Copy & Comedy: Repetition for Results

Over the last eight months, I have embarked on a new career as a copywriter with Progressive Insurance. Having performed stand-up for six years and starting a speech-writing company with Laugh Staff, the transition seemed natural as writing was already in my blood.

If your company is looking to convert customers, then effective copy should be the lifeblood of your messaging. Effective copy can cut through the clutter of the thousands of ads that we’re exposed to every day. A sharp subject line or an effective tweet will go a long way in establishing your brand voice as a thought leader in your chosen industry.

How do create the most effective copy? You present options that continuously get a little crazier. A colleague of mine encourages me to always present at least three copy options for every project. No matter if it’s a subject line, headline or the body copy itself, the client always feels valued if you take the time to give them choices.

The first option can be the safe option with messaging that is pretty dry and conveys the purpose. The second option can be messaging that pushes you a little out of your comfort zone (this could be something as small as an exclamation point or a quote for the subject line) and the third option should be something that still gets the purpose across, but definitely disrupts the normal train of thought. There’s a fat chance that the third option may get chosen, but why not showcase your creativity? If the client says no you still have two solid options for them to choose.

One exercise that I have recently started that helps me write better copy is writing sample monologue jokes. These are the types of jokes you see in the beginning of The Tonight Show with Jimmy Fallon or The Late Show with Stephen Colbert.

Writing monologue jokes has helped me to stay up with current events while writing a high volume of material. My goal every day is to write 15 jokes broken down into 5 setups with each setup getting 3 punch lines.


A man died in North Carolina as he was running in a Marathon sponsored by Krispy Kreme Doughnuts…

1)    At his funeral, mourning family members were glazed over with emotion.

2)    The autopsy revealed jelly filling in his bloodstream.

3)    Death hasn’t been determined but they did find powder under his nose.

This habit has helped me stay on top of the news and has enabled me to keep churning out content fast. They say content is king. If so, copy is the crown jewel of your messaging.

Josh Womack is the Co-Founder of Laugh Staff, a company that uses stand-up comedians to help write wedding toasts, dating profiles and engaging content. He is also a Copywriter at Progressive Insurance. And no, he hasn’t met Flo.

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