Dear Billionaire

You’d think with a full staff and a family office, things would run smoothly, but estate management is where even the wealthiest households fall apart. In this episode of Dear Billionaire, we uncover 6 estate management mistakes that quietly derail luxury homes—and how to fix them. Without structure, strategy, and leadership, your household won’t just feel chaotic—it will be. Whether you're a home...

You know the type—talented, high-performing, but impossible to work with. In this episode of Dear Billionaire, we dive into how to coach the uncoachable—or cut ties with toxic staff for good. Skipping straight to termination might feel tempting, but it’s lazy leadership. Real leadership means offering clear, documented opportunities for improvement. Whether you're a house manager, estate manager,...

If you think team building means dragging your household team to an escape room while Cindy the housekeeper solves every puzzle...think again. In luxury homes, siloed staff can quietly derail service and morale. To build a world-class household team, you must first break down the barriers that keep siloed staff from working collaboratively. Whether you're an estate manager, house manager, or high-...

When staff take PTO, does your home fall apart? If the answer is yes—or almost—this episode is a must-watch. In world-class estates, operations stay seamless even when staff take PTO, thanks to cross-training, smart planning, and clearly defined systems. I’ll show you how to create the same results in your home. In this episode, we cover: - Why most private homes are one vacation away from chaos -...

Your staff deserves time off, but your house and family keep running full steam. How do you balance both without chaos? In this episode, we’re exploring smart, seamless strategies for managing household staff personal time off (PTO) so your home runs smoothly even when key team members are away. From proactive scheduling to cross-training tips, I’ll show you how to maintain consistency, reduce str...

"You’re Not A Good Fit." Homeowners use this phrase to dismiss staff when they want to take a chance and see what happens next. It’s their right and privilege to choose who they want in their home and to relieve staff of their duties, even those who are competent, for reasons that may seem irrational or unfounded from an outsider’s (or even an insider’s) perspective. These decisions, whether logic...

In the world of the ultra-wealthy, few purchases are as significant as acquiring a mega-mansion (10,000+ square feet). This is the ultimate status symbol — of wealth, success, security, and, often, a new phase in life. However, life in such a home involves significant adjustments beyond the luxury. In this episode, I explore 7 related considerations. Thanks for listening! Read the blog post: https...

As a homeowner, your staff is your most important asset when building a residential real estate portfolio. With them, your property values will stay high, and the enjoyment of owning these homes can feel manageable. Ensuring your staff feel heard, supported, and appreciated goes a long way toward fostering a productive and loyal team and protecting one of your most valuable personal assets. This s...

Managing a large household with full-time staff is as complex as running a not-so-small business. Estate Managers who run that business make daily decisions that could impact their employment. For an estate manager, fear of losing their job may cause them to hesitate on both big and small decisions that impact progress at your property. Incorrect assumptions can cause a homeowner to deem them "not...

Why is it important to understand and identify toxic people inside your organization? - You won’t get the service you are paying for. - Your revolving door of entering and exiting staff will require additional resources and patience during these transitions. - Your family will continue to feel disrupted in their daily lives. - Your household staff will feel insecure and seek more secure opportunit...

When I think of a successful, live-in staffing scenario, I can only come up with Alice from The Brady Bunch . Fast forward to today and real-life situations…I’m not sure live-in situations are a good idea. I’ve seen many bad examples lately of House Managers losing their livelihood and housing – and not being prepared with a Plan B. If you think about the most stressful situations in life, aside f...

In the past, I have written and spoken a lot about Unicorn Employees (i.e., required tech skills for house managers, world-class service goals, leadership requirements, system-building skills, and team building). If you Google Unicorn Employee, you’ll find numerous articles that outline the ideal candidate or employee. But, if you Google Unicorn Employer , you’ll come up with NOTHING. Let's change...

I did a Coffee Talk about a month ago on what private service professionals need to do to keep a principal’s secret as a secret. Today I'm going to talk about what the homeowner – the principal, the employer – needs to do so that their secrets aren't divulged to their household staff. We keep secrets from other people. But if a homeowner is constantly pressing their staff with statements like, “Wh...

Dear Billionaire, You need an ORG CHART for your household team. Yes, you do! I know you're rolling your eyes, but listen up.... Whether you have a small housekeeping team or a family office, in this episode I explain the benefits of this important one-page document. (Or use Post-It notes!) And...drum roll, please...I have a free org chart template to make this task a little easier. You can get it...

This week I thought I would walk you through a property assessment and why these are so important to any homeowner – but especially if you're new to the property. I was on a site visit last week at a house where the homeowner had purchased it within the last 6 months to a year. They have had full blown renovations happening since they purchased it, and they purchased it as is. However, nobody did...

At midnight on Sunday, I was awakened by my phone vibrating. Not in a standard, silenced phone call way; more like an Amber Alert. Without my glasses on, I dismissed it and went back to sleep. Minutes later, I heard one of many tornado sirens blast – longer than their average weekly testing. After the third or fourth round, I couldn’t ignore them. I got out of bed to look outside and check the wea...

If you employ staff in your home, you are likely already using a non-disclosure agreement (NDA). And if you do, you probably have stipulations in it like the following, to which your staff have signed their understanding: - They will not be involved in the preparation of a book, article, story, video, or film about the homeowner, their family business, their business interests, or their personal l...

When it comes to hiring new staff, does it ever feel like you’re jumping off a cliff into the abyss? Like you and a private service professional are getting married without knowing each other really well? I can tell you from experience as a former estate manager, and from the estate managers and house managers I speak with, that this feeling goes both ways. The solution to this for both parties: a...

It’s time to look at household staffing differently When a homeowner decides they need staff, they: - hire people, - sign the paychecks, and - assume they’ll get the service they need from those employees. Then, when staff questions overwhelm them – when the homeowner doesn’t get the service they desire, and they feel frustrated with the lack of control over their day and the lack of privacy withi...

From the first day I stepped into my role as an estate manager, I had an idea of how I thought it should be. I had been working on luxury properties for more than 20 years, but not in them. And I felt like I had hit the jackpot when I was hired for this very demanding role. One that I felt I was 110% suited for. I thought that by being employed by a high-tech giant that I would walk into a world o...

One of the most important tasks you should complete before hiring staff is this Master Maintenance Task List. You can create this yourself in Excel. There are only (5) columns. They are: 1) Item or Category 2) Who completed the task 3) Frequency that the task needs to be completed 4) How long each task takes to complete 5) What is the task The investment of time to create this task database provid...

King Charles’ coronation was an extraordinary experience filled with pomp and circumstance, gold and glitz, and all of the eye candy that we royal watchers can stand. But many who posted on social media this week – I’ll call them the lip readers – counted the times Charles said, “Thank you.” So, we all know that he was hyper aware of the millions and millions of people that were watching him durin...

Recent job descriptions of estate managers have become a laughable list of unrealistic expectations and impossible deliverables. As with any job, an employee should have reasonable agility to adapt to ever-changing work environments. While the growing trend of homeowners wanting fewer staff in their homes is understandable, it shouldn’t be seen as an opportunity for unethical behavior. Thanks for...

Remember, staff won't leave employers or managers when they feel successful, well-paid, supported, and valued. The best candidates have options, and seasoned vets' salaries are at an all-time high. You’ll need to be an excellent employer to attract and maintain a trusted household team. Here are the top 10 ways to retain world-class staff. Thanks for listening.  For more information, visit ou...

During April, our team has been diving into the nitty gritty nuances between Service and Servitude. Since watching Succession, I decided to go deeper into the different aspects of service available to families of wealth. If I had to describe a sliding scale of service, I would say that managing a 2,000-square-foot Malibu beach house for a wealthy individual with no children is Service Level 1, whi...