Kind Of Like Winning The Lottery

Summary

A former full-time writer and salesperson for a sex tabloid recounts his journey from earning $700/week to making millions, maintaining secrecy about his wealth, and eventually facing legal consequences and adapting to a modest lifestyle post-incarceration.

Abstract

The narrative describes the author's unexpected career shift from driving a New York City yellow cab to becoming a successful writer and salesperson in the adult entertainment industry. Over time, he amassed a fortune through commissions by selling advertising space to sex workers in reputable publications. Despite his significant earnings, he chose to keep his wealth a secret to avoid complications with clients and family. His secret was eventually exposed during a legal battle with the IRS, leading to a brief imprisonment and the loss of a substantial portion of his wealth. Post-release, the author leads a modest life, including part-time work as a Doordash delivery person, while still possessing enough savings to live comfortably for the remainder of his life.

Opinions

The author believes that discretion about his financial success was crucial due to the nature of his work and clientele.
He implies that flaunting wealth could have led to negative consequences, such as clients withholding payment or attempting to negotiate lower rates.
The author suggests that maintaining a low profile was a strategic decision, akin to a "spy versus spy" scenario, to protect his income and livelihood.
He expresses a sense of irony and detachment regarding the public revelation of his financial status and the subsequent reactions from his social circle and clients.
The author seems to take pride in his ability to adapt to changing circumstances, including his transition to a more modest lifestyle after legal and financial setbacks.
He conveys a sense of contentment and satisfaction with his current situation, despite the dramatic shifts in his financial status over the years.

Nobody knew

It was a life-changing event the day I was hired to be a full-time writer and salesperson for a sex tabloid published out of Philadelphia, PA. In the beginning, it was a $700/week job that would get me out of the driver’s seat of a New York City yellow cab. It ended up with my making millions and going to prison for a year. Who’d-a-thunk?

We hear and read stories about lottery winners and how they handled the windfall. Did they blow it on bull shit? Did every family member and friend come out of the woodwork for a loan? Did they even tell anybody?

Well, I never won the lottery. I’ve never even bought one ticket to try. But I did experience having money seemingly fall from the sky — accumulating millions while nobody knew.

To be sure, it didn’t happen overnight. I went from $1000/week — to two — and then to ten thousand within a year. Given my unique circumstances (and temperament to be sure), it would have been foolish to advertise my good fortune.

I earned the money selling advertising in newspapers and websites to hookers who needed to attract customers. The media outlets for which I sold (Village Voice, New York magazine, New York Press) were all legitimate publications that just happened to create a special section for the girls. Knowing how much hookers made, the media charged a fortune for the space — and I made my fortune in commissions selling it for them.

Those publications wanted ad agencies to handle the bulk of the army of hookers who advertised in their pubs — and were willing to pay those agencies handsomely for taking on the job. I took on that job and made the big bucks. Most guys in my position either burned out on drugs — or hooker sex — or both. But I partook in moderation — and did my job diligently with whatever skills (copywriting, graphic design et al) I had. And I stayed the course for two decades.

Bragging on my windfall would have been about the stupidest idea I could have ever entertained given the circumstances. If one of my hooker or whorehouse-owning clients realized how much I was making, how do you think they would have felt — or treated me?

You got it. They wouldn’t pay their bills. Or they’d try to hustle me. Or they’d negotiate a lower rate once they realized I was flush with cash. It was truly a spy versus spy scenario.

And as such, I rode around on a bicycle picking up ad money wearing sneakers and a hoodie. Nobody knew. Not even my family. It was all a big secret. I did tell a few of my old cab-driving buddies. But they thought I was just a dreamer/bull shit artist. They didn’t believe me.

Then the IRS came a-knocking at my door. The bubble burst in an instant with respect to my riches. But still, nobody knew that I’d made all that money — nor lost it to the USA.

With respect to my lifestyle, nothing changed after “the visit.” There was 500k the IRS couldn’t seize. And I lived on a tiny fraction of what I was making. It was almost like a setback in a Monopoly game.

Then the other shoe fell. Three years later, when my plea deal was finalized, a Daily News writer ran a full-page feature about me — complete with most of my financials. The cat was out of the bag. My family was in shock. They had no clue. The hooker world went crazy. They refused to believe it, citing that the press always amplifies numbers exponentially to garner readers. I went with that.

But eventually, they got the memo. Fortunately, I’d pretty much retired by the time the news was out. Selling ads took a back seat to me negotiating my legal woes.

After 5 plus years of playing a cat and mouse game with the feds (I was the mouse) — and then spending a year in prison for tax fraud — I emerged with 1/3rd of my life savings — enough to live on for the rest of my life.

To occupy myself, I (among other activities) Doordash part-time. The people to whom I deliver (who’ve ranged from the wife of the prime minister of Dubai to welfare cases living in the projects) have no clue that the scruffy old white guy who just delivered their food is in fact a multi-millionaire (if you consider 3 to be multi — which it technically is). And I like it that way.

In some bizarre manner, it makes me feel like I’m the most unique character in all of New York City. The rich guy delivering food on a pedal bike in the dead of winter? No way. But it’s true. What can I say? I’m that lottery winner who told nobody — and went on with his life unchanged by the windfall.

P.S. I realize it could be interpreted that I’m bragging with this story. But I know nobody on Medium — and am never likely to meet anybody. So it’s kind of like a diary entry.