How to Become a Personal Assistant: Common Sense Is Key

NDA, NDA, you're signing NDAs across the board.
It is a very confidential position.
They're letting you into their life.
You're gonna see them at their worst and at their best.
Hi! I'm Rabbo Zeri and welcome to How Much Can I Make.
I am a curious journalist, fascinated by what people do for a living, what their jobs are really like, and how much they can earn.
Join me as we dive into stories behind careers, uncovering insights and details, which I hope you'll find as intriguing as I do.
So let's get started.
Today we are gonna talk about a job that is very desirable, at least by some of my friends, which is the personal assistant.
Today's guest is Bob, who's been doing it for many years.
So we're gonna find out from him what it takes and how much can you make.
Bob, hi.
First of all, thanks for doing it.
Absolutely.
I want to start by learning what is the difference between a personal assistant and executive assistant.
There are essential differences.
I will say that I got into personal assistance by starting as an executive assistant.
And the reason is because I will say 75%, 80% of any executive assistant position always incorporates some personal assistance.
Because you're dealing with someone at work and heavily scheduled, you know, traveling a lot.
You need to know what their personal life is to some degree in order to schedule them appropriately for their professional life.
So personal assistant is a higher level?
I think the funny thing is that as an executive assistant, the personal assistance is implied.
It's never really discussed.
But what happens is that you end up doing personal things for the executive.
And this is often problematic within human resources if you're working with a corporation, uh say for a lawyer.
That would be my case.
I worked for a lawyer at one point.
And did a lot of personal assistant work as the executive assistant.
And it that ended up turning around and kind of biting me in the butt later because human resources didn't see that as my role.
Right.
In spite of the fact that that's what I was tasked to do.
They didn't refuse to pay you though, right?
Oh no, no.
They didn't refuse to pay me, but when I left, it was a matter of discussing that part of the job.
You know, it it it was a contentious departure simply because of that.
So I fought my way out of it.
Um, and I ended up with a full year severance, and they covered my costs for the full year because they knew essentially that what I was doing was what I was being asked to do.
Right.
So, okay, let's back up for a second.
What does a personal assistant do?
They they do anything that uh is asked of them.
Uh personal assistance can mean filing an insurance claim.
Personal assistance can mean on the lower end, it can mean walking a dog.
You know, I mean as a personal assistant.
For me, my personal assistance jobs started as a result of the executive assistance.
But then as a personal assistant, solely with no executive responsibilities, meaning you're not dealing with them at work, you become oftentimes more of a manager, and that may be a manager of properties or a manager of a single household.
But it is more than say personal assistance.
You're a house manager at this point.
Oftentimes people call it an estate manager, but estate managers are often managers who cover multiple properties, and within those multiple properties, each property has a house manager.
So you're overseeing all the managers.
As an estate manager, as an estate manager.
If it is a multi-property uh individual.
Right.
How did you get into this business to begin with?
Well, I started as an office manager 20 some odd years ago.
At some cooperation or something, at a small marketing firm here in New York, a theatrical marketing firm.
Friend needed an office manager, went in and was with her for five years and took her from four seats in a sublet space to her own office over the five years.
And her own office and two others across the country, and probably 30 employees.
So I was with her while she grew.
Uh and um during that time I learned so much about everything, really.
I learned more about tech, learned more about scheduling, you know, which is the key, which is the hardest thing is the scheduling, watching someone's calendar.
You know, at that point, as an office manager, I was still doing personal things for the owner.
There's always a personal assistant component to the job.
Are there any kind of like agencies or yes?
One's called British staffing.
There's the calendar group is one.
I have worked with a few um staffing companies.
My most recent position, or the position I'm in now, was with a recruiter.
I mean, there are recruiting, I mean, most any recruiter you know recruits for these positions as well.
And what kind of requirements they'll have?
It depends.
Most of them are more concerned about your experience than say your education.
It's not really it's not as something that you learn in school, it's something you learn on the job over the course of time.
I I it's funny, a friend of mine, actually my personal trainer, his father was retiring and he wanted to start doing something different.
And so he was talking to his father about me, and I talked to his father.
His father just wanted to have a conversation.
We had a conversation, and the poor guy was just he thought he could just walk in and do what I do.
I mean, granted, he's you know, he's he's my age, so I mean he's older, but he had no experience.
And I was trying to tell him it's like you're not gonna get a job.
I'm sorry, but you're not going to get the job that I have at least.
But let me ask you, because most of it is common sense, right?
You have to run somebody's life and business.
Most of it is common sense.
You also have to know how to read your employer.
And most of these people are high net worth individuals, and with a high net worth individual, you're gonna come across a personality.
Right.
And you've got to be able to adapt to that personality.
See, uh I've worked for people who like a lot of detail and they want, you know, they want lots of detail in their emails, etc.
And the guy I work for now wants brevity.
He does not want any unnecessary verbiage or etc.
So you have to adapt.
You have to because you are working for that one person.
That's what I want to ask you.
Is it possible to work for two different people at the same time?
Oh, yeah, I think so.
It is.
If you are not on site, house managers, most of the time you're on site.
Right.
Running the cleaning crew, you know, running anything that's going on.
Any of the service providers, you know, utility providers, there's a renovation going on, you're dealing with the contractor, project managers, etc.
So you're on site uh most of the time.
Many times in this position, it's a remote position with some travel to the to the home or homes over the course of the week or the month.
But most of these operations can be done from home, from a computer, with a phone.
The most common thing I think across the board would be travel.
Yeah, set up the travel agenda and all of that.
Getting an agenda, finding the flights, hotels, etc.
If somebody wants to get into the business, I understand you need the experience, but what are the skills or character traits that you need?
Uh communication skills need to be sharp, need to know how to convey an idea or directive, idea to your boss, directive to the subordinate.
It's like, and you also, in my opinion, I don't ask anyone to do something that I can't do or won't do myself.
And I'll show them how to do it.
If I have a specific way it needs to be done, if I and if a client wants a toilet clean in a specific way, I will show the cleaning person how that toilet needs to be cleaned.
I won't do it again because they'll have learned, but I will show them and I don't have a problem with that.
Right.
Okay, communication's big.
Can't be sensitive, can't take things personally.
You can't get offended by that.
No.
People are often very brief, and when you're dealing also with high net worth individuals, there can be a bit of snobbery.
I mean, it's kind of inherent.
You just have to be able to brush that off.
You're going to be many times when you know you're smarter than the person you're working for, at least in terms of what you're dealing with specifically.
You gotta eat that.
Right.
Since the show is called How Much Can I Make, how much can you make on a job like this?
Upwards of$300,000,$350,000 a year.
What?
Yeah, depending on how many properties someone is overdo overseeing.
Say an estate manager would probably be up three, three hundred and fifty thousand dollars a year, especially if they're covering three or four residences across the country.
House managers, I would say two hundred, two hundred and twenty-five thousand dollars.
Yo, that's a lot of money.
What are the hours usually?
Um, generally the hours, uh, it's availability, it's not hours.
Availability is 24-7.
Wow.
Okay.
So, but hours, that's a little tougher to describe.
I mean the amount if you're effective at what you do, your hours can be much shorter than 40 hours a week.
If you know what you're doing.
And if the load isn't that heavy.
If you're running three or four properties at once, you're doing a full day, trust me.
So, how do you juggle being on call all the time with your private life?
Well, there are certain I set boundaries for sure.
I mean, you know, over the weekends and the evenings, I say to whoever I work for that if you need to reach me, you need to call me.
Don't send me an email, don't send me a text, you need to call me.
Especially if it's, you know, post the nine to five say parameters.
And if you set that boundary or that that requirement, or make it understood that that's the most effective way to get you, people will fall in line.
How can somebody break into this business if they have no experience?
I don't know.
I can't imagine what you would do to get I mean, a lot of it is um luck.
Luck, for sure.
I guess I lucked into the personal assistance part through the executive assistance role.
Right.
I think for anyone starting out, someone young, someone in their 20s or you know, early 30s wants to start out, become an executive assistant.
Can you start at that young?
You don't have much experience in life.
That's why you start as an executive executive assistant.
Okay.
Then you're gonna get some personal assistant work through that.
Trust me.
I mean, as I said, 75-80% of that employers are those employers are gonna ask you to do something personal.
And if they ask you to do something personal if you like it, I mean for me it was a matter of I found more reward as a personal assistant or accomplishing those tasks than I did, say, you know, writing up a contract off of a boilerplate.
I mean, that's just, you know, punching, that's just pencil pushing, as far as I'm concerned.
There is thought, but it's not critical thinking.
It's just sort of uh, you know, filling in the blanks.
As a personal assistant, house manager, etc.
You you you're constantly thinking, trying to avoid problems, anticipate problems, and then correct problems.
And one of the biggest things you have to do is put out a fire without anyone knowing.
That's the biggest thing.
That's what I wanted to ask you.
What was the biggest disaster that happened to you?
Uh it biggest disaster.
I worked for a private family who owned a townhouse, you know, a standalone townhouse in Manhattan.
They were gone.
It was the 4th of July, and I got a phone call from Central Station, which is the fire department.
Because, of course, they have a standalone townhouse, they have to have a fire assistant fire system.
Right.
And it has to be hooked up to Central Station.
And while they were gone, they were having work done in the apartment, in the house, and or the townhouse, the uh contractor neglected to put over one of the CO2 detectors, and this is a very common thing with contractors, they'll just put a mask over that so they cover it so that when their debris, dust, or whatever, drop like drywall dust or whatever flies up in the air, it doesn't trigger these alarms.
Well, they'd forgotten to do that, and then they they'd left, the alarm went off, and the fire company called me and said that they were on their way.
And I'm like, don't worry, there's no fire, trust me, I will meet you down there.
Fourth of July, so there wasn't much traffic.
I hop into a cab and I'm like, I've got to go down to which was a straight shot down Broadway, but mind you, I'm sitting there the whole time just thinking, oh Jesus, just don't break the doors, don't break the doors down.
And I got out of the car at the corner of uh Broadway and Warren, and I was running to the next block because they were close to the next block.
And I see the I see two fire trucks, two fire trucks in front, and a gaggle of firemen in front of the building, and two with axes.
And they had already gotten through the glass doors, which are the the vestibule, and then the vestibule is where the front doors were, which were$45,000, 20-foot height wooden, laminated, beautiful designer doors.
And they were going to take an axe to them because you know that they But they didn't tip.
Because I'm running down the street going, Don't do it, don't I'm screaming, don't do it the entire way.
And I got there and I opened the code and let them in, and of course, there was no fire.
They, of course, but when they're there, they have to go through every floor, floor by floor by floor.
When we got down to the cellar, which is where they were cutting the drywall, etc., I could see that they had not covered a CO2.
And I didn't say anything to the fireman, but we just determined there was no fire and they went on their way.
Did the owner ever know about it?
Oh, yeah.
Of course.
Well, they do.
No, I I'm fully disclosed.
I don't I tell them everything.
Right.
Because there's cameras everywhere anyway.
So, you know, there's no point in lying.
What's the craziest thing that somebody asks you to do?
My boss asked me to erase her calendar because she was being sued.
So she wanted me to go into her outlook and do something fairly illegal, which I refuse to do.
It's illegal to clear your calendar?
Well, if someone's asking for your calendar in a as discovery, and someone tells you to clear their calendar for the last two years, something fucking suspicious is going on.
And I was subpoenaed after that, and I had to testify in court against this person.
So I'm glad I didn't do it.
If you didn't know and she asked you, she's your boss, ask clear my calendar.
Would you be liable if uh I I couldn't answer that question.
All I know is that I knew, don't do that.
Did she fire you after that?
Oh no, she got fired.
So I lost my job because she got fired.
That's the worst person I've ever worked for.
Oh wow.
Worst person I ever worked for.
And I only worked for her for five months.
Oh, I thought you said the first person.
No, worst.
The very worst person I've ever worked for.
Complete nut job.
Brilliant, brilliant mathematician and economist.
Do you like this job, by the way?
My job now?
Yeah.
I mean the job position?
And just being a personal assistant.
Do you do you like being doing it?
Okay, I've been doing it for 20 years.
I know.
I have friends that want to get in.
They don't know how.
It's it seems like a really closed-knit network.
It I it's just it's a niche kind of thing.
It's very niche.
But I think that's a fantastic pay.
What if you just start?
How much will you make if you just start?
If you just start, well, I mean, you're not gonna start as a house manager unless you have experience.
You're gonna have to start somewhere, and I'm gonna tell you, executive assistant is gonna be your best path.
I mean, there are personal assistant jobs out there, but somebody's gonna ask to pay you$50 an hour and not give you any benefits.
Right.
And they say, if you want to learn this, you may as well be making good money and getting benefits while you're doing it.
Because you're not necessarily gonna get those benefits later if you're working for an individual.
My current employer was very generous and created an LLC so that he could cre um provide me with insurance.
But that's not normal, right?
Not at all.
Most people just will change your compensation to allow for insurance.
And there's also not 401k, none of that, right?
You have to put your own savings.
Yes.
Unless you're with a corporation, then you're gonna have a 401k if you're an executive assistant.
But yeah, otherwise you're on your own.
What are the additional perks that you get?
You work for multimillionaire and billionaires.
Some of them are very, very generous, and some of them are not.
It's like some of them made their money by being cheap, and some of them just have a lot of money and know how to spend it.
Perk is, I had gotten some great used designer furniture.
I mean, when I say used, I just should say expensive.
Previously owned.
It's not dirty, it's not damaged, it's just they decided to redo a room.
Nice.
There's a lot of uh trust issue here, right?
Absolutely.
NDA will sign one in the interview process, to tell you the truth.
Oh.
NDA, NDA.
You're signing NDAs across the board.
Oh.
Oh, yes.
It is a very confidential position.
Yeah, trust is absolutely because also they're letting you into their life.
You're gonna see the kids act up, you're gonna see them fight with their kids, you can see them fight with their spouse.
You're gonna see them at their worst and at their best.
And you have to just zip your lip.
Oh, you must have some stories.
I wish you could tell.
I wish you could tell them.
In front of other people.
Really?
Yeah, it's kind of funny.
Damn.
Wow.
Yep.
But like I said, I love it.
I love what I do.
I think I'm good at it.
And um, you know, most of my jobs have always been long term.
And I'm always interviewing.
I'm always, you know, looking at what's available.
And I was recently um interviewed by someone in the uh process with the recruiter, they said, Well, you know, this person just you know doesn't like to see people in their house who work for them.
They want you to be invisible.
Well, how what do you mean?
They it's just that you don't You hide in the bathroom?
Well, actually, and I read some really horrifying stories about previous employers or employees who had been forced to kind of wait in their area because they were entertaining and they primarily did not want to see any of the staff at all.
But for in order for them to leave, they had to walk past where these people were.
So they had to stay where they were for hours.
Whoa.
And to tell you the truth, um, you know, I was in the interview process, and when I read this, I called up the recruiter and I said, You can take me out of um consideration for this job.
I don't want to work for this man.
You work with the same recruiter all the time?
No, I have two or three that I work with.
Once I start a process on a job with one, I'll stop with the others because I don't think that's fair.
But if that doesn't pan out, then everybody gets I go back into everybody's pools.
Do you give any commission money to the recruiter?
No, that's paid by the uh employer.
Yeah, they have the money anyway.
Yeah.
No, I'm not paying it.
It's not like an apartment.
It's a job.
I'm gonna let the employer pay that.
All right.
Well, Bob, thank you so much.
I didn't know the details of all this thing in your job.
And it's fluid.
When I told people I'm gonna do a personal assistant, said, wow, that's an interesting job.
It can be.
And there are a myriad of designs of that position.
You can be a shopper, be a dog walker, you know.
I mean, think about it.
Depends upon who you're working for.
But you do it all.
I don't walk dogs.
No, you delegate it.
At this point, yeah, I delegate, yeah.
I get you a dog walker.
Right.
You know, I don't climb on ladders, I get that, you know, I get a handyman.
But in the beginning, you know, I would do handyman things because I want to be able to tell somebody how to do something, you know, and I would watch any con any contractor, any plumber, you know, you learn any IT guy, oh my god, the IT people.
A V, you know, and I worked for the family that had the townhouse, you know, it was completely wired.
Just learn so much with the IT guy.
You know, home sound systems, etc.
Biggest thing I learned was like, you know, if it's not working, just unplug it and plug it back in.
Seriously.
And that's for a seven-story townhouse.
When in doubt, reboot.
Reboot, exactly.
But uh other things I I've learned as well.
Yeah, you you know a lot about a lot of things.
I know that.
Well, yeah, that's a jack of all trades, master of none.
A lot of people would say, I don't believe that.
I think that uh the trade is the house manager slash personal assistant.
Right.
The rest you do delegate, so I don't need to know how to do the things that I tell them to do.
Yeah, you just have to have the common sense to know they're doing it right.
Exactly.
I could do this job.
Anybody.
Yeah, especially if I get 300,000.
Exactly.
There's a lot of stuff I do for$300,000 a year.
And I know there are a lot of people that hire personal assistants.
There are a lot of rich people in the growing industry, actually.
It is, huh?
It actually is.
I think the gap is widening.
There's a lot more rich people here, and they're gonna need help.
But if somebody just earns a million dollars a year, they still would hire a personal assistant, right?
If their salary is a million dollars a year, sure.
They will that's the range of people we're talking about.
Yeah, well, I mean, uh yeah.
I mean, I was working for founding partner lawyers, yeah.
They were making a million dollars a year for sure.
Yeah.
Nice.
Yeah, not me, unfortunately.
Some of the people I work for don't work.
What do you mean don't work?
We're retired.
You know, they're just independently wealthy, high net worth individuals.
They have money, they don't need to work.
So they just need you to run their lives and they sit on the sofa all day long.
Uh or not.
You know, they do other things, they play tennis, you know, they travel.
Nice.
I would love that life.
Yeah, I would too.
I would love the lives of many people I've worked for.
But nevertheless, I do have their life in some small way.
Right.
All right, and on that note, this is it for the day.
Thank you.
You're welcome.
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