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My Secret Life as a Mysterious Multimillionaire’s Personal Assistant

It started with a simple Craigslist ad. Before long I was being sent on sketchy tasks, pocketing wads of cash, and trying not to think about where his money came from.


Read when you’ve got time to spare.


Illustrations by Julie Benbassat.

My boss, Zander, stood outside a restaurant window, waving a wad of cash at the steakhouse’s waitstaff. He wanted them to open, hours early  just for us. “I’ll make it worth your while,” he shouted, their backs turned to us.  

It didn’t work, so we continued wandering around downtown Austin. We decided to dine at Searsucker, an impulsive choice given Zander’s waning pride and the 100-degree heat. Sweat beaded down my neck and pooled in my armpits as the hostess led my boss, his chauffeur and me to the dining area. She escorted us to a table guarded by a wide-branching palm tree that seemed almost practical compared to the braided ropes draping from the ceiling and the vanity lighting demanding that we EAT EAT EAT.  

 Zander (I’ve changed his name, as well as those of others mentioned in this piece) settled into the first open chair and started flirting with the hostess. He drained his Old Fashioned and asked for another.  

“I shouldn’t,” he shook his head. “My wife is going to bitch at me if I come home drunk.” His words flowed faster as he sucked the ice cubes swirling in his tumbler. His wife was a nag. A bitch. He hated being around her. 

I told him that he shouldn’t talk about his wife like that. He shrugged before telling me that he called his wife a bitch to her face all the time. “She thinks it’s funny,” he remarked before emptying another cocktail in two gulps and heading to the restroom.

Terry, the chauffeur, leaned over and cleared his throat: “You shouldn’t say anything when he starts in on his wife. I hate it when Zander talks about her like that too. But this is a good gig. It pays a lot of money. Like, a lot. You can’t even imagine  you don’t want to mess this up,” he warned me. “You have to learn to let some things go.” 

I stared at the cheese congealing on my hamburger, chastened by Terry’s scrutiny. By not being complicit in Zander’s antics, I had somehow forgotten “my place.” It wasn’t just about being an obedient assistant. As a black woman, I had stepped across an invisible line separating me from these two white men. 

* * *

In 2013, I worked part-time at a literacy program for refugees. For 30 hours a week, I shuffled war-weary adults into classes appropriate for their level of English comprehension. I cared for many of them; some even adopted me as their surrogate niece. I perceived my job as confirmation that I was morally good. That saccharine righteousness dripped away over time. I became bored and frustrated with the way my skill set was being underutilized, and by the small monthly paycheck that I was often told not to cash right away, in case it bounced. I was demoralized. 

Trolling Craigslist was my favorite pastime. It distracted me from my depression as I indulged in the absurdity of the missed connections and casual encounters. I also obsessively checked for fast-cash jobs (and ovary donation requests) to supplement my income. That’s how I found an ad for “16 Days Straight: Editing and Motivating Gig.” 

I responded to the ad and scheduled an interview with Zander at a Starbucks near my apartment. We clicked immediately, and after I reviewed a section of his self-help book to make sure I was comfortable “reading material that was laden with vulgarity,” he offered to pay me $10 an hour with a $5 daily bonus for arriving to my shift early. He implied that there was potential for me to earn more over time. Believing that this could also provide valuable editing experience, I agreed and started the following day. 

For six hours a day, I supervised as Zander wrote nonstop during 50-minute writing sprints. He was prohibited from leaving his seat unless it was during the assigned 10-minute break. His fingers always had to be poised on the keyboard. If I noticed him clicking aimlessly or staring at his phone, I shamed him  his preferred motivation. Whatever he wrote during one sprint, I edited in the subsequent one, while also monitoring him.  

Zander bragged that he was working toward a doctorate in public health. His goal was to “help people better themselves,” and until then he would attempt to do so with his self-help books. I edited stories about liposuction surgery, steroid use and vague financial advice, scrolling past photos of his post-op absHe wanted to inspire others to undergo liposuction. We shouldn’t be ashamed to do whatever it takes to achieve our goals, his claimed. The gratuitous shots of his penis in his beforeandafter photos were an added bonus for his readersHe loved the way he looked and wanted others to see that too. He believed everyone should feel this way about themselvesAt the end of the day, we did a “sustain and discontinue” session where we discussed what helped and hindered our productivity.  

The only time we talked about our personal lives was in the few minutes before the start of the workday, or during Zander’s breaks — if he wasn’t ordering more lattes and flirting with the baristas. He was unfailingly candid in our conversations, except when it came to questions about how he made his money. According to a creased business card he handed me, Zander worked in real estate. Doing what? He wouldn’t say. He also didn’t comment much on his other companies as he flashed their respective businesses cards before tucking them back into his suit jacket pocket. Among many things, I learned that he and his wife each maintained a separate menagerie of lovers. His included one of the baristas. Although he was a multimillionaire, he was terrible with money, yet aspired to be one of the world’s first trillionaires. I didn’t believe he was rich until we walked outside together one afternoon and he unlocked a brand-new Mercedes-Benz that was backed into two parking spaces. A note was pinned under a windshield wiper.

It read: “You are a fucking tool, you pretentious fuck. Enjoy your small cock. – Everyone” 

I took a picture to show my husband Kevin (my then-boyfriend) so we could mock Zander later, but as I raised my camera I became afraid people would associate me with him. I worried they would see Zander laughing and think that I thought it was a joke, that I was pretentious too. I was so ashamed. I quickly took the picture, realizing later that part of the note was out of frame. 

* * *

I didn’t mind the work. The extra cash allowed Kevin and me to make extra payments on our credit cards or update a few pieces in our threadbare wardrobe. We laughed at Zander as we ate out more often on his dime. We saw him as an eccentric narcissist squandering his riches. We didn’t think twice about having our hands out to catch his scraps. 

One day during a break, Zander announced that he was ending my contract a few days early. He was traveling to India soon for business, where he would also outsource the editing of his e-book for $1.25 an hour to reduce his losses. He paid me the day’s wages and most of the bonus for working all 16 days. 

“I’m not a bad guy,” Zander said, fanning bills onto the sticky table. He was short $100 and asked to meet the next day so he could pay me the rest. “I need to know that you’re OK with this, that you don’t think I’m some asshole.”  

I wasn’t, and I did think so, but I agreed to meet him anyway. I needed that money. 

The next day, Zander waited for me outside Starbucks at a table near the entrance. He sat with his hands stuffed in his jacket, his body erect as if he were ready to leave for somewhere more important. 

He grinned as he placed the $100 bill he owed me on the table. His silence was unnerving. Paranoia itched the back of my mind. I maintained eye contact as I slid the bill across the tabletop, tensing my muscles in expectation of a gotcha! moment. 


Once the money was in my pocket, he slapped another pile of hundreds on the table. He waited, still grinning. I sensed he wanted me to freak out like a game show contestant who had just won a showcase. He expected effusive thanks for his generosity. But the implication that I should be thankful for money meant to ease his guilt turned my stomach.  

“What’s this for?” I frowned at the thought that this might be a Pretty Woman situation. He was well aware of my financial needs, and combined with his constant compliments about my looks, I had been holding my breath for the moment he asked me to be his escort or another lover.  

Zander chuckled at the customers gaping at the money as they entered Starbucks. 

“I am not afraid of money,” he remarked. “I have it. Why shouldn’t I flaunt it? These people need to get used to seeing it.” He said the money was an additional gift for ending the gig early. He really wanted us to be friends.  

I didn’t want to be his friend, but I couldn’t help but think back to a moment when I was 16. My mother’s longtime beautician had offered me the chance to be a stewardess for a trusted male client. He had a private jet and wanted a “young, intelligent woman” to steward him on his flight to Paris the following week. My mother urged me to do it, even though I didn’t have a passport. I always regretted being unable to go. Mostly, I yearned for an adventure I might not ever get to have again, and I vowed never to let the opportunity pass me by twice.  

“You should hire me on as your assistant,” I blurted. “You need me.” 

* * *

“Everyone has a price; at the end of the day everyone is a money-grubbing whore; everyone will justify anything if they get their palms greased enough.”  

“I know he’s not talking about me,” I told Kevin as I read Zander’s email accepting my offer to build his brand as his strategic development officer. I reminded myself that I could not be bought and pushed around. Heeding Kevin’s advice, I had proposed a position that would offer me more clout and potential mobility with future employers. I also wanted Zander to see that I had the acumen to do more than edit his books. In reality, Zander treated me like a glorified assistant. He promised me designer handbags and international trips as I juggled his tasks with my part-time work at the refugee nonprofit. He didn’t offer me a salary but instead paid me a few hundred dollars per day, the amounts based on how he felt or what was in his wallet at the end of each day. If we worked on a business project, he prematurely offered me commission on its expected earnings while also promising an additional commission when the project was complete. I bought into his absurdity and I often changed my work schedule to accommodate his whims. If he asked me to jump, I asked how high, then used the fistfuls of cash he paid me to soften the fall. 

Zander once requested my presence at a meeting with a realtor selling property near Lake Travis. He planned to purchase it and make it exclusive to the wealthy by either sinking the road connecting the property to the mainland or posting armed mercenaries at the community’s entrance.  

“The only way in is by helicopter. Doesn’t that sound cool?”  

It sounded bizarre, but I half-heartedly agreed. I wasn’t about to say no and risk losing a potentially lucrative job. Zander’s chauffeur later whisked away in the all-black interior of his newest Bentley. It was all completely sexy and insane. 

I never complained when my boss asked me to do something mildly unscrupulous like taking photos of blueprints that were confidential or recording a meeting unbeknownst to the attendees. I worried that if I said no, I’d lose access to the luxury travel and foreign adventures I craved. I chalked my deceit up to the job or  as Zander would say  “the cost of doing business.” I agonized about my decisions at home, but once I pulled out my earnings for the day, Kevin and I reasoned that I should keep going until I was asked to perform a monstrously unethical task. I balanced out these wrongs by challenging Zander and Terry’s male posturing.  

“You know we’re intimidated by you, right?” Zander smiled and said to me one day after I criticized a story about one of his mistresses. “You see right through our bullshit.”  

I stared at his porcelain veneers, studying the sharpness of his smile, and belatedly realized he was a shark and I was a guppy. I was unsure how long I had been in danger of being eaten alive. 

* * *

Two weeks after I became Zander’s assistant, I quit my job at the nonprofit. Working for him offered immense freedom. The money provided ease. Plus, an employee at another local refugee organization had just quit to work overseas, and I saw this as the universe giving me license to also choose a life of comfort over social responsibility. 

My first major assignment was to spearhead a financial project. The specifics were sketchy at best. Zander hushed my concerns by announcing that I’d earn a percentage of the project’s earnings. It was enough to make me a millionaire in a month. I sat speechless as he bloviated about how I would ascend to a new life, how I would be even greater than I was at that moment.

“Help me become the richest asshole in the world,” he texted me later 

I didn’t believe it was possible. I didn’t believe he, a rich white man, would give away that much money to me. I agreed to work on the project but, for the first time, I forced myself to examine my situation. Where was this money coming from? When he said he owned a company that sold military products, what did that mean exactly? While I silently questioned every move, Zander hindered mine. 

My demise culminated in two simultaneous events.  

As we prepared to go to India to meet investors for his Lake Travis property, Zander gave me funds to acquire my travel visa. He later gave me additional money and demanded that I receive my immunizations within 24 hours.

While I worked on getting my visa, our relationship changed overnight. Zander excluded me from meetings and rebuffed my inquiries about ongoing projects. When I asked Zander about the recent changes in my duties, he asserted that he was figuring out the highest and best use of my intelligence, time and talents. 

It turns out the best use of my intelligence, time and talents was bribery.  

Zander arranged to meet me outside of our favorite Starbucks one drizzling, gray day. It was like a scene out of film noir. Terry held an umbrella over Zander, dressed in an expensive dark-colored pea coat, while the rain fell on me. Zander handed me a manila envelope with paperwork, a business card for a company of his he had never mentioned before, and cash. He ordered me to hand-deliver the envelope’s contents to a city official by the end of the day. 

“What the hell is that?” I asked, pointing at the money. 

“Don’t worry about it. You’ve gotta grease some palms sometimes.” He rubbed his hands together and flashed a predatory smile. 

I drove home, collapsed on my apartment floor, and cried. I was overcome with the realization that I had swindled myself for greed, that there was a real possibility I had compromised my morals. Money wasn’t just the carrot; it had become my prime motivation. It was also the stick. 

When my tears dried, I got angry at Zander. He knew the bribe’s obvious illegality would have harsher repercussions for me, a black woman, yet he still ordered me to do it. Any doubts I had about his previous overtures were clarified. I was not a trusted confidante, I was simply there to ease his ego while providing a service. For me, holding that envelope meant doing the tasks that were beneath a rich white man, under the guise of good will. 

I didn’t want the envelope and refused to hand-deliver it, but Zander ignored my calls and texts. I researched the mailing address for the city official, deciding that I would anonymously mail the envelope insteadCrime procedurals flashed in my mind as I put on dishwashing gloves, wiped down the envelope and the documents, tossed the money inside, and taped it shut. I drove to UPS wearing a hoodie and sunglasses. I paid for next-day delivery, then blocked my face from the security cameras as I left. An hour later, irrational and consumed with panic, I sat in my apartment debating whether I should drive back to UPS and beg them to give me back the envelope. 


Days later, Zander inquired about the immunizations. Of course, I’d been unable to get them so soon. He accused me of lying and taking his money. He texted: “My gut feeling is that I’m being spun.”’  

“Spun.” The word crackled across my brain waves. It translated to cheating. Robbery. Theft. Each subsequent text drew a broader line in the sand. He claimed everything he gave me was a gift. This had been a trial run. He’d never trusted me.  

“What would you do in my position?” he texted.  

I yelled expletives at my phone, humiliated. I couldn’t believe he was rejecting me for failing to complete this mundane immunizations task, which could still have been completed in the upcoming weeks. Of course I had been unable to schedule a next-day appointment for something that required advance notice. And there was also an underlying threat in his texts. My instincts bucked at the steel trap closing around me. 

Finally I texted him, “I quit.” 

Zander offered me $500 to dissolve our contract  unironically contradicting his earlier claims that he hadn’t hired me. There’d be no hard feelings, he said. He wanted to be…friends. I ignored my phone buzzing like an angry hornet and wept on my bed. I had narrowly escaped what I suspect would have been something truly awful had I gone to India with him. I had flown too close to the sun. 

In a matter of weeks, I had lost two jobs and stalled my professional development. I was ashamed to admit that I had put myself in a precarious situation, and because of it I now had nothing. It was the first time I had ever felt truly disappointed in myself. 

I briefly considered asking for my old nonprofit job back  it was available if I wanted it  but I was resigned to this much-needed course correction. I had only initially accepted that job out of a lack of opportunity. To go back meant to ignore the deep-seated dissatisfaction that gripped my core: I was unhappy with my life and was seeking permission to let go of my responsibilities. 

Taking the job with Zander had freed me from social pressure to pursue a single career track until retirement. It gave me the flexibility to cultivate passion projects like writing. And while I wanted to jet-set around the world, I wanted it to be through my own hands and not in service of someone who did not respect me.  

Quitting meant I was financially unstable, but it also gifted me with a chance to pursue my dreams. 

A year later, I received an email from Zander. Attached was a picture of him and his wife standing on their home patio overlooking Lake Travis. He described their recent trip to India and asked if I had used my visa yet.  

“You have 10 years to use it,” he wrote. 

My fingers hovered over the keyboard for a few seconds, then I deleted the email without a response. But I smiled as the picture of Zander and his wife blinked out of existence. I had not gone to India yet, but now I know that one day I will. 

DW McKinney is an essayist who has written for Bitch Media, Elite Daily, HelloGiggles, and others. She serves as the creative nonfiction editor for The Tishman Review and Reviews Editor for Linden Avenue Literary Journal, and she is currently working on a nonfiction chapbook that examines (and imagines) shedding her cloak as a Black woman for a life unburdened by racism.

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This post originally appeared on Narratively and was published September 23, 2019. This article is republished here with permission.

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