HOSTED BY Kevin Rogers

COPY CHIEF RADIO

EP 332: From Freelancer to Founder: How Chris Orzechowski Built a Business That Prints Email Profits

Episode332
Copy Chief Radio

EP 332: From Freelancer to Founder: How Chris Orzechowski Built a Business That Prints Email Profits

In This Episode

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.

What You’ll Learn:

09:44 – 13:00 – From Freelancer to Founder
Chris shares the story of how he stopped thinking like a “service provider” and started operating like a business owner — a moment that completely transformed his income and focus.

21:37 – 24:45 – You Don’t Need More Clients
Kevin and Chris talk about how freelancers often chase more clients when what they really need is better systems — and how to stabilize income without burnout.

29:58 – 35:00 – Price Like a Pro (Without Losing Clients)
Chris breaks down his approach to pricing — how to raise your rates ethically, communicate value confidently, and stop undercutting yourself.

51:29 – 55:30 – Balancing Hustle and Home
Chris gets real about building an agency and being a present dad. The discussion turns deeply human as Kevin and Chris unpack what “success” really means when family comes first.

59:40 – You Can’t Scale Chaos — But You Can Systemize Freedom
Kevin wraps the episode with one of his best insights yet — how every freelancer eventually learns that success isn’t about doing more work… it’s about building structure around what you already do best.

Key Quotes:

  • “You can’t scale chaos — but you can systemize freedom.” – Kevin Rogers
  • “The moment I stopped calling myself a freelancer and started acting like a business owner, everything changed.” – Chris Orzechowski
  • “Most copywriters think they have a pricing problem. What they really have is a positioning problem.” – Chris Orzechowski
  • “The goal isn’t to escape client work. The goal is to structure it so it fuels your life instead of drains it.” – Chris Orzechowski

Resources:

🔗 Connect with Chris Orzechowski:

🔗 Mentioned in this Episode:

🔗 Connect with Kevin Rogers & Copy Chief

Plus… whenever you’re ready:

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Produced by Copy Chief Media



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Ready to Land Dream Clients and
Build Your Copywriting Edge?

Get your free copy of The Goods and unlock the strategies top copywriters use to succeed:
Don’t wait—download your guide to copywriting success now!
 
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Ready to Land Dream Clients and
Build Your Copywriting Edge?
Get your free copy of The Goods and unlock the strategies top copywriters use to succeed:
Don’t wait—download your guide to copywriting success now!