Fleeing the Con Man’s Sinking Ship

“If you were on a ship and the captain told you that it was sinking, what would you do?”

I was taken aback by the question posed during a job interview several years ago, but I chalked it up to one of those analytical tests that management consultants are asked – like how would you go about determining the number of tennis balls that could fit into a room. After conjuring a serviceable crisis management response on the fly, I accepted a job offer.

When I first met the founder of the company–a serial entrepreneur who I had heard was a mercurial genius–he told me that he had already heard good things about me. He ushered me into his all-glass meeting room in our lavishly-decorated office, one of four commercial properties the company had around the world. I peppered him with questions, time melting around us, and then we speed-walked around Madison Square Park so he could smoke a cigarette. He laid out his dreams and vision for the company. I felt an exhilarating momentum in my bones, and I started to fantasize about the future. That night, I told my parents that my boss was impressed with me, and they said that they were proud. After all, they had read news reports that the company was funded to the tune of hundreds of millions.

Later that week, he whisked me back into his glass room to meet with him and his executive assistant, a frumpy woman who took a lot of notes and did not ask many questions. He wanted me to travel with him to a conference. “Fly her out early, the weekend before most people arrive,” he told the assistant. “That’s when the wives come.” He grinned at me like a Cheshire cat. 

This man was endowed with an amount of confidence that I had never seen before in any single human being. A dyslexic who had to adapt at a young age without the ability to read or write, he had an uncanny ability to read people instantly. He could recognize what motivated people on a deep and subconscious level, pushing their buttons to achieve his desired outcome. I watched, a fly on the wall in a meeting, as he converted a paunchy, skeptical businessman who had started the meeting with a scowl into a supporter who was laughing and enthusiastically patting backs.

I started to see and believe that he could control or predict outcomes because of this almost clairvoyant understanding of people’s psychology and how they would react to different variables. But he also recognized that the future can be random and unknown, that things have the potential to spiral into chaos into any moment. And through it all, most people just want to be told what to do. 

During one dinner on our first business trip, he told me to order “everything on the menu” and slapped down his corporate AmEx. The next day, still bloated in my hotel, I woke up to a call from my direct manager, wondering where our boss was. No one had heard from him all day. He resurfaced a few hours later, calling me to say he had been in a very long investor meeting where phones were not allowed. I wondered what sorts of conversations went on during these business meetings. Important ones, surely–all part of his master plan. The executives were relieved when I texted that he had reappeared.

Over time he shared with me some of the wisdom he had learned over the years as an entrepreneur. “You do things because you can,” he said. It made me feel powerful, not in that I craved power over other people, but in the sense that I could push the boundaries of my own abilities and imagination. I felt special. One day he proclaimed “You’re the boss!” I thought about being responsible for the very serious finance men in the conference rooms, who I imagined had beach homes and college tuitions to pay for. What would they say if they knew that behind the curtain, a 24-year-old selling her dresses to Brooklyn consignment shops for extra cash was their boss’s “boss”? 

What I could not have predicted is that I had more cash on hand from selling my old Proenza Schouler dress than our company did. 

On our second and final business trip, we went to Las Vegas. He was in a frenetic mood, mirroring the energy of the city built for living in the present. Before the trip, I was accidentally cc-ed on an email. His assistant had emailed my direct boss to let him know she was booking a hotel “room” for the two of us. “Rooms, surely?” replied my direct boss. I knew I would be spending much of my time in the man’s hotel room, but it seemed absurd that it didn’t matter.

When he opened the door to his gaudy hotel suite, smoke billowed out. He was pacing back and forth, speaking animatedly on the phone. I teetered in my high heels, feeling like a baby fawn, and heard him announce to the person at the end of the line that he needed a million dollar bridge loan. Soon after he hung up, he took his clothes off. He told me that he felt an electricity between us. 

The company run by the man with no clothes had no money–electricity would not run it alone. It was reported that he had fundraised a fifth of what the media had initially reported, which he claimed was merely a reporting error that he forgot to correct. Journalists began writing that he had used company funds to subsidize his own personal bills, and sources piled on with their accounts of his mismanagement. When I gingerly asked him what had actually happened, he responded that he was unfairly becoming the sole scapegoat, because everyone was so embarrassed. 

One day he called and said he needed to go away for a long time, and that he could not keep up with whatever our relationship was. I begged him not to go. But he hung up.

It felt like my heart had dropped into the pit of my stomach, like an elevator plummeting down a shaft. Betrayed, broke, jobless, and walking the streets of Columbus Circle alone, I felt that my insides had been excavated, hollowed out. Maybe I was not special. I considered that he never had any plan, at all–that dreams are for fools.

His executive assistant and I were in touch, as she had provided me with intermittent updates about the bankruptcy proceedings. She invited me over to her tiny studio apartment, and offered me some Xanax. Initially calm, she flew off the handle when she realized he had vanished and would not write her a recommendation to help her move into a new job. She began sending me definitions of sociopathy over email. “MOVE ON!” she wrote. “We all make mistakes and if you read through the definitions below, he was a snake charmer with you.” 

People were not getting paid and people were angry; I was at a loss for how to feel, or what to do. I still desperately, delusionally wanted to believe he had control of the situation – or maybe that his apparent fraud did not mean that I was also one. 

“There is a thin line between an unrealized vision worth chasing, and a fraudulent delusion of the future.”

I was paralyzed with confusion about how to proceed in life. Was I supposed to lock in plans and attempt to cling to some security, or live moment to moment, knowing a rug pull could happen at any time? Was I under the spell of a sociopath and narcissist who manipulated me and took advantage of me, or was I motivated to push myself by a misunderstood entrepreneur? There is a thin line between an unrealized vision worth chasing, and a fraudulent delusion of the future. When does a dream become real? 

We hope and we dream, and sometimes our wildest fantasies do come true. Most other times reality comes crashing in, obliterating our idealized version of the future. The world throws curveballs at us or even bludgeons us sometimes, and we recalibrate our expectations and feel humbled. We stitch together palatable memories of the past into stories that help us make sense of things and keep going–all as we fight both the waking ruminations and sleeping nightmares about sinking ships.

One thing I do know is that while our lives can be at the mercy of the predictable or unpredictable acts of people as well as collisions with the world and with each other, we still can create our own dreams. We do not need to be players within someone else’s dream, especially when someone has another idea of the agency our characters have within their dreams. 

The con man reappeared when I no longer needed or wanted him, as people who abandon you tend to do – as if they have some antenna that can detect when you have properly moved on. Two years after that final phone call, he sent me a Facebook message, congratulating me on a new job and apologizing for letting me down as a boss, as a friend, as more than that. We met for drinks, and I told him I’d write something about him one day. He grinned through his vape. I think he liked the idea of immortality, because – predictably – many entrepreneurial men like him do. 

I do not regret our relationship. But a part of me regrets that in meeting him, he made it impossible for me to have more time living under the protection of certain illusions. Because at the end of the day, don't we all want someone to let us know that everything will be okay? To remind us that dreams do come true?

In my dreams, increasingly, I know I must wrest control of the ship.

Ariella Steinhorn is writer and the founder of Lioness and Superposition, companies that tell stories about power, and Nonlinear Love Stories, a project that tells stories about unconventional love.