Chris Tomasulo was the first guy to introduce me to direct response copywriting.

He showed me some sites and a few letters that looked weird and unappealing to my untrained eye. Chris patiently explained the psychology behind the copy and why the pages looked the way they did (ugly on purpose was still very effective in 2002).

Then he turned me on to Carlton, Halbert and Makepeace and Bencivenga and all the dead guys, then recommended the Masterson course. It was the only DR course available at the time far as I know.

I dug into the course, wrote my “restaurant letter” and started writing some classics by hand. However, I was sort of stuck in student mode without a line on how to get clients.

Then one day a young guy named Mike knocked on my door offering his landscape services. He was a real hustler. I was more interested in his sales tactics than his botanical chops and we had a long chat on my doorstep about marketing. I told him I was a copywriter and we should test something together.

He agreed and actually followed through. Exciting times.

I wrote a one page letter for his services and he pulled a list of 200 names and addresses in the neighborhood he wanted to target.

I insisted that he and his wife hand-address and lick stamps onto every envelope to get the maximum “A-pile” open rate.

They griped but agreed.

One dumb thing I did was have the letters printed on green paper. I thought they would stand out more, plus, ya know green means nice lawn, right? Genius. Otherwise the piece looked exactly like a personal letter.

The letter mailed and we waited.

Took about three days for the first calls to come in. I don’t recall the exact numbers, but Mike booked quite a few quotes and ended up closing about four new accounts from the letter. Not a staggering conversion rate, but the cost per acquisition was nuts.

Since I worked for the experience, the ad run cost them all of $74 in stamps and a box of envelopes to land $240 monthly in new business.

And that’s just the baseline offer, he had upsells for hedge trimming and the like, plus it gave him a foothold in the neighborhood where he wanted to grow his account base. Do good work, win some customer endorsements, drop a few door hangers with a special offer and you’re the king of Barclay Estates, man.

I considered it was a resounding success, but when I asked if he wanted to run a second campaign, he said “I’m just not sure it was worth it.”


Welcome blue collar business logic 101. I think licking all those stamps did us in. Plus, it’s very hard to break out of old habits and commit to creating word of mouth, rather than hoping for it.

Anyway, that was the first letter I wrote that mailed.

And any freelancer will tell you, tied for first with “good pay” the best reason to to become a copywriter is to see your copy run.

So, let’s hear the story of your first gig?

And if you dig these conversations and want to be on the inside with the hottest working copywriters and the savvy business owners who hire them, join Copy Chief at the current best price by clicking here now.

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