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Are you willing to give up the work you built the agency around in order to build the agency itself? Today's featured guest recounts how he and his partner built their agency after a decade working together at the Oprah Winfrey Show. Fifteen years in, they are still figuring out what the founder job actually is versus what they have always been good at.

He talks through how the transition from doing to leading actually happened, what it cost him creatively and personally to step out of directing, and what he means when he says that making the video was always the easy part.

Brett Singer is a co-founder and principal at Bottle Rocket Media, a digital agency based in Chicago specializing in video production, motion graphics, SEO, paid media, and AI search optimization.

He and his business partner Dan Fisher both worked at Harpo Studios on the Oprah Winfrey Show for over a decade before launching Bottle Rocket in 2011. The agency built its initial client base entirely from the network that came out of Harpo when the show ended, then invested heavily in their own SEO to shift from outbound to inbound. Brett is now focused on business development, vision, and team culture.

In this episode, we'll discuss:

Letting go of the work you love for the future of the agency
When the business no longer needs you
The hardest part of running an agency

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Sponsors and Resources

E2M S olutio n s: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service.

The Work You Love Is Not the Work the Business Needs From You

Brett spent years at Harpo perfecting motion design and later started Bottle Rocket partly because he wanted to keep doing it. It was work he greatly enjoyed. Unfortunately, he realized that was the wrong job for him, not from a strategic decision but from simple math: when he was in the edit suite, no one was finding the next client. The business did not care how good he was with a camera. It needed someone holding the relationship and the vision.

Letting go of the work he was trained for and genuinely good at did not happen cleanly. He describes it as kicking and screaming and slowly, and that is probably the most honest description of how most founders navigate this. In this case, the difference for him was having his partner, which meant there was always someone to hold the other accountable to the right job. Solo founders have to engineer that accountability differently. But the outcome is the same: the work you loved getting you here is eventually the work that stops the business from going further.

The Identity Gap When the Business No Longer Needs You

Stepping into the CEO role can feel like loss before it feels like freedom. When the business no longer needs you for the thing you spent a decade mastering, there is a real identity gap. The hours that used to be filled with something you were visibly good at are now filled with work that is harder to measure and slower to produce visible results.

Brett went through his own version of this as he transitioned away from directing. He still goes to set occasionally and feels the pull. He made peace with it not by letting go of the creative part of himself, but by redirecting it: into the sales process, into how the agency presents itself, into the culture he is building.

The creative instinct did not go away. It found a different channel. That reframe, from "I gave up my craft" to "I applied my craft differently," is what makes the CEO stage sustainable instead of a sustained identity crisis.

Making the Widget Was Always the Easy Part

Brett is clear about something that sounds counterintuitive until you have run an agency for a few years: the actual service delivery, producing the video, building the campaign, running the edit, is the easiest part of running an agency. The hard part is everything surrounding it. Hiring. Culture. Vision. Business development. Managing the people who manage the work. None of that was taught. All of it had to be built from scratch by people whose entire prior training was in making the thing.

This is the reason most agency founders stay stuck in the work longer than they should. It is the thing they know. Every hour in the edit bay is an hour that feels productive and measurable. Every hour in a hiring conversation or a strategy session feels less certain and harder to justify. The founders who scale are the ones who learn to value the less comfortable work, not because it becomes easier, but because they understand what it makes possible.

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