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New conversation is live! Wealth Lessons From the Hilton Dynasty | Why Their Money Has Lasted So Long w/ Mark Miller Listen here- https://podcasts.apple.com/us/podcast/money-school-podcast/id1451332111

Most investors think wealth preservation is about performance. At the high-net-worth level, the real conversation is about structure.

Because the families that keep wealth across generations are not just trying to get better returns. They are thinking about education, tax strategy, access, capital protection, charitable planning, and the systems required to make wealth last beyond one person’s lifetime.

And once you understand that, the way you evaluate wealth starts to change.
Most successful investors don’t lose wealth because they have never learned how to make money. They lose it because the structure around the money was never built to preserve it. The next generation inherits assets without inheriting judgment.

Tax strategy gets treated like an afterthought instead of part of the portfolio. And high-income earners often assume better tax outcomes require extreme lifestyle disruption, when the real issue may be access to more sophisticated planning.

In this episode of Money School Elite, I sit down with Mark Miller of Hilton Wealth and the Hilton Family Office to unpack how wealthy families actually think about preserving capital, reducing tax drag, and building systems that last.

Mark works inside the family office world, where the conversation is not about chasing returns. It is about protecting wealth, structuring it intelligently, and making sure the capital and the knowledge behind it survive over time.

New conversation is live! What Wealthy People Do After the Obvious Tax Strategies Run Out w/ Michael Malloy - Check it out here: https://www.chrisnaugle.com/michael-malloy

If you think life insurance is about protection, you’ll miss what it can do at a high net worth level.

For wealthy investors, business owners, and families with meaningful assets, the question is not just where to invest. It is where long-term capital should sit, how it should be owned, how it should grow, how private it should remain, and how efficiently it can move to the next generation.

That is where Private Placement Life Insurance, or PPLI, changes the conversation.
Most investors dismiss life insurance because they think they already understand it. They picture ordinary policies, limited investment options, and a product built mainly around a death benefit. But at the high end, that framework is incomplete.
PPLI is not ordinary life insurance. For the right investor, it can function as a long-term asset structure, allowing capital to grow in a tax-advantaged environment, support estate planning, simplify reporting, preserve privacy, and create a more strategic way to hold assets over time.

In this episode of Money School Elite, I sit down with Mike Malloy to unpack how PPLI actually works, why wealthy families use it, and why the structure around an asset can matter just as much as the asset itself.

Mike works with high-net-worth clients, families, and advisors on advanced tax and estate planning strategies using Private Placement Life Insurance. In this conversation, he explains why PPLI is not simply about buying insurance.
It is about building a structure around long-term capital, especially for investors who have already used the obvious planning tools and need a more sophisticated way to think about tax efficiency, privacy, liquidity, and wealth transfer.

Check out this conversation! The Tax Strategy Making Family Offices Rethink Bitcoin w/ Eric Runge

Most investors think Bitcoin is about price. At the high-net-worth level, a far more important conversation is happening around taxes.

Because Bitcoin isn’t treated like a stock or a business. It’s treated as property. And that classification opens up strategies around taxation and capital movement that simply don’t exist in traditional asset classes.

And once you understand that, the way you evaluate Bitcoin starts to change.
Most high-net-worth investors don’t dismiss Bitcoin because they don’t understand it.

They dismiss it because, from where they sit, it doesn’t meet the standard.
If your entire framework is built on fundamentals, intrinsic value, and cash flow, Bitcoin feels like a contradiction. It’s volatile, it doesn’t produce income, and it doesn’t behave like the assets that built their wealth. But that framework may be incomplete.

In this episode of Money School Elite, I sit down with Eric Runge to unpack how Bitcoin is actually being used inside high-net-worth portfolios, and why the conversation at that level looks very different from what most investors see.

Eric works directly with family offices and high-net-worth investors, helping them think about capital, risk, and structure beyond traditional asset classes. And in this conversation, he breaks down how Bitcoin fits into that picture, not as a speculative bet, but as a strategic layer.

Check out this conversation! Real wealth is built before the IPO, but you can't access it w/ Mona DeFrawi

Most people don’t realize that a large portion of real wealth is created before companies ever reach the public markets. In private companies, early-stage investments, and entrepreneurial ventures, growth happens the fastest.

For a long time, that part of the market has been largely inaccessible to retail investors, reserved instead for institutions and high-net-worth individuals. And that has played a significant role in the growing gap in wealth. In this episode of Money School Elite, I sit down with Mona DeFrawi to unpack how this system actually works and what’s starting to change.

Mona has spent decades working inside private markets, helping companies grow, go public, and navigate how capital flows behind the scenes.

In this conversation, we break down several important realities that experienced investors understand, but most people never see.

We discuss why retail investors have historically been “protected” out of private markets, how early-stage investing drives the largest returns, and why most of the growth happens before companies go public.

New conversation is live! - High Income, Financial Advisors, Still No Wealth? Here’s Why w/ Dave Wolcott - Check it out here: https://www.chrisnaugle.com/dave-wolcott

Most high earners think wealth is built by earning more, saving more, and staying disciplined within the traditional financial system. At the high-net-worth level, the real conversation is structure.

Because the issue is not always income. It is where the capital sits, how it is taxed, how accessible it is, how many jobs each dollar is doing, and whether there is an actual architecture around the wealth being built. Without that, even people making good money can still feel behind, overtaxed, overexposed, and dependent on a system they do not really control.

Most investors follow the conventional path because it feels responsible. Max out the 401(k). Build home equity. Defer taxes. Keep money in the market. And to be fair, that advice is not irrational. It is familiar, simple, and widely accepted. But it may also be incomplete for people who want real control, liquidity, cash flow, and long-term freedom.

In this episode of Money School Elite, I sit down with Dave Wolcott, Founder and CEO of Pantheon Investments, to unpack how wealthy investors think about capital differently.

Dave spent the last 25 years studying how the top 1% actually build wealth, and his perspective is not about chasing returns or rejecting every traditional strategy. It is about building the infrastructure around your capital: tax planning, asset repositioning, private investments, liquidity, relationship capital, and making every dollar work across multiple dimensions.

He shares how wealthy investors build infrastructure around their capital, reposition idle assets, and make every dollar work across multiple dimensions.

New episode is live! The Silent Wealth Leak Most High-Earners Miss w/ Robert Rolih - Listen here- https://www.chrisnaugle.com/robert-rolih

When your income starts to scale, the instinct is to focus on earning more and delegate everything else.

You build momentum, create cash flow, and then hand your capital over to advisors, funds, and institutions that are supposed to manage it efficiently in the background. The system looks sophisticated, regulated, and optimized, so it feels like the right move.

But what many high-income earners and investors don’t realize is that the biggest risk to their wealth often isn’t the market… It’s the structure their money sits inside.
Because once capital is placed into systems you don’t fully understand, small decisions start compounding in almost invisible ways. Fees that seem insignificant begin to erode long-term growth.

Portfolios that look diversified turn out to be overlapping and inefficient. And over time, instead of compounding wealth, you’re quietly leaking it.

In this episode of Money School Elite, I sit down with Robert Rolih, investor, entrepreneur, and author of The Million Dollar Decision, to break down what really happens to your money after you’ve made it.

In this conversation, we discuss why small, seemingly harmless fees can significantly delay your financial freedom, how a lack of visibility into your own portfolio creates hidden risk, and why many investors don’t actually know what they own.