Why Do Agency Owners Feel Trapped in Their Own Business? And How To Break Free with Dan Fisher | Ep #837

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Ever feel like running your agency is just one long grind of “good enough” projects, endless deadlines, and late-night work sessions? Most agency owners start out chasing freedom, only to find themselves trapped by clients, culture challenges, and their own workaholic habits. Today’s featured guest is certainly familiar with this cycle, so how was he able to build a business that works for him instead of the other way around? By focusing on clarity, culture, and constant evolution.

Dan Fisher is the founder of Bottle Rocket Media, a Chicago-based video production and digital marketing firm. Before running his agency, Dan spent a decade in television, including a long stretch as an editor at The Oprah Winfrey Show. What started as “making a few videos for people” turned into a full-fledged agency after his partner joined. Today, Bottle Rocket Media blends storytelling with digital strategy to help brands communicate with impact.

In this episode, we’ll discuss:

• Data meets creativity.

• The agency he “thought he should build”

• Culture as a compass.

• Redefining work and energy.

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Dan wasn’t setting out to build an agency. He was a New York kid, worked on TV production in LA, and then got tapped on the shoulder for a gig at Oprah. When he landed in Chicago, he figured he’d be there a couple of years. Ten years later, he had a family, a house, and roots that weren’t going anywhere.

After leaving TV (not a moment too soon, according to him), he just started making videos for people. Then his partner came on board, and suddenly it was more than a side hustle. It was a real business. That’s when Dan realized he was no longer just a TV guy—he was running an agency.

TV wasn’t all glitz. Dan loved the storytelling, the cameras, the lights. However, running a daily show can crush even the strongest souls. Deadlines piled on top of deadlines. Three to four episodes a week meant three to four immovable deadlines every week. Still, it gave him his 10,000 hours. He learned how to tell stories fast, direct, edit, and manage creative teams.

Most importantly, TV taught Dan the importance of knowing your audience. At Oprah, there was always an “audience of one”—Oprah herself. He’d have the version he wanted to tell, and then the version she’d actually approve. That lesson carried into agency life: storytelling isn’t about you, it’s about your client. You’re not making an indie film; you’re telling their story in a way that serves their brand.

Bottle Rocket Media isn’t trying to be Hollywood. They focus on nonfiction storytelling, documentary-style content, education-driven pieces, spokespeople, and commercial spots. What makes their approach stand out is how they marry creative instincts with marketing data.

Working in the creative field never ceases to surprise Dan who, even now, expects something to land well with audiences and sees the complete opposite happen. This is why he and his team lean into A/B testing. Sometimes it’s the tiniest tweak: a subject line in an email, a color shift in a graphic, or moving the ending to the front of a video. It’s a reminder agency owners need: you can be confident in your craft, but the market has the final say.

When he started, Dan assumed he’d be miserable doing the “operations” side. But mentoring, managing, and building a team turned out to be just as rewarding as calling “action” and “cut.”

He’s learned the balance between doing and teaching. Having 10,000 hours of experience doesn’t mean you always tell the story better than a fresh intern. It means you know how to refine, manipulate, and see perspectives others might miss. At Bottle Rocket Media, they encourage collaboration. Editors critique each other’s work. Ideas bounce around. And Dan stays focused on a critical question every creative leader should ask: Am I making it better, or just making it different?

It took Dan years to reach what he calls his maturity, after trying to be “the agency he thought he should be”. Eventually, after banging his head against the wall for a long time, he realized the power of clarity—both personally and professionally. He started the business as a way to make ends meet after leaving TV, but it was time to define his goals with the agency and make it his own.

Once he stopped chasing someone else’s model and leaned into his own strengths, everything changed. The real turning point wasn’t in working harder, but in defining what success actually looked like for him and his team.

Clarity doesn’t just guide you, it’s also something you can instill in your team. Once Dan started defining his agency’s beliefs, he could attract people who truly fit. To him, if your team is not going in the same direction, then what’s the point?

But culture hasn’t been easy, especially post-pandemic. Bottle Rocket Media runs on a hybrid model: three mandatory in-office days, with Mondays and Fridays remote. For Dan, it was about letting go of his old Gen X “first one in, last one out” mentality and adapting to a younger workforce. The result is a stronger, more unified team—even if they’re not physically together every day.

Coming from TV, where it’s not rare to work up to 70 hours a week, Dan initially started his agency using the volume model, which is what he knew. Once the business was up and running, his hours were still pretty similar to what he was used in TV.

Eventually, however, it got to a point where a trusted employee expressed he was at his breaking point, and Dan knew it was time to dial down. Working beyond a certain limit didn’t make him better, it was just making him an ineffective leader.

That shift changed how he managed his team, starting by cutting off the bottom 20% and elevating the types of projects they do. This way, with clear goals and clear deadlines, he’s building the kind of leadership that creates loyalty and sustainability.

The agency game changes daily. Right now, AI is shaking up video and digital marketing. What worked yesterday won’t always work tomorrow. If you want your agency to survive, curiosity is the ultimate skill. Test, adapt, and don’t get too comfortable.

That philosophy is why Dan’s agency has evolved from purely video into a full digital offering. On the video side, he had to learn how to let go and empower others. On the digital side, he leans entirely on his team’s expertise. In both cases, growth depends on staying open to new approaches and trusting the right people to execute them.

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