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How I Nearly Became a $1000 a Day Dogwalker for a World Famous Fashion Designer

The first in a series of jobs I've taken, or almost taken, to support a writing career.

I tried to stay warm but my flimsy suit pants weren't cutting it.  The snow fell briskly, coating the luxe Soho street with a fine glaze.  At 11:30 AM I was scheduled to finally meet the man, THE man, the rich and famous celebrity man for whom I was trying to get hired as a $1000 a day dog-walker, a ludicrously lucrative sum.  Over the previous two weeks I'd been put through a meat grinder of an interview gauntlet to try and score this plush gig.  But this was the worst, forced to stand outside in the freezing snow waiting for a text from the man's third assistant letting me know Bob* was ready for me.

My journey had begun the previous Tuesday morning when my friend Lawrence, a headhunter, had called to tell me about the position.  At the time I was underemployed as a writer, but, then again, with the exception of probably five writers in the world, we all feel we're underemployed.  Believe me.  But I wasn't "underemployed" as in only selling one book and two screenplays per annum, I was underemployed as in I had awoken that very day with a feeling of existential dread, wondering where my next paycheck would come from.  I was even angling for a writing job with the free newspapers handed to people as they entered the subways in the morning.  I was also considering moonlighting as a bartender but every time I went to an understaffed bar to see if they needed help, I'd inevitably end up ordering a drink before I could even inquire about career opportunities.  This would lead to another drink which would lead to me waking up the next morning with a wicked hangover and a lofty and unremembered bar tab.  I was spending $50 I couldn't afford each time I went looking for work and no one was even getting my resume or writing samples for their files.

This celebrity dog-walking gig sounded promising though.  The job description was as follows:

Arrive at twenty-five room mansion every morning at 11 AM when celebrity leaves for work at his offices next door.  Sit in living room of twenty-five room mansion, amidst one of the world's finest collections of Richard Phillip's works where I could read a book, watch a 100" TV screen, surf the internet, or just do my own writing work.  Twice a day, locate Ginger the dog within twenty-five room mansion and walk her.  Hand leash over to celebrity when he returns from work at 6 PM.

Write in a gorgeous mansion while making a fortune and occasionally rubbing elbows with celebrities?  I could dig this.  I mentally began spending my money on stupid things.

If you're a man you probably haven't heard of this celebrity.   A woman, and you would shriek and consider this guy pure A-list.  A gay man who lives in New York, LA, or one of three international cities and you've almost certainly had sex with this celeb.  As for me, I knew enough about culture to at least recognize the guy's name, though I didn't really know anything about him.  I quickly read his Wikipedia entry.

My first meeting was with the celebrity's first level assistant Raymond.  I met him at Lawrence's offices in midtown.  Headhunting offices have always given me the creeps and I always hated visiting Lawrence's specifically.  The waiting room was constantly stocked with desperate people in cheap suits and tacky dresses filling out forms on a clipboard noting which skills they possessed (usually none) and how many words per minute they could type (usually 30 poorly spelled ones.)

Raymond met me in the waiting room with a big bear hug as he looked me up and down. I had actually worn a suit, my only suit, an ill-fitting Ralph Lauren number, sans tie, but the rotund Raymond was clad in a pink paisley button-up untucked, teal jeans, and maroon boots.  Lawrence led us to a private conference room where my interview would take place.  I had prepared myself for a litany of questions related to dog-walking.  I'd memorized breeds, spied on people in my Hell's Kitchen neighborhood's poop-picking-up technique (inside-outted plastic bag over the hand), and even put some pictures of my sisters' dogs on my iPhone so as to pretend I was already a loving dog owner.

But Raymond didn't really care about me or my skills at picking up dog shit.  All he cared about was fawning over the greatness of his boss, his idol, Bob.  Seems with this celebrity's busy international, jet-setting lifestyle, and countless companies, he didn't have much time to walk his own dog.  But he still "loved" the thing and wanted it taken flawless care of.  No price was too large to pay for a caring companion.

It was not an interview of me, but, rather, as if I was interviewing Raymond about Bob, with the paisley-clad fella rambling on and on about his boss and his boss's lifestyle.  Raymond had been the previous dog-walker, apparently the lowest job rung in Bob's hundred million dollar empire, before getting promoted to his current position.  Dog-walking was entry-level but full of prestige in Bob's mind and company.  Raymond was moving up Bob's ladder briskly, but he still had the stories to share from his few month's past:

*"I remember arriving at Bob's one morning to find Gwyneth passed out drunk and naked on the living room couch.  I slung her over my shoulder and carried her to the guest room where Chris was sleeping."

*"The only tough parts of this job are when a crazy drunken party is going on all throughout the mansion and you can't find fucking Ginger and you're looking everywhere, underneath beds with people getting mounted on top of them, yelling Ginger's name down hallways full of naked bodies, blow jobs happening everywhere.  It's stressful!"

*"Now Bob isn't your typical fag. He's very buff. He's always like, 'Hey Ray, wannna go shoot some hoops, drink some beers?' Of course I don't. He'll love you though. You look like a guy that can shoot some hoops and drinks some beers."

*"By the way, you're willing to sign a non-disclosure agreement, right?"

Now I was intrigued. I went home and Google Imaged Bob.  Indeed, in most pictures at major celebrity events, he towered over other people and, with a penchant for appearing shirtless, if not 99% nude in ad campaigns and magazine covers, one could tell he was indeed quite buff, despite being in his mid-40s.  I'd quit playing pick-up basketball recently after getting tired of getting dunked on by 12-year-old urban youth who were already 6'5" so I looked forward to have a new boss that could be a potential one-on-one partner.  Maybe I'd go from dog-walker to one-on-one partner to millionaire business partner!

Apparently, despite my shoddy straight male style and lack of speaking during my interview, I moved onto phase two of the process, this time getting bumped to a meeting with Bob's #1 assistant, a female Sheri.

I met Sheri at the offices of Bob's high-end fashion company.  She kept me waiting for a good half hour in the lobby with nothing to do but stare at the nude male "art" pictures covering the walls.  Eventually she arrived, with her fashion forward shirt and it's massive jutting shoulder-pads entering the waiting room a few seconds before her.

Her job "interview" with me consisted of a single question.

"Do you do drugs, Aaron?"

I didn't.  I was a bit taken aback and Sheri assumed my silence to mean I was having an eternal debate as to how to answer.

"It's OK if you do drugs, Aaron.  Weed.  Coke. Crystal Meth.  It's truly cool if you do them.  So does Bob.  Once a month.  Just please let me know if you do and what you do and how often you do it.  And, if you do, I'd prefer if you don't do it around me.  I used to be a coke addict myself.  Bob's second to most recent dog walker though was a meth addict who we had to check into rehab.  I had to fucking walk Ginger for a few weeks.  So if you do drugs, I just hope you can keep your shit together enough to walk precious Ginger."

I still hadn't met her.  Precious Ginger.  Or, him.  Bob.

Sheri must have liked my response to her interview as I found out that afternoon I was one of three finalists who would actually get to meet Bob the next week.  Raymond, who had taken a liking to me and wanted me to be selected, called to brief me.  He noted that the interview would be less than a minute.

"Bob makes decisions quickly, based purely on 'feel.'  That's why he's so successful."

I felt it.

And, that's how I found myself standing outside, on the street corner a block away from the twenty-five room mansion, one that had just been featured in some magazine, "Awesome Homes Monthly" or some shit, eyeballing my watch, now several minutes past our schedule 11:30 AM meeting.

I'd arrived far too early I suppose and seen one of my competitors, perhaps the 11:20 appointment, already enter Bob's residence.  This potential dog-walker looked more a fashion designer's speed, a thin pixie-ish man with a bowl haircut and patent leather sneakers.  I'm sure he'd never walked a dog in his life.  Then again, I really hadn't either.  I'd grown up with plenty of dogs, but I'd always let other members of my family do the dirty work.

Finally, I saw my competition exit with a smile and, two minutes later, I got the text.  Bob was ready for me.

I banged the loud door knocker and a minute later a frantic Raymond greeted me.  We walked through a never-ending halfway to an elevator which we took to the top floor of the five story apartment.  There, sat Bob, bigger in person and casually dressed, face down looking over some sketches as several designers surrounded him.  Raymond pointed me to a seat at the massive table which was at least ten feet in diameter.  The dog, Ginger, an enormous sheepdog, was sleeping under the table.

Bob hadn't looked at me once, but the second I sat down he began throwing one word questions at me in between the conversations he was having with his assistants.


"Uh...yes.  Syracuse."





The whole time I histrionically reached under the table, petting an unresponsive Ginger, trying to let Bob know I loved dogs. Even dogs that smelled like shit, like Ginger, who seemingly hadn't been bathed in a year.  Bob didn't even seem to notice my efforts.

After a few quick one-sentence questions, Bob never looking up once, I was dismissed from the table with a wrist-flick.  Raymond returned to the room to escort me on the long walk out of the mansion.

By the time I'd excited the building and turned the street corner my phone was ringing.  Raymond.

"Sorry, Aaron.  Bob's already hired some one else.  He didn't like your shoes."


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