Episode Details

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Have you ever questioned whether you're actually built for the hard seasons of agency life? When things get messy, unpredictable, or overwhelming, do you wonder if you have what it takes to keep going or if everyone else somehow got a playbook you missed? Most agency owners don't wake up one day and decide, "I'm going to build an agency." They trip into it. One project turns into two, side work turns into real revenue, and suddenly you're invoicing clients without knowing what an invoice number is supposed to look like.

Today's featured guest unpacks what it really looks like to build an agency without a roadmap. Through failed partnerships, stalled careers, and moments where quitting felt easier than continuing, he developed the resilience and mindset required to keep moving.

Cliff Skelliter is a serial entrepreneur and owner of Launchpad Creative, a design-thinking agency, working across brand identity, video production, and strategy. They blend artistry, functionality, and brand communication to create captivating digital and physical spaces that not only engage and inspire but also reflect the essence and values of the organizations they work with.

In this episode, we'll discuss:

• The Easiest Choice: Leaving his Career and Going All-In on the Agency

• What He Learned from His Partnership Experiences

• Self-Belief as the Most Important Lesson for Agency Owners

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E2M Solutions: 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.

Cliff didn't grow up in a family of entrepreneurs, and never set out to "start a business." His entry into agency life wasn't strategic, it was reactive. While working an internship at Canadian news station CTV, he saw the ceiling in broadcast media and realized that no matter how talented or ambitious he was, there was a limit to how far that career could go. Meanwhile, he was already getting requests to work on some projects outside of the station.

Eventually, the projects kept getting bigger and the people at the station complained Cliff was creating a conflict of interests with his side hustle, as clients chose him, instead of the station, to produce their commercials. It was an ultimatum, and the choice was clear. By then, that "side hustle" was more lucrative and offered more creative control. Plus, it was just more fun.

What's important here isn't just how Cliff started—it's what he didn't have. No business background. No sales training. No master plan. Like many agency owners, he learned by doing, Googling, guessing, and occasionally getting it wrong, which is mostly the default path. The dan