Jack Macco Wastes Your Time
CEO Prank Calls
“Are you wearing a helmet?” Charlie screamed at the CEO through the receiver. “Because prices are falling!”
It was the climax of a good Jack Macco. We’d made a habit of prank-calling high-level executives, and Charlie’s character Jack was our hero. After a week of getting beaten down by the boss, there was nothing better than meeting up in Charlie’s office overlooking the tennis courts on Bayaud and exacting the people’s justice. Together, we’d make the masters of the universe pay, and we’d do it by laying waste to their dearest asset: time.
Who knows how many millions of dollars’ worth of minutes we stole from America’s corporate elite over the years.
We were just kids, twenty-somethings fresh out of college or retail jobs. Before being hired at the national magazine, Anthony had been a towel boy at a local spa. Charlie had worked at a hockey store. And I, having received my masters in fine arts degree, had recently been employed as a waiter at the Stapleton Olive Garden.
But that office made us feel like we’d made it, as did the idea of working at a magazine, a glamorous thing to announce on Facebook in 2016. (Note to younger readers: beware the glamorous job).
I had a fancy title and was interviewing Scarlett Johansson, but my salary started at $35,000/year, less than I’d be making if I’d stuck to slinging breadsticks. As “managing editor,” I was working 70+ hours a week and always on-call via a noisy Slack chat. By Thursday/Friday, our brains were slag, and, since the boss would usually check out early, we took refuge in Charlie’s swanky office–he being the company’s most successful employee and still the best salesman I’ve ever known. And it was there that we’d hatch our schemes for harassing the people whose professional status we could only pretend at.
Since we were in the media business, we had a variety of sleazy tactics to get your cell number. Most importantly, we understood the psychology. Even though we were young scrubs, we were acquainted enough with the business class to understand how they ticked. And this was how Jack Macco was born.
When you’re pranking C-suite executives, yes, obviously you do want to have some traditional crank call fun. Absurd scenarios, funny voices, all that good stuff. But the most important thing is wasting their time. This is what makes the CEO prank call such a worthy comic enterprise. If you’ve eaten up even a minute of their seven-figure day, you’ve already won, joke’s on them. So when you formulate your strategy, your first priority is how to keep them on the line.
See, Charlie understood that global-level CEOs are often type A psychos, who are every day surrounded by sycophants and yes-men. They’re smart, vicious, and highly analytical creatures–velociraptors testing the fence for weaknesses. And because their time is so precious, they’re tuned to every detail of your voice–minor inflections, cadence, diction, anything that might give you away as someone who’s not on their level.
But Jack Macco would not only be on their level. He would rise above it. Jack could speak to billionaires like inferiors. He would bully them, and, because most serious executives are smart enough to refrain from acting in the blind, if the voice on the other end seemed like an equal (or a potential superior), they would meet it as such. In other words, they would let you talk long enough to drag them deeper into the joke. For Jack, this would usually involve telling the CEO that they’d forgotten some major partnership, and why hadn’t they signed the damned terms agreement?!? And then, after a long, confusing, and heated back and forth that would sometimes result in a screaming match, he would abruptly pivot to trying to sell them an absurd product that didn’t exist in the corniest way possible, saying that they were fools for not working with him (our favorite was to pitch a CEO a banner ad on our personal blog website), at which point they would hang up (ideally 10-15 minutes later after we’d gotten our yucks).
Here’s an example (with names and numbers bleeped out). Please excuse the laughter. We were pros at muting the line during giggle fits.
JACK MACCO
Was it childish? Absolutely. But there’s something to be said for good old-fashioned fun. And when I reflect on Jack, I also think that it was a way of relieving a careerist tension we all felt (and still feel today, but especially back then). Every week, we were on the phones, in meetings, etc., saying the words, wearing the mask, going to tradeshows, pressing the flesh, and it was so nice to inject some silly humanity into the dance of the dead by regressing to the teenage delight that is the prank call.
Ah, I wonder if the kids are still doing it. It’s got to be much harder now, since people rarely answer their phones anymore, which I don’t understand. Could the person on the other end be trying to scam you? Sure. But you should answer anyway. Life is a scam. Get into it! Have some fun. Tell someone no! Exert what little power you have; it feels good! Or maybe get dragged into an adventure with Jack Macco! Anyway, I digress.
Charlie and I are both soulless CEOs ourselves now–though his enterprise is much more lucrative than mine. We both still live in Denver, and whenever we get together for beers, we’ll inevitably talk about all the laughs we had as overworked kids, desperate for juvenile humor, petty revenge, and alas, yes, advancement.
Till next time.
Yours,
-Paul M. French, editor


