Generational Wealth Secrets: Trusts, Insurance & Legacy

Introduction by Jean Chatzky 

Most people believe that building generational wealth is something reserved for billionaires with family offices, tax attorneys, and offshore accounts. But here’s the truth: the same strategies the ultra-rich use — trusts, life insurance, leveraging assets, and disciplined stewardship — can be applied by everyday families, starting right now.

A trust fund isn’t a billionaire’s toy. It’s a simple legal tool that ensures your home, savings, and life insurance pass directly to the people you love without court battles or unnecessary taxes. A million-dollar life insurance policy isn’t a fantasy. For the price of a monthly phone bill, it can become the engine of a financial dynasty.

Generational wealth isn’t just about money. It’s about creating a system — a container — that protects your assets, grows them, and transfers them with intention. It’s about teaching your children not only what you’ve built, but how to build upon it.

This series is going to break the cycle of thinking wealth-building is out of reach. We’ll show you how to use the tools available, step by step, so you can move from just covering today’s bills to creating a legacy that outlives you.

(Note: This is an imaginary conversation, a creative exploration of an idea, and not a real speech or event.)

Topic 1: Trust Funds as the Foundation of Legacy

Moderator: Jean Chatzky (she’s approachable, practical, and perfect to guide this)
Speakers: Suze Orman, Jane Bryant Quinn, Ed Slott, Raymond C. Odom, Thomas J. Stanley

Introduction – Jean Chatzky

Welcome, everyone. Today we’re starting with the foundation of generational wealth: trust funds. Too many people think trusts are only for the ultra-wealthy, but the reality is that even middle-class families can use them to protect assets, avoid probate, and ensure money passes smoothly to the next generation. We’ll talk about how to get started, what to include, and who you need on your team.

Question 1: What’s the very first step an average family should take to set up a trust affordably?

Suze Orman:
The very first step is to get clear on why you want a trust. Most families think of it only for rich people, but if you own a home, have savings, or want to make sure your kids avoid probate court, you need one. Start by deciding who should inherit and under what conditions. Then, see if your state offers simple revocable trust templates. Many families can get started for under $1,000 with a good estate attorney — far less than the costs of probate later.

Raymond Odom:
I agree, Suze. Legally, the first step is to sit with an estate attorney who understands your state laws. But you don’t have to get fancy at first. Even a basic revocable living trust provides protection. You list your assets, choose your trustee, and that’s it. The mistake people make is thinking they need millions before it’s worth doing. No — if you own property or have dependents, you need one.

Jane Bryant Quinn:
I’ll add this: the first step is also emotional. You must decide whether you’re comfortable letting go of direct control. Some families delay because they think “I’ll just deal with it later.” But if you start now, you give yourself time to test and adjust. The earlier you set up a trust, the smoother it is when you really need it.

Ed Slott:
From a tax perspective, step one is deciding between revocable or irrevocable. Revocable means you can change it. Irrevocable gives more tax protection but less flexibility. If you’re just starting out, revocable is usually the right step. That’s where most families should begin.

Thomas J. Stanley:
And don’t forget — the real first step is to adopt the mindset that protecting wealth is as important as making it. Too many people build assets without thinking about transfer. For middle-class families, the affordable trust is not about complexity — it’s about discipline.

Question 2: How do you decide what assets (home, savings, life insurance) to place inside a trust?

Raymond Odom:
The rule of thumb is this: if it’s valuable and you want it to avoid probate, put it in the trust. That usually includes your home, bank accounts, and investment accounts. Life insurance is a big one too — naming the trust as beneficiary can give you control over how the payout is used.

Suze Orman:
Yes, but with one caution: don’t automatically put retirement accounts like IRAs into a trust unless you understand the tax consequences. Sometimes it’s better to list individual beneficiaries. Always check with a professional before transferring retirement funds into trusts.

Jane Bryant Quinn:
For ordinary families, think of the trust as a bucket. Your home goes in the bucket, your non-retirement investments go in, your life insurance payout can be directed there. What doesn’t go in? Your everyday checking account — you need liquid cash outside. This balance is important.

Ed Slott:
Exactly. From a tax angle, the trust is most effective for after-death transfers. Retirement accounts have special tax treatment, so tread carefully. But homes, second properties, brokerage accounts — those are perfect for trusts.

Thomas J. Stanley:
I’d add: the asset that most often gets overlooked is small business ownership. If you own a business and it’s not structured inside a trust, the transition can be chaotic. For generational wealth, securing that continuity matters as much as securing property.

Question 3: What professionals (lawyers, advisors) do you really need, and how can you keep costs low?

Jane Bryant Quinn:
At minimum, you need an estate attorney to draft the trust properly. But it doesn’t have to be prohibitively expensive. Many firms now offer flat-fee packages for simple trusts. The cost of probate can easily run 5–10% of the estate — so paying $1,000–$2,000 now is actually saving money later.

Suze Orman:
And please, don’t cut corners with online do-it-yourself kits if you have property or children. They might be fine for very simple cases, but one mistake can invalidate your whole trust. Spend the money on a real attorney.

Raymond Odom:
Beyond an attorney, sometimes you need a financial advisor who understands trusts. Not every advisor does. If you want your investments aligned with your estate plan, bring them into the conversation. That said, you don’t need a team of ten people. Start lean.

Ed Slott:
Yes, and I’d stress: also involve a CPA or tax advisor if you have significant assets. Estate planning touches taxes at every level. Keeping costs low is good — but keeping mistakes low is better.

Thomas J. Stanley:
The professional is important, but even more important is having a family meeting to explain the trust. The cost of confusion among heirs can be greater than legal fees. Transparency is the cheapest way to preserve wealth.

Closing Thoughts – Jean Chatzky

Thank you, everyone. The message here is clear: trusts are not just for the wealthy. They’re practical, affordable, and powerful tools for any family that wants to protect their assets. Start simple with a revocable living trust, put in your home, savings, and life insurance, and hire an affordable estate attorney to set it up. Remember: the cost of not planning is far greater than the cost of planning.

Topic 2: Life Insurance as the Wealth Engine

Moderator – David McKnight

Life insurance isn’t just about replacing income when someone dies. Used strategically, it can be the engine that drives generational wealth. The ultra-rich buy large policies, place them inside trusts, and then use the cash value to borrow against. But how can ordinary families do this? Let’s start by asking:

Question 1: How do you calculate how much life insurance coverage your family actually needs?

Douglas Andrew:
Start with what I call the “economic replacement value.” If you’re earning $75,000 a year and want your family to live comfortably for 20 years, that’s $1.5 million. But you don’t necessarily need to buy that much coverage right away. The key is: buy what you can afford today, and structure it in a way that grows over time.

Suze Orman:
I’ll simplify: think of life insurance as love, not numbers. Ask, “If I were gone tomorrow, what money would my family need to stay in the house, send the kids to school, and live without panic?” That’s your baseline. Then, layer in additional coverage if you want wealth creation on top of protection.

Patrick Bet-David:
I like to tell clients to do a “life plan audit.” How much debt do you have, how much future expense (like college), and what legacy do you want to leave? That determines the coverage. Too many people underinsure because they only think short-term. The wealthy over-insure because they know it’s an investment vehicle.

Chris Hogan:
I call it the “legacy number.” What would it take to not only cover your family but leave something behind? A million-dollar policy sounds like a lot, but broken down it might only cost $100–$200 a month if you’re young and healthy. That’s a price most families can find in their budget if they prioritize it.

Van Mueller:
The math is important, but don’t overlook timing. The best time to buy life insurance is yesterday. The second best is today. The younger and healthier you are, the more coverage you can lock in for pennies on the dollar. Waiting costs you wealth.

Question 2: Why do the wealthy put life insurance policies inside trusts, and what advantages does that create?

Patrick Bet-David:
Simple: control and tax efficiency. When you place a policy inside a trust, you’re not just leaving a lump sum. You’re dictating how it’s used — whether to pay estate taxes, fund education, or support a business. That structure is power.

Douglas Andrew:
Yes, and the trust removes the proceeds from your taxable estate. Without that, your heirs could lose up to 40% of the payout to taxes. Inside a trust, the money is protected, tax-advantaged, and shielded from creditors. That’s why the ultra-wealthy do it — but families with modest means can too.

Suze Orman:
I’ll add that for women, widows, or single parents, this is critical. Without a trust, beneficiaries can make bad decisions or be manipulated. The trust ensures that your life insurance — your love letter to your family — is used exactly the way you want.

Chris Hogan:
This is also about dignity. A trust-owned policy lets you pass down wealth in a way that doesn’t burden your children with confusion, probate, or fights. You’re creating a clear legacy roadmap.

Van Mueller:
And one more: flexibility. A trust can allow loans against the cash value during your lifetime, while still protecting the death benefit for your heirs. It’s the best of both worlds: use now, legacy later.

Question 3: How can someone choose the right type of policy (whole life, indexed universal, term) for generational wealth purposes?

Chris Hogan:
If you’re only looking for short-term protection, term insurance is fine. But if you want to build wealth across generations, term won’t cut it — it ends. You need permanent coverage: whole life or indexed universal life.

Douglas Andrew:
I prefer indexed universal life because it allows cash value growth linked to market performance without direct risk. Over decades, that’s powerful. And remember: inside a trust, the structure matters more than chasing returns.

Van Mueller:
Whole life is still king for many families because of its guarantees: guaranteed cash value, guaranteed death benefit. It’s predictable, and predictability is wealth. The best policy is the one you can keep paying for consistently.

Suze Orman:
Here’s my rule: don’t overcomplicate. If you’re just starting, term is okay as a bridge. Once you’re financially stable, upgrade to permanent coverage. What matters most is getting started, not getting the “perfect” policy.

Patrick Bet-David:
And don’t forget customization. Ultra-rich families often layer policies: a base whole life policy plus supplemental indexed policies. The mix depends on your budget, age, and goals. One size never fits all.

Closing Thoughts – David McKnight

Life insurance, when placed inside a trust, becomes more than protection — it becomes a wealth engine. First, calculate coverage based on love and legacy needs. Then, use a trust to protect the payout and dictate how it’s used. Finally, choose a permanent policy that grows with you. Remember: the wealthy don’t buy insurance to die rich. They buy it to live free and leave a lasting impact.

Topic 3: Borrowing Against Your Life Insurance Policy

Moderator – Mark Willis

Most people think of life insurance as something that only pays out after death. But permanent policies also build cash value that you can access while you’re alive. The wealthy have used this for decades — borrowing against policies instead of selling assets. Let’s explore how this works in practice.

Question 1: How do you know when your policy has built enough cash value to safely borrow against it?

R. Nelson Nash:
This is the essence of what I called the Infinite Banking Concept. Typically, a policy needs 3–5 years of consistent funding before the cash value becomes meaningful. Once you see steady growth, you can borrow. But don’t rush — the foundation has to be solid first.

Grant Cardone:
Think of it like real estate equity. You don’t pull cash out of a house after a few months. You wait until it has value. Same with life insurance. When the cash value equals at least a few months of expenses or the down payment for a small asset, you’re ready.

Mary Buffett:
From an investor’s lens, the safe time is when the interest you’ll pay on the loan is lower than the return you can reasonably expect on the asset you’ll buy. If you’re paying 5% to borrow and making 10% elsewhere, that’s when borrowing makes sense.

Vanessa Shaw:
For families starting small, I say: wait until you have at least $20,000 in cash value before borrowing. That way you’re not depleting the policy too quickly. Always think of the insurance as the engine you must protect.

Van Mueller:
And here’s the truth: the exact moment doesn’t matter as much as the discipline. The policy is designed to grow no matter what. The danger isn’t borrowing too soon — it’s borrowing without a plan to repay.

Question 2: What are the exact steps to request a loan from your insurance policy?

Grant Cardone:
It’s simple, but most people don’t know it: call your insurance company, ask for a “policy loan,” and they’ll cut you a check against your cash value. No credit check, no bank approval. That’s the beauty of it — you’re the bank.

R. Nelson Nash:
Yes, and remember: it’s not taxable. Because technically, it’s a loan, not income. You’re borrowing from yourself, and the death benefit is collateral. That’s why the wealthy prefer this over selling assets.

Mary Buffett:
Step one is paperwork: you specify how much you want to borrow. Step two, the insurance company sends the funds. Step three, you decide on repayment. Many families forget step three — but that’s the most important one if you want to preserve the policy’s power.

Vanessa Shaw:
Exactly. I teach clients to set automatic repayments, even if small. Treat it like a bank loan. That keeps your policy healthy and ensures the wealth engine continues for your kids.

Van Mueller:
And the simplest advice: borrow less than 70% of your available cash value. That buffer protects the policy’s stability and keeps the loan from eating into your death benefit too much.

Question 3: How do you structure repayment so that your policy continues growing while you use the money?

Mary Buffett:
The repayment should come from the profits of whatever asset you bought. If you borrow to buy a duplex, let the rental income pay back the policy loan. That way, the system is self-sustaining.

Grant Cardone:
Exactly — debt is only dangerous if you’re lazy. If the borrowed money buys a cash-flowing asset, it repays itself. That’s how you grow — buy more income, not more stuff.

Vanessa Shaw:
I advise families to think of it as “pay yourself back with interest.” Pretend you’re the bank — because you are. This mindset ensures the money doesn’t disappear; it recycles.

R. Nelson Nash:
Yes, and remember — you don’t have to repay on a strict schedule. That’s the flexibility. But wise families repay aggressively because every dollar repaid strengthens the policy for the next loan cycle.

Van Mueller:
Here’s the long-term vision: borrow, invest, repay, repeat. Over time, your trust ends up holding both the growing policy and the assets you bought. That’s how generational wealth multiplies.

Closing Thoughts – Mark Willis

Life insurance loans aren’t about spending — they’re about recycling capital. First, let your policy grow enough to build equity. Then, borrow against it for smart investments. Finally, repay from profits so the engine never stops. That’s how families move from saving pennies to creating dynasties.

Topic 4: Turning Borrowed Money into Generational Assets

Moderator – Robert Kiyosaki

The rich don’t just save money — they buy assets that create more money. With life insurance loans, you now have liquidity without selling your wealth. The question is, how do you turn that money into something that produces income for generations? Let’s dig in.

Question 1: What’s the simplest type of income-producing asset a beginner could buy with borrowed funds?

Ken McElroy:
Real estate, hands down. A duplex or small apartment is the easiest entry point. People always need a place to live, and even one rental can cover your loan repayment and leave a profit. Start small and learn the ropes.

Barbara Corcoran:
I agree. Even a single-family rental is a good first step. The key is location and cash flow — don’t fall in love with the property, fall in love with the numbers. If rent covers expenses and loan repayment, you’re on the right track.

Daymond John:
I’ll speak for the entrepreneurs — a small franchise can be a great first step. Unlike starting a business from scratch, you get a proven system. Think of something low-cost but steady, like a food kiosk or service franchise.

Cody Sanchez:
For those who want something less intimidating than real estate, small businesses are a gold mine. Buy a laundromat, a car wash, or a local service business. These cash-flow right away and don’t require fancy skills.

Chris Hogan:
I’d say it depends on your personality. Some people prefer tangible assets like property; others thrive in business. The simplest asset is the one you’ll actually manage responsibly. Start where you have interest and commitment.

Question 2: How do you run the numbers to make sure the asset’s profits can cover loan repayment?

Barbara Corcoran:
In real estate, it’s simple: income minus expenses must be positive. If the net profit is greater than your loan repayment, it’s a green light. Always overestimate expenses to stay safe.

Ken McElroy:
Yes, use the “1% rule.” If a property costs $200,000, it should rent for at least $2,000 a month. That’s a quick way to see if it cash flows enough to cover the loan and provide margin.

Daymond John:
For franchises, I tell people to demand the Franchise Disclosure Document (FDD). It shows average earnings and costs. Plug those numbers in against your loan repayment. If the system isn’t profitable on paper, walk away.

Cody Sanchez:
With small businesses, I like to buy ones already profitable. Look at their cash flow statements, make sure net profit is higher than your expected loan repayment. If not, negotiate the price down or pass.

Chris Hogan:
And don’t forget risk buffers. Assume you’ll have vacancies, slow months, or unexpected repairs. If the deal still works after factoring in those bumps, it’s a safe move.

Question 3: Once the loan is repaid, how do you protect both the new asset and the policy inside the trust?

Ken McElroy:
Put the property title inside the trust. That way, your heirs inherit smoothly and avoid probate. Meanwhile, your policy keeps growing, ready for the next cycle.

Barbara Corcoran:
Yes, and reinvest the cash flow into maintenance and expansion. Too many people spend the profits instead of reinvesting. Protecting the asset means keeping it healthy for decades.

Daymond John:
For businesses, set them up as LLCs owned by the trust. That creates legal separation and ensures continuity. Even if something happens to you, the business stays intact.

Cody Sanchez:
I recommend creating a “family investment playbook.” Document how you bought, managed, and paid off the asset. That way your kids can repeat the cycle. Knowledge transfer is just as important as asset transfer.

Chris Hogan:
And don’t overlook insurance on the asset itself — property insurance, liability coverage, business insurance. Protecting the cash flow source is as important as owning it.

Closing Thoughts – Robert Kiyosaki

Here’s the lesson: the wealthy don’t spend borrowed money on liabilities — they buy assets. First, pick something simple like real estate or a small business. Second, run the numbers carefully to ensure profits cover the policy loan. Third, once it’s paid off, lock both the policy and the asset inside the trust. That’s how you turn borrowed dollars into generational wealth machines.

Topic 5: The Discipline and Mindset of Generational Wealth

Moderator – James E. Hughes Jr.

We’ve talked about trusts, life insurance, borrowing, and assets — but here’s the truth: without discipline, it all falls apart. Statistics show most families lose wealth by the third generation. The missing piece isn’t money — it’s mindset and systems. Let’s ask:

Question 1: Why do most families lose wealth by the third generation, and how can this cycle be broken?

Thomas J. Stanley:
The biggest reason is lifestyle inflation. Children grow up enjoying wealth but never learning how it was created. They spend instead of stewarding. Breaking the cycle requires raising kids with financial discipline — frugality, budgeting, and responsibility.

Michelle Singletary:
Yes, I see it every day. The second and third generation often feel entitled. The cure is education. Families must normalize talking about money early, not hiding it. Show kids the work behind the wealth.

Chris Guillebeau:
I’d add that wealth disappears because it lacks purpose. If money is just numbers, the next generation doesn’t respect it. But if wealth is tied to values — funding education, entrepreneurship, community projects — it endures.

Suze Orman:
And sometimes it’s simply lack of structure. A trust without rules is just a pile of money. Families need guardrails: conditional distributions, financial training, benchmarks for heirs.

Stephen Covey Jr.:
The cycle breaks when families build trust — not just financial trust, but relational trust. If children see themselves as part of a larger legacy, they’re more likely to preserve it.

Question 2: What systems (family meetings, financial education, governance) ensure heirs are responsible stewards?

Michelle Singletary:
Family meetings are powerful. Once a month, talk openly about money — budgets, investments, even mistakes. If kids grow up with transparency, they’ll grow into stewards instead of spenders.

Thomas J. Stanley:
I encourage families to do what I call “frugal rituals.” Even wealthy families should practice living below their means. Simple cars, modest homes — these choices teach discipline better than lectures.

Suze Orman:
Yes, and create a family mission statement tied to the trust. It could say: “This wealth exists to fund education, entrepreneurship, and health.” The system then has a compass, not just a vault.

Chris Guillebeau:
Governance matters. Some families create family councils or boards, where heirs must learn investing before accessing money. It may sound formal, but structure is what makes wealth last.

Stephen Covey Jr.:
And don’t forget mentorship. Each generation should mentor the next — not just with money, but with values. This relational continuity is the real governance system.

Question 3: How do you teach children to see money as a tool for freedom and impact rather than just consumption?

Chris Guillebeau:
Let them experience it. Instead of just giving money, fund a small project for them — a lemonade stand, a charity initiative, a side hustle. They’ll learn money creates choices, not just shopping trips.

Thomas J. Stanley:
Children must see money as the byproduct of hard work. That means letting them earn, not just inherit. Give them responsibility early, even if it’s small, so they associate wealth with effort.

Michelle Singletary:
I tell parents: “Don’t give allowance for free — tie it to chores or saving goals.” The message is: money flows from action and choices. That’s how you shape habits.

Suze Orman:
Also, show them the impact of money. Fund a family scholarship, donate to a cause, or invest in a local business together. When kids see money changing lives, they see it as power, not just consumption.

Stephen Covey Jr.:
And always connect money back to trust — both financial and relational. Teach children: “This isn’t just wealth, it’s a legacy you’re trusted to grow.” That changes how they see every dollar.

Closing Thoughts – James E. Hughes Jr.

Discipline is the bridge between money and meaning. Families lose wealth when they pass down assets without passing down wisdom. The solution is threefold: talk openly about money, create systems of accountability, and embed purpose into your wealth. Remember: generational wealth is not just what you leave to your children, but what you leave in your children.

Final Thoughts by James E. Hughes Jr

Wealth alone does not endure. History shows that most fortunes vanish by the third generation. The reason is simple: families pass down money, but they fail to pass down meaning, discipline, and wisdom.

If you want your wealth to last, you must see yourself not as an owner, but as a steward. A steward protects the trust, funds the policy, borrows wisely, invests in businesses that feed future generations, and — most importantly — educates the heirs who will take the torch.

Generational wealth is not just a financial inheritance; it is a cultural and spiritual one. It is the stories you tell, the values you model, and the systems you build so that your children and grandchildren don’t just inherit what you have, but also who you are.

If you can align your money with your mission, your trust with your teaching, your assets with your values — then you will have created more than wealth. You will have created a living legacy, one that will carry forward long after you are gone.

Short Bios:

Jean Chatzky – Personal finance journalist and CEO of HerMoney, known for making money approachable for families.
Suze Orman – Financial advisor, bestselling author, and TV personality, famous for her practical advice on money protection and estate planning.
Jane Bryant Quinn – Veteran financial columnist and author of Making the Most of Your Money, an expert in wills, trusts, and family finance.
Ed Slott – Tax and retirement expert specializing in IRAs, inheritance planning, and wealth transfer.
Raymond C. Odom – Estate planning attorney and strategist with deep expertise in trusts and multigenerational planning.
Thomas J. Stanley – Late author of The Millionaire Next Door, highlighting the habits and discipline of America’s wealthy.
David McKnight – Author of The Power of Zero, known for explaining tax-free retirement and insurance-based strategies.
Douglas Andrew – Financial strategist and author of Missed Fortune, advocating life insurance as a wealth-building tool.
Patrick Bet-David – Entrepreneur, founder of Valuetainment, and insurance professional who simplifies wealth strategies.
Van Mueller – Insurance strategist and educator, expert in policy loans and infinite banking concepts.
Chris Hogan – Financial coach and author of Everyday Millionaires, focused on legacy and retirement wealth.
R. Nelson Nash – Founder of the Infinite Banking Concept, pioneering the idea of using life insurance as a personal bank.
Grant Cardone – Real estate mogul, entrepreneur, and author, well-known for leveraging debt to scale wealth.
Mary Buffett – Author and educator on Warren Buffett’s investment principles, with insights into borrowing and reinvesting.
Vanessa Shaw – Wealth coach who helps families adopt private banking and disciplined wealth-building strategies.
Robert Kiyosaki – Author of Rich Dad Poor Dad, advocate of leveraging debt to acquire income-producing assets.
Ken McElroy – Real estate investor and author, expert on cash-flowing multifamily investments.
Barbara Corcoran – Real estate mogul and investor on Shark Tank, known for scaling small property investments.
Daymond John – Entrepreneur and Shark Tank investor, expert on building and franchising businesses.
Cody Sanchez – Investor and entrepreneur specializing in buying small businesses for generational wealth.
James E. Hughes Jr. – Author of Family Wealth, considered a leading authority on sustaining wealth across generations.
Michelle Singletary – Washington Post financial columnist, focused on practical money habits and family discipline.
Chris Guillebeau – Author of The $100 Startup, advocate for financial independence and purpose-driven wealth.
Stephen Covey Jr. – Leadership expert and author of The Speed of Trust, focused on values and legacy in wealth.