John Simons On How Copywriting Helped Start The Clothing Brand bigsexy inc.

Haris Halkic: Hi John, thanks a lot for agreeing to share some tips on copywriting and your background. Let’s start with how you got started in copywriting? Please tell me more about your story.

John Simons: Hey, Haris. Thanks for hosting me on your platform!

My road to becoming a copywriter is a tad unusual. I began as a graphic design major with a focus in advertising, at Kean University. During my time there, I participated in the annual Creative Boot Camp in New York, hosted by The One Club.

Every year I found myself in the copywriting position. This came in part to the majority of fellow participants being art directors. I’m a pretty savvy wordsmith, so the writing came natural to me. From those bootcamps I sort of re-discovered my love for writing and learned that I’m not too bad at it either, haha.

Haris Halkic: How did you transition to freelance copywriting from your previous job? What’s your best piece of advice for someone who is employed and wants to become a freelance copywriter?

John Simons: I’m the first mate on the Silver Bullet Dolphin Watch and Speed Boat Ride in Wildwood, NJ. As fun as the job is, I knew I didn’t want to watch dolphins all day. My advice for someone who wants to be a copywriter:

Get your portfolio together. Copywriting is more than catchy headlines and original taglines.

Ask your friends if they need body copy written for their blog; text for their Instagram; or even if you can write their wedding invitation. Anything to get in your portfolio.

Haris Halkic: Getting clients is one of the greatest challenges for freelance copywriters. Could you tell me more about how you get clients?

John Simons: I actually am not a freelance copywriter. However, I run my own clothing brand and therefore have an understanding of marketing myself. For starters, I had to figure out what my goals were. My brand, bigsexy inc., opens the conversation to what it means to be sexy. I believe that everyone deserves to feel sexy.

After I realized my brand goals, I focused on locating a niche market: my friends. Your best advocates are your friends.

My greatest challenge kickstarting the brand was identifying what it could offer, besides clothing.

It took a lot of experimentation and suggestions. I’ve learned that it’s impossible to do it myself. Any great innovator had a team.

Haris Halkic: You already mentioned that you started the big sexy inc. brand and movement. What’s it all about?

John Simons: Bigsexy inc. exists to remind people that they deserve to feel sexy. The majority of magazine covers are unattainable figures, Instagram accounts are basically normalized porn and the music industry has popularized rape culture. With all of this content out there, it’s easy to empathize with people who are self-conscious about their body.

I believe that anyone has the ability to feel sexy. It isn’t your appearance.

The most sexy people share these qualities: confidence, determination, intelligence and honesty. Anyone has the ability to be sexy.

Haris Halkic: How did you learn to write copy? Are there teachers, books or resources that you can recommend?

John Simons: I learned by first re-teaching myself the fundamentals of writing. Read this book: Elements of Style by Strunk and White. I also took numerous courses on Search “ad copy” or “marketing copy” or “writing with flare” in the search bar and you’ll strike gold.

As for teachers, my professor Robin Landa and mentor Gil Kuruneri helped me construct effective ad copy. They taught me tone and how to write for a specific audience.

Here’s a list of books I recommend:

  • Advertising by Design by Robin Landa
  • Hey Whipple, Squeeze This! by Luke Sullivan
  • Elements of Style by Strunk and White
  • On Writing by Stephen King

Also, listen to The Copywriter’s Club podcast!

Haris Halkic: How do you prepare for a writing session?

John Simons: I first stare at my notes and then begin to drink heavily. I do this for 2 hours. (kidding) I actually set up my notes, get a feel for the structure of info I’m going to write and then free-write for about 30min. Once all the gears are greased, I start from the beginning. I know that if I just write and pump out as much content as I can, it’s going to be trash.

Haris Halkic: Who’s your favorite ad or piece of copywriting?

John Simons: My favorite piece of copy is the 1997 manifesto “The Crazy One’s” for Apple. It’s on-brand, colloquial, everlasting and inspiring. It makes you believe that you can do anything and become anything you aspire to be.

Haris Halkic: In your opinion, what are the greatest advantages of running your own business? What makes this lifestyle so special?

John Simons: The greatest advantage is a flexible schedule. You can grant yourself time-off and enjoy yourself.

Haris Halkic: What one daily habit has contributed to your success more than any other?

John Simons: Being adaptable.

Your customers want the best and they want it now.

I’ve learned to take “suggestions” as grains of salt.

Haris Halkic: If someone wants to hire you or find out more about your brand, what is the best way to get in touch?

John Simons: You can check out my portfolio here: You can also shoot me an email:

Thanks again for hosting me on your platform!

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