From Broken Agency Partnerships to Bulletproof Self-Belief with Cliff Skelliter | Ep #873

How do you know if you’re actually built for the hard seasons of agency life?

Most agency owners don’t fail because they lack talent they quit during the messy middle. Cliff Skelliter’s story proves that resilience, self-belief, and learning the hard way aren’t bugs of agency life… they’re the initiation. If you’ve ever wondered whether you’re cut out for this, this episode will feel uncomfortably familiar, in the best way.

What You’ll Learn

• Why most agency owners stumble into entrepreneurship without a roadmap
• The hidden dangers of partnerships built on convenience instead of values
• How self-belief becomes a real competitive advantage in hard seasons
• Why “going all-in” often feels easier than trying to play it safe
• The long-term business impact of resilience over raw talent

Key Takeaways

• Most agency owners are making it up as they go. Yes, even the ones you admire
• Bad partnerships don’t just slow growth, they amplify existing weaknesses
• Sales isn’t about personality, it’s about asking better questions
• The universe will always offer you an “out”… resilience is choosing not to take it
• Belief isn’t hype, it’s the fuel that keeps you moving when logic says stop

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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Sponsors and Resources

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.

When Going All-In on the Side Hustle is an Easy Yes

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 danger is assuming everyone else has it figured out, while you’re making it up as you go.

Agency Partnerships: When They Work and When They Break You

Cliff’s first business partnership was both formative and brutal. His partner helped get the business off the ground but was dishonest, reckless, and ultimately destructive. While Cliff focused on creative work, his partner handled sales and accounts… and quietly created financial chaos. When the partner disappeared, Cliff was left holding the debt and the consequences.

Many agency owners bring on partners not because it’s strategic, but because it feels safer. Someone else handles sales. Someone else deals with money. Someone else shares the weight. But if values, ethics, and accountability aren’t aligned, the cost can be enormous.

Thankfully, Cliff was able to recover from the blows to both the agency’s finances and its reputation. He also gave partnerships another chance. The second partnership was different and far more successful. Cliff partnered with someone who combined complementary skills to build a business that lasted nine years. It worked because each person did what they were good at and didn’t want to do the rest. Even then, the partnership eventually ended, not because of business failure, but personal life complications.

Partnerships aren’t good or bad by default; they amplify whatever already exists. Clear roles, boundaries, and shared values make them powerful. Avoidance, people-pleasing, and lack of communication make them fragile.

Resilience, Self-Belief, and the Placebo Effect of Entrepreneurship

Cliff got important lessons from both experiences, mainly that he’s much more capable than he thought. He could handle sales, which is something he doubted for years. Like many agency owners, he assumed you had to be a certain “type” of salesperson or personality to run a business. In reality, you just need to ask better questions and not be afraid of uncomfortable conversations.

He also learned he’s far more resilient than he gave himself credit for. Most agency owners would testify to the fact that the universe constantly gives you outs. Jobs. Acquisitions. Easier paths. And yet, something in your gut says, “I’m not done.” That resilience isn’t logical. It’s identity-level. Entrepreneurship stops being something you do and becomes something you are.

He now understands the importance of believing in himself, even when it seems absurd. Your mind alone can trigger real physical outcomes. When doubt creeps in, remind yourself that belief itself is a lever. Not hype and not manifesting nonsense; just the willingness to keep going when the story in your head tells you to quit.

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