Who’s the Most Valuable Member of Your Entourage?

Just like in the legendary cable show, rich people everywhere have an entourage (whether or not they call it that). Keeping up appearances while investing, working, traveling, entertaining, and perhaps raising two or three kids and a dog, requires a great deal of effort – and a squad of highly-skilled assistants.

My girlfriends and I were chatting about this over lunch last week, because one of them is looking for a new nanny, and it made me wonder: who is the most valuable member of the entourage? The irreplaceable helper without whom you feel that your life would cease to function as the well-oiled machine it needs to be?

Every wealthy person will have a different answer, and women will certainly have a slightly different one than men. Here are some potential MVPs:

–The person who does your hair: your barber, colorist, hair stylist, the person who does your waxing, grooms your eyebrows, or perhaps even the doctor who did your hair transplants

–Your personal trainer – or your tennis instructor, golf pro, Soul Cycle leader, ski teacher, or boxing coach

–Your personal chef – or your caterer, the maître de at your favorite restaurant, your butcher, or your favorite barista

–Your manicurist – who also does your pedicures

–Your facialist – or your cosmetic dermatologist, your make-up artist or your plastic surgeon

–Your doctor – or your therapist, your midwife, or the person who’s about to do your surgery

–Your kids’ nanny – or their test-prep, French and math tutors, their college counselor, or your family therapist

–Your personal shopper – or your jeweler, your watch salesperson, or your fine art advisor

–Your tailor/fitter – the only person who really knows how much you weigh other than your internist; or possibly your dry cleaner

–Your doorman – who sees all and discusses nothing

–Your caretaker – if you own multiple homes, you probably have more than one – this person oversees the operations of your main house, accessory buildings (pool house, guest house), and the surrounding grounds, and is highly likely to be on the short list for MVP, given everything you’re asking of them

–Your housekeeper – anyone who is doing your laundry knows all of your secrets – treat this person extremely well

–Your groundskeeper – or your gardener, pool person, exterminator, or tree person

–Your household handyman (or woman) – or your building’s superintendent – whoever you call when the pipes burst, the heating goes out, or there’s a door that won’t close properly; could also be your IT expert (the person you call when your home server conks out)

–Your driver – or the pilot and the cabin crew of your private jet, your helicopter, or your yacht

–Your decorator – or your architect, or general contractor – if you’re in the middle of a large renovation project, you’re probably seeing these people more than you see some members of your own family

–Your real-estate broker – moving up in the world, or moving out, down-sizing or buying your dream ski house, this person is privy to your private emotions in a way that many are not

–The people who care for your dog – the walker, the vet, the groomer, or the head of school at doggie daycare

–Your financial advisor – or your attorney, your accountant, or your insurance broker

–Your executive assistant – you probably have one at the office and one at home, and one of them is probably your favorite but you should clearly never make this known

–Your travel agent – or your ticket agent, who can score last-minute tickets to the Yankees game or the Super Bowl

–Your masseuse – or your yogi, reiki practitioner, life coach, acupuncturist, or meditation guide

–Depending on your line of work, hobbies, life stage and lifestyle, you might also vote for: your agent, your producer, your speechwriter, your ghost writer, your PR person, your advance man, your body guard, your mechanic, your crisis manager, your family photographer, your flight instructor, your wedding planner, your OB-GYN, your backup singers or your go-to DJ

By the way, at the risk of offending someone upon whom my personal happiness depends, I will totally not be telling you who my MVP is.

We have a few friends who have household staffs that are sufficiently large that they need a lead person to coordinate all the others, especially the ones involving their various homes and children. This indispensable person rarely has a title, but they are the first line of defense on almost any problem, and some days, I really wish that I had such a person. A running joke between my husband and me is “just call Henry, he’ll take care of it.” That’s what one of our friends says anytime anything goes wrong anywhere in her life. We’ve actually never met Henry – he just makes things happen from behind the scenes. Sort of like Charlie in Charlie’s Angels.

Some people hoard their list of service providers because it takes years to build the right team, and they have no desire to lose anyone. A mom at my kids’ elementary school once hired our nanny right out from under us, and to this day we are still furious with both of them. That is so not cool.

There’s a river of advice about the protocol around severing one of these entourage relationships, particularly if they have been long-standing. I have never seen people so anxious as when they have to fire their nanny. I have seen real tears shed when a beloved housekeeper decides to retire and move to a warmer climate.

Back in the days of the landed gentry in Europe, there were rules around this that were understood by all. Now, we’re making it up as we go, and getting it wrong a great deal of the time.

By the way, I think there’s a huge business opportunity for someone to create a viable referral service for the wealthy so that one could easily hear from others about who’s really good and who’s available for all of these roles – like Angie’s List, but for millionaires.

And of course, there are many unwritten rules between the principal and the members of the entourage. Like: what gets said when you’re getting your hair done stays in the salon; no talking to the principal’s spouse or partner about anything without checking first; no betrayals of confidences to anyone, including other members of the entourage; no judging; no stealing (obviously); no yelling; no insider trading; no asking for money, favors or cast-out clothing (wait for them to be offered). Compassion and a sense of humor on both sides are mandatory.

I read an article recently about the obsession of the Silicon Valley elite for having all manner of helpers and assistants sign non-disclosure agreements (NDAs). This is another of those odd East Coast-West Coast behavioral divides. Or perhaps this too is generational? I have never heard of anyone on the East Coast demanding an NDA – it’s just understood that there are certain rules and norms that everyone has a moral obligation to uphold. Interesting how some people who have made their fortunes getting others to share the most intimate details of their lives online are unwilling to have even their carpenters talk about what they’re working on.

Years from now, I wonder if the chat-bots will make this potential MVP list. Will Alexa, Siri, Cortana and the other virtual assistants become that sympathetic supporter who both gets you, and gets things done? (And will some of them have names that sound male, not female?) Given the amount of human intelligence that it takes to get these relationships right, that’s going to require some serious advances in AI.

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