Tips & Tricks of an Ultra-High-Net-Worth Estate Manager

“If someone asked the one word that describes what I do as an estate manager, I’d say ‘facilitator.’” So said Alfred Penny,[1] who spent the past 24 years as the estate manager for an ultra-high-net-worth family – a family worth billions.

What exactly is a facilitator? You might say Alfred’s job is to manage day to day tasks so his boss doesn’t have to. “I don’t generate income, but I facilitate an environment which is conducive to doing business,” he said.

The life of the super-rich isn’t challenging in the way life is for many of us. However, life with multiple properties, a private jet, a fleet of luxury vehicles, and an art collection worth millions presents its own set of challenges. That’s where Alfred comes in. As estate manager, he managed all this so his boss, aka the “principal,” could do what he did best. And that was “making millions and millions of dollars. We all have certain redeeming qualities,” Alfred said wryly.

Getting your start & getting your share

A funny, exuberant, and humble man, Alfred dedicated his adult life to being a private service professional. He started out at the Culinary Institute of America (CIA) in Hyde Park, NY on the private chef track.

After CIA, he did “a few stages [2] under chefs at the best restaurants in the country.” Developing this kind of “provenance,”[3] as Alfred put it, is essential for working your way into the world of high-net-worth families and above.

At the same time, he insists that if they’re ambitious enough, a housekeeper working at a local hotel could make it into this world. “How hungry are you?” he asked. Indeed, Alfred wanted to share his experience to help the next generation see that there’s more out there—that there’s real potential for a great career in private service. So, if you’re hungry and interested in learning what it takes, listen up.

“Some days I went to work in a helicopter,” Alfred said. “I remember flying cross country on a private 737. Nothing was normal.”

During political fundraisers hosted by his most recent principal, Alfred served dinner to and met several U.S. presidents and vice presidents, as well as numerous ambassadors and dignitaries.

Many domestic staff can’t imagine getting health benefits from an employer. Alfred tells a different story. One of the housekeepers he worked with made $80,000 a year, received 100% health insurance, and a matching 401k contribution. Every few years, the boss would buy her a new car. When they were remodeling one of the houses, she got several pieces of high-end furniture for free.

Alfred himself made in the $200,000 range, but he made it clear that packages vary in every possible way. Salary is just one piece of the puzzle, depending on the perks and location (cost of living differences vary widely by location), that number could move up or down significantly.

Let’s be realistic though, these are demanding positions. Going private is “a tough world,” Alfred said.

Butlers, house managers, and housekeepers — pride & modesty at the top

Private chefs start at schools like CIA and Johnson & Wales. But, according to Alfred, there are also butler schools around the world. Charles MacPherson is a well-known Butler and housekeeping school based in North America, and there are additional trade schools where you can get your start. The housekeepers he has worked with started at mid-range hotels, then worked their way into more prestigious hotels. From the Four Seasons or the Peninsula [hotels], for example, you could make the move to a housekeeper position for a high-net-worth family.

Alfred’s winning character might be described as a paradoxical mix of pride and modesty.

“When I was hiring staff,” Alfred said, “I never discriminated; I wanted somebody who took pride in their presence. Their resume had to be folded and in a beautiful envelope, and most importantly, they wanted to learn and were willing to grow. When they got the job, they stood by my side and asked me lots of questions.”

His message: Cultivate pride in your work, but never forget that there’s always, always, more to learn. For example, Alfred described himself during his stages as standing beside great chefs, watching everything closely, and asking for tips. “I emulated their style and skills: clean clothes, the best tools, and true mastery of their calling.”

Alfred had just graduated from one of the finest culinary schools in the country, but he was humble. “Some people think they can do no wrong, there’s an arrogance to them,” he said. “But you have to work your way up and learn the trade, understand finer products and materials, and take pride in that.”

Few people recognize the level of expertise required in this kind of work. The higher you go, the more there is to learn. Alfred started with his former employer as a private chef and house manager. As his principal grew from high-net-worth to ultra-high-net-worth, Alfred grew along with him. As their trust deepened, his principal asked him to manage the extensive and very expensive art collection that he had begun to acquire.

“Unfortunately, my knowledge of art was minimal,” Alfred said. “I was humble, extremely humble. I asked questions; I studied. Eventually, I was handling an art collection worth hundreds of millions: de Kooning, Warhol, Calder, and these are the common names. It boggles the mind.”

Gatekeeper of the castle

Aside from the profound privilege that wealth of this magnitude brings, it also brings risk. During his tenure, Alfred said that he had to remain invisible to the world. He couldn’t be found on Google. “There was information blackout, total anonymity.” If you’re on social media, your information is public, and that is completely unacceptable. “So, as estate manager,” Alfred said, “I was the gatekeeper to the castle. Discretion, privacy, and security were of the utmost importance.”

The “castle” itself had to have serious protection as well. All the properties he managed were equipped with elaborate security systems and surveillance cameras. When a vendor came to the house, for example, they used the service entrance. They were required to sign an NDA;[4] their pictures were taken. They couldn’t take pictures in the house, and if they broke the rules, they would be asked to leave immediately.

Most of us don’t think about the risks that these families face. And as facilitator, part of Alfred’s job was protector. “You have to build a loyalty to your principal and the family you work for. And you have to understand and respect the position you’re in,” he said. “My anonymity was part of that. It wasn’t easy, but it comes with the territory.”

For private service professionals at this level, the demands are extremely high, and there are definite sacrifices, but for Alfred, “this whole career is about passion and love for what you do. Sure, when you’re higher up the ladder, there is some loneliness,” he said. “But if you’re willing to go in 100%, there are also rewards. Huge rewards.”