I was a hedge fund billionaire’s PA. It nearly killed me | Life and style

It was early evening on an almost-spring day, six months after I started working as sole personal assistant to Boone R Prescott, the billionaire founder of the hedge fund Carbon. Boone had left the office, so I stepped on to a treadmill. For years, I had run for an hour five or six days a week. I had mostly kept up the running at Carbon, but in the office gym, because it was more convenient than doing a loop around the park. The hour was frequently sewn together from smaller pieces because I’d receive an email or text to which I had to respond.

Ding. I looked down.

I was halfway through my run and my phone was resting on the ledge, so I did not have to pick it up to see that the email was not time-sensitive. I let it sit.

Then I ruminated over whether I should let it sit and, after several excruciating minutes, decided no, I could not. I feared Boone would say something to me if I was slow to respond – yet I refused to stop running. For months I had been letting work intrude on my life and for the sake of my sanity I needed to complete this one personal goal, to run for one whole hour, or else.

I’m not sure how long I agonised as I ran, ran, ran, putting one foot ahead of the other, until finally I resolved to answer the email while running. I picked up the phone and began typing a reply.

I looked down. Black.

I felt my chin slam the belt as I was thrown off the end. “I’m fine!” I yelled before I heard gasps and, “Oh my God.” I calmly checked my body. I was wearing Carbon-provided Lululemon leggings. They were intact; I had hope. As I rolled them upfrom my ankles, all I could think about was not letting my dumb decisions affect my ability to work. Starting midway up my shin, I saw my skin was no longer whole. The friction of the rubber, looping at over 10ft a second, burned my epidermis, past the red, outer layers into the glistening white. A streak of burns ran on each leg from the kneecap down, as if a craggy stone had skipped across the water that was my skin. My palms, my chin – they burned, too.

My head, hips, back, joints – everywhere I was in pain. Emma from investor relations and May from accounting were there. So was José from the kitchen staff. He ran for ice, then helped me up and walked me back to my desk.

A few colleagues told me I should go to the hospital. “I’m fine,” I said. But I wasn’t. I couldn’t walk. Quilts of skin were missing from my knees. I took an Uber home at 6.48pm.

The next day I took an Uber back to work at 7.42am. In the late morning I recounted what had happened to me to Boone. “Carrie,” he said, “go to the hospital. Now.” He called the assistant to the president of the hospital, who got me in that same day, in the early afternoon, to see a doctor specialising in women’s sports medicine.

Boone’s wife, Elisabeth, called to offer support. “Try Boiron arnica and calendula creams,” she said. “My friends and I – our kids get bruises all the time.” I did not tell Boone it was his email that had tripped me up. That detail was beside the point. The point was it was my fault. When would I learn that I couldn’t do two things at once? That perhaps I should just stop the treadmill? And so I cleared the deck, again: I doubled down on work and only work. No more personal goals of any kind.

Elisabeth’s creams did not help. For weeks, new skin would grow over the wounds and I would take a step, bend my knee, and tear the scabs right back open.

I was 29 when a headhunter reached out to me wanting to chat about job openings in New York. In college, at MIT, I had majored in math and finance. Then I worked for four and a half years as a quantitative equity analyst before quitting to go to business school. But I dropped out – I wanted to change paths. I needed time and space to figure out my life. So I enrolled as a non-degree student at various universities and cobbled together a liberal arts education by taking classes in the humanities. I was midway through a fiction writing workshop when this headhunter asked to meet.

“The job,” he said, “is essentially being Boone’s right-hand person: you’d manage his time and business life, help with research, support one of his analysts. This is a once-in-a-lifetime opportunity. Can I pitch you to them?”

Carbon did not have a website or a Wikipedia page, and Boone was not active on social media. He did not give interviews. Nor did he sit for photos. In the early part of the decade, Boone debuted on a prominent list of the youngest billionaires in the US. If he continued compounding his wealth at, say, 20% a year – a conservative estimate given some of his reported returns; a number that does not even factor in the profits he’d receive from owning and managing the funds – he’d have a net worth of over $5tn by the time he reached the age of Warren Buffett.

The recruitment process included 14 interviews, most of which passed in a blur. An hour with Boone. An hour with Elisabeth. A forensic grilling by Gabe, Boone’s software analyst, to whom I’d also provide support. A psych test, over Skype, with Boone’s executive coach, covering my family background, life history, values and dreams. Carbon asked for references – eight of which they had chosen from my LinkedIn page.

I was at home in Michigan when Boone called. My base salary would be what I had asked for, plus I would be eligible for a bonus after one year. No range was given for the bonus. Would I be able to start in two weeks?

“Here’s your welcome bag.” Erin, another assistant, held up a navy canvas tote emblazoned with CARBON in pure white. It contained a water bottle stamped with the same logo; a folder with an employee handbook noting that Individuals should refrain from using vulgarities, obscenities, jokes, sarcasm; and the sable fur of the investor class, a Patagonia fleece jacket with another Carbon logo embroidered on the left arm.

Later I had a sit with Boone in his office on the 46th floor of the iridescent New York skyscraper we shared with other behemoths of the money-management industry. I was ready to learn everything from him and came prepared with a Moleskine already containing copious notes on the books he had sent “to get us in sync”.

Boone came prepared, too. He gave me a sheet of paper titled Orientation for Carrie Sun. As he spoke, I took notes. The first three words I jotted down were straightforward, integrity, honesty. He explained what my mentality should be: Not to promote BRP. No quote. No press. Not cancelling mtg last min. Not too big or important. Political – no. He described how I should interact with others: Super nice. Helpful. Resourceful. Get back to people. Super nice. (Again.) There was a whole section on his food preferences: Protein – not heavy. Salad/soup. Clean. Not spicy, salty. Not mayo. No caffeine/red wine. Anti-cancer. He mentioned Carbon was a “flat” organisation and I needed to understand its “cadence”.

There was more: five sheets of paper titled CS Responsibilities and Expectations that listed 96 responsibilities (from Calendar to Research to Finances to Communication) followed by 13 general expectations. We went over each line; there were no duplicate items.

“The key for you,” Boone said, “is to watch closely and learn from others. Don’t step on anyone’s toes. Don’t act like you know everything. Defer to others.”

Then he went over the expectations. Maximise efficiency. Positive, “can do” attitude. No ego, productive, high return on time. When he was explaining the fourth expectation – kindness, professionalism, going the extra mile – I found myself diving headlong into the rapids.

He said he cared deeply about doing the right thing. About morality. Before Carbon I had told myself I would never get emotionally involved with work or school again. I had been burned before by loving institutions that did not love me back; by believing that goodness and equity and justice were possible at places with elite reputations and capitalist interests to protect. It was then, toward the end of my first sit with Boone, I became a believer again. I believed in the possibility of good billionaires. I believed that you and I and anyone who wanted to could be a good person at a hedge fund. I also believed that the game was about more than just money.

The final expectation: There are no “dumb” questions in the first 18 months (or really ever)! Boone put his finger on the line and said, “You can ask me anything you want at any time.” I nodded. “And don’t say hedge fund. We’re not a hedge fund.” He paused to make sure I knew he was not kidding. “We are an investment firm.”

The goalposts moved the next day. At home, after my first day of work, I had heard my phone chime once around 9pm. Hours earlier I had added Boone to my favourites and dragged him up top – above Mom and Dad and my best friend, Yuna – and changed the settings so his contact would bypass everything and ding once for email, twice for text; everyone else was on mute.

I went to check my phone. The email was sent to me and Jen, who ran his family office and personal life, and included a photo of his kids at Carbon’s recent Family Day. How cute! Later in the night I checked my phone again and saw that Jen had replied all.

The next morning, Boone and I had a sit. I was ready to tackle Carbon with my “can do” attitude when he, first thing, asked, “Did you get my email last night?”

“Yes,” I said. “Your kids are adorable.” I made the same sloped brows and tilted head I make at seals and sloths and corgis.

“Can you reply to all my emails when you see them?”

“Well, I – Yes. I will. I’m sorry. I was going to respond today in person as I didn’t want to clog up your inbox.”

“I want to know that you read everything I send.”

“I thought … ” The email was after hours, it was on a personal topic, it did not have a question. “Got it. Going forward, I will respond to all your emails instantly.”

Later that day, I was charged with my least favourite task: interrupting a meeting to pass Boone a note. Elisabeth had called. “Can this wait an hour?” I’d asked.

“No,” she said.

In the cube next to mine sat Lena, who had been on vacation when I came in for my interviews. I liked her right away: she held a book of literary true crime, which she would slam shut every time I popped out from behind the monitors I had positioned so I would not see her in my peripheral vision. She supported Michael, a portfolio manager with responsibilities closest to Boone’s.

“Hey, Lena?” I asked. “How do you pass a note?”

“I take a Post-it” – she picked up a pad – “and I take a marker” – she seized the nearest pen – “and I write a note like this.” She scribbled some words. “Then I fold it in half so others can’t see and I walk it over.”

“Do you knock?”

“No. You barge in.”

I sighed loudly.

“No one likes it,” she added, “you just learn to do it.”

I took a pen and wrote a note but miscalculated how much space I’d need; the letters smashed into each other like a Scrabble accident. If I could not plan the spacing of a message, how was I going to plan Boone’s life? It took me three tries, then I put my heels back on and walked the corridor from the front office to the conference rooms. Boone saw me from afar. I pushed open the glass door – someone was in the middle of a sentence and stopped for a few infinite seconds before continuing to speak – circumnavigated the guests, handed Boone the note, which he read but did not acknowledge, then fled calmly.

After the meeting, Boone called me into his office.

“Carrie,” he said. “So. Your energy.”

Oh, God.

“You’re too hesitant,” he said. “I need you to walk with more confidence and just come in, then get out, but also be more easy-going, relaxed, and chill.” During my interview process, Boone had asked me to dial down the moxie, telling me to try hard not to be so intimidating; apparently I had overshot it. I asked him to clarify his Möbius strip of a sentence, which he did, although all I heard was that he wanted me to walk like a Victoria’s Secret Angel. He wanted me to be like him: breezy. I observed his energy: immovable. No tics. No part of his unconscious would he let manifest in reality.

“Most important,” he added, “don’t be weird.”

In June I wanted to do something special for Boone’s birthday. I settled on a surprise guest and called the president of one of the world’s top speakers’ bureaux with a roster that included author Michael Lewis and Alex Rodriguez, the former Major League baseball player. Within 24 hours, Todd had given me a handful of people with whom he had confirmed availability. I stared at the list. No one felt right. Many of the people who had come to mind had already spoken at Carbon. Roger Federer turned us down, citing his tournament schedule. I started over. What did Boone like?

At least once a week for about half the year, he drove to and from a hamlet on Long Island during evening rush hour to play in a hockey league. Boone had played hockey in prep school. He held rink-side tickets to the New York Rangers that he would use a few times a season. He cringed whenever I said ice hockey. He corrected me every single time: “Carrie. Stop saying ice. It’s just hockey.” There was only one possible name.

At 4.14pm on the day of the surprise, I hurried to the ground floor. Boone’s favourite hockey player was with two men in black. I shook hands with the Center, a sports legend; in his other hand, he held a bag. We walked to the elevators and went up to the conference room.

Against the wall of windows, balloons the size of toddlers spelled HAPPY BIRTHDAY BRP. On the main table: party hats, noisemakers, streamers; at least five kinds of beer; red velvet cookies stuffed with Nutella, chocolate chip cookies stuffed with cheesecake; a three-tier cupcake tower; and, the zenith, a layered cake sculpted in the shape of a hockey puck in the team colours of the Rangers with a fondant player in full uniform. On the dry bar: handles of Tito’s and Fireball and Patrón; a bucket of bottles of Cloudy Bay; another bucket of pink and gold bottles of Veuve Clicquot, all of which surrounded an ice sculpture of Mount Everest, through which a vendor had carved two luges for shots.

“Here,” said the Center, handing me his bag. “I brought jerseys.” I counted two and knew that they were worth at least a thousand each.

Through the glass doors, I saw Boone in a white dress shirt, black pants and a light blue tie, an ensemble he wore so often that the assistants asked me if Boone owned more than one outfit. He almost walked past us before he glanced up and caught my eye.

He came in. We yelled, “Surprise!”

Boone’s cheeks turned red. He spun to his left and saw the Center and jumped back a foot. I watched the two men shake hands. Boone, the Center and Michael sat down on the three barstools the kitchen staff had helped me deposit at the front of the room. The crowd settled in. The Center began speaking. Not about how to win (that would be way too elementary) but about how to keep on winning. “You need to go out there and play each day,” he said, “as if it were the championship game. There is no such thing as a slump.”

“So, after you’ve won a championship,” Boone asked, “what was your routine or psychology right after?”

“I went right back out there. We’d celebrate a bit – you know, have dinner, drink out of the Cup.” The Center’s gaze traveled around the room. “But I was always the first guy back on the ice, in the rink the next day.”

The three men spoke about skating to where the puck is going and not where the puck is, which was a treasured hockey quote of business leaders. “But then,” Michael asked, “how do you know where the puck is going?”

“Practice. That’s all it is. If you practice enough, you can sense where the open ice will be.” Watching the three men interact, I could not help but notice the banality of genius. It occurred to me that Carbon did not have any superpowers beyond its boring and total efficiency. People worked like machines: they made goals, they accomplished them – this was the genius of following through. There would be no deliberations, no excuses. There was will, followed by action. Mean it, do it. There was no such thing as a slump.

But I wondered if the genius here could also be the horror. You might, through no conscious fault of your own, encode a lack of moral sensitivity if every second of every day your attention was fixated on self-interest, winning, profits, killing it, destroying your competition.

I handed the Center his bag and a thick black Sharpie. “I have a little something for you,” he said as he turned toward Boone, who smiled. A cause, an effect. I was able to make someone happy; the world made sense.

Boone looked at me. “We’ll give away the second one?” he said.

I nodded as Boone slipped a blue jersey with a red number over his head.

“Can I get Scarlett Johansson for my birthday?” someone else barked at me.

7.47pm: SO SORRY, I texted two friends with whom I had made dinner plans that I had just cancelled. I am so sorry. The Center had left, but Boone was still there and I never left the office before him.

The party wound down. Boone manoeuvred around a growing field of dirty plates, torn streamers and pizza crumbs to come find me. “Let’s tip the night cleaning crew 500 each,” he said, pulling out his wallet and handing me cash.

11.15pm: I surveyed the damage. Bottle caps, filthy napkins, half-eaten cookies everywhere. Boone hadn’t eaten dessert. The custom Rangers cake, which cost more than a thousand dollars: untouched, into the garbage – not a single slice of it was cut.

When I started the job, I joked to a friend that I didn’t have time to go to the bathroom. A year on, I didn’t have time to breathe. Pressures were mounting – the lack of support, the intolerable workload, the fact that when I tried to ask for help I was bought off with spa trips or a salary bump. At the same time, Carbon’s performance, which had been stellar, was down. News agencies reported on our lack of success. Boone was in such a low mood that no one dared to go into his office until they received confirmation from me that he was agreeable enough to approach that day and hour.

Boone never once yelled at me – but his feedback and continuous asks had increased in intensity.

My mind had been frazzled, in a perpetual state of distraction, from relentless task-switching. Forces top, down, internal, external competed constantly for my attention, so I spent every second reacting as though a virus had infected my phone and toggled all the switches to allow notifications to flash/buzz/sound all the time. If, as Boone believed, how you spent your days was how you lived your life, then I was not in control of mine. Boone did not merely influence my days – he owned them.

I began making mistakes at work. Chrome was a hedge fund that had debuted with much fanfare a few years back. It had struggled last year, ending in the red. Boone said he might want out and had me schedule a power breakfast for him and one of Chrome’s founders, Troy. In the weeks leading up to the meeting, Carbon was not able to turn around its performance. Chrome was also down for the year, though by less.

Arctic air had shifted. “I’m going to hold,” Boone said. “But keep the meeting.”

The day before the breakfast, I was, as usual, at work before Boone. At 8.10am Troy called. “Where’s Boone?”

There are moments in life you fear not because the moment itself is so terrifying but because it will reveal something to you, about you, after which things will never be the same.

Boone was at home. He was at home because I hadn’t told him he had a breakfast meeting. I hadn’t told him he had a breakfast meeting because it wasn’t on the calendar for today.

“He’ll be right there,” I said to Troy, knowing Boone could walk over in eight minutes.

I called Boone. No answer.

I called his apartment’s landline. No answer.

I called the housekeeper. No answer.

I called his cell again – no answer.

I called Jen, told her it was an emergency. Could she tell me who might be at the apartment right now?

I called the laundress. No answer.

I called the chef. No answer.

I considered sprinting to Boone’s apartment and banging on the door.

I called the concierge at his building, told him it was an emergency. Could he please, please go knock on Boone’s door? “Trust me,” I said, “he’ll thank you later.”

After one of the longest minutes of my life, Boone called.

“Boone – ”

“I’m playing with my kids. What’s up?”

“Emergency, my fault, I’m sorry. Your breakfast with Troy is today, not tomorrow. Please hurry. He’s waiting.”

Click.

Troy waited over 30 minutes for Boone. For the first time in my life I thought I was going to get fired. The emotion I felt at that thought: relief.

An hour later, Boone walked into the office.

I sprang up from my chair. “Boone, I’m so – ”

“Don’t worry about it,” he said. “You never make mistakes; I’m not worried. This is not a systemic thing.” Boone is nice, I thought.

Sooooo nice. But I was not sure about the validity of his last statement. I looked over at Lena, who was looking to the side of me with a blank face. Whenever she made a mistake, she did not tell us about it. She did not have to. She would sit in Michael’s office, her face apple red, as the rest of us would watch, on mute, through thick glass walls, Michael deliver a monologue à la Alec Baldwin in Glengarry Glen Ross.

My mistakes continued. Each task added a risk of interruption; each interruption broke my concentration by five or 10 or 30 minutes. Before I could return to where I had left off, another interruption would come, and I could never get back to the thing I needed to do.

Gabe, the software analyst I supported, was away on a research trip. He had back-to-back meetings before heading to the airport for a return flight; I forgot to check him in. I was in the middle of several tasks requiring focus when my calendar reminder went off and I snoozed it. By the time I remembered, it was after the cutoff. When he arrived at the security checkpoint, there was no way for him to board the flight. I called and called – travel agency, credit card, frequent flyer programme, all the luxury concierge services for Carbon and Boone – but having status could not rewind time. I got him booked on another flight, a disruption of about an hour.

The next day at the office, Gabe was even more silent than his normal taciturn self. After I finished apologising, he said, “This cannot happen again.”

“I know; there’s no excuse. I will set even more reminders for myself.”

“Maybe you need to do less work.”

Late Saturday night. I was at a friend’s birthday party. Boone texted, asking me to do something work-related. Then he sent another text, 15 words – a flippant dismissive remark that was personally insulting to me.

So. In the very next instant I watched my thumbs tap-tap-tap and then tap the blue arrow to send a reply in less than a second:

I *totally* understand what you mean!

A new low.

Instead of telling him he must watch his words – that this was a callous way to talk about me and those I love and represent – I had agreed with him. Not only that: the speed and ease with which I had abandoned myself and my people for the sake of Boone, to help him feel good.

I told myself I was just doing my job, executing orders, being a professional. I put my own needs aside for Carbon and Boone because I had believed that serving my employer meant serving humanity. I had believed in the prestige of Carbon which, to me, lay not in any zeros after commas but in the moral legitimacy of the enterprise. I ignored the fact that individual portfolio managers at Carbon used individual private jets. I ignored how each of those private jets contributed to climate change and government revenue shortfalls via tax breaks. I ignored the fact that many middle-class workers paid more in taxes, percentage-wise, than hedge fund managers. I ignored the very real privileges of everyone, including me, working at Carbon, how people treated us differently, how they tripped over one another to make our lives easier: they answered our calls; we jumped the queues; they gave us discounts and freebies and – what killed me – saved their best behaviour for us.

Something was wrong with this setup. I knew it. I think he did, too.

I began therapy because Boone had told me to get professional help. That was his suggestion to address the issues created by his workplace. The therapist agreed to see me for two hour-long sessions to start. At the first, I described my physical symptoms, including repeat colds, headaches, allergies, fatigue, acid reflux, indigestion, dry eye, eczema. I described how for months after a bad ankle sprain I could not walk right. I described my disordered eating, although I said the worst of it was over. I described my emotional issues.

How I felt on the precipice of collapse. “Why am I so bad at dealing with stress?” I asked her. “I used to be the person who could do anything, nothing fazed me. Now I can’t even do this one job. What is wrong with me?”

Without pause my therapist said, “Nothing’s wrong with you. Your job is killing you.”

One day after I had been working at Carbon for two years, sometime after Team Lunch because I did not want to interrupt his Monday-morning flow, I walked into Boone’s office. “Hey, Boone, can I talk to you?”

He swung his chair round and I sat down.

“Don’t tell me you’re leaving me,” he laughed.

I delivered my lines, devoid of emotion. I feared if I let myself feel anything, I might back down. “And so, for reasons I’m happy to get into if you like, I’ve decided it’s best for me to transition out of this role and move on.”

His square shoulders and flat eyebrows betrayed no emotion. Seconds later, he asked, “Are you joking?”

“No. I’m serious. I’m beyond grateful to have been given the opportunity to work at Carbon and, especially, to work with you so closely, and I thank – ”

“What’s the matter?”

My eyes watered. I raced to wipe away any tears before Boone could see. “The matter is that I feel overworked. I am constantly stressed. You tell me to ask for help, and when I do … I feel I’ve received no help in reducing my workload.”

“There must be something else.”

“I’m telling you I’m burned out.”

“Carrie.” The tone in which he said my name meant a lesson was coming. “When I founded Carbon, I was burned out for a decade.”

He looked up and away. “No. More than that.” He looked back at me. “If I can take it, I think you can, too. You’re tough; you’re among the toughest I know. Want a sabbatical? If so, take it, and your job will be here waiting for you because finding your replacement will take a couple years at least.”

A pause.

Then he asked, “What do you want?”

“What do you mean?”

“Tell me how to fix this; I’ll do it. Anything.”

He made me promises: I would be heard, my concerns would not be ignored and, most important, I would have less work and more support. In exchange he wanted me to promise that I’d give this a fair chance. I did. I hung on for over a month. But nothing really changed. I found myself back in his office again, and this time there was no talking me out of leaving.

My one goal for the last day was not to cry. I sent a thank-you-and-goodbye email to Carbon-NewYork-All, mentioning that I was leaving to “embark on some new adventures” and how “immensely grateful” I was to have been a part of the organisation. I sent a personalised email to Elisabeth, who sent the kindest note back. I found Luis who, when I gave my badge back to him, told me the truth. He had taken me to sit for a photo for building security on my first day and, after that, I would see him every so often, roaming the halls.

“Carrie, wow, yep,” he said after I told him about my burnout. “I remember your first day and you looked so amazing … and now I see that Carbon has ruined you!” I had never felt so good about being told I looked so bad.

I deleted Boone from my favourites. Then changed my phone’s settings so that his contact would never ding again.

Names and details of individuals and companies have been changed.