The secret world of billionaire's assistants
Brian Daniel was featured in a 3,500-word article for New York Magazine's "The Cut."
Everyone loves to judge what rich people do with their money, and no one has a better front-row seat than those they keep closest: their personal assistants. For decades, Brian Daniel worked as a PA for ultra-wealthy clients; now, he helps recruit and train other high-level PAs for some of the world’s richest families and top-earning CEOs and has built a deep network of people in the private-service industry along the way.
Here, he talks about what a typical day of work might entail, how he snags a table at the most in-demand restaurant at the last minute, and what it’s like when your boss has never heard the word “no.”
Here, he talks about what a typical day of work might entail, how he snags a table at the most in-demand restaurant at the last minute, and what it’s like when your boss has never heard the word “no.”
What do most people not understand about what it’s like to be a personal assistant to the super-rich?
A lot of people think it's red carpets and Lamborghinis all the time, but most of your job is sitting behind a desk. Even when you’re on the road with a client, you’re isolated in many ways.
One family I was traveling with for three months, they had profound inherited wealth and they just wanted privacy, even from each other. So, we were getting these big villas that were very quiet. Each person would go to their own wing, with their own kitchenette and fridge, and we’d keep it stocked with what they wanted, and they wouldn’t have to see anybody.
Sometimes they would give me their phone and be like, “I don’t want to talk to anybody. If something important comes in, deal with it.” And that might go on for days.
One family I was traveling with for three months, they had profound inherited wealth and they just wanted privacy, even from each other. So, we were getting these big villas that were very quiet. Each person would go to their own wing, with their own kitchenette and fridge, and we’d keep it stocked with what they wanted, and they wouldn’t have to see anybody.
Sometimes they would give me their phone and be like, “I don’t want to talk to anybody. If something important comes in, deal with it.” And that might go on for days.
What kind of salary are we talking, for a personal assistant at a high level?
It’s strange; people are getting stingier and stingier. I had someone, a celebrity in New York, who recently reached out to me, and they only wanted to pay $80,000 for a PA. And I’m like, listen... Do you want to solve your problem? If you want someone who is going to be loyal to you, who will manage your staff and stay with you for ten years and give you peace of mind — which is priceless — we’re talking about $250,000 a year.
Figuratively, it’s like a marriage, a professional marriage. These CEOs and billionaires, they spend more time with their personal assistants than they do with their spouses. It’s 12 hours a day, six days a week sometimes, and they’re on call 24/7. These assistants, they’re running the show and they should be well compensated for it.
If you’re jetting around and want a lifestyle manager who travels with you, an ultra-experienced personal assistant handling everything as you go from place to place, that’s going to cost you even more, like $10,000–$20,000 a week just in that person’s salary. Of course, you also need to pay for their hotel rooms, food, and they’ve got to have their clothes cleaned. The numbers get astronomical. When I was with one royal family and we were traveling with these big entourages, we would get two full floors of rooms — can you imagine two floors?
The bill was in the millions because the cheapest rooms at these 5-star hotels are $1,200 a night. The suites are $5,000–$10,000 a night, and they’re ordering room service for breakfast, lunch, and dinner, and going to the salon and getting massages. I would have the hotel print the bill so that I could go through it meticulously looking at all the charges, and it was like a phone book.
Figuratively, it’s like a marriage, a professional marriage. These CEOs and billionaires, they spend more time with their personal assistants than they do with their spouses. It’s 12 hours a day, six days a week sometimes, and they’re on call 24/7. These assistants, they’re running the show and they should be well compensated for it.
If you’re jetting around and want a lifestyle manager who travels with you, an ultra-experienced personal assistant handling everything as you go from place to place, that’s going to cost you even more, like $10,000–$20,000 a week just in that person’s salary. Of course, you also need to pay for their hotel rooms, food, and they’ve got to have their clothes cleaned. The numbers get astronomical. When I was with one royal family and we were traveling with these big entourages, we would get two full floors of rooms — can you imagine two floors?
The bill was in the millions because the cheapest rooms at these 5-star hotels are $1,200 a night. The suites are $5,000–$10,000 a night, and they’re ordering room service for breakfast, lunch, and dinner, and going to the salon and getting massages. I would have the hotel print the bill so that I could go through it meticulously looking at all the charges, and it was like a phone book.
Why do you think people get stingy about these salaries when they have so much money?
They delude themselves because when they put out a job opening, and it says $80,000, they get hundreds of applications.
What they don’t understand is that it’s not about quantity, it’s about quality. When you hire people who are gawkers, who are opportunistic, who don’t have a lot of experience and will work for $80,000 to be in proximity to fame, you’re guaranteed to have problems down the line.
Eventually, everything falls apart and people start suing. And when a celebrity or billionaire gets sued, they never win. They lose every single time. The case never goes to court because nobody wants their dirty laundry out there.
Another reason these people get stingy is that there’s some kind of psychological distortion that happens when everyone fawns over you all the time. The VIP’s mentality is, “Hey, this person should be paying me, because they get to be around greatness.”
They’re used to having people want a piece of them, so they think that the job is such an amazing opportunity that they shouldn’t have to pay the person what they’re actually worth. They live in a bubble and their reality is warped.
What they don’t understand is that it’s not about quantity, it’s about quality. When you hire people who are gawkers, who are opportunistic, who don’t have a lot of experience and will work for $80,000 to be in proximity to fame, you’re guaranteed to have problems down the line.
Eventually, everything falls apart and people start suing. And when a celebrity or billionaire gets sued, they never win. They lose every single time. The case never goes to court because nobody wants their dirty laundry out there.
Another reason these people get stingy is that there’s some kind of psychological distortion that happens when everyone fawns over you all the time. The VIP’s mentality is, “Hey, this person should be paying me, because they get to be around greatness.”
They’re used to having people want a piece of them, so they think that the job is such an amazing opportunity that they shouldn’t have to pay the person what they’re actually worth. They live in a bubble and their reality is warped.
What’s something difficult that you might have to pull off on the job?
I’m a big believer in having "boots on the ground" and doing things in person. For example, I was in Los Angeles, and the VIP wanted to go to the hottest restaurant in town that was booked solid for three months. It was Friday night, seven o’clock, and they wanted an eight o’clock reservation.
So, I get in the car, I go down there. I reach out to my network — “Who knows the general manager?” You can’t just call the restaurant. It’ll ring forever. You have to be there in person because they need to see who you are. That’s very important. There’s a manner that you need to have.
So, I go down to the restaurant, I meet the maître d’ or the general manager. I literally point at the table and say, “We’ll be back in 45 minutes. That’s the table I want, and I also want the best server in the restaurant.” And I spread a bunch of money around. At the very minimum, you have to be spreading hundreds [in tips] — I wouldn’t dream of offering $20s or $50s, because they’d be insulted.
Most of my clients have understood that I need tip money if I’m going to do my job. Then I get the VIP, I come back to the restaurant, and I tell the GM when we’re a minute away. And then, before the VIP gets out of the car, I go in and make sure the table is clear, because you don’t want to be standing there for several minutes while they’re finishing the table. Then I escort the VIP in, they sit down, the server’s right there, the drink he wants is already on the table.
This is what I call "Jeff Bezos-level billionaire treatment."
So, I get in the car, I go down there. I reach out to my network — “Who knows the general manager?” You can’t just call the restaurant. It’ll ring forever. You have to be there in person because they need to see who you are. That’s very important. There’s a manner that you need to have.
So, I go down to the restaurant, I meet the maître d’ or the general manager. I literally point at the table and say, “We’ll be back in 45 minutes. That’s the table I want, and I also want the best server in the restaurant.” And I spread a bunch of money around. At the very minimum, you have to be spreading hundreds [in tips] — I wouldn’t dream of offering $20s or $50s, because they’d be insulted.
Most of my clients have understood that I need tip money if I’m going to do my job. Then I get the VIP, I come back to the restaurant, and I tell the GM when we’re a minute away. And then, before the VIP gets out of the car, I go in and make sure the table is clear, because you don’t want to be standing there for several minutes while they’re finishing the table. Then I escort the VIP in, they sit down, the server’s right there, the drink he wants is already on the table.
This is what I call "Jeff Bezos-level billionaire treatment."
What else would your job entail?
It was my job to manage all the yachts and the subordinate assistants and the exotic-car fleets and the nannies.
At one point, someone wealthy that I was working for had a sick family member, and we were at the Mayo Clinic for six months in the private wing. Most people don’t know about these private suites. They’re for heads of state. They’re behind bulletproof glass, and nobody else can be in there.
We got the whole wing, and it was over a million dollars a month. That doesn’t even count the entourage. We had hotels and private homes rented, too. We were housing all the chefs and the drivers. It’s a lot of logistics.
At one point, someone wealthy that I was working for had a sick family member, and we were at the Mayo Clinic for six months in the private wing. Most people don’t know about these private suites. They’re for heads of state. They’re behind bulletproof glass, and nobody else can be in there.
We got the whole wing, and it was over a million dollars a month. That doesn’t even count the entourage. We had hotels and private homes rented, too. We were housing all the chefs and the drivers. It’s a lot of logistics.
Brian talks about the $6mn bill at the Mayo Clinic.
How do people define “PAs” vs EAs, or chiefs of staff, or house managers? I’ve heard all those titles used interchangeably.
Every employer has their own "language," and you use the language of the employer. Maybe the employer is using the terms wrong, but who cares? What’s the difference between a tutor and a governess? Is it a house manager or an estate manager? Is it a PA or a “strategic business partner”?
The most important thing is that you understand the way that the client wants things to be run. When they come home, they want the towels folded this certain way, rolled up like sushi. They want to be addressed in this manner. They want staff everywhere [visibly working], or they don’t want to see staff at all. We create house manuals with pictures, and it’s all digitized so that it’s the same "rules" across all their homes, and there’s no confusion.
The most important thing is that you understand the way that the client wants things to be run. When they come home, they want the towels folded this certain way, rolled up like sushi. They want to be addressed in this manner. They want staff everywhere [visibly working], or they don’t want to see staff at all. We create house manuals with pictures, and it’s all digitized so that it’s the same "rules" across all their homes, and there’s no confusion.
How did you get into this field?
I moved to Los Angeles when I was 19, and I had stars in my eyes. I wanted to be an actor. I grew up in a cornfield in Michigan, so when I first got to California, it was like when Dorothy lands in Oz and all of a sudden, the world is in color. I was like, “Holy cow!”
I got a job working at a gym in Beverly Hills, right down the street from 20th Century Fox. A lot of actors and producers and agents and publicity people would go there, so I just started meeting people. Then I started working at the Beverly Hills Hotel, and that’s how I met my first boss, who was an extended member of the Johnson & Johnson family. That was my first real PA gig.
One job led to another, because a lot of these people are in the same circles. After more than ten years of working for high-net-worth families and individuals, I decided to start my own operation, recruiting and placing PAs for the same type of clients. A lot of other staffing agencies deal primarily with nannies and housekeepers. But finding a highly skilled person who you can trust with all your secrets is incredibly difficult — people want to hire an Ivy League–educated executive assistant who’s worked for a billionaire before and has recommendation letters.
And just because someone worked for one billionaire doesn’t mean they’re going to be good in another environment with someone else. We are aligning the hard skills, soft skills, and the personality traits to make a perfect match that’s going to last for 5, 10, or 20 years. The high-net-worth families don’t want to be blowing through assistants every year. They have a lot to lose, and it’s hard for them to trust people.
I got a job working at a gym in Beverly Hills, right down the street from 20th Century Fox. A lot of actors and producers and agents and publicity people would go there, so I just started meeting people. Then I started working at the Beverly Hills Hotel, and that’s how I met my first boss, who was an extended member of the Johnson & Johnson family. That was my first real PA gig.
One job led to another, because a lot of these people are in the same circles. After more than ten years of working for high-net-worth families and individuals, I decided to start my own operation, recruiting and placing PAs for the same type of clients. A lot of other staffing agencies deal primarily with nannies and housekeepers. But finding a highly skilled person who you can trust with all your secrets is incredibly difficult — people want to hire an Ivy League–educated executive assistant who’s worked for a billionaire before and has recommendation letters.
And just because someone worked for one billionaire doesn’t mean they’re going to be good in another environment with someone else. We are aligning the hard skills, soft skills, and the personality traits to make a perfect match that’s going to last for 5, 10, or 20 years. The high-net-worth families don’t want to be blowing through assistants every year. They have a lot to lose, and it’s hard for them to trust people.
What’s typically the problem when these families can’t retain their assistant?
A few times a year, I will go on location with clients and work as their personal assistant myself to help figure out what they really need. Often, these are the families that are having trouble finding or retaining staff. They don’t want to tell me what’s going on behind the scenes, or they don’t actually know.
Being there in person solves a lot of problems. When on location, I meet all the players. Here’s the security team, here’s the executive housekeeper, here are the people they’re dealing with, too. What typically happens is you have a bunch of "fiefdoms."
Just like in big companies where the departments don’t want to cooperate — the same thing happens in mega-mansions. There is often backstabbing and infighting, and the clients are totally blind to it. And it’s too much for one PA to manage. Especially these huge mega-estates that are like 50,000 square feet — they’re like college campuses or little cities.
Also, you’d be surprised at how these billionaires hire people. They’ll hire a friend of a friend, or their neighbor’s niece, or they’ll see someone at Starbucks and be like, “Oh, she’s young, she’s cute, she’s got a lot of energy, she seems like she’d be a good assistant,” and they just bring people in with no experience.
Suddenly, that inexperienced person is in charge of world-class butlers that have worked for princes, and the respect isn’t there. You have these tricky dynamics about the way things should be done.
Being there in person solves a lot of problems. When on location, I meet all the players. Here’s the security team, here’s the executive housekeeper, here are the people they’re dealing with, too. What typically happens is you have a bunch of "fiefdoms."
Just like in big companies where the departments don’t want to cooperate — the same thing happens in mega-mansions. There is often backstabbing and infighting, and the clients are totally blind to it. And it’s too much for one PA to manage. Especially these huge mega-estates that are like 50,000 square feet — they’re like college campuses or little cities.
Also, you’d be surprised at how these billionaires hire people. They’ll hire a friend of a friend, or their neighbor’s niece, or they’ll see someone at Starbucks and be like, “Oh, she’s young, she’s cute, she’s got a lot of energy, she seems like she’d be a good assistant,” and they just bring people in with no experience.
Suddenly, that inexperienced person is in charge of world-class butlers that have worked for princes, and the respect isn’t there. You have these tricky dynamics about the way things should be done.
I imagine there’s a lot of secrecy, too.
Of course, everybody signs Non-Disclosure Agreements. That is standard operating procedure. They won’t even give me the job description unless I’ve signed an NDA. Then I’ll say, “Okay, is there anything else you want to tell me?” And then sometimes that’s when you get very important information.
I had one [potential] client who was a financial genius, and it turns out he was a nudist. He walks around in his birthday suit. They said the assistant would have to be okay with that because it’s random — you come to work, he opens the door, and voilà. These very wealthy people have eccentricities, and not everyone can deal with them.
I don’t want a world-class estate manager to quit their existing job for a new one and then walk into a complete surprise like that. That’s why I like to go on location and see what's going on for myself.
I had one [potential] client who was a financial genius, and it turns out he was a nudist. He walks around in his birthday suit. They said the assistant would have to be okay with that because it’s random — you come to work, he opens the door, and voilà. These very wealthy people have eccentricities, and not everyone can deal with them.
I don’t want a world-class estate manager to quit their existing job for a new one and then walk into a complete surprise like that. That’s why I like to go on location and see what's going on for myself.
What are some of the “soft skills" that you mentioned that assistants need to be successful?
You have to have thick skin. You’re like a rhinoceros or an armadillo. And you have to have incredible patience. The way you word things is so important. Your intonation and speed of delivery — I mean, it’s an art. You’re working for people who are not used to hearing the word no.
One example: I was working for a prince, and in the Middle East, he’s a pretty big deal. But outside of that world, nobody knows who he is; he’s just another wealthy guy. So, he got this crazy idea that he wanted to meet this big-deal Hollywood celebrity.
I got on the phone with the right person who worked in that celebrity’s inner circle. And they said, “We might be able to do it, but here’s the set of circumstances under which it could happen.” So when I explained to the VIP that, if he wanted to meet this celebrity, he would need to make a donation to the celebrity’s favorite charity and do these other things, he exploded in uncontrollable anger. It went on for two days. He was running around screaming, “No, people pay to meet me.” He lost his mind.
So, I learned an important lesson: It would’ve just been better for me to just say that I couldn’t do it. You have to get to know the "rhythms" of the person you’re working for, and there’s certain ways that you have to say things. And you have to know when it’s better to not say anything or tell "little fibs."
The use of "collective pronouns" is very important — saying “we” instead of "you" or "I." Sometimes when you’re working with people who have inherited wealth — they just walk into money and never had a job and don’t understand how the real-world works — they’ll ask you to do something profoundly ridiculous, and you can’t tell them how dumb the idea is.
If you have ever watched the TV show Succession, then you know how silly the trust fund kids can be.
One example: I was working for a prince, and in the Middle East, he’s a pretty big deal. But outside of that world, nobody knows who he is; he’s just another wealthy guy. So, he got this crazy idea that he wanted to meet this big-deal Hollywood celebrity.
I got on the phone with the right person who worked in that celebrity’s inner circle. And they said, “We might be able to do it, but here’s the set of circumstances under which it could happen.” So when I explained to the VIP that, if he wanted to meet this celebrity, he would need to make a donation to the celebrity’s favorite charity and do these other things, he exploded in uncontrollable anger. It went on for two days. He was running around screaming, “No, people pay to meet me.” He lost his mind.
So, I learned an important lesson: It would’ve just been better for me to just say that I couldn’t do it. You have to get to know the "rhythms" of the person you’re working for, and there’s certain ways that you have to say things. And you have to know when it’s better to not say anything or tell "little fibs."
The use of "collective pronouns" is very important — saying “we” instead of "you" or "I." Sometimes when you’re working with people who have inherited wealth — they just walk into money and never had a job and don’t understand how the real-world works — they’ll ask you to do something profoundly ridiculous, and you can’t tell them how dumb the idea is.
If you have ever watched the TV show Succession, then you know how silly the trust fund kids can be.
I’m sure that offering money for favors can be useful, but in other cases people might find it insulting. How do you avoid offending people?
You have to gauge the situation. For example, once I was in Las Vegas with a client who had a very big entourage. We were driving by In-N-Out Burger, and it had just closed. And with corporate places like that, the rules are the rules. When they are "closed," the register’s off, the door is locked, and nobody else can come in -- period.
But the client wanted In-N-Out. So, I ran over to the drive-through window. They were serving the last person, and I put my body in the window so they couldn’t close it. And I gave the guy a $100 bill and said, “Go get your manager right away and tell him it’s a business emergency.”
So, the manager came over and I was like, “We need to come in.” And they’re like, “We are closed.” And I said, “You see that whole line of Rolls-Royces, Lamborghinis, and Ferraris?” And I pulled out a whole lot of money and said, “I’ll cover the overtime. It’s all off the clock. The corporate office won’t find out. Open the front door and let us in.”
It probably cost $10,000 for those hamburgers, including the "payoff money" and the cost of the food. But it worked.
Sometimes you need to offer more than money, though. There was another situation a number of years ago when a celebrity client wanted to go see a movie. It was opening weekend, seven o’clock on Friday. The movie was sold out in every theater, and the client wanted to see it privately.
So, I went to the movie theater, and I talked to the GM and I said, “Listen, I’m prepared to pay you $5,000 for the favor, and I will buy every seat.” When I’m making a request like that, I pay very close attention to the person's reaction. What’s he feeling while I’m proposing this to him? I know that my manner, my physicality, my intonation, all of those things matter.
I have to stay one step ahead with solutions to any problems. I said, “We can put a sign on the door that says, ‘Out of Order,’ and you can tell people the projector broke down. We will sneak the VIP in through the emergency exit so he can see the movie.” Then I watched his facial expressions. I could tell he was almost there, but he was doubting it. So, I said, “On top of that, as the movie’s ending, we’ll bring you in and you can meet the VIP and his family.” And the guy says, “Okay, I’ll do it.”
I knew that that would close it. It wasn’t just about the money. Now he’s got a great story, too; and he’ll be telling it forever. Good personal assistants, they’re doing stuff like this every day. They’re moving mountains for a living.
But the client wanted In-N-Out. So, I ran over to the drive-through window. They were serving the last person, and I put my body in the window so they couldn’t close it. And I gave the guy a $100 bill and said, “Go get your manager right away and tell him it’s a business emergency.”
So, the manager came over and I was like, “We need to come in.” And they’re like, “We are closed.” And I said, “You see that whole line of Rolls-Royces, Lamborghinis, and Ferraris?” And I pulled out a whole lot of money and said, “I’ll cover the overtime. It’s all off the clock. The corporate office won’t find out. Open the front door and let us in.”
It probably cost $10,000 for those hamburgers, including the "payoff money" and the cost of the food. But it worked.
Sometimes you need to offer more than money, though. There was another situation a number of years ago when a celebrity client wanted to go see a movie. It was opening weekend, seven o’clock on Friday. The movie was sold out in every theater, and the client wanted to see it privately.
So, I went to the movie theater, and I talked to the GM and I said, “Listen, I’m prepared to pay you $5,000 for the favor, and I will buy every seat.” When I’m making a request like that, I pay very close attention to the person's reaction. What’s he feeling while I’m proposing this to him? I know that my manner, my physicality, my intonation, all of those things matter.
I have to stay one step ahead with solutions to any problems. I said, “We can put a sign on the door that says, ‘Out of Order,’ and you can tell people the projector broke down. We will sneak the VIP in through the emergency exit so he can see the movie.” Then I watched his facial expressions. I could tell he was almost there, but he was doubting it. So, I said, “On top of that, as the movie’s ending, we’ll bring you in and you can meet the VIP and his family.” And the guy says, “Okay, I’ll do it.”
I knew that that would close it. It wasn’t just about the money. Now he’s got a great story, too; and he’ll be telling it forever. Good personal assistants, they’re doing stuff like this every day. They’re moving mountains for a living.
How do you deal with boundaries, personally, when clients cross them?
It’s hard. You get sucked in, and the water becomes very muddy [lines are blurred]. A lot of these wealthy people are lonely. They’re in their mega-mansion alone with you, and then they’re telling you all their problems, and you become like a psychiatrist. It’s tricky.
Personally, I know other people in the business, and I would sometimes call them and say, “What do you do in this situation?” And we’d give each other advice. Celebrities have an army of people who work for them -- the agents, managers, doctors, and the lawyers. But those people are only interacting with them intermittently at best. The PA is the one that’s there in the trench, day in and day out, year in and year out.
You have to know your place, though, too. A lot of VIPs are obsessive about the people around them. They’re constantly in a state of mental torture because they think other people want things from them — usually their money. So, you want to make sure you keep both feet on the ground, because it can all be suddenly taken away [when the job ends].
Personally, I know other people in the business, and I would sometimes call them and say, “What do you do in this situation?” And we’d give each other advice. Celebrities have an army of people who work for them -- the agents, managers, doctors, and the lawyers. But those people are only interacting with them intermittently at best. The PA is the one that’s there in the trench, day in and day out, year in and year out.
You have to know your place, though, too. A lot of VIPs are obsessive about the people around them. They’re constantly in a state of mental torture because they think other people want things from them — usually their money. So, you want to make sure you keep both feet on the ground, because it can all be suddenly taken away [when the job ends].
How do you keep from being starstruck or intimidated by the famous people you work with?
You get used to it. It’s a business. And when you meet these people, most of the time, you’re going to be disappointed. Either because they’re mean, or they’re just not like what you thought they were going to be like. The Hollywood publicity machine creates a certain image, and it’s very rare to meet a celebrity who is genuinely an amazing, brilliant, kind, humane person to everyone all the time. Once you’ve been around it enough, those butterflies start to go away.
This article was updated by CPAN in 2026 for timeliness. Read the original article >>
