Early Side Hustles and Income Mix

Josh Cantrell didn’t set out with some polished master plan.

He got fired.

What could have become a long, discouraging detour ended up becoming the first step in building a self-employed career with more ownership, more leverage, and more intention.

In this conversation, Josh talks through the evolution of that journey.

Early on, he did what many freelancers do. He said yes to whatever paid. Alongside marketing work, he flipped storage units, ran an eBay store, and DJ’d weddings to keep the lights on. Over time, though, he realized he didn’t just need more work. He needed a clearer way to create value.

That’s where frameworks entered the picture.

Josh shares how discovering StoryBrand gave him a structure he could lean on, not just to do better work, but to explain his reasoning, package stronger offers, and shift client perception. Instead of feeling like he was winging it, he had principles. Instead of selling tasks, he could sell outcomes.

We also dig into the mindset shifts that came with experience.

Josh talks about moving from scarcity to abundance, from thinking the world was small and stingy to realizing there’s plenty of opportunity out there. He explains how raising his standards changed his behavior, financially and professionally, and why standards often shape results more than motivation does.

Another major theme in this episode is relationships.

Josh has become increasingly intentional about building what he calls IRPs: ideal referral partners. Rather than relying on random lead gen or posting into the void, he focuses on real conversations with people who already know the kinds of clients he wants to serve.

We also talk about LinkedIn, but not in the eye-rolly, “optimize your content funnel” kind of way.

Josh uses LinkedIn as a conversation starter. He posts consistently, follows up with people who engage, and looks for chances to turn digital attention into human connection. That approach has led to podcast invites, referral relationships, and new opportunities.

And beneath all of it is a simple but important truth: Clarity comes before amplification.

If your message is muddy, more marketing just means you’re mumbling into a louder microphone. Josh explains why great content starts with great thinking, and why helping prospects believe the right things may matter just as much as writing the right words.

If you want to specialize, strengthen your positioning, create more demand, and build a business with better leverage, this one is worth your time.

Key Points

• Josh started in survival mode. After losing his job in 2017, he pieced together income through freelance marketing, weddings as a DJ, an eBay store, and whatever else kept the lights on.
• Confidence followed competence. Early “imposter syndrome” had less to do with being broken and more to do with lacking reps, clarity, and proof.
• Frameworks changed the game. StoryBrand gave Josh a structure for making decisions, justifying recommendations, and packaging higher-value offers.
• His business evolved slowly but meaningfully. He moved from general marketing services into messaging, positioning, copy, and later more strategic engagements, including fractional CMO-style support.
• His mindset shifted from scarcity to abundance. Instead of treating every lost client like a verdict on his worth, he learned to see the market as big, generous, and full of opportunity.
• He now works from standards, not hope. Revenue standards, relationship standards, and service standards all shape how he shows up and how he grows.
• Ideal referral partners are a major growth lever. Josh aims to build relationships with peers and adjacent experts who already serve the kinds of clients he wants.
• He treats LinkedIn like a system, not a stage. Post consistently, follow up with engaged people, start real conversations, and see where the thread leads.
• He’s prioritizing documenting over performing. Lived experience, experiments, humor, and observations from real life make better content than sterile “5 tips” posts.
• A dream client already believes messaging matters. Josh does best with B2B companies selling something expensive, complex, or confusing that understand clear messaging must come before louder marketing.
• The deeper opportunity is belief change. Great content does not merely attract attention. It upgrades thinking. It creates demand by putting a fire in people’s minds about better ways to solve old problems.

Notable Quotes

• “Confidence comes as a result of competence.”
• “If we’re spending money on marketing, but the message isn’t clear, we’re just mumbling into a microphone. We’re just louder.”
• “When you’re creating demand, it’s about putting a fire in someone’s mind about opportunities and possibilities and new ways to solve old problems.”

Resources Mentioned

• Follow Josh Cantrell on LinkedIn: https://www.linkedin.com/in/joshcan
• Check out his website, Signal Brandworks: https://signalbrandworks.com/
• Join the Freelance Cake Community: https://www.freelancecake.com/community