market. Not because I wanted to build a cheap brand. Because the first job is about credibility, you need something to point to. Something that tells the next client: this is the standard, and this is the pace.

Payroll day changes your personality

The day it became a business for me was payroll day.

I paid the people who worked for me, and I felt the weight of it in my chest. Not in a sentimental way. In a mechanical way.

Creative becomes obligation. Quality becomes responsibility. Deadlines become other people’s rent.

That’s the first real maturation. Employee to operator. Maker to employer.

The part nobody sells you on

Agency life gets sold as freedom. What you actually buy is consequence.

In corporate life, there are layers between you and the blast radius. In agency life, the blast radius sits on your desk, in your inbox, in your calendar, and in your body. The system is smaller, which means everything hits you directly. There’s no bureaucracy to hide behind, but there’s also no bureaucracy to absorb impact for you.

That’s why founder stamina becomes a myth that people applaud right up until the founder starts breaking.

When “scrappy” stops being a virtue

Toward the end of year one, we had enough work that “scrappy” stopped being our brand voice and started being a delivery risk.

We needed more everything.

More equipment. More media storage. More edit systems. More design stations. More redundancy. More people.

I still remember the day it arrived. Hard shell equipment cases stacked. Rental drives everywhere. The feeling of a small machine turning into real infrastructure.

And the marker wasn’t the gear. It was the margin. I could bring on more people and more equipment, deliver at a higher level, and still keep a healthy profit. That’s the difference between a hustle and a business. A business can scale without feeding on the founder.

I built a band before I built a machine

Early on, I hired people I liked. People who felt like my kind of people. People I could imagine sitting next to at midnight without wanting to jump out a window.

That works for a while. Then it gets expensive.

I hired a junior person to help keep the office organized. He came through a referral tied to someone I trusted. I let trust replace diligence. The truth was simple. He wasn’t hungry. He was filling time. He fell asleep in the office when he thought nobody was watching. I had to fire him and then explain it to my trusted colleague (who just happened to be his father).

I hired a full-time designer. He was so cool in the way, only a true artist can be. He was super talented, but he was built for product design, not agency delivery. His relationship to perfection was almost devotional. The work was beautiful. The pace was impossible. In a corporate environment, deadlines can stretch. In an agency, deadlines arrive like weather. I had to let him go, too, and the Department of Labor came looking for overtime he claimed I owed him. Plus fines.

The deeper mistake underneath those hires wasn’t a lapse of judgment. It was architecture.

I built a band of misfits because it felt good. I liked them. They liked me. Then I realized I had built something where I was the only stabilizer. I didn’t build a system. I became the system.

The agency world was changing while we were building

This is the part most founders miss when they tell their origin story. They narrate their agency like it existed in isolation.

By the mid-2010s, client-side thinking was being reshaped by procurement logic. More project work, fewer retainers. Faster turnaround, lower tolerance for cost. More internal scrutiny. Less patience for anything that looked like overhead.

At the same time, distribution had fragmented. One campaign idea could no longer live as a single artifact. It had to exist as a constellation. Many versions, many formats, many platforms, all with their own physics.

Clients wanted the craft of premium work. They also wanted the velocity of constant output. They wanted everything, they wanted it yesterday, and they wanted the price to feel like 2005.

That conflict doesn’t show up in the pitch deck. It shows up in what founders accept. It shows up in what founders agree to “just this once.” It shows up in the slow rewriting of what “good” is allowed to mean.

My role changed before I admitted it did

At some point, I had to face the question that sits behind a lot of agency founder burnout.

Was I going to be sales, operator, product, or creative?

I left corporate because I wanted to be closer to the work again. I wanted to make. I wanted to feel the craft in my hands, not just in my approvals.

Then the agency grew and I learned the uncomfortable truth.

I wasn’t back in the work at all, I was accountable for the work.

Those are different identities.

The call I said yes to when I should have said no

Early on, the agency sold itself on my background. The resume. The credibility. The story.

That works until it doesn’t.

Eventually, the shine wears off and you either have a sales system or you have anxiety.

I didn’t build a true sales system early enough. I kept selling the story, then started substituting pressure for process when the story stopped doing the work for me.

That’s where over-promising enters.

Not dishonesty. Fear.

I said yes to a full-length video game competition show. A pilot plus episodic builds, crescendoing into a grand finale. The timeline was too tight. I didn’t have enough capacity. I knew I couldn’t deliver fast, cheap, and good. I could deliver two. I agreed to all three anyway because I wanted to be in that lane. Because gaming shows were getting hot. Because I wanted the portfolio piece.

The client made it easier to say yes by promising he’d be there through production and post, giving instant approvals.

Operationally, it cooked my team.

We kept hiring support staff because people were burning out. My lead editor had a personal relationship with the client. Nothing unethical. No favors. Just that subtle extra push people give when a friendship is in the mix. The work got done, but it left a mark. It taught me how fast a team will run through itself when the founder sells aspiration as capacity.

The logos were real, but logos don’t pay for mistakes

We worked with major media brands. MTV, Nickelodeon, and all of the Paramount family. Premium networks like HBO and Showtime. Platforms like Netflix and Amazon. Big sports and entertainment teams where the turnaround expectations were brutal and the audience expectations were worse.

The work was real. The logos were real.

They didn’t protect us from bad operating decisions.

The moment I knew it could collapse

The single moment I knew the whole thing could collapse had nothing to do with a client leaving.

I got sick. I physically collapsed. I flatlined.

What I remember most is the bargaining. Not with a divine entity. Not with the universe. With myself.

If I could live, I would do so many things differently.

I would take care of myself better. I would stop treating stress like a tax I had to pay to earn the right to lead. I would stop confusing deterioration with commitment. I would be a better person, the way people mean it when they’re scared they won’t get another chance.

It felt like pain and it felt like distance. It felt like watching my life from somewhere that didn’t care about my deadlines.

After that, founder mythology stopped sounding admirable and started sounding like denial.

A business can survive competition. It can survive bad hires. It can survive market cycles. It can survive COVID.

It does not survive a founder who treats self-destruction as the admission price.

What I believe now

I still believe the agency model can be beautiful. A group of talented people moving in concert, making work that carries taste and conviction.

I also don’t romanticize what it takes anymore.

I grew my first agency to $5m in its peak years.

What I know now is simpler and more expensive.

A business that runs on my slow depletion is not a business. It’s a bargain I eventually settle in ways no invoice can name.