Use a personal excess liability policy with limits of $10 million or more, not a standard $1 million umbrella.
The Standard Umbrella vs. the Industrial-Strength Hurricane Shelter.
A standard $1 million umbrella policy is a fantastic tool for a middle-class family. It’s a sturdy umbrella. But for a high-net-worth family, it’s like bringing a simple umbrella to a Category 5 hurricane. It is dangerously inadequate. A personal excess liability policy with limits of $10, $20, or even $100 million is the steel-reinforced, concrete hurricane shelter for your assets. It recognizes that your wealth and profile make you a target for catastrophic, “nuclear” lawsuits, and it provides the industrial-strength protection needed to survive that kind of storm.
Stop insuring your custom home with a standard HO-3 policy. Do use a high-value carrier that offers guaranteed replacement cost and a cash-out option instead.
The Off-the-Rack Suit vs. the Bespoke Savile Row Garment.
Insuring your custom-built home with a standard, mass-market policy is like trying to fit a bespoke, handmade suit into a cheap, off-the-rack garment bag. It doesn’t fit, and it doesn’t protect the true value. A high-value carrier like Chubb or PURE offers a custom-tailored solution. They provide “guaranteed replacement cost,” promising to rebuild your unique home exactly as it was, even if the cost exceeds your policy limit. They also offer a “cash-out” option, giving you the freedom to take the money and start fresh somewhere else.
Stop just listing your fine art on your homeowners policy. Do get a standalone, agreed-value fine art policy with worldwide coverage instead.
The “Junk Drawer” vs. the Climate-Controlled Museum Vault.
Listing your fine art on your homeowners policy is like storing a masterpiece in your junk drawer. It’s lumped in with your other belongings, has a high deductible, and is only covered for a limited list of perils. A standalone fine art policy is the climate-controlled, high-security museum vault. It insures your collection on an “agreed value” basis, so you know the exact payout. It provides worldwide, “all-risk” coverage, including for mysterious disappearance and accidental breakage. It is the professional-grade protection that your valuable collection deserves.
The #1 secret for protecting your assets is titling them correctly in trusts and LLCs and then insuring those entities properly.
The “Army” and the “Fortress” Working Together.
The #1 secret to asset protection is a two-part strategy. First, you build the fortress: you title your various assets in a series of carefully constructed legal entities, like LLCs and trusts, to compartmentalize your risk. But a fortress alone is not enough. You must then hire the army: you must purchase high-limit liability insurance policies that specifically name these legal entities as the insureds. It is this powerful, one-two punch of legal structuring (the fortress) and risk transfer (the army) that creates a truly impenetrable defense for your wealth.
I’m just going to say it: Your mass-market insurance company does not understand the risks or have the right products for a high-net-worth family.
The “Fast Food” Restaurant vs. the “Michelin-Starred” Chef.
A mass-market insurance company is a fast-food restaurant. They are designed to efficiently serve a million identical, simple meals. They have no idea how to prepare the complex, multi-course, gourmet meal that a high-net-worth family’s risk profile requires. A specialty high-net-worth carrier is the Michelin-starred chef. They have the expertise, the sophisticated “ingredients” (policy forms), and the white-glove service that is specifically designed to cater to the unique and complex tastes of a wealthy clientele. You cannot get fine dining at a drive-thru.
The reason your standard policy is inadequate is that it has low sub-limits for jewelry, silverware, and other valuables.
The “Fine Print” That Puts a Low Ceiling on Your Best Stuff.
Your standard homeowners policy has a secret, low ceiling for your most valuable possessions. Buried in the fine print is a list of “sub-limits,” which are the maximum the policy will pay for the theft of certain categories of items. While you might have a million dollars in property coverage, the sub-limit for jewelry might be just $2,500, for silverware just $5,000, and for firearms just $2,500. A standard policy is designed for standard stuff; it is dangerously inadequate for protecting a collection of high-value, specialized assets.
If you’re still employing domestic staff (nannies, housekeepers) without Employment Practices Liability Insurance (EPLI), you’re losing protection from wrongful termination and harassment lawsuits.
The “Family” That Is Also a “Workplace.”
The moment you hire a nanny, a housekeeper, or a personal assistant, your home is no longer just a home; it is also a workplace, and you are an employer. This exposes you to the exact same legal risks as a major corporation. A disgruntled employee can sue you for wrongful termination, discrimination, or harassment. A standard homeowners or umbrella policy does not cover these risks. Employment Practices Liability Insurance (EPLI) is the essential, specialized shield that protects you from the messy, and often very expensive, human side of being a household employer.
The biggest lie you’ve been told is that your umbrella policy covers all your activities; it often excludes things like non-profit board service.
The “All-Access Pass” with a Velvet Rope.
The lie is that your personal umbrella policy is a magical, all-access pass that covers every aspect of your life. The reality is that it has a velvet rope. Most standard umbrella policies have a “business pursuits” exclusion and may not cover the professional decisions you make as a board member for a non-profit. Serving on a board is a serious, professional activity with its own unique liability risks. You must ensure that the non-profit organization has its own, robust Directors & Officers (D&O) liability policy to protect you in that specific role.
I wish I knew about Kidnap & Ransom (K&R) insurance before my first international business trip.
The “Special Forces” Team on Speed Dial for Your Worst Nightmare.
For a high-profile executive or a wealthy family traveling abroad, the risk of a kidnapping, while remote, is catastrophic. Kidnap & Ransom (K&R) insurance is not just a policy; it is a crisis response team on retainer. The most valuable part of the policy is not the money it provides for a potential ransom; it is the immediate, 24/7 access it gives you to an elite, world-class team of security consultants and hostage negotiators. They are the special forces team who will manage the entire, terrifying crisis and work to ensure a safe return.
99% of wealthy families make this one mistake: they fail to have a comprehensive risk management plan that goes beyond just buying insurance.
The “Financial Fire Department” vs. the “Fireproof Building Code.”
Buying insurance is a crucial, but reactive, step. It is hiring the best possible fire department to put out a fire after it has already started. A comprehensive risk management plan is proactive. It is the process of designing and building your entire financial and personal life to a “fireproof” building code. It involves legal structuring, physical security, cyber-safety, and behavioral changes to prevent the fire from ever starting in the first place. The insurance is the backstop, not the entire strategy.
This one small action of getting a professional security audit of your home will not only improve safety but can also lower your insurance premiums.
The “White Hat Hacker” for Your Physical Castle.
A professional security audit is like hiring a “white hat hacker” to test the defenses of your physical, not digital, castle. An expert will walk your property and identify all the hidden vulnerabilities—the overgrown landscaping, the poorly lit entryway, the weak lock on the back door. Implementing their recommendations will not only make your family dramatically safer, but the documented report from that audit can be submitted to your high-net-worth insurance carrier, who will often reward your proactive security posture with a significant premium discount.
Use a specialty broker who works with high-net-worth carriers like Chubb, PURE, or AIG Private Client, not your local Allstate agent.
The “Boutique” Expert vs. the “Department Store” Generalist.
Your local, mass-market insurance agent is a department store. They sell a wide range of good, reliable products for the average person. But they do not have the access or the expertise for the luxury market. A specialty, high-net-worth broker is the exclusive, high-end boutique. They have the deep knowledge and, most importantly, the exclusive appointments with the “designer brand” carriers like Chubb and PURE that are not available to the general public. For a sophisticated client, the boutique is the only place to shop.
Stop thinking your assets are safe behind an LLC. Do realize that a “corporate veil” can be pierced, and high liability limits are essential.
The “Chain-Link Fence” vs. the “Concrete Fortress.”
An LLC is an important and necessary legal tool. It is like putting a sturdy, chain-link fence around your assets. It will stop a casual trespasser. However, a determined and skilled attorney can often find a way to “pierce the corporate veil”—to find a hole in that fence and come after your personal assets. High-limit liability insurance is the ten-foot-thick, steel-reinforced concrete fortress that you build around that fence. The legal structure is the first line of defense; the insurance is the ultimate, impenetrable one.
Stop insuring your wine collection for its purchase price. Do insure it for its current market value instead.
The “Seed” vs. the “Full-Grown Oak Tree.”
Insuring your wine collection for what you originally paid for it is like insuring a mighty oak tree for the price of the acorn you planted 20 years ago. A fine wine collection is a living, breathing, and appreciating asset. The purchase price is irrelevant. You must have a specialized, “agreed value” policy that is based on the current, and often dramatically higher, market value of your collection. This requires regular appraisals to ensure that the insurance you are paying for is protecting the full-grown tree, not just the long-forgotten seed.
The #1 hack for a smooth claim is using a high-net-worth carrier that provides a dedicated claims concierge service.
The “Private Banker” for Your Worst Day.
The standard claims process is a frustrating, bureaucratic nightmare. The #1 hack is to work with a high-net-worth carrier who provides a “claims concierge.” This is the private banker for your financial disaster. You are not just a claim number; you are a valued client. You will be assigned a single, dedicated, and highly experienced adjuster who will quarterback the entire process for you. They will handle the contractors, they will manage the paperwork, and they will ensure a smooth, white-glove experience during your most difficult time.
I’m just going to say it: Your financial advisor who only manages your investments is ignoring the biggest threat to your wealth: liability lawsuits.
The “Offense” Coach Who Has Completely Forgotten About the “Defense.”
A traditional, assets-under-management financial advisor is the brilliant offensive coordinator for your financial team. They are a master of growth, of scoring points, of building your wealth. But they have a massive blind spot. They often completely ignore the other side of the ball. A single, catastrophic liability lawsuit is the surprise “blitz” that can sack your quarterback and wipe out your entire lead. A true wealth manager understands that a powerful, well-coached defense—your liability insurance program—is just as important as a high-flying offense.
The reason you need workers’ compensation for your domestic staff is that it’s required by law in many states, even for one employee.
The “Household Employer” and the Law You Didn’t Know You Were Breaking.
The moment you hire a full-time nanny, housekeeper, or gardener, you are not just a homeowner; you are a “household employer.” In many states, the law requires every employer, even one with a single employee, to provide workers’ compensation insurance. This is not an option; it is a legal mandate. This policy will pay for your employee’s medical bills and lost wages if they are injured on the job. Failing to have this coverage is not just a financial risk; it is a violation of the law that can come with significant fines and penalties.
If you’re still chartering yachts or private jets without non-owned aviation/watercraft liability, you’re losing critical coverage.
“Renting the Keys” to a Multi-Million Dollar Liability Machine.
When you charter a private jet or a yacht, you are not just a passive passenger; you often have a degree of control that creates a massive liability exposure. Your personal umbrella policy may have a specific exclusion for the use of aircraft and large watercraft that you do not own. A “non-owned” aviation or watercraft liability policy is the specialized tool that fills this dangerous gap. It is the crucial, and surprisingly affordable, coverage that protects you from the catastrophic, multi-million dollar liability of a disaster in the air or on the sea.
The biggest lie is that you can just “self-insure” your risks. A single catastrophic lawsuit could wipe out a significant portion of your net worth.
The “Fortress of Cash” vs. the “Financial Fire Department.”
“Self-insuring” is a dangerously arrogant term. It implies that your pile of money is a fortress that is strong enough to withstand any attack. The reality is that a catastrophic, “nuclear” liability lawsuit is a financial firestorm that can burn through a multi-million dollar fortress with terrifying speed. Insurance is not just a pile of money; it is the professional fire department. It is the legal and contractual transfer of that catastrophic risk to a multi-billion dollar institution that has the overwhelming, specialized firepower to extinguish that blaze.
I wish I knew that a high-value homeowners policy would pay to fly in a specialist artisan from Europe to restore custom woodwork after a fire.
The “Rebuild” vs. the “Re-Create” Promise.
A standard homeowners policy promises to “rebuild” your house with modern, standard-grade materials. A high-value policy from a carrier like Chubb makes a different, and much more powerful, promise: to “re-create” your home. I wish I had known that this means if the custom, 18th-century woodwork in your library was carved by a specific artisan in France, they will pay to fly that same artisan’s workshop to your home to perfectly and authentically re-create that masterpiece. It is a level of detail and commitment that a standard policy cannot even comprehend.
99% of art collectors make this one mistake: they don’t have a policy that covers the art while it’s in transit to a gallery or another home.
The “At Rest” vs. the “In Motion” Risk.
A standard art policy is great for protecting your collection while it is hanging safely on your wall. But an artwork’s moment of greatest peril is when it is “in motion”—being transported to a gallery, another home, or a museum. This is where most of the damage occurs. The crucial mistake is not ensuring that your policy has broad, “wall-to-wall” transit coverage. A good fine art policy is designed for a collection that moves, providing seamless protection from the moment it leaves your wall until the moment it is safely hung on the next one.
This one small action of placing your life insurance inside an Irrevocable Life Insurance Trust (ILIT) will remove the death benefit from your taxable estate.
The “Winning Lottery Ticket” in Your Pocket vs. in a Separate, Secure Vault.
For a family with a taxable estate, owning a large life insurance policy personally is like carrying a winning, multi-million dollar lottery ticket in your back pocket. When you die, the IRS will reach into that pocket and take up to 40% of it in estate taxes. The simple, but profound, action of creating an Irrevocable Life Insurance Trust (ILIT) to own that policy is like building a separate, secure vault for that ticket. The vault is a separate legal entity, and it delivers the full, un-taxed payout directly to your family, completely shielded from the IRS.
Use premium financing to acquire large life insurance policies, not just tying up your own liquid capital.
Getting an “Interest-Only Mortgage” on a Financial Skyscraper.
Premium financing is a sophisticated strategy that allows you to acquire a massive asset without using your own cash. It is like getting an interest-only mortgage to purchase a multi-million dollar financial skyscraper (a life insurance policy). A third-party lender pays the large, illiquid premiums for you. You simply pay the small, annual interest on the loan, which keeps your own capital free to stay working in your more liquid, higher-returning investments. It is the ultimate leverage play for efficient and massive legacy creation.
Stop insuring your collector cars with a standard auto policy. Do use an agreed-value collector car policy with flexible usage provisions.
The “Used Car” vs. the “Work of Art.”
Insuring your ’65 Mustang with a standard auto policy is a tragic mistake. That policy will treat it like a simple used car and pay you a depreciated, “actual cash value” after a loss. A collector car policy understands that your vehicle is a work of art. It insures it on an “agreed value” basis, meaning you and the company agree on its specific, collectible value upfront. It also has much more flexible usage provisions, recognizing that you are a careful enthusiast, not a daily commuter. It’s the art insurance your rolling masterpiece deserves.
Stop letting your children drive high-performance cars titled in your name without massive liability limits.
The “Loaded Weapon” You’ve Handed to an Inexperienced User.
Giving your teenager the keys to a high-performance sports car that is titled in your name is the legal and financial equivalent of handing a loaded weapon to a person with no training. You, as the owner of the “weapon,” are on the hook for any and all catastrophic damage it might cause. If you are going to take this massive liability risk, you must have an equally massive fortress of liability protection in place. This means a multi-million dollar excess liability policy that is large enough to absorb the nuclear fallout of a worst-case scenario.
The #1 secret your family office should know is that a dedicated insurance advisor is as important as the investment manager or CPA.
The “Third Leg” of the Wealth Management Stool.
A family office is a three-legged stool that is designed to support a family’s wealth for generations. The first two legs are well-known: the investment manager (to grow the assets) and the CPA/tax attorney (to minimize the taxes). The secret is that the stool is dangerously unstable without the third, and equally important, leg: the dedicated, professional risk management advisor. Their job is to build the defensive fortress of liability and property insurance that protects the family’s balance sheet from being destroyed by a single, catastrophic event.
I’m just going to say it: Being “rich” makes you a bigger target for frivolous lawsuits.
The “Deep Pockets” Bullseye on Your Back.
This is a simple, and unfortunate, reality of the modern legal world. The more successful and wealthy you become, the larger and more attractive the financial bullseye on your back becomes. You are no longer just a person; you are a “deep pocket.” This makes you a much more attractive target for frivolous, and not-so-frivolous, lawsuits. A plaintiff’s attorney is far more likely to take a questionable slip-and-fall case against a person with a known, multi-million dollar net worth. Your wealth is a magnet for legal trouble.
The reason you need D&O insurance for serving on a non-profit board is that you can be held personally liable for the board’s decisions.
The “Good Deed” That Can Cost You Your House.
Serving on the board of a non-profit is a wonderful and noble act. It is also a serious, professional role with significant legal liability. You, as a board member, can be held personally liable for the decisions and the financial mismanagement of the board. If the non-profit is sued, the lawsuit will often name the individual board members, putting your personal assets—your house, your savings—at risk. Directors & Officers (D&O) insurance is the essential shield that protects your personal wealth while you are doing your good deed.
If you’re still not conducting background checks on all your domestic staff, you’re losing your first line of defense against theft and liability.
The “Known” vs. the “Unknown” Risk You’re Inviting into Your Home.
When you hire a nanny or a housekeeper, you are inviting a stranger into the most intimate parts of your family’s life. Not conducting a thorough, professional background check is an act of blind trust that is bordering on negligence. A background check is your crucial first line of defense. It allows you to verify a person’s history and to avoid hiring someone with a record of theft, violence, or a terrible driving record. It is the simple, proactive step that allows you to manage the risk before you hand over the keys to your house and the care of your children.
The biggest lie is that all umbrella policies are the same. A high-net-worth policy provides much broader coverage.
The “Standard Sedan” vs. the “Armored Limousine.”
The lie is that an umbrella is an umbrella. The reality is that a standard umbrella policy is a reliable family sedan. A high-net-worth umbrella, from a carrier like Chubb, is a custom-built, armored limousine. The high-net-worth policy provides much broader coverage. It often includes defense costs outside the policy limit, it can cover risks like libel and slander, and it will often “drop down” to provide primary coverage for risks that your underlying policies don’t cover at all. It is a completely different, and far superior, class of vehicle.
I wish I knew that my homeowners policy excluded coverage for my horse stable and I needed a separate equine liability policy.
The “Pet” That Is Actually a “Liability Powerhouse.”
I wish I had known that a standard homeowners policy views a horse not as a pet, but as a large, unpredictable, and highly dangerous liability risk. My policy had a specific exclusion for any liability arising from the ownership of horses. The separate stable, the fencing, and, most importantly, the massive risk of that 1,200-pound animal kicking or biting someone, required a specialized “equine liability” policy. It’s the specific tool needed to protect against the unique, and often catastrophic, risks of the equestrian world.
99% of high-net-worth parents make this one mistake: they don’t have a plan to protect their children’s inheritance from lawsuits or divorce.
The “Briefcase Full of Cash” vs. the “Generational Trust Fund.”
The biggest mistake is to leave a massive inheritance directly to your children. It is the equivalent of handing them a briefcase full of cash. That money is now their personal property, and it is completely exposed to being lost in a future divorce, a lawsuit, or a bad business deal. A properly structured, multi-generational trust is the secure, personal vault for that inheritance. The money is protected for their benefit, but it is not legally “theirs,” keeping it shielded from their future financial and marital predators for generations.
This one small action of consolidating all your policies with one high-net-worth specialist will ensure there are no gaps in your coverage.
The “Single, Woven Quilt” vs. the “Pile of Mismatched Blankets.”
Having your various insurance policies scattered across multiple, standard-market companies is like trying to stay warm with a pile of small, disconnected, and mismatched blankets. There are guaranteed to be gaps and holes. The simple, powerful action of consolidating all of your policies—your home, your cars, your valuables, your liability—with a single, high-net-worth specialist is like trading that pile of blankets for a single, massive, and beautifully woven quilt. It is a seamless, integrated, and gap-free solution that provides a single, warm layer of comprehensive protection.
Use Private Placement Life Insurance (PPLI) to shield your alternative investment gains from taxes.
The “Tax-Free Greenhouse” for Your Most Exotic and High-Growth Plants.
For an accredited investor, Private Placement Life Insurance (PPLI) is the ultimate tax-shelter. Think of your most aggressive and tax-inefficient alternative investments—like your hedge funds—as a collection of rare, exotic, and incredibly high-growth orchids. A PPLI policy is the massive, private, and legally tax-free greenhouse that you can build around them. By placing these investments inside the insurance “wrapper,” you allow them to grow and compound in a completely tax-free environment, shielding your most explosive gains from the harsh, annual glare of the IRS.
Stop thinking your wealth is a secret. Public records make it easy to identify you as a “deep pocket” target.
The “Invisible” Bullseye on Your Back.
The myth is that your wealth is a private matter. The reality is that in today’s digital world, you are living in a glass house. Public records—your property deeds, your political contributions, your business filings—are all easily searchable online. A plaintiff’s attorney can, in a matter of minutes, use these public records to identify you as a high-net-worth, “deep pocket” individual. You must operate under the assumption that your wealth is not a secret, and that you have a large, and very visible, bullseye on your back.
Stop displaying your wealth on social media. Do practice discretion to reduce your family’s risk profile.
Don’t Advertise the Contents of Your Financial Safe to the World.
Your social media profile is a public billboard that advertises your life to the entire world. Posting pictures of your exotic cars, your multi-million dollar homes, and your lavish vacations is not just sharing; it is advertising. You are broadcasting to a global audience of potential thieves, kidnappers, and frivolous litigants that you are a high-value target. Discretion is a powerful, and often overlooked, security tool. A lower-key, more private online presence is a crucial part of a modern, high-net-worth family’s personal security plan.
The #1 hack for insuring a vacation home is using the same carrier as your primary home to ensure seamless coverage.
The “One Brain” That Understands Your Entire Life.
The #1 hack for insuring a vacation home is to use the same, high-quality insurance carrier that insures your primary residence. This is not just for the multi-policy discount. It is about having a single, “one brain” insurance partner that understands your entire risk profile. In the event of a major liability claim that spans both properties, you are dealing with one, single adjuster and one, single legal team. This eliminates the catastrophic risk of two different insurance companies pointing their fingers at each other, leaving you caught in the middle.
I’m just going to say it: Your personal assistant should not be managing your multi-million dollar insurance portfolio.
The “Well-Meaning Amateur” vs. the “Seasoned Professional.”
Your personal assistant is a fantastic and trusted part of your life. They are not, however, a licensed and experienced risk management professional. Asking them to manage your complex, multi-million dollar insurance portfolio is like asking your friendly family doctor to perform your brain surgery. It is a task that requires a deep, specialized, and professional level of expertise. Your financial fortress should be designed and managed by a seasoned, professional architect, not a well-meaning and talented amateur.
The reason you need a reputation management component in your liability policy is to cover the cost of PR services after a high-profile incident.
The “Financial Fire Department” and the “Public Relations Paramedic.”
A major liability lawsuit doesn’t just threaten your finances; it threatens your good name. A standard liability policy is the financial fire department; it provides the lawyers and the money to fight the lawsuit. But a modern, high-net-worth policy often includes a “reputation management” component. This is the public relations paramedic. It provides a separate pool of money to hire a top-tier PR firm to manage the media, to control the narrative, and to protect your family’s reputation from the public fallout of a high-profile, and often messy, legal battle.
If you’re still using a standard bank safe deposit box, you’re losing coverage, as they are not insured.
The “Un-Insured” Steel Box at the Bank.
This is one of the most shocking and misunderstood secrets of the banking world. The contents of your bank’s safe deposit box are not insured. Not by the bank, and not by the FDIC. If the bank is robbed, or if there is a fire or a flood, you are on your own. You are simply renting an empty, un-insured steel box. The only way to protect the valuable jewelry, gold, or documents inside that box is to have a separate, “valuable articles” policy from your own insurance company that specifically covers the items stored there.
The biggest lie is that you don’t need a personal cybersecurity policy. High-net-worth individuals are prime targets for ransomware and spear-phishing.
The “Digital Bullseye” on Your Financial Back.
The lie is that cybersecurity is a problem for businesses, not for individuals. The reality is that high-net-worth families are the #1 target for sophisticated, personal cyber attacks. A “spear-phishing” attack that targets your family office, or a “ransomware” attack that locks up all your personal data, can be a multi-million dollar disaster. A personal cybersecurity policy is the specialized, modern shield that provides the expert response team and the financial resources needed to survive these targeted, and increasingly common, digital attacks.
I wish I knew that a high-value auto policy included a generous rental car provision, often for a comparable luxury vehicle.
The “Ford Taurus” vs. the “Mercedes-Benz” Loaner Car.
A standard auto policy’s rental car coverage is designed to get you a Ford Taurus. It’s basic, and it has a low daily limit. I wish I had known that a high-value auto policy, from a carrier like Chubb, understands that you are not a “Ford Taurus” person. Their rental coverage has a much higher, or even no, daily limit, and it is designed to get you a rental car that is of a “like kind and quality” to the luxury vehicle that you are used to driving. It’s a small detail that makes a huge difference in the claims experience.
99% of people with household staff make this one mistake: they don’t have a formal employee handbook, which is a key defense in an EPLI claim.
The “Unwritten Rules” vs. the “Legal Rulebook.”
If you have household employees, an “employee handbook” might seem like a cold, corporate formality. It is not. It is your single most powerful legal shield in an employment lawsuit. A lawsuit for wrongful termination or discrimination is almost always about proving that you acted unfairly or inconsistently. A written handbook that clearly outlines your policies, and a signed acknowledgement from the employee, is your Exhibit A. It is the legal rulebook that proves you are a fair, professional employer who has established and communicated clear rules.
This one small action of getting a professional appraisal for all your valuables every 3-5 years will ensure they are adequately insured.
The “Snapshot in Time” vs. the “Real-Time Movie.”
The value of your art, your jewelry, and your wine is not a static number; it is a constantly changing movie. An appraisal is a snapshot of that value on one specific day. The simple, disciplined habit of getting an updated, professional appraisal every three to five years is the key to ensuring that your insurance coverage is keeping pace with the real-time, appreciating value of your collection. It turns your old, outdated photograph into a modern, accurate motion picture, ensuring you are never caught dangerously underinsured.
Use a dedicated marine insurance policy for your yacht that covers the hull, liability, and crew.
The “Floating Corporation” That Needs Its Own CEO of Risk.
A yacht is not a boat; it is a complex, multi-million dollar asset with the operational complexity of a small corporation. It has a crew (your employees), it has massive liability risks, and it travels internationally. A standard boat policy is dangerously inadequate. You need a dedicated, “all-risk” marine insurance policy from a specialty carrier. This policy is designed to cover the hull for its agreed value, to provide the massive, multi-million dollar liability limits you need, and to include the crucial workers’ compensation coverage for your professional crew.
Stop assuming your teenager’s social media posts can’t get you sued for libel or slander. Your umbrella policy may be your only defense.
The “Digital Fistfight” That Leads to a Real-World Lawsuit.
In the old days, a teenage dispute was a fistfight in the schoolyard. In the modern world, it is a vicious, and very public, digital war fought on social media. A single, ill-advised post by your child that is deemed to be libelous or slanderous can easily result in a massive lawsuit that names you, the parent, as the responsible party. Your homeowners policy likely excludes this. A good, broad umbrella liability policy is often the only, and the most important, shield that can protect you from the modern, digital risks of parenting.
Stop thinking your divorce decree fully protects you. Do ensure your ex-spouse is removed from your policies and that you have adequate coverage for your new life.
The “Legal Divorce” vs. the “Financial Divorce.”
A divorce decree is the legal document that ends your marriage. It is not a magic wand that automatically severs your complex, intertwined financial life. You must be proactive. You must ensure that your ex-spouse is removed as a driver from your auto policy and as a beneficiary on your life insurance. And you must do a full, comprehensive review of your own coverage to ensure that it is adequate for your new, single life. The legal divorce is just the first step; the financial divorce is a separate, and equally important, process.
The #1 secret is that high-net-worth carriers offer complimentary risk management services, like wildfire defense and hurricane preparation.
The “Insurance Company” That Also Wants to Be Your “Fire Department.”
This is the #1 secret that separates the elite carriers from the masses. A high-net-worth insurer like Chubb or PURE does not just want to write you a check after the disaster; they want to help you prevent the disaster in the first place. They offer a suite of complimentary, “white-glove” risk management services. If a wildfire is approaching, they will send a private crew to your home to spray it with fire retardant. Before a hurricane, they will help you move your valuables. They are not just your insurer; they are your proactive risk management partner.
I’m just going to say it: If your insurance agent plays golf with you but never conducts a formal annual review, you have a friend, not an advisor.
The “Country Club” Relationship vs. the “Boardroom” Relationship.
A friendly, social relationship with your insurance agent is a wonderful thing. But it is not a substitute for a professional one. If your agent is happy to play a round of golf with you, but they never proactively schedule a formal, annual review of your entire insurance portfolio, you have a golfing buddy, not a professional risk advisor. The boardroom—the place where you do the serious, detailed work of protecting your family’s wealth—is far more important than the country club.
The reason you need broader uninsured/underinsured motorist protection is that the person who hits your Lamborghini probably has state-minimum coverage.
The “Mismatch” of a Supercar vs. a Super-Small Insurance Policy.
The mathematical certainty of the road is this: the person who crashes into your quarter-million-dollar exotic car is almost certainly not a fellow millionaire. They are a normal person with a normal, and likely state-minimum, insurance policy. Their paltry $25,000 of property damage liability will not even cover the cost of your front bumper. High-limit, “unstacked” Uninsured/Underinsured Motorist coverage on your own policy is the only way to protect your masterpiece from the financial reality of a catastrophic mismatch.
If you’re still not using a trust to own your life insurance, you’re losing up to 40% of the death benefit to estate taxes.
The “IRS” as Your Unwanted, and Very Expensive, Beneficiary.
If you personally own your life insurance policy and your estate is taxable, you have an unwanted and unlisted beneficiary on that policy: the Internal Revenue Service. Upon your death, the IRS can treat that death benefit as part of your personal estate and take a 40% cut right off the top. By having the policy owned by a properly structured Irrevocable Life Insurance Trust (ILIT), you are removing it from your personal estate. The trust, not you, owns the policy, and it delivers the full, 100% tax-free benefit to your heirs.
The biggest lie is that your assets are “judgment-proof.” A determined lawyer can find a way to reach them.
The “Mythical” Fortress with a Hidden Back Door.
The lie is that with clever legal structuring, you can make your assets completely “judgment-proof.” The reality is that a smart, determined, and well-funded plaintiff’s attorney is a master at finding the hidden back doors and the secret passages in any fortress. While legal structures are a crucial and necessary layer of defense, they are not a magical, impenetrable force field. The ultimate, final, and most powerful layer of protection is not the legal wall; it is the massive, deep moat of a high-limit liability insurance policy.
I wish I knew that I could get a discount for having a whole-house generator and a central-station alarm system.
The “Self-Sufficient and Secure” Home Discount.
I wish I had known that high-net-worth insurance carriers are obsessed with proactive risk mitigation, and they will reward you for it. A whole-house generator is not just a convenience; it ensures that your security systems, your sump pumps, and your climate control will continue to function during a power outage, preventing a host of potential claims. This, combined with a central-station alarm system, signals to the insurer that your home is a well-protected, self-sufficient, and “good” risk, a status that is rewarded with a significant premium discount.
99% of high-net-worth individuals make this one mistake: they have significant liability gaps between their underlying policies and their umbrella.
The “Gap” Between the Foundation and the First Floor.
An umbrella policy is designed to sit on top of your underlying home and auto policies. The mistake is to have a “gap” between them. For example, your umbrella might require you to have $500,000 of auto liability, but your actual auto policy only has $300,000. In a lawsuit, that $200,000 gap is your personal responsibility. You have a hole between your foundation and your first floor. A good broker will do a “gap analysis” to ensure that all your policies are perfectly stacked on top of each other with no dangerous spaces in between.
This one small action of reviewing your risk exposure before a child goes to college (e.g., hazing, alcohol-related incidents) is a critical parental duty.
The “Empty Nest” That Is Suddenly Full of New Risks.
When your child goes to college, your risk profile as a family changes dramatically. You are now exposed to a whole new world of liability risks—fraternity hazing incidents, alcohol-related accidents, accusations of libel on social media. The small, but critical, action of sitting down with your insurance advisor before they leave for school is a crucial parental duty. It allows you to review your umbrella liability limits and to have an honest conversation with your child about the new, and very real, risks they are about to face.
Use a not-for-profit D&O policy to cover your role on a condo or co-op board.
The “Volunteer” Job with “Professional” Sized Risks.
Serving on your condo or co-op board is a volunteer position, but it is not a risk-free one. You are a director of a corporation, and you can be held personally liable for the board’s financial decisions, for breaches of your fiduciary duty, and for employment-related claims from the building’s staff. A specialized “not-for-profit” D&O (Directors & Officers) policy is the essential shield that is designed to protect the personal assets of the volunteer board members who are taking on these very real, and very professional, risks.
Stop treating your insurance portfolio as a set of disconnected policies. Do demand an integrated risk management strategy from your broker.
The “Pile of Bricks” vs. the “Engineered Fortress.”
A collection of disconnected insurance policies from different agents is a simple pile of bricks. It is not a structure. A true, high-net-worth risk advisor does not sell you bricks; they provide you with an architectural blueprint. They will design an integrated, seamless, and engineered fortress of protection where all the different policies—the property, the liability, the life, the valuables—are designed to work together in a coordinated and gap-free strategy. You should not be buying policies; you should be implementing a plan.
Stop letting your children live in a home you own without a formal lease and their own renters insurance policy.
The “Tenant” Who Can Accidentally Sue You.
When your adult child lives in a separate home that you own, they are, for legal and insurance purposes, a tenant. You are a landlord. A formal lease agreement is not an insult; it is a crucial business document that clarifies the rights and responsibilities of both parties. And requiring them to have their own renters insurance policy is the essential risk transfer tool. It ensures that if their guest is injured, or if they accidentally cause a fire, their insurance policy, not yours, is the first line of defense.
The #1 hack for international travel is a K&R policy that provides access to elite security and crisis response teams.
The “Panic Button” That Summons the Special Forces.
For a high-profile traveler, a Kidnap & Ransom (K&R) policy is the ultimate “panic button.” The #1 hack is to understand that the policy is not about the money; it is about the access. The moment a crisis occurs—a kidnapping, a political detention, a violent extortion threat—you are not just calling an insurance company; you are activating a direct line to one of the world’s elite, private security and crisis response firms. They are the special forces team that will manage the entire, terrifying event and work to ensure your safe return.
I’m just going to say it: The more successful you become, the more complex and critical your insurance needs become.
The “Skyscraper” Needs a Deeper Foundation Than the “Shed.”
When you are just starting out, your financial life is a simple backyard shed, and a simple insurance policy is a perfectly adequate foundation. But as your success and your wealth grow, you are building a massive, complex skyscraper. That skyscraper requires a much deeper, more complex, and more professionally engineered foundation to support its weight and to protect it from the much stronger winds it will face at that altitude. The simple, off-the-shelf solutions of your past are dangerously inadequate for the complex realities of your present.
The reason you need a thorough review of your policy language is to look for exclusions related to your lifestyle, like aviation or high-risk hobbies.
The “Fine Print” That Knows You Fly a Plane.
A standard insurance policy is designed for a standard, low-risk lifestyle. If your life is more exciting than that, you must read the fine print. A standard umbrella policy, for example, will almost certainly have a clear and unambiguous exclusion for any liability arising from the ownership or use of a private aircraft, a high-speed boat, or certain high-risk hobbies. To be protected during your passions, you must work with a specialist broker to find a policy that is specifically designed to cover your unique and more adventurous lifestyle.
If you’re still lending your exotic car to a friend, you’re losing control of a massive liability exposure.
You’re Not Just Lending a Car; You’re Lending a Multi-Million Dollar Lawsuit.
Handing the keys of your Ferrari to a friend is not like letting them borrow a Toyota. You are not just lending them a piece of machinery; you are handing them a loaded, multi-million dollar liability weapon. Even if they are a great driver, a simple accident in a high-performance vehicle can have catastrophic results. And because the insurance follows the car, it is your policy and your assets that are on the line for their mistake. It is an act of trust that comes with an almost unmanageable level of personal risk.
The biggest lie is that you have enough life insurance. You need to account for estate tax liquidity, business succession, and philanthropic goals.
The “Income Replacement” Calculation vs. the “Legacy” Calculation.
The lie is that the purpose of life insurance is just to replace your income. For a high-net-worth family, that is just the first, and often smallest, part of the equation. Your real need is for “liquidity.” You need a massive, tax-free pool of cash to pay the estate taxes, to fund the buy-sell agreement for your business, to equalize the inheritance between your children, and to fund your charitable foundation. The “income replacement” number is a middle-class calculation; the “legacy liquidity” number is the one that matters to you.
I wish I knew that a high-value policy would cover the cost of rebuilding to the latest, more expensive green building codes.
The “Rebuild It Better” Promise.
I wish I had known about the subtle but powerful “Ordinance or Law” coverage that is built into a high-value homeowners policy. After a major loss, you are legally required to rebuild your home to meet the newest, and often much more expensive, modern building codes. A standard policy will not pay for these forced upgrades. A high-value policy will not only pay to rebuild your home as it was, but it will also provide the extra funds needed to bring it up to the latest, and often more environmentally friendly, “green” building standards.
99% of people with private aircraft make this one mistake: they don’t have adequate liability coverage for their corporate hangar.
The “Parked” Risk vs. the “Flying” Risk.
An aircraft owner is acutely aware of the massive liability risk of flying their plane. They will have a high-limit aviation policy. The mistake is to forget about the massive risk that exists when the plane is not flying. Your corporate hangar is a high-value, high-risk property. A fire, a fuel spill, or a slip-and-fall accident in that hangar can lead to a multi-million dollar lawsuit that is not covered by the aviation policy. You need a separate, high-limit “premises liability” policy to protect you from the “on the ground” risks of your aviation operations.
This one small action of creating a separate legal entity to own your high-risk assets (like boats or rental properties) will help shield your other assets.
The “Watertight Compartments” of Your Financial Battleship.
Your personal balance sheet is like a giant battleship. The simple, powerful action of creating a separate LLC to own your high-risk assets is like building a series of internal, watertight compartments in that ship. You can put your rental properties in one LLC, and your boat in another. Now, if a torpedo (a lawsuit) hits your “boat” compartment, the damage will be contained to that one, single area. The watertight doors of the LLC will prevent that flood from sinking your entire, personal financial battleship.
Use a captive insurance company for your family office to gain tax advantages and insure unique risks.
The “Family-Owned” Insurance Company for Your Family’s Unique Risks.
A “captive” is a sophisticated tool that allows you to create your own, private, family-owned insurance company. This captive can be used to insure the unique and hard-to-place risks of your family—like the art collection, the equestrian operation, or the kidnap and ransom risk—often with significant tax advantages. It transforms a pure expense (your insurance premiums) into a contribution to a new, family-owned asset. It is the ultimate tool for control, customization, and tax-efficiency in a large family’s risk management plan.
Stop thinking your personal umbrella covers your business activities. It doesn’t.
The “Home” vs. the “Office” Bodyguard.
Your personal umbrella policy is the high-limit bodyguard that is hired to protect you and your family in your personal life. It is not licensed or trained to protect you at the office. Every personal umbrella policy has a strict and absolute “business pursuits” exclusion. It will provide no coverage for any liability that arises from your professional or business activities. For that, you need a separate, and equally large, “commercial” bodyguard—a commercial umbrella policy—that is specifically trained for the unique risks of the corporate world.
Stop being “penny wise and pound foolish” with your insurance. The premiums are a rounding error compared to your total net worth.
The “Cost of the Moat” vs. the “Value of the Castle.”
For a high-net-worth family, the premium for a robust, multi-million dollar insurance portfolio is the cost of building a deep, wide, and alligator-filled moat around your financial castle. To complain that the moat is “too expensive” is a classic “penny wise, pound foolish” mistake. The cost of the premium is a tiny, insignificant rounding error compared to the massive, multi-million dollar value of the castle it is designed to protect. The real “cost” is not the premium; it is the catastrophic, and completely unrecoverable, loss of the castle itself.
The #1 secret is that your choice of insurance carrier sends a signal to a potential litigant about how hard you’re willing to fight a lawsuit.
The “Reputation” That Becomes Your First Line of Defense.
A plaintiff’s attorney is a strategic businessperson. When they are deciding whether to sue you, one of the first things they will do is find out who your insurance company is. The #1 secret is that your choice of carrier is a powerful signal. A standard, mass-market carrier has a reputation for settling claims quickly and easily. A high-net-worth carrier like Chubb has a decades-long, ironclad reputation for having the best lawyers and for fighting every single frivolous claim to the bitter end. That reputation is a powerful deterrent that can stop a lawsuit before it ever starts.
I’m just going to say it: Your wealth manager probably knows very little about sophisticated property and casualty insurance.
The “Brain Surgeon” vs. the “Orthopedic Surgeon.”
Your wealth manager is a brilliant financial professional. They are a brain surgeon, a master of the complex world of investments, taxes, and estate planning. They are not, however, an orthopedic surgeon. The world of sophisticated, high-net-worth property and casualty insurance is a completely different, and equally complex, medical specialty. You would not ask your brain surgeon to set your broken leg. You need a separate, and equally skilled, specialist who has dedicated their entire career to the specific art of protecting your physical assets and your liability.
The reason your art collection needs a separate policy is for coverage against risks like “breakage” and “mysterious disappearance.”
The “All-Risk” Shield for Your Most Fragile Assets.
Your homeowners policy covers your art against a short list of “named perils,” like fire and theft. But what if a guest accidentally knocks a sculpture off its pedestal? Or what if a valuable piece simply vanishes while on loan to a museum? A specialized fine art policy provides a much broader, “all-risk” shield. It covers your collection against almost any type of loss, including the two most common and uninsured risks for art: accidental breakage and the maddeningly common “mysterious disappearance.”
If you’re still co-signing loans for your adult children, you’re losing sight of the insurable interest you now have in their life and health.
The “Bank of Mom and Dad” Needs to Insure Its Loans.
When you co-sign a large loan for your adult child—for a house, a business, or a medical school education—you have ceased to be just a parent. You have become the bank. And a smart bank always insures its largest and most important loans. You now have a direct, and massive, “insurable interest” in your child’s life and their ability to earn an income. A life and disability insurance policy on your child, for the amount of the loan, is not a morbid act; it is a prudent and necessary business decision to protect your own balance sheet.
The biggest lie is that you’re “fully covered.” There is no such thing.
The “Perfectly” Safe Ship That Can Still Be Sunk.
“Full coverage” is the biggest lie in the insurance world. It is a myth, a marketing term. There is no such thing as a policy or a portfolio that can protect you from every single risk in the universe. A great insurance plan is like a modern, incredibly safe battleship. It has multiple layers of defense, it is built to withstand almost any attack, and it is the best protection that money can buy. But even the safest battleship can be sunk by a clever enough enemy or a big enough storm. The goal is to be resilient, not to be invincible.
I wish I knew that my umbrella policy would “drop down” to provide primary coverage if my underlying policy didn’t cover a specific loss.
The “Shape-Shifting” Shield That Fills the Gaps.
I wish I had known about the “drop-down” superpower that is built into a high-quality umbrella policy. A standard umbrella just sits on top of your other policies. But a true, high-net-worth umbrella is a shape-shifter. If you are hit with a lawsuit that is not covered by your standard home or auto policy at all—like a libel or slander claim—the umbrella can “drop down” and provide primary, first-dollar coverage for that risk, subject only to a small deductible. It is a powerful, gap-filling feature that is a hallmark of a great policy.
99% of wealthy parents make this one mistake: they give their college student a high-limit credit card without teaching them about the risks of fraud and theft.
The “Financial Firearm” You’ve Handed to an Untrained User.
Giving your college student a high-limit credit card is like handing them a powerful financial firearm. It is a tool that can be incredibly useful, but it can also be incredibly dangerous in untrained hands. The mistake is to hand them the weapon without also providing a mandatory, detailed “gun safety” course. You must teach them about the risks of online fraud, the dangers of phishing scams, and the importance of strong, unique passwords. Without this training, you are setting them up for a financial misfire that can damage their credit for years.
This one small action of reviewing your family’s social media presence for security risks is a modern necessity.
The “Digital Breadcrumbs” That Can Lead a Thief to Your Door.
The social media posts of your entire family are a trail of digital breadcrumbs that can lead a criminal right to your front door. A simple geotagged photo can reveal your home’s location. A vacation post can announce that your home is empty. A picture of a valuable new piece of art can make you a target. The small, but critical, modern action of sitting down with your family and reviewing your collective social media presence for these security leaks is a non-negotiable part of a modern, high-net-worth family’s personal security plan.
Use a combination of life insurance and disability insurance to fund your business buy-sell agreement.
The “Death and Disability” Twin Pillars of Your Business’s Future.
A buy-sell agreement is the blueprint for your business’s survival after the departure of a partner. Most businesses have the “death” pillar in place with life insurance. But they forget that a partner’s permanent disability can be just as, if not more, devastating. A complete plan requires two pillars. A disability buy-out policy is the second, crucial pillar that will provide the lump-sum cash needed to buy out a partner who is still alive, but who is no longer able to work. Without both pillars, your structure is dangerously unstable.
Stop thinking your homeowners policy covers the full replacement cost of your custom wine cellar or home theater.
The “Standard” vs. the “Custom” Features of Your Financial House.
Your homeowners policy is designed to rebuild a standard, builder-grade house. It does not automatically account for the expensive, custom features you have added. Your multi-hundred-thousand-dollar, climate-controlled wine cellar or your state-of-the-art home theater are not standard features. To be properly protected, these high-value, custom installations must be specifically and separately scheduled on your policy. Otherwise, in the event of a fire, you will only get a check to rebuild a standard basement, not your custom-designed masterpiece.
Stop assuming your second home in a catastrophe-prone area is easily insurable in the standard market.
The “High-Risk” Property That the Standard Market Won’t Touch.
That beautiful beach house in a hurricane zone or that lovely cabin in a wildfire-prone area is a piece of paradise. It is also, in the eyes of the standard insurance market, a ticking time bomb. The major, household-name insurance companies are increasingly refusing to cover these high-risk properties. You cannot assume that you can just call your regular agent. You will likely need to work with a specialized broker who has access to the “surplus lines” market to find a specialty carrier who is willing to take on that high, catastrophic risk.
The #1 hack for a high-net-worth family is to have a coordinated team of legal, tax, and insurance advisors who all talk to each other.
The “Board of Directors” for Your Family’s Fortune.
The #1 hack for managing a complex financial life is to stop having a series of disconnected conversations. You must create a professional “Board of Directors” for your family, and you must insist that they all sit at the same table. Your attorney, your CPA, your wealth manager, and your insurance advisor must be in regular communication, working together as a coordinated, holistic team. This ensures that every decision is viewed from all angles, and that your legal, tax, and risk management strategies are all perfectly and seamlessly aligned.
I’m just going to say it: You should be as diligent in selecting your insurance broker as you are in selecting your investment manager.
The “Defense” Is Just as Important as the “Offense.”
You will likely spend months interviewing and doing due diligence on a potential investment manager. You are, after all, entrusting them with the “offense” of growing your wealth. You must apply that exact same level of rigor and diligence to selecting your insurance broker. This is the professional you are entrusting with the “defense” of that wealth. A single mistake or a piece of bad advice from your defensive coordinator can easily wipe out a decade’s worth of gains from your star quarterback. The defense is not a secondary concern; it is an equal partner.
The reason you need a broker who understands your lifestyle is that they can identify risks you haven’t even thought of.
The “Sherlock Holmes” of Your Personal Risk Profile.
A great high-net-worth broker is not just a salesperson; they are a private detective. They will take the time to deeply understand not just your assets, but your entire lifestyle. Do you travel frequently? Do you serve on non-profit boards? Do your children have a public social media presence? They are the “Sherlock Holmes” who can analyze the unique clues of your life to identify the hidden, and often significant, risks that you would never even think of on your own. It is a proactive, and incredibly valuable, diagnostic process.
If you’re still paying your insurance premiums directly, you’re losing the administrative efficiency of having your family office manage the payments.
The “CEO” vs. the “Mailroom Clerk.”
As the principal of your family, your time is your most valuable asset. Your job is to be the CEO, focused on the high-level, strategic decisions. Paying the dozens of individual insurance premium bills is the job of the mailroom clerk. A family office or a good business manager can take on this administrative burden. They can consolidate all your premium payments, ensure that nothing is ever missed, and provide you with a single, simple summary. It is a powerful way to delegate the non-essential and to reclaim your most valuable resource: your time.
The biggest lie is that you can hide your wealth in today’s digital world.
The “Glass House” of the Modern, Digital Age.
The lie is that with clever planning, you can make your wealth invisible. The reality is that in a world of public records, search engines, and social media, you are living in a glass house. A determined plaintiff’s attorney can, in a matter of hours, use completely legal, public sources to get a very accurate picture of your net worth. The goal of asset protection is not to create an invisibility cloak; that is a fantasy. The goal is to build a fortress that is so strong and so well-defended that even when they can see the treasure, they know they cannot get to it.
I wish I knew that I needed to specifically schedule my wife’s engagement ring on our policy, even after we were married.
The “Jewelry” That Is Not Just “Stuff.”
I wish I had known that the moment that engagement ring went on my wife’s finger, it was no longer just a piece of personal property. It was a valuable, and specifically limited, asset. Our homeowners policy had a low, $2,500 sub-limit for the theft of any single piece of jewelry. The simple, and crucial, action of “scheduling” the ring—getting it appraised and listing it separately on the policy for its full value—was the only way to protect that significant, and deeply sentimental, investment. The wedding does not magically change the insurance rules.
99% of people with vacation properties make this one mistake: they don’t understand their liability for guests who are injured on the property.
The “Host” Who Is Also the “Legal Guardian.”
When you invite a guest to your vacation home, you are not just a host; you are taking on a significant legal duty to ensure their safety. You are the property owner, and you are responsible for any known, or even unknown, hazards—the loose railing on the deck, the slippery boat dock, the unfenced pool. If a guest is injured, you will be held liable. Understanding this immense responsibility, and having a high-limit liability policy in place, is the most critical and most overlooked part of owning a second home.
This one small action of putting your umbrella policy’s details in your wallet will ensure you have it handy after an accident.
The “In Case of Emergency” Card You Hope You Never Use.
After a serious car accident, you will be stressed, disoriented, and required to provide your insurance information. The small, simple action of carrying a small card in your wallet that lists your umbrella insurance company’s name, your policy number, and their 24/7 claims hotline is a powerful tool. It ensures that in the chaotic moments after a major incident, you have the crucial information for your most powerful layer of protection right at your fingertips, ready to be given to the police or the other party.
Use a high-net-worth carrier that will pay for loss prevention, such as installing a water shut-off system for you.
The “Insurance Company” That Also Wants to Be Your “Handyman.”
A standard insurance company will send you a bill. A high-net-worth carrier will send you a handyman. The best carriers are proactive risk management partners. They will often pay for a portion, or even all, of the cost to install loss prevention devices in your home. They will help you install a whole-house, automatic water shut-off system, a gas leak detector, or a centralized alarm system. They know that the small, upfront investment in prevention is a much smarter and cheaper strategy than paying a massive claim later on.
Stop thinking your political or philanthropic activities don’t create liability risks.
The “Public Figure” Who Is Also a “Public Target.”
The moment your name appears in the newspaper as a major donor to a political cause or as the host of a large, charitable gala, you have transformed yourself from a private citizen into a public figure. This elevates your profile and can make you a target. Your philanthropic activities, especially hosting events, create a new and significant set of liability risks that must be managed. You must ensure that your personal liability insurance is broad enough to cover these new, public-facing, and often uninsured activities.
Stop letting your insurance be the last thing you think about. Do make it the first line of defense for your balance sheet.
The “Moat” You Build Before You Build the Castle.
Too often, insurance is the last, and most grudgingly purchased, item on the financial to-do list. This is a strategic error. A robust, well-designed insurance portfolio is not an expense; it is the first and most important line of defense for your entire personal balance sheet. It is the deep, wide moat that you must build before you start construction on the beautiful, valuable castle. Without the moat, your entire life’s work is completely exposed and vulnerable to being captured by a single, lucky attacker.
The #1 secret is that true wealth preservation is about mitigating risk, not just chasing investment returns.
The “Un-Glamorous” Defense That Wins Championships.
The financial media is obsessed with offense—the exciting, high-flying world of investment returns. But the secret that every truly wealthy, multi-generational family knows is that championships are won with defense. The un-glamorous, disciplined, and often boring work of mitigating risk—through legal structuring, smart insurance, and proactive security—is the key to long-term victory. It is far easier, and far more important, to not lose the money you have than it is to try and earn more. Wealth preservation is a defensive game.
I’m just going to say it: The peace of mind from knowing your family is protected by a fortress of insurance is priceless.
The “Freedom from Fear” That You Can Actually Buy.
We spend our lives in the pursuit of happiness. But a foundational component of happiness is the freedom from fear and anxiety. A comprehensive, well-designed insurance portfolio is one of the most direct and efficient ways to purchase that freedom. It is the financial transaction that allows you to buy the priceless, and tangible, emotional state of peace of mind. The knowledge that you have built a powerful, impenetrable fortress around the people and the assets you love the most is a feeling of security that is worth more than any premium.
The reason you need to read the fine print on your D&O policy is to check for exclusions related to regulatory actions or shareholder lawsuits.
The “Hidden Holes” in Your Leadership Shield.
A Directors & Officers (D&O) policy is the essential shield for a corporate leader, but you must inspect that shield for hidden holes. The most important part of the policy to read is the “Exclusions” section. A weak D&O policy may have a broad exclusion for claims brought by regulatory agencies, or a restrictive “insured vs. insured” exclusion that prevents one board member from suing another. Reading this fine print is the only way to ensure that your shield will actually protect you from the most common and dangerous types of corporate arrows.
If you’re still relying on your company’s travel insurance for personal trips, you’re losing coverage for your family members and non-business activities.
The “Work” Phone That Doesn’t Work for Personal Calls.
Your company’s corporate travel insurance policy is like a work-issued cell phone. It is a fantastic tool that is designed for one specific purpose: to protect you while you are traveling for business. The moment you are on a personal vacation with your family, you are trying to make a personal call on the work phone. The policy will almost certainly not cover your spouse or your children, and it may have an exclusion for any non-business related activities. For your personal travel, you need your own, personal phone.
The biggest lie is that your standard auto policy will provide a rental car of “like kind and quality” after you crash your Porsche.
The “Go-Kart” They Give You When You’re Used to a “Race Car.”
The biggest lie of standard rental car coverage is the idea that it will make you whole. After you crash your high-performance luxury vehicle, a standard auto policy will give you a rental car benefit with a low, $30-a-day limit. This will get you the keys to a sub-compact sedan. It is a go-kart. A true, high-net-worth auto policy understands that you are used to driving a race car. It provides a much higher, or even unlimited, rental benefit that is designed to get you a vehicle of a “like kind and quality.”
I wish I knew that my umbrella policy had a “self-insured retention” (a deductible) for claims not covered by my underlying policies.
The “Deductible” for the Gaps in Your Coverage.
I wish I had known about the “Self-Insured Retention” (SIR). It is the secret deductible for your umbrella policy. For a claim that is covered by your home or auto policy, the umbrella sits on top with no deductible. But for a claim that is not covered by your underlying policies, but is covered by the umbrella (like libel or slander), the umbrella will “drop down” to be your primary coverage. But it will only do so after you have first paid your SIR, which is a deductible that can be anywhere from $1,000 to $25,000.
99% of high-net-worth individuals make this one mistake: they don’t review their insurance and asset protection strategy after a major liquidity event.
The “Sudden Fortune” That Is Suddenly at Risk.
A major liquidity event—the sale of a business, a large inheritance—is a wonderful moment. It is also a moment of maximum peril. You have just transformed from a successful person into a publicly-known, “lottery-winner” deep pocket. The mistake is to not immediately and dramatically upgrade your defensive posture. The liability limits and the asset protection strategy that were adequate for your “before” picture are now dangerously inadequate for your “after” picture. You must immediately build a much larger fortress to protect your new, much larger treasure.
This one small action of having a “personal risk manager” on your team will change your perspective on wealth preservation forever.
The “Chief Security Officer” for Your Family’s Fortune.
A large corporation would never operate without a Chief Risk Officer. A high-net-worth family should not either. The small, but transformative, action of hiring a dedicated, professional “personal risk manager”—an expert insurance broker—to be on your family’s advisory team will fundamentally change your perspective. They are the Chief Security Officer whose entire job is to think defensively. They will proactively identify your risks, design your fortress, and ensure that the wealth your other advisors are building is never lost to a single, catastrophic event.
Use your insurance portfolio as a strategic tool to enable your lifestyle and protect your legacy, not just as a necessary expense.
The “Cost Center” vs. the “Strategic Asset.”
Viewing your insurance as just a necessary, and annoying, expense is a defensive, and limited, mindset. A sophisticated family understands that a well-designed insurance portfolio is a powerful, strategic asset. It is the tool that enables your lifestyle. It is the high liability limits that give you the freedom to host a large, charitable gala. It is the fine art policy that gives you the confidence to loan your masterpiece to a museum. It is not just a shield; it is the strategic foundation upon which your life and your legacy are built.