CCR280: (Freelancer’s Journey) Carolynn Ananian - Adventures of a “Path 2” copywriter

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!  

Brian McCarthy is a brilliant mindset coach who has transitioned from a career in direct response copywriting to helping creative professionals break free from imposter syndrome. In this episode, Brian shares his unique perspective on overcoming the mental and emotional blocks that keep many copywriters stuck. We dive into the origins of imposter syndrome, its impact on freelance copywriters, and practical steps to build self-confidence while staying aligned with your values. What You’ll Learn in This Episode: Why imposter syndrome hits copywriters harder than most professionals How Brian helps people dismantle self-doubt with personalized coaching The transformative power of aligning with your core beliefs Simple steps to ease self-imposed pressure and achieve more peace

In this episode, I sat down with Dan Walker, son of Jeff Walker (product Launch Formula) and a seasoned leader at Internet Alchemy, to explore the intricacies of hiring top-tier copywriters through the innovative "Goods" process.  We dove deep into the strategies behind finding copywriting talent that balances creativity, adaptability, and strategic thinking—essential skills for freelance copywriters and direct response marketers alike. In This Episode: The step-by-step breakdown of "The Goods" hiring process (the "American Idol" of copywriting)... How Dan Walker and his team evaluated over 50 candidates to find writers who excel in both creativity and execution... The importance of congruence and strategy in copywriting, beyond just strong writing skills… Insights into balancing AI tools like GPT for efficiency while maintaining the human touch in direct response copy... Tips for freelance copywriters looking to stand out in competitive hiring processes like this one...  

In this thought-provoking episode of Copy Chief Radio, Kevin Rogers sits down with Eddie Shleyner, creator of "Very Good Copy," to discuss the artistry, psychology, and daily practice of being a copywriter. Eddie shares the journey of writing his first book, the life lessons passed down from his grandmother, and how the craft of copywriting extends far beyond selling products—it's a way of seeing and engaging with the world. Kevin and Eddie delve deep into the emotional and intellectual toll of writing for a living, how to live a "writer's life," and why copywriting is about empathy, clarity, and being invisible in the work. Eddie reveals his process for choosing clients, the unexpected challenges of publishing a book, and the discipline required to balance work, family, and creativity. Whether you're a seasoned copywriter or just starting out, this episode will inspire you to think differently about your role as a writer and how you approach both your craft and your life.  

In this powerful episode of Copy Chief Radio, Kevin Rogers sits down with mindset master Jeremy Bellotti, founder of Personal Mastery®, to discuss the deeper levels of personal growth, high performance, and mastery. Jeremy takes listeners through the stages of personal development and how to move beyond survival-mode thinking to achieve sustainable growth, both as a freelancer and as a human being. The two discuss the importance of rewriting your "internal code," the concept of mastery as an infinite game, and the critical role of relationships in success. Kevin and Jeremy share personal stories and insights from their journeys, exploring concepts like the courage required to be a freelancer, how to recognize the roles people play in your life, and the critical nature of embracing curiosity and truth as guiding principles for growth. If you're ready to break free from old patterns, create real transformation, and step into your full potential as a copywriter, entrepreneur, or human being, this episode will leave you fired up to take action.  

Being a writer is so much more than the words.   John Carlton and I did a 25 episode podcast series together and the actual “writing of words” accounted for maybe a third of the conversation. The majority of the episodes were about the “living and thinking” behind the words.    I’ve been pondering this more than ever since large language models came into the craft.    Where exactly does the writer belong in this evolving process?   Of course, for established writers, its use will vary greatly. They know what they need from it and when it’s in the way.   Soon, though, there will be a new generation of writers who never knew life without it.    For them, I believe, just like today, their advantage will come from how they live and experience life.    So, I offer this framework: W.R.I.T.E N.O.W. I lay out (almost) every step in this episode. 

Lizzie Mills was just 20-yrs-old and a new mom when she joined Copy Chief as one of the first members through the door in 2014. She felt like the greenest copywriter in the place, but not for long.  The veteran copywriters were more than happy to guide her and show her the ropes.  Today, Lizzie, along with her husband, Steve, lead their family business and have achieved more success than “she ever dreamed.” All this, while growing their family of three to six, and homeschooling their four children. During our conversation, Lizzie shares… Her two biggest pieces of advice for new copywriters… How she and Steve survived (and actually grew!) their business through the harsh Australian lockdowns (with only two clients)...  Why going “in-house” was the best decision of her career… And… What her “empire” would look like if she decides to build one!

Tom Hammaker’s life in copywriting took a radical turn last month when he was hired to become Rich Schefren’s copywriter.  Better yet, Tom won the gig in a six-week competitive search against dozens of other copywriters – some with more than 20 years in the game.  We called it “The Goods,” and clearly Tom has them.  In this episode you’ll hear directly from Tom how he approached “The Goods,” his strategy for the final copy test, and what it’s like to work with one of the best marketing teams in the world, led by a bonafide legend of Direct Response.