If you’ve ever hit that wall in your freelance career where you’re booked solid, your income looks good on paper, but somehow you feel stuck, this episode is going to hit you square in the chest.

Chris Orzechowski is one of the few freelance copywriters who managed to break free from the “busy but broke” trap. He’s written for huge eCommerce brands, trained hundreds of writers through his courses, and built a thriving email agency that lets him do creative work and be home with his kids every night.

In our conversation, Chris and I dig deep into the real evolution of a freelance copywriter, how to move from surviving on gigs to building something scalable, sustainable, and sane.

We talk about systems, mindset, and the hard lessons it takes to go from writing words to running a business. But we also talk about what it means to stay a craftsman in a world obsessed with automation and shortcuts.

This isn’t a “rah-rah hustle” episode, it’s an honest look at how to grow up as a copywriter, stay creative, and actually build a business worth living for.

In this episode, Kevin Rogers sits down with Victoria Franco to unpack transcreation—the blend of marketing strategy, cultural intelligence, direct response copy, and translation that turns English‑first offers into winners in Latin America.

They break down why literal translation fails, how WhatsApp/DM culture flips the funnel, and why emotional resonance, social proof, and community matter more than ever for Freelance Copywriters and growth teams.

You’ll hear how Victoria rebuilt Kevin’s offer for the Latin market (with help from Dave Maswery) and the “nuance worker” approach brands need to avoid embarrassing—and costly—misfires.

In this episode of Paid to Create, I sat down with Dave Munson, founder of Saddleback Leather and author of the new book They’ll Fight Over It When You’re Dead. Dave’s story is one of relentless curiosity, unwavering faith, and a passion for building things that matter.

We got deep into how a single leather bag turned into a brand people brag about owning—and why creating something people love starts by solving your own problems. This one’s for anyone who feels that call to build something great from the ground up.

In this episode, you’ll learn:

✅ Why Dave says starting is the most underrated business tactic
✅ How to create products people brag about owning
✅ Why “success” has nothing to do with your bank account
✅ How Saddleback used storytelling to build an insanely loyal fanbase
✅ The connection between faith, failure, and craftsmanship

In this episode, I handed the mic to Lolita Allgyer—our brilliant messaging and story strategist here at Copy Chief—for a deep dive into what makes story-driven copy land with real emotional punch. This was more than just an interview. Lolita came in with the mindset of a strategist working with a client (me), and what followed was an honest, curious, and wide-ranging conversation about creative process, storytelling instincts, personal evolution, and how parenting shaped both my writing and my life.

We talked about everything from writing emotionally connective emails to how marijuana and music open creative portals, plus how the art of observation fuels direct response copy that connects on a deeper level. If you're a freelance copywriter working to bring more soul and strategy into your messaging–ya know, the human stuff–then, this one’s for you.

In this powerhouse episode of Copy Chief Radio, Kevin Rogers chats with Daniella Wade—a strategic copywriter and entrepreneur from Trinidad and Tobago—about what it really takes to thrive as a freelance copywriter and what it’s like to land an elite in-house gig with Jeff Walker's team at Internet Alchemy. Daniella shares her entrepreneurial journey, how she transitioned from hustling freelance gigs to becoming a valued team member in a premium direct response company, and the game-changing mindset that helped her stand out during Copy Chief’s "The Goods" competition.

In this special Behind The Copy session, I’m joined by one of the most legendary and unfiltered voices in copywriting—Chris “Mr. Moneyfingers” Haddad. If you've ever wondered how someone turns emotional pain and dark humor into multi-million dollar sales letters... Chris holds nothing back.

We go deep into the psychology of persuasion, the evolution of his infamous Michael Fiore persona, and why he thinks AI still can’t touch a human’s heart (or balls, apparently). Plus, he breaks down his most famous offer—Language of Desire—line by brilliant line.

Brace yourself. This one’s a ride.

Most freelance copywriters are introverts—which makes the idea of networking feel about as natural as small talk at a corporate retreat (aka painful). But what if you could build powerful, career-changing relationships in a way that feels natural, rewarding, and even fun?

That’s exactly what Selena Soo teaches in this episode. She’s built a thriving business by helping experts, authors, and entrepreneurs get in front of the right people—without faking it, forcing it, or feeling like a sleazy networker.

We dig into Selena’s “Six Circles of Connection” framework and how freelance copywriters can use it to land more dream clients, grow their influence, and build credibility in their niche—without changing who they are. (When you hear the six circles, you’ll immediately start dropping people you know into the circles!)

If you’ve ever thought, “I hate networking”—this episode is for you.

Peter Hoppenfeld and I dive headfirst into the state of marketing in 2025 and what it means for freelance copywriters like us. We’re talking about the major shifts happening right now, including how the FTC is tightening the reins on marketers, why bloated copy is losing its edge, and what it’s going to take to connect with a younger, savvier audience.

We also explore the importance of innovation, staying compliant, and creating marketing that’s as ethical as it is effective. Peter has been reading a ton of copy lately (as always), and he’s got some big insights into where the industry is headed. Trust me, this one’s not just for note-taking—it’s for action-taking!