It was never enough.

I thought this meant I was bad with money. I can now see that what I had was what I call “money dysmorphia,” and you may too.

But, here’s the thing: money is infinitely renewable, when we know how to use our non-renewable resources well. Most of us don’t. As a result, we get trapped on what I’ve come to see as a never-ending quest for financial freedom, which then gets leveraged against us in so many ways. When you see it, you can break free of it, and get financially liberated.

The voice of money dysmorphia sounds like this: I should be farther ahead by now. I should understand this better. I should have saved more. Maybe if I just invest in that one next thing or build that one next thing or make that one next deal…maybe then I’ll have enough. What if there isn’t enough?

Most of us assume that voice is telling us the truth. We think it is pointing to a personal flaw, a discipline problem, a budgeting problem, a planning problem, something we could finally fix if we earned more, spent less, optimized harder, or became the kind of person who understands all the financial things we imagine everyone else already knows.

But what if the voice is not the truth? What if it is the symptom of a system that needs you to believe the problem is you?

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• • •

The first time I encountered this line from Leisa Peterson, a Certified Financial Planner and the author of The Mindful Millionaire, she named something I had been circling for years: the feeling of personal failure that is embedded within our economic system.

Peterson describes the mechanism with extraordinary clarity this way:

A few large companies consolidate an industry and place a middleman between the person buying the service and the person actually doing the work. That middleman charges you as much as you will pay and pays the worker as little as the worker will accept. The worker cannot survive on the wage, so public programs fill part of the gap. You fund those programs through your taxes, which means you pay once when you buy the product, and then you pay again to subsidize the worker the company is not paying enough to live.

The company collects on both ends. And then you and the worker are both told to manage your money better.

The federal minimum wage has remained $7.25 since 2009 and is now at its lowest real value in nearly seventy years. There is not one county in the United States where a full-time minimum-wage worker earns enough to cover a basic single-person budget.

That gap is not evidence that millions of people have individually failed at money. It is what the model was built to produce. That is the design. Not your character.

In other words, our extractive economic system creates chronic insecurity. Then, it teaches us to interpret our insecurity as evidence of our own financial inadequacy. Our internalized blame is a root cause of money dysmorphia.

(I’m going to be talking to Leisa on an upcoming episode of The Great Wealth Transfer Podcast, so subscribe here to get the heads-up for when it drops.)

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• • •

Charles Eisenstein names the engine underneath it in his work Sacred Economics. Because our economic system is committed to endless growth, it is always finding something new to sell. Once our basic needs are met, that growth comes from packaging something people used to do for themselves or for each other and selling it back to them as a “value-added” product.

For example, care is no longer what we do for each other: it’s marketed as a service. We’re discouraged from co-creating and fostering community and encouraged to buy a subscription to a community instead. Our spending counts as “growth,” even though the life underneath it has been exploited.

We are living inside a machine engineered to make us feel as if there is never enough, because the machine itself runs on never enough.

Eisenstein says that, yes, it’s horrifying to realize that much of the service economy is designed to deprive you of your money, your agency, and your humanity, but it’s also a revelation that you can act on. When we see what’s happening, we can make active, engaged decisions to steward our money based on what we value, not what’s being marketed to us as “value.” I call it “eyes wide open” decision-making.

This is the whole invitation of my work around the Great Wealth Transfer. See the machine. Then quit feeding it on autopilot, and start directing our resources toward the world we actually want to live in.

We have a huge amount of power when we wake up, see what we have, become our own best advisors and start directing what we have, not just money, but our time, energy and attention (our non-renewable resources) to what we want to create. We can see that we are the creators of the economy, not victims of it.

(And, I’m also going to be talking to Charles on an upcoming episode of The Great Wealth Transfer Podcast, so subscribe here to get the heads-up for when that one drops, too.)

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• • •

If you are what the financial industry calls a High Earner Not Rich Yet, or a HENRY:

• You may earn more than your parents ever did but not feel wealthy.

• You may have a retirement account but no real cash cushion.

• You may have a home with substantial equity alongside credit card debt, or stock options that look impressive on paper while student loans are deducted every month.

• You may be supporting children and helping aging parents at the same time.

And so you keep thinking: when I finally have enough, then I will learn how all of this works. Then I will pay attention. That, my friend, is your money dysmorphia talking.

Here is the reality.

$31.9 TRILLION in retirement assets alone are held by the mass affluent, roughly 31 to 33 million HENRY households.

U.S. households collectively hold approximately $67.8 trillion in corporate equities and fund shares. The wealthiest 1 percent own about half, which means the other half, roughly $34 trillion, is owned by everyone else.

By us.

You are in the game, and your retirement accounts, pension, mutual funds, insurance products, 529 plans, and brokerage accounts already direct capital every day.

Part of how we get “mined” is by failing to see how much power we have, how much we control, and that we actually can be good with money, and use what we have to create the new future reality we want to live in, together.

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• • •

So here’s what I want you to do now:

I know this can feel overwhelming. That is part of how money dysmorphia works: it convinces us that not looking is okay because we don’t have enough to worry about anyway, or we’ll think about it when we have more.

This is the lie that keeps us disempowered.

Take back your power by looking at what you have. It’s the starting place.

And note that you do not have to fix everything today. In fact, you don’t have to fix anything today. All you have to do is look.

See what you have. Let’s start there. Then, once you see, you can choose. (To make this actually doable for you, I created an AI prompt to help you inventory what you own and look inside your funds, without requiring you to share private financial data. When you join the Financial Liberation Challenge, you get the prompt. It's here.)

You can choose to move some of what you have out of extractive systems.

You can choose to invest in the world you want to see.

You can expand the options on your menu.

But you have to look at what you have.

Stop outsourcing to your guy.

Stop abdicating your leadership.

Start taking full responsibility.

And, together, we can create an entirely new economic reality, one that doesn’t extract, but instead regenerates, and creates the world we want to live in.

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• • •

This is where the Great Wealth Transfer becomes much more than a story about who inherits what. Between now and 2048, approximately $124 trillion will transfer between generations. A significant portion will move through families who do not think of themselves as wealthy, families with retirement accounts, homes, businesses, insurance policies, land, and debt. Families like yours.

If you are HENRY, you are not watching this transfer from the outside. We are all inheritors, and we are also the stewards of the future.

The question is not whether the money moves. It is already moving. The question is where it sits now, and whether it moves consciously and intentionally, or whether it flows by default toward the same systems that have been mining you and your family’s time, labor, attention, and resources.

Someone in the family has to open their eyes and ask: What do we actually have? What has it been funding? What do we want it to make possible now?

That someone can be you.

• • •

I’m continuing this conversation on The Great Wealth Transfer Podcast, on Apple Podcasts or on Spotify. Or watch it on YouTube!

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If you don’t know Dan, he coaches founders, helps build companies as an angel investor, and is as honest as they come about money. One of his first angel investments, a check he wrote in 2011 to an Irish founder named Eoghan McCabe, is about to become one of the largest paydays of his life.

The company was Intercom, recently renamed Fin, and Salesforce has signed an agreement to buy it for approximately $3.6 billion, a transaction that’s expected to close later in Salesforce’s 2027 fiscal year. After fifteen years, Dan is finally about to see what his original bet became.

His email was about the importance of holding an investment instead of panicking and selling. Every few years, somebody would ask whether he wanted to sell his shares, and Dan would write to Eoghan and ask, “Are you still building?” Eoghan would say yes. Dan would hold, and he continued to hold through years when it looked to the outside world as if nothing was happening, as well as through years when taking the money would have been paid nicely. But because he trusted Eoghan, he waited. Now, Dan’s patience looks like a prophecy.

“The slow way is the fast way,” Dan wrote. Then he said something else that stayed with me: “I won because I wouldn’t walk away on him.”

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Dan wants to be inspired by the founder, to understand the problem the company is solving and to know that he can be useful for more than the check. For him, investment is a relationship, which helps explain why his question to Eoghan was not, “What is the latest valuation?” It was, “Are you still building?”

Dan held the investment, because he had faith in Eoghan. I love that part of this story. But, it got me thinking: while that small investment was becoming a fortune, whose name did it grow in?

If Dan lived in the U.S. (he doesn’t, he lives in Canada), and that investment was in his own name (I have no idea if it was), when that wire landed with Dan’s share of the $3.6B sale, the whole gain would be sitting in his name, in his estate, fully exposed. To tax. To anyone who ever comes looking. To his spouse and kids, if they aren’t properly prepared to receive what he’ll leave behind.

• • •

In my previous article, when I wrote about building a family office before you feel rich enough to need one, this is what I meant. Not that you should rent an office and hire twelve people to sit around a polished boardroom table discussing your $25,000 investment. I meant that someone should be looking across your legal, financial, tax and family life while the decisions are still small enough to be made without setting off alarms.

They would be asking questions like, for example, what’s the title on the asset? What could it grow to over time? If it does grow in value, where will that value sit? Who is supposed to benefit from that growth, and what could leave it at risk?

Those are family office questions.

So I decided to take a look at Dan’s investment in Intercom through this lens. A VC analyst went back and estimated what Intercom’s earliest backers made: about thirty-six times their money. So a fifty thousand dollar stake, held for fifteen years, becomes around $1.8 million.

The investment earns the same whether the shares are held in your own name or transferred early into a trust. But the ownership structure determines who and what ultimately receives it, and how much.

If an asset is personally held, it’s usually part of the owner’s larger financial and estate picture. For a U.S. taxpayer (again, Dan lives in Canada, so I’m not talking about his specific situation here), it could create estate tax exposure if the estate is large enough.

For a family already above the estate tax threshold, federal estate tax can take roughly forty percent when you die (it’s been as high as 77 percent between 1941-1976, we could get there again), and just at the 40 percent rate, that could be $700,000 gone, on money you already earned.

And that’s just Federal. If you live in a state with estate tax, it’s more. And this isn’t even including what can happen to personally held assets that get caught up in litigation, creditor claims, divorce, incapacity, or a badly planned transfer after death.

There is another way to hold an investment like Dan’s that could have provided his family with protection. Same investment, same fifteen years, same return, but with one difference. This difference is the thing I’ve spent twenty years trying to get people to see before it is too late instead of after the fact.

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• • •

Here’s the move.

You do not wait until an asset is worth millions to protect it. Instead, you make your investments (in your own business or in someone else’s) through a protected structure, an irrevocable trust I call a Steward’s Trust.

I use the word “steward” very specifically because stewardship is the point: the asset is not being hidden from the family or shoved into a vault where nobody can touch it. It is being held with an understanding that the asset has a purpose and it will be well and intentionally cared for while it grows into something meaningful.

You set it up while your investment is still just a relatively small check nobody is thinking much about. A stake worth even ten thousand dollars is worth it. I’m talking about investments like pre-IPO shares or the rental property you want to buy before the neighborhood turns. Or equity in the thing you are building right now. You get the idea.

If you structure it right, this is your vehicle for creating and caring for generational wealth, and it’s the simplest way to set it up right from the start. The best part is you can benefit from what is in that trust your entire life, and you can pass it on to your family free of estate taxes, and totally protected, for many generations. This is how the wealthiest families created wealth from way back, and kept it in the family.

There is one catch, and it is the thing that trips up even the smartest people: it’s way better if you don’t do this for yourself.

If you set up this kind of trust and fund it with your own money or an asset you already own, if it’s not in there long enough or set up in the right jurisdiction, a judgment could pull it right back into your estate and the whole structure collapses. The safe harbor is to have someone who loves you set up the trust, and have the trust make investments for you.

Now, all the upside grows inside the trust. And, we structure the trust so you maintain investment control. So, imagine that Dan put $50,000 into Intercom, and that $50,000 grew to $1.8 million; if he had done it through a Steward’s Trust, now that $1.8 million is protected. Same growth, same money, but the estate tax on it down the road will always be zero.

The full $1.8 million passes to the kids, the grand kids, and even the great grands, no matter how much it grows over time, and no matter what the estate tax rate or exemption is, protected the whole way. Same asset, same fifteen years (in Dan’s case). One version could hand $700,000 to the IRS. The other keeps every dollar in your family.

Does that mean you put something into a trust and continue behaving as though nothing changed? No, and anybody promising that should make you nervous. Who creates the trust and serves as trustee matters. The powers retained by the person who built the asset also matter, as do the beneficiaries, the jurisdiction, and the tax treatment, as well as the way the trust is administered ten years after everybody has forgotten the enthusiastic meeting in which it was signed.

A good structure is not necessarily complicated, but it is precise. It has to work in the life of the family using it, not just on the day the lawyer produces the hefty binder with the fancy documents.

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• • •

I talked with a founder a few weeks ago who learned this the hard way, though he may not know yet that he has a problem waiting to happen. He has done something both clever and complicated by setting up foreign trusts for his kids, with people living overseas as the trustees, the ones actually in charge. It works, technically. For now.

But let’s look at what he built. The people holding the keys to his children’s future live on the other side of the world. They can die, go missing, or stop answering his calls or emails. He wired his family’s security to strangers in another country because that was the structure that was recommended to him.

Here is what he could have done instead. He could have had his own parents set up a Steward’s Trust for him, one for him and one for each of his kids. It would be kept here in the United States, with independent trustees he actually knows and could replace if he needed to. His parents could make the gift, which keeps the structure intact. And every asset he built inside that trust would have grown inside a protected, American, family-controlled structure that does not depend on someone he might not be able to reach if things change.

This offers the same protection with none of the fragility. The difference was not intelligence. The founder I’m talking about is a brilliant man. The difference is that no one ever told him, and he didn’t know what he didn’t know.

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• • •

Because Dan’s story involves an angel check and a multibillion-dollar technology company, the lesson is easy to see. It can also make the rest of us dismiss the whole thing as something that happens to guys who invest in software companies. The other reason that people dismiss the value of setting up a trust like this, is, frankly, because most appreciating assets look pretty unimpressive at the beginning. In fact, they can look like a potential mistake.

People tell themselves that they’ll revisit “structuring something” after the next funding round, after the investment property is renovated, when their business turns a profit, or when somebody who seems legitimate tells them that the thing they’re building is worth something.

But if you wait too long, things can get complicated and expensive, with the result that you could lose a major chunk of the returns on your investments to taxes, creditors, and more. In fact, this is one of the reasons wealth so often remains unprotected even in ultra-wealthy families.

Dan understood that the founder and the company were worth staying with before the outcome proved him right, but his form of vision is rare. I am not telling you to start chasing early-stage companies or that every investment will reward your patience. Most absolutely will not. Dan himself makes clear that the long game works only when you are in the right game, with people you understand and want you to be actively involved.

My recommendation (not legal or financial advice): look at what you are building, holding or acquiring, and ask yourself, “Do I really believe in it and that it could grow into something meaningful?”

If so, it’s worth planning for and protecting now. If you think to yourself, “Eh, I don’t know, I don’t really have enough to take it seriously now.” That could be your money dysmorphia talking, and it’s the very thing that keeps many of us from creating real wealth.

Money dysmorphia doesn’t just make us feel poorer than we are. It can cause us to look directly at something with the power to change a family’s future and decide that it’s not enough to plan well for now. The very reason so many families perpetuate not enough instead of creating the generational wealth they have so close at hand.

• • •

In my next article, “You Are Not Bad With Money. None of Us Are,” I will dig deeper into money dysmorphia: the distortion that tells capable people they are failing at money while keeping them from seeing the financial power they already hold. If you want it in your inbox, subscribe.

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I’m continuing this conversation on The Great Wealth Transfer Podcast, on Apple Podcasts and on Spotify, talking through the steps to creating a Steward’s Trust to protect your future payout. Or watch it on YouTube, here!

This is not legal or tax advice, and every structure I described has to be built with real counsel for your real life, ideally a Personal Family Lawyer who knows how to set up these structures and ensure they are maintained the right way.

New to this conversation? Read “The Great Wealth Transfer Is Not Just a Rich-People Story,” where I explain why this historic transfer includes far more families than most of us realize.

And they may have good reasons not to trust you. Heck, you may not even really trust yourself with money.

The good news though is that if you can acknowledge it, see it, and understand it, you can change it. Before any of the assets involved in the Great Wealth Transfer move in a good way, something else needs to transfer first: trust.

I know it because I did it, I built trust with myself, then with my mom and sister, and it changed the course of my family’s life for generations to come.

But, first, I’d F-it all up, royally. If you have too, it’s not too late.

• • •

When I was rebuilding after my bankruptcy, I needed capital to rebuild. I had ruined my credit, and after turning everywhere else (I even asked my ex-ex-ex boyfriend, and he said no), the last person to ask was my mom.

Asking her was terrifying. Our relationship was complicated. And she was not sitting on a pile of money. My mom was an art teacher in her seventies and still working because she needed the paycheck; she had barely $200,000 saved for her own retirement.

What she did have was a credit score she had spent her whole life protecting. It was around 800, and she was so proud of it. I knew she was going to say no, but I also thought to myself: “If my own mom won’t invest in me, what kind of a loser must I be?!”

I’m glad I let myself face that fear. Once I admitted that I felt like a loser, I could stop treating my mother’s answer as proof that I was one and start showing her, and myself, what had actually changed. (It’s a good hack. Try it!)

I also realized life was giving me a huge opportunity to stop repeating the very patterns that resulted in me losing again and again. So, I asked.

And she said no.

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But I didn’t treat the “no” as evidence my mom didn’t believe in me (even though at that time, I’m sure she did not). I could have made it about all the ways I thought she had failed to support me (I had always been looking for evidence of that).

Instead, I did the inner work around it, and then showed her the numbers, the plan, what I had learned, and the structure I intended to put around the risk. I showed her I understood what I was asking her to put on the line.

Most importantly, I committed to her that no matter what, I would take care of her for the rest of her life. I didn’t say that lightly. With fear, willingness, and hope for the future, she said yes. (If it would be helpful for you to see me asking my mom to invest in me, her saying no, and then yes, you can get the BTS + so much more in the Financial Liberation Challenge here.)

With access to $150,000 in business credit from my mom, I rebuilt the foundation of the companies I lead today, which last year hit $13.5M in revenue, and have made the Inc. 5000 list 7x since then. Today, my mom is living her best life, retired, and earning a supplement to her social security as the treasurer of our eco-system.

Here’s what was even more important than the money: my ask and my mom’s decision to say yes changed our relationship with each other and with our entire approach to our collective family wealth. My mom, my sister and I have been making financial decisions together ever since, instead of allowing money to remain a source of silence, fear, or leverage.

The point of all of it is, I had to grow up into the person I was asking my mother to trust. You may need to also.

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• • •

Keith, who joined me this week on The Great Wealth Transfer Podcast and YouTube video, had to grow up too, and because he did, he likely saved his family from financial catastrophe. I don’t mean this lightly. If Keith had not stepped up when he did, he could be sitting in financial devastation stuck in a court process right now instead of living his best life caring for his family’s resources.

Keith’s dad worked on Wall St. for fifty years and kept pretty much all the family money in cash, while believing Keith spent money “like a drunken sailor.” There was no way he would entrust the family money to Keith.

That began to change six years ago. Keith asked his dad to sit down with me and his stepmom to talk about it. His dad said yes. I think he was relieved that Keith was initiating this conversation, and doing it with a friend and lawyer. When we talked about the resources he’d spent a lifetime accumulating, his dad told me he liked to worry about the money. I could see that Keith needed to step up so his father could spend the last years of his life not worrying.

When we looked at why Keith’s dad earned the money to begin with, his dad was able to see that what he really wanted was to make sure his kids wouldn’t need to worry like he did. I suggested the starting place was for Keith and his dad to start by looking at everything he had together, and his dad agreed.

Keith spent an entire week going through every file, folder, account, and asset his father owned, and, for the first time, he was able to see his family’s financial life as a whole, rather than as an invisible source of money handled offstage.

He inventoried everything, and that inventory functioned as Keith’s apprenticeship in becoming a steward of their family’s resources. Keith saw what there was, how the pieces fit together, what his father was trying to protect, and what would eventually need to be managed across three generations.

Here’s the crazy part: within six months of that conversation, Keith’s dad began a significant cognitive decline. Today, he’s living in a memory care facility where he’s happy as a clam, has no anger, fear, or any lashing out, and is post-worry, which I understand is quite rare for someone with dementia.

I believe that Keith’s dad is at peace because Keith was able to step up into his role as a steward of their family’s wealth before it was too late. I call it karmic reward. When you do the work to so that the senior generation can pass on resources during life; in a way everyone can enjoy the resources together.

If Keith’s dad had gone into decline before we had the conversation, their family could have literally lost almost everything to the costs of Keith’s dad’s care, court costs, potentially conflict, and a whole lot of confusion. Instead, Keith no longer has to work a soul sucking job to prove his worthiness to his dad, and instead now gets paid to be in his right role as the steward of their family’s wealth. Best of all, his parents can rest easy because Keith is handling everything for his dad, his stepmom and mom, his siblings, and all the grandkids.

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• • •

It’s true that many parents use money to control their adult children. Some refuse to share information or keep moving the goalposts. And, they even keep treating us, capable adults, as if we are irresponsible teenagers.

But here’s the question you need to ask: are we?

Sometimes our parents do not trust us because we are still acting like teenagers around the family money. Maybe we want access without accountability or we take questions as criticism. Maybe we’re asking our parents to trust that we have the best of intentions when we haven’t shown them that we can tolerate oversight or put the family’s long-term well-being ahead of what we want right now.

It doesn’t make us bad or wrong, but it does mean that there is a lot of growing up left to do. There was for Keith and for me.

Here’s part of what I came to understand, as I did my own growing-up work around money: every family has a business, even if nobody owns an actual company.

The “family business” is the care and coordination of your family’s assets, debts, insurance policies, legal documents, tax decisions, homes, caregiving responsibilities, professional relationships, private promises, and the years and years of accumulated knowledge about how everything came to be.

And, someone usually holds most of that knowledge. It may be your father, your mother, a sibling, the family accountant, or the lawyer who drafted documents twenty years ago. Sometimes, no one holds the entire picture at all, which is part of the problem. This is, ideally, where you come in as what I call a “Family Wealth Steward” - and you don’t have to be rich, or even think you are rich to be one.

Becoming your family’s wealth steward doesn’t mean declaring yourself the head of the family or lording control over everyone. Please no. You also don’t need to become a lawyer, insurance professional, financial advisor or accountant. But as I wrote in “Don’t Wait Until You’re ‘Rich Enough’ to Build This,” you do need to understand how the family’s legal, insurance, financial, and tax decisions affect one another, and the cost of fragmentation.

You need to know, for example, whether an asset is titled correctly, whether the will, trust, health care directive and power of attorney still reflect the family’s real life, insurance coverage matches the actual risks, tax decisions are being made proactively, and if the professionals involved are all working from the same information. And, more than that, you need to know when you do not know enough, and, most importantly, be willing to ask the right people and learn.

Family wealth stewardship is a path of waking up to recognize that what you have matters, whether it’s $50,000, $500,000, $5 million or $25 million. It starts with you seeing what you have, then becoming your own best advisor, knowing what you can do yourself, and what you need support for, and hiring the right support, and then, ultimately, building with the people you love.

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• • •

Before you can ask your parents to trust you with stewarding their money or business, you have to ask yourself some tough questions. And, you have to answer them truthfully:

• Have you clearly documented what you own and what you owe? Do you have your own up to date estate planning documents in place?

• Do you open the statements, understand the insurance you carry, file your taxes, keep agreements, tell the truth and learn the right lessons when something goes wrong?

• Can you make a plan and follow it long enough for someone else to rely on you?

• Can you receive feedback without treating it as an indictment of your character?

If not, it’s not too late. Your parents likely don’t expect perfection, but they are looking for evidence that you can face reality. Then comes the harder step: approaching them without the conversation devolving into the same pattern as your teenage fights.

So, instead of asking, “Do you have a will?” you might say something like: “I’m stepping into the next stage of my adulthood around my financial life, and I want to make sure I understand what I need to about your care needs for the rest of your life. Would you be open to a conversation about that?”

This is stewardship, and it could very well be the most important next initiation of your life.

• • •

I’m continuing this conversation on The Great Wealth Transfer Podcast, here on Apple Podcasts or here on Spotify, with important notes on what it is actually like to navigate becoming a steward of family wealth from someone whose life was radically changed for the better by it. Or watch it on YouTube, here!

In this episode, you'll learn:

• Why the first real step toward family wealth stewardship is a full inventory, not a will — and what happens if you skip it

• How to open the estate-planning conversation with your parents without it reading as "what's in it for me"

• The real story of a "caring" email that got read as greed — and cost a family its trust

• Why "he wanted to create family security" is a stronger reason to plan than fear of dying

• How to raise financially capable adult kids without doing the work for them

• The "bucket" system for managing cash and investments across three generations at once

• Why timing the market matters less than knowing your own risk tolerance and time horizon

Guest — Keith Alpert

Instagram — @rockinout68: https://www.instagram.com/rockinout68/

LinkedIn — /in/keithalpert: https://www.linkedin.com/in/keithalpert/

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Website: https://alikatz.com/

Free Resource: Get my Inheritance Guide — practical guides on what's actually transferring, and how to talk about it: https://www.alikatz.com

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In my early years as a lawyer, working on transactions for Warren Buffett and others like him, I got an insider view of the traditional family office. I knew what legal and financial order looked like, and I was quite sure it didn’t apply to me. My guess is you likely think it doesn’t apply to you either. As a result, the $62T that “we the people” have in our control is at risk of being lost, or extracted from us.

After graduating from Georgetown Law, I worked within wealth structures for some of the most financially sophisticated families in the country. I understood, in precise professional detail, how legal, insurance, financial, and tax realities (what you’ll often hear me refer to as “LIFT”) fit together into one coherent system.

Yet I had none of that for myself. Of course I didn’t. Frankly, I didn’t think any of it applied to me. That was for rich people. Really rich people. And I was sure I was not that.

Yes, I was earning a six-figure paycheck at 28, and then I built two seven-figure businesses by the time I was 35, but I didn’t come from money. I had student loans and debt. I didn’t even really know what a 401k was or why I needed one.

I figured that the LIFT coordination handled by the family offices of Munger, Buffett, Allen, Ovitz, Eisner, and the other big-name clients we served surely didn’t apply to me. That thinking ended up costing me over a million dollars in mistakes I wouldn’t have made if I’d understood how it all fit together.

When I first started working at Munger Tolles, one of the first things they did was hand me a piece of paper and they said, “Congratulations, you’ve got a 401k! Now, tell us how you’d like to invest it.”

The paper they handed me had all sorts of letters on it, and I had no idea what those letters meant. I was too embarrassed to ask, and we didn’t have Google back then. So, I literally squeezed my eyes closed, put my finger down on the paper, and that’s how I picked my 401k investments.

It’s why everything I now build is organized around one core idea:

Wake up, see what you have, and learn to steward it before someone else does it for you.

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• • •

The moment it first became impossible for me to ignore was during my divorce.

My husband hired a forensic accountant, worried I might hide assets. Fair. He was the stay-at-home spouse; I was the breadwinner who had started a business he really knew nothing about. He was probably right to be worried.

I had no intention of hiding assets from him, but he didn’t know that. The real issue was that I had no idea how to manage the financials of my business. It hit me square in the face when his forensic accountant looked across the table and said: “Alexis, your books are really messed up.”

It was 2005. I was 32, raising two little kids, getting divorced, and only 18 months into the world of business. I had a CPA who had told me I didn’t need to incorporate my business. Bad advice.

I had bought a whole life insurance policy from an insurance guy I thought was my friend. Bad advice.

And I definitely didn’t have an integrated view of what I had, what it cost, what it was building toward, or what was falling through the cracks.

I was managing my finances the way most people do: by looking at my bank account to see if I had enough money, and running numbers in my head during yoga class to make sure I wouldn’t run out.

The result would become more than a million dollars in mistakes I wouldn’t have made if I’d had a system, structures, rhythms, and flows that would allow me to think about money when I needed to, and not worry about it when I didn’t need to worry.

But at the time, I was the only one holding the whole picture, and I didn’t even understand the frame. I felt alone. Too ashamed to ask for help, too exhausted to know where to start, and too convinced that if I just earned a little more, the chaos would somehow resolve itself.

Then, two years after the divorce, a letter arrived from the IRS. They were auditing my taxes from 2005—the same year I already knew was messed up. I stood in my kitchen and read it twice.

I cried for two days. Not just about the audit. About all of it. About how someone who knew as much as I did could have let things get this far. About the shame of it. About being so alone with something so big.

Then I woke up and realized crying wasn’t the answer: I was being taught a critical lesson. I called my personal assistant (a 17-year old working for me part time) to work with the accounting team I hired to handle the audit (oh, how I wanted to cheap out, not hire them, and try to do it myself) and told them all:

“Handle this audit and don’t bring it up to me unless there’s something specific I can do. Otherwise, just take care of it.”

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And I took every bit of energy I could have spent berating myself, worrying and stressing and—any time I thought about it—I’d rip my mind away like ripping velcro, and took some action that would build my second business instead.

Within 18 months, I turned that new business into a million dollar revenue stream, and I got a “no-change” on the audit.

It felt like a miracle. And it was. But, also, it was a huge lesson in how critical my focus was, and that I could control outcomes with where I put my energy and attention.

But I still didn’t really learn what my “books” or “financials” really were. And, eventually, that once again caught up with me. There was way too much flowing through my system, and I couldn’t handle it all.

Instead of turning to face it, and figure it out, I decided I was bad at business, and I’d walk away from it all. Not because I had lost everything—I hadn’t. My businesses were still earning. I had even created irrevocable asset protection trusts to hold the businesses so if I filed bankruptcy, the businesses would survive.

Filing bankruptcy was the most strategic thing I could do: get a clean start, face my biggest fear, and rebuild on a foundation I actually understood. And I did, slowly, but on a completely different one.

Here is the thing I came to understand only after the bankruptcy: I needed my own family office. Even though I was broke and rebuilding from rock bottom, I needed to figure out how to see what I had, become my own best advisor, and then hire the right support from there.

• • •

The role of family steward—the person who holds the whole picture of a family’s wealth, household, and future—is not a modern invention. It is at least 1,500 years old. The Romans called this person the major domus, the master of the house. The role survived the fall of the Roman Empire, moved through medieval European households, and eventually became so powerful that the Frankish maior domus, the Mayor of the Palace, held more authority than the king.

The modern version arrived in America in 1882. Here is how it evolved and why it matters now.

For 140 years, this model was available to one tier of family. The families who had it built durable wealth across generations. The ones who didn’t, lost it. There is a widely cited industry statistic: 60 percent of families lose their wealth by the end of the second generation. 90 percent lose it by the third.

Family offices were invented to interrupt that pattern. What I built after my bankruptcy, without yet knowing what to call it, was my own version of the same thing.

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• • •

Back then, I didn’t think of it as a family office. I just knew I needed help. I wasn’t even clear what that help was, so I started with two people I already trusted. That same personal assistant who had helped me through the audit, and his girlfriend, who was also my nanny. I trusted them, and figured I could train them to help me.

This young couple had been helping me hold my life together through the divorce, the audit, and everything after, while I was raising two kids and running two businesses. I didn’t trust them to know everything about money. I did trust them not to take advantage of me when I was vulnerable. That turned out to be exactly the right place to start.

We learned together. They went to college, got married, started a bookkeeping company. We built tools and systems that let me actually see what I had for the first time: not just the number, but the whole picture. What was coming in, what was going out, what was protected, what wasn’t, what I was building toward, and what I was quietly losing.

Twenty years later, I can see that what we were building over all those years was my family office. Together, we learned how to coordinate my legal, insurance, financial, and tax reality so that I would never again be the only one holding the whole picture alone.

That is what I now call LIFT: Legal, Insurance, Financial, Tax. Four pillars. One connected system.

Death has a way of introducing people who should have met twenty years earlier. A business loss, a divorce, or an unexpected tax bill has a way of revealing the absence of a system that should have been there all along.

I know. I lived it. With all the professional knowledge in the world and no integrated view of my own financial life.

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• • •

This is where the Great Wealth Transfer enters the picture. As I wrote in “The Great Wealth Transfer Is Not Just a Rich-People Story,” nearly half of the money and assets expected to transfer over the next two decades will move through families that do not think of themselves as wealthy.

This is not a wealth problem. It is a seeing problem. And I say that with complete compassion because I had the same seeing problem for most of my adult life, even while I was professionally solving it for everyone else.

Most of us assume the Great Wealth Transfer doesn’t apply to us because we don’t think we have enough to be part of it. But we are all inheritors. All of us will be inheriting something, even if that something is a whole lot of debt and trauma.

But, this transfer isn’t only about what gets passed down. It’s about how much of it your family actually keeps—in your own hands, your own relationships, your own community—versus how much quietly flows out to whoever is positioned to receive it.

The real risk isn’t the size of the number. It’s everything that doesn’t happen because the number seems too small to matter: the conversations that don’t take place, the documents that sit unread, the assets nobody is tracking, the adult kids who assume their parents have it handled, the siblings who stop speaking over an estate that should have brought them closer.

• • •

So here’s the great news: family offices are no longer a luxury available only at the top. AI is collapsing the cost of the professional services that used to define what a family office required. The category is being stretched, and the work—the actual coordinated stewardship of a family’s whole picture—is ready to scale.

What I am building, what I have spent the last twenty years building for myself, and I’m now able to make available to all of us is what I call Family Office at Scale: a model that brings the discipline of the Rockefellers and the Buffetts to every family, with a Personal Family Lawyer trained as a Family Wealth Advisor supporting you to become a Family Wealth Steward, at the center.

The lawyer is the only professional structurally positioned to hold this seat, with fiduciary duty, attorney-client privilege, and no product-sale incentive pulling them off the family’s side of the table.

This is not a new idea. It is a 1,500-year-old idea whose time has finally come for everyone. You do not need more money to start. You need to decide that what you already have is worth seeing. That is where everything begins, and it is available to you right now, at whatever level you are starting from, in whatever condition your financial life is currently in.

• • •

In my next article, I will be looking at Dan Martell’s news and how investments that pay off massively can be at risk if you don’t protect them by taking a simple, forward-thinking step. If you want it in your inbox, subscribe.

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New to this conversation? Read “The Great Wealth Transfer Is Not Just a Rich-People Story,” where I explain why this historic transfer includes far more families than most of us realize.

I’m also continuing this conversation on the podcast, with more on why family-office thinking should not be reserved for people with eight-figure balance sheets—and why it can help you right now. Or watch it on YouTube, here.

• • •

Sources: Family office history: World Economic Forum and J.P. Morgan, The Single Family Investment Office Today, August 2016. Rockefeller family office history: Rockefeller Capital Management. 60/90 percent generational wealth loss statistic: World Economic Forum and J.P. Morgan, 2016. Great Wealth Transfer projection and inheritance estimates: Cerulli Associates, 2024. Planning gap data: Northwestern Mutual Planning and Progress Study. Quote on stretching of the “family office” category: Financial Planning, May 2025.

The financial industry calls it the Great Wealth Transfer. And if you haven’t paid much attention to it (or even heard of it) I’m guessing that’s because you think it has nothing to do with you.

Or, maybe you think they are talking about “the Great Reset,” the sweeping, elite-driven plan that came out of the World Economic Forum during Covid times.

So you may assume it’s about governments, billionaires, and powerful families. It isn’t. The Great Wealth Transfer is happening right now through ordinary families, retirement accounts, homes, businesses, and the decisions you’re making (or not making) around your kitchen table right now.

If you haven’t heard of it yet, or don’t think it applies to you, I don’t blame you because you may not even think of yourself, or your family, as rich.

And, it’s true that the high-net-worth and ultra-high-net-worth households—the wealthiest 2 percent of American families—account for more than half of the total transfer. But, here’s the thing: the remaining 98 percent of households account for the other half. And that’s where we have a tremendous amount of power, and opportunity.

The numbers around “wealth” are often presented to emphasize how much of it is concentrated at the top. We get it. But here’s what the numbers also reveal, and it’s big:

That is the premise of this Substack, and it is why I am here with you now.

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• • •

The Great Wealth Transfer is not simply a story about billionaires and their estates. It is a much more important story about those of us with houses, retirement accounts, small businesses, life insurance policies, land, farms, modest portfolios, and the obligations that come with caring for aging parents, raising children, and navigating debt. We are the families who may hold significant assets without ever thinking of ourselves as people with wealth to steward.

But before we go any further, let’s be clear about what the word wealth means here. It does not mean a fortune.

In this context, I’m using “wealth” as the container word for money and assets. And yet wealth is so much greater than just money and assets. As you’ll hear me often say, family wealth, the term I’ve built my life’s work around, includes our intangible, and most often lost, compromised or sacrificed non-renewable resources.

We will talk much more about our individual and collective non-renewable resources and how to stop sacrificing them in service to what is renewable: money.

For now, though, let’s look at the financial wealth—money and assets—and why we must see that what we have is worth taking a lot more seriously (and, at the same time, putting it in its right place, not centering it quite so much, and also realizing we have a lot more than we think).

There’s a lot of paradox and nuance here, so stick with me through whatever may seem contradictory. It’ll be worth it.

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• • •

Here are some ways your financial reality could be impacted by the Great Wealth Transfer:

• Your mother gives you money from her savings to help with a down payment. That is a wealth transfer made during her lifetime.

• Your uncle dies and leaves you the proceeds of a modest life insurance policy. That is a wealth transfer.

• Your parents leave the family house to you and your sister. Whether you keep it, sell it, or discover that debts and deferred maintenance have consumed most of its value, that is a wealth transfer, too.

• Your aunt adds you to the deed to her house or to her bank account because you’re her only heir, and you lose the capital gains benefit of her death, or she loses her bank account because you didn’t file your taxes. That’s wealth transfer.

• Your father says his retirement account will be divided among his children, but the beneficiary form still names his former wife. The account will pass according to that form, not according to what he told you he intended. That is also a wealth transfer—just not the one he thought he had planned.

• Your mom got remarried to a younger man who has kids from a prior marriage. She didn’t update her estate planning documents because you didn’t want to bring it up. Then, she’s hospitalized for too long to do anything about it. When she dies, her husband gets everything, and you get cut out. A very common unintended wealth transfer.

None of these families would necessarily describe themselves as “wealthy.” But all of them have wealth moving from one generation to the next. And this is happening now, not someday. The oldest Baby Boomers are turning 80 in 2026.

The decisions that will determine what your family receives—and what it loses—are being made in estate plans that have not been reviewed in a decade, retirement accounts whose beneficiaries haven’t been checked since a divorce or remarriage, and family conversations that keep getting postponed until there is more time, more money, or more certainty.

The useful window is now—while the people who built and hold the wealth are still here to clarify what they want, and what they intended, fix what no longer fits, and prepare the people who will eventually be responsible for carrying it forward.

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• • •

Many of today’s most powerful family dynasties began with an ancestor who recognized a major economic shift before most people did, and acted on it.

Let that sink in for a minute, and recognize that they were people, just like you, who happened to be living during a time of great change. And they saw a future that they acted upon when few others did.

That can be you, and your family could be the beneficiary of your choices now for many generations to come, depending on where you choose to focus your resources today. With more information and also more distraction at our fingertips than ever before, where you focus your resources could make all the difference in the world. I’m here to support you to hone in on what matters most.

• • •

One of the biggest differences between high-net-worth families and the rest of us (other than money and assets) is that they’re far more likely to have infrastructure: lawyers, tax professionals, private banks, investment advisors, current estate plans, regular family meetings, and professionals whose job is to notice when the pieces do not line up.

Many have formal family offices—dedicated structures built to coordinate the legal, insurance, financial, and tax decisions that affect every member of the family. The absence of that infrastructure for the rest of us is not just inconvenient. It is expensive.

These are often not failures of love or intention. They are failures of infrastructure.

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I want to be precise about what I mean by “infrastructure,” because the word can sound like something that only makes sense at eight figures. But it really matters at far less, and perhaps even more.

Every family that wants to steward what it has needs some version of the same four functions:

That is the work a family office performs. Most families do not need a building, a staff, or a minimum balance. They do need the function of a family office though: a decision-making structure that allows you to see your resources clearly and act on them deliberately. We’ll be looking at how we can create that together, here.

We’ll also look at:

• how to find out what your family actually has;

• how to talk to your parents without sounding as though you are counting their money;

• how to prepare your kids for what’s coming without creating entitled brats;

• how to keep court costs, care costs, taxes, and family conflict from consuming what your parents hoped to leave; and

• how to decide what the money is for, once it arrives.

We will also examine what it costs to avoid this work—and how families at every asset level are beginning to do it differently.

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• • •

There is a reason so many of us fail to see any of this clearly, and there is a name for it:

Money dysmorphia (n): the distorted view we have of our financial reality that causes us to sacrifice our non-renewable resources in service to money, which is infinitely renewable when we know how to use our non-renewable resources.

Money dysmorphia often causes us to measure our financial reality against an imagined standard (usually someone else’s) and could make whatever we do have look too small, too disorganized, or too inadequate to require serious planning.

It is the same distortion that convinces a family with equity in a home, retirement accounts, and a life insurance policy that it does not have “real” wealth and that the conversation about protecting it belongs to someone else.

You will see how this plays out over my future articles, and I’ll help you see what you may be missing now when it comes to the impact of this Great Wealth Transfer and money dysmorphia on you, your family and your community because until you can see what you already have, you cannot protect it, build it or redirect it deliberately.

You do not need to wait until you feel rich enough. In fact, if you do, you may never become rich. Instead, you start right now, by getting clear about how to care for what you have now.

• • •

I’m continuing the conversation with my new podcast, The Great Wealth Transfer with Ali Katz. In it, I talk through what the $124 trillion figure actually means for a family like yours—and why the decisions being made now will shape your future and one we can create together. Or watch it on YouTube, here.

Also published today: “Don’t Wait Until You’re Rich Enough to Build a Family Office,” which shows you what family-office thinking could look like in your life right now.

Sources: Cerulli Associates, “Cerulli Anticipates $124 Trillion in Wealth Will Transfer Through 2048,” December 5, 2024; Cerulli Associates, The Cerulli Report: U.S. High-Net-Worth and Ultra-High-Net-Worth Markets 2024.

This article provides general educational information, not individualized legal, tax, financial, or investment advice. Consult qualified legal, financial, and tax advisors who understand your complete family and financial picture before making decisions about estate planning, wealth transfer, or family financial structures.

In this solo episode, Ali breaks down the belief that quietly cost her the most: "this doesn't apply to me." Despite starting her career working on tax transactions for Warren Buffett and Charlie Munger's law firm, she didn't think legal, insurance, financial, or tax planning applied to her own life — a belief rooted in growing up as the "poor" family in a wealthy Miami community. That single belief ended up costing her more than $1 million over the years, including an unexpected $116,000 tax bill, $250,000 in debt from selling a business to the wrong buyer, and a $50,000 lawsuit she settled because she didn't have the right insurance.

The turning point came two years after her divorce, when a forensic accountant's warning that her "books were really messed up" turned into an IRS audit letter. After two days of spiraling into self-blame, Ali hired real support, redirected that energy into her business instead, and built her second million-dollar business in just 18 months.

In this episode:

• Why "this doesn't apply to me" is one of the most expensive beliefs you can hold about money

• The four pillars of a family office: legal, insurance, financial, and tax

• Why the right time to build your family office is before you feel rich, not after

• How an IRS audit forced Ali to rebuild her entire approach to money

• Why raising capital or bringing in a business partner too soon almost always backfires

• How to turn "eyes squeezed shut" money decisions into "eyes wide open" ones

Free Resource: Get my Inheritance Guide — practical guides on what's actually transferring, and how to talk about it: https://www.alikatz.com "The time to build your family office isn't when you're rich. The time to start is actually when you think you don't need one." — Ali Katz "I built my second million dollar business in just 18 months." — Ali Katz

Follow and subscribe to get notified of every new episode, and — most importantly — share this one with somebody you need to be in conversation with right now.

Connect with Ali Katz: Instagram: https://www.instagram.com/thealikatz Facebook: https://www.facebook.com/TheAliKatz/ LinkedIn: https://www.linkedin.com/in/thealikatz/ Website: https://alikatz.com/

In this solo episode, Ali Katz breaks down money dysmorphia: the distorted relationship with wealth that keeps people feeling broke no matter how much they make. She shares her own story of feeling broke while earning $165,000 a year as a lawyer — and again while running $2 million businesses — and explains why $1–$30 million in family wealth counts as rich, even when it doesn't feel that way.

Ali also gets practical, walking through why most people never take real ownership of their finances (like her mother asking a male teacher to invest her retirement account, or Ali herself blindly picking a 401(k) option at 28), and why $70 billion currently sits unclaimed in state coffers because families never find out what their loved ones had.

In this episode:

• What money dysmorphia is, and why it keeps you feeling "not rich enough"

• Why $1–$30 million in wealth counts as rich

• How to treat your finances like your own family office

• What happens if you never take real ownership of your money

• Why "eyes squeezed shut" financial decisions cost you more than you think

• How to reframe estate planning as a rite of passage into adulthood

Free Resource: Get my Inheritance Guide — practical guides on what's actually transferring, and how to talk about it: https://www.alikatz.com "I'm making $165,000 a year and I still felt broke." — Ali Katz "If we have money dysmorphia, no matter how much we have, we're never going to feel rich." — Ali Katz

Follow and subscribe to get notified of every new episode, and share this one with someone you love — someone who needs to hear this too.

Connect with Ali Katz: Instagram: https://www.instagram.com/thealikatz Facebook: https://www.facebook.com/TheAliKatz/ LinkedIn: https://www.linkedin.com/in/thealikatz/ Website: https://alikatz.com/

You’re already an inheritor. The question is whether you’ll become a steward: someone who sees the whole picture, has the conversations that don’t happen by accident, and directs what your family has built with intention rather than handing it off and hoping for the best.

This newsletter is for the reader who decides to look at what they actually have, at what’s actually at stake, and at the legal, financial, and family dimensions of the largest wealth transfer in American history. One piece a week. Eyes wide open.