Known for his sharp wit, controversial takes, and unmatched expertise, Nabeel Azeez sat down to talk with Sean and share his journey from volunteering to becoming one of the most expensive copywriters in Dubai.

We discussed his approach to branding, his TROLL framework for attracting and polarizing an audience, and the lessons he’s learned from years spent cold emailing clients and handling B2B sales.

Sean recently sat down with Kim Krause Schwalm to discuss her journey to become a 9-figure copywriter and how she used her early success to have clients BEGGING to work with her when she went freelance.

In this episode we wanted to go back and cover what mistakes we made as new copywriters and what we would do differently if we were to start all over again. And while we sadly CAN’T undo our mistakes… we hope you can learn from them!

In this episode of Copy That! we answer two of our favorite “It Depends” questions: “How much do copywriters really earn?” and “How much can a new copywriter expect to make when starting out?”

Like most “It Depends” questions… it’s complicated.

That’s why we decided to double the length of this month’s episode and get into all the details that go into how copywriters make money writing copy. Details like:

• The real impact of being freelance vs in-house
• How long it really takes to start making money as a beginner copywriter
• How much you should be making at each stage of your career
• When and how to ask for royalty checks
• Going “wide” vs “deep” when skilling up (Generalizing vs Specializing)
• And the BEST way to sell your services (without even using the word “copy”)

“How do professional copywriters do research?”

“What do I even research for my copy?”

“How much research is enough?”

We get questions everyday about how to do research for copywriting gigs, so this episode of Copy That is! is dedicated to the research process. Some of the things we say are so controversial that we may have attracted the attention of one the world’s best email copywriters…

Tune in to find out:

• The 4 Types of Research You Should Be Doing
• How to Know WHAT to Research
• The Simple Trick to Make Clients Give You Info Worth Using
• How to Make Other People Do Your Customer Research… For Free
• When You SHOULDN’T Do Research
• Embarrassing Research “Hacks” We Actually Use

Sean sits down with the one and only Mark Ford (more widely known as Michael Masterson) to talk about Mark’s experiences as one of the trailblazers of direct-response copywriting into the digital space. Hear what Mark Ford has to say about:

-What traits tell him a new copywriter is going to succeed -Why so many people learn the “wrong” lessons from studying classic copy -Which commonly forgotten emotions you NEED to be able to work into your copy -How “H.A.T.” is going to be the key to writing breakthrough copy in the Internet Age -And so much more!

Sean recently sat down with Aaron Gentzler - CMO of Mauldin Economics and with 20 years of experience in the financial publishing niche - to talk shop. But this is more than conversation about how Aaron climbed the financial copywriting ladder. It's a conversation about one simple truth that new copywriters should WANT to hear: The financial niche is desperate for new talent. So how do you break into the financial niche? What are publishers looking for when they hire junior copywriters? How should you pitch your copywriter skills when you're cold emailing?

Pauline Longdon has an amazing story. She's a former Australian Army Major and former Nurse who reached a dramatic fork in the road of her life. And the choices she made turned her into one of the most sought after and respected copywriters working today. Hers is a story of triumph, overcoming obstacle after obstacle, and leveraging the power of copy into incredible results for her clients. Her path will inspire you and give you an idea of what it takes to succeed.

Alex sat down with the one and only Glenn Fisher from @TheFixCopywriting (who btw worked as a Copy Chief at Agora and has written for companies like Pinterest and Huel) to talk all things copywriting and marketing.

Making high 6 or even 7 figures as a copywriter is the exception, not the norm. But exceptions *do* exist. And in this video Sean sits down with one. This 7 figure copywriter began his journey at 17 with no formal education, no courses, and no money. 5 years later, he's made over $1 million for himself. If you want to follow anyone's path, follow his. It's a story of hard work, cleverness, and finding sparks of creativity.

Sean sat down with Kyle Milligan (of Copy Squad/"Take Their Money" fame) with the intent of talking about some of our favorite topics like:

- AI copywriting - Common copywriting mistakes - The biggest problems new copywriters run into  - The state of copywriting YouTube

...but of course they ended up talking about everything under the sun. 

So sit back, relax, and get ready for a wild ride as they talk about fun subjects like:

- Their deepest insecurities as copywriters  - Why competence and confidence are less connected than you think - What makes Copy That!'s marketing uniquely strange

In this roundtable discussion, copywriters Tania Yeo and Daniel Throssell discuss their experience getting into financial copywriting, and the sacrifices and risks they had to take. Then the conversation broadens out to include what copywriters can do to improve and succeed in this business, and what mistakes to avoid (with helpful tips from Steven Young along the way). 

Yes, it is still possible to become a successful copywriter in 2023 or 2024. Here are the best strategies for launching and growing a copywriting and internet marketing career this year.

Is brand advertising dying? Is AI taking over direct response copy? In this podcast interview, Sean and Rod discuss and then debate what the future of advertising looks like, as well as many of the common problems facing brand agencies today. From atomization and AI to Liquid Death and an automated discount email sequence selling Gucci, we unpack what’s working and what’s broken in modern copywriting.

We marked the beginning of 2026 with a free panel discussion between people from different backgrounds, nationalities, and career paths to discuss the questions we get most about launching and building copywriting career: What are the mistakes beginners make when they go looking for their first job or client? Should you go to portfolio school? Should you get a degree in mass communications? How do I build a portfolio as a newbie? Has AI killed this opportunity?

In this episode, we’re joined by Matthew Volkwyn to help us strip away the "get rich quick" veneers of the copywriting world to look at what actually builds a sustainable, high-income career. If you’ve been hunting for a magic outreach "hack" or a shortcut to six figures, this is your reality check: true success is a three-to-five-year game of skill mastery, and the real money is in cultivating long-term relationships with the clients you work with. 

In this discussion, we talk about why most copywriters struggle with client acquisition. We explore the prioritization of skills over tactics, arguing that when you become undeniably good, the industry’s top 1% starts doing the heavy lifting for you through referrals and high-level networking.

Whether you’re just starting your clock on the "3-to-5-year rule" or you’re a seasoned pro looking to tighten your client retention, this episode offers a roadmap for evolving from a freelancer into a high-value partner.