Letter From Milo: Ad Man

December 8th, 2019

I was awakened from a sound sleep, about three in the afternoon, by a phone call from Big Mike, the Barn Boss of this scabby, talentless blogging outfit. The Barn Boss sounded uncharacteristically agitated.

“Milo, we’ve got a problem.”


“This time it’s serious. The Third City is broke.”

“Jesus! How can that be? When you hired me you said we had hundreds of thousands of readers.”

“Well, heh, heh, I may have exaggerated a bit.”

“How many readers do we actually have?”

“Ah, seven.”

“Seven! You’re shitting me.”

“Well, I’m still waiting for the numbers to come in from New Zealand. But, never mind that. The point is that we’re in a jam and the only way out is by advertising. We’ve got to sell ads on our site.”

“What kind of idiot would even consider advertising with us?”

“I’ve given it a lot of thought. See, advertising is a lot like writing. You write about things you know. In advertising, you sell ads to people you know, people you do business with on a regular basis, people whose products and services you buy.”

“I guess that makes sense.”

“Right now, Benny Jay is out on the street selling ads to all the fried chicken joints and Chinese restaurants in town.”

“Benny does like his chicken.”

“So, all you have to do is visit your favorite business establishments and sell them ads. Trust me, it’ll be a piece of cake.”

“Okay, I’ll give it a shot.”

I had spent quite a few years in the ad game, and I had hoped never to go back to it. I worked as a copywriter and creative director for several small and midsized agencies. I was a professional bullshitter, the person who comes up with catchy headlines and informative copy that are supposed to convince you that the products or services I’m writing about are things you can’t live without. I was, in essence, a salesman with a keyboard.

I’ve met a lot of interesting people in the advertrising world. The industry is filled with talented, driven, ambitious people who could succeed in almost any other fields they set their minds to.

On the other hand, I’ve also met a lot of raging assholes, unscrupulous people who were either borderline psychotics or shameless thieves. Sadly, the ad game seems to attract nutcases. It is an industry driven by creativity, the almighty dollar and merciless deadlines, a combination that’s guaranteed to bring out the absolute worst in people.

Still, as much as I hated getting involved in advertising again, I owed it to Big Mike and Benny Jay to help keep The Third City going. Besides, Big Mike was right. If I stuck to soliciting business from people and companies I knew, I figured I could sell a few ads and keep this fine blog site afloat.

A phone call from Big Mike woke me up the next afternoon.

“Well, how’d you do?”

“About what?”

“Selling ads, asshole.”

“Oh, I did real good. Sold three ads.”

“That’s great, man! I knew you could do it. Who’d you sell ad space to?”

”I sold one to Nickel Bag Bernie…”

“The pot dealer?

“Yeah, he wants to expand his business.”

“Ah, okay. How much did you get?”

“50 bucks.”

“Jesus, that’s great. We can use that 50 bucks.”

“There’s one little hitch, though. Bernie got in a new shipment of fine weed from Hawaii.”


“I bought a quarter ounce for a hundred bucks.”

“Are you saying that you sold an ad and lost 50 bucks on the deal?”


“Great fucking job.”

“Thanks. After I left Nickel Bag Bernie’s I stopped by Madame LaFarge’s Whorehouse and sold her an ad for 100 bucks.”

“That’s more like it.”

“Except, there was another little hitch.”

“Oh, Christ!”

“You see, Madame LaFarge hired a new girl, a cute little thing from Sri Lanka. She’s double jointed and does this weird thing with her hips that…”

“How fucking much?”

“250 bucks, plus a tip.”

“Let me get this straight. You sold Madame LaFarge an ad and only lost 150 bucks on the deal?”

“Plus the tip. Then I stopped at Swillagain’s and sold an ad for 25 bucks.”

“Don’t tell me.”

“Well, I had few drinks, then bought the boys a round…”

“I get the picture.”

“By the way, how did Benny Jay do selling ads to fried chicken joints and Chinese restaurants?”

“I don’t know. He’s still in the hospital getting his stomach pumped.”

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