Money School Elite

Franchising is promoted as passive income, mailbox money, even a 5-hour a week side hustle. SBA loans come easy, and you can even use a government incentive program to roll over retirement assets into a franchise. But for wealthy investors, there is both opportunity and risk. I wanted to take an honest look at both, and break down how savvy investors evaluate a franchise opportunity. So I brought...

The real estate investing landscape is a mess right now.  Real estate investors who were going heavy during the Covid era, enjoying low interest rates, are struggling to keep their doors open and wondering what's next.  But not everyone. Some investors are looking at this market as a buying opportunity. In this episode, you'll meet Chris Lopez, co-founder of Property Llama.  He spotted an opportun...

Self-storage gets a lot of attention, but is it true passive income? Neil Henderson says passive income is a spectrum. And he's absolutely right. As head of Investor Relations at Nomad Capital , and host of Road to Family Freedom podcast, Neil's team is doing the daily work that puts their investors further on the passive end of the spectrum. He joined me to share the reality of investing in self-...

What's the near future of private credit and where are we in the consumer credit cycle? Should individual investors look to private credit as an investment vehicle? Vervent founder and CEO David Johnson is one of the best people to ask, as Vervent helps rescue distressed loan portfolios. David is also a high school dropout who went on to a Stanford MBA and stints at Bain and McKinsey before buildi...

High net worth families can suffer huge losses by assuming your estate plan works for current conditions, even after those conditions change. The estate tax exemption, which is generous right now, is a perfect example. Estate attorney Steve Gibbs joins me to share his approach to wealth transfers for high net worth families. Steve is the founder of Wealth Transfer Coach and author of books such as...

A major commercial real estate syndication just collapsed, and $30 million worth of investors are going to lose their money. Other syndications are struggling to stay afloat…issuing capital calls and freezing distributions to investors. To understand what's driving this wave of failures, I reached out to Ryan Caldwell CCIM®, CPM®, Co-Founder and CEO of Resolute RDM and an 18-year veteran of commer...

What if the reason you pay more in taxes than necessary is not that you earn too much, but that you begin planning too late? When business owners see wealthy investors paying lower effective tax rates, it is easy to assume they have access to loopholes or special rules. But the more important difference often lies in how deliberately they structure their income, investments, entities, transactions...

What if commercial real estate is already in a period of serious distress, but most investors cannot see the full extent of it yet? When a market turns, people expect the evidence to be obvious. They expect public defaults, collapsing prices, and clear signs that the cycle has changed. But this downturn is unfolding differently. Distressed assets are changing hands privately, lenders and instituti...

Most business owners think their exit value will come down to EBITDA and an industry multiple. But buyers are not only evaluating what the company earns; they are deciding how much risk they would inherit.  That risk can show up in customer concentration, weak financial reporting, founder dependence, an incomplete leadership team, or a business that has not been prepared to operate without its own...

Most people think the hard part is making money. But Lawrence Dunning's story shows that making money, keeping money, and using money well are three very different things. By 30, Lawrence had built a multi-million-dollar net worth on the trading floor in Chicago. Then he stepped away to pursue a dream that had a much smaller window: becoming a professional MMA fighter. When he came back, the tradi...

Most high-income W-2 earners eventually run into the same problem. Their income gets better, but their structure does not. Airline pilots are one of the clearest examples. They can earn exceptional money, receive strong retirement contributions, and build what looks like a very successful financial life on paper. But as the income grows, so does the constraint: almost all of it is active, highly t...

Most investors assume there are only two practical ways to approach Bitcoin: buy it directly and accept the volatility, or avoid it because it does not fit the framework that built their wealth. But Bitcoin mining introduces a different conversation. For most people, mining sounds too technical, too operationally complex, or too institutional to be a serious investment strategy. Servers, power, co...

Most business owners do not realize they have outgrown their accountant until the tax bill becomes impossible to ignore. The person who helped you when the business was small may have been perfectly fine at that stage. But as revenue, profit, assets, investments, and complexity grow, tax preparation is no longer enough. At a certain point, the business does not just need someone to file the return...

Most investors think wholesaling is just the entry-level side of real estate. At the strategic level, the better conversation is about deal flow. Because in a market where seller motivation is rising, buyers are more selective, and many casual wholesalers have left the business, the opportunity is different from what it was a few years ago. The edge is not simply finding properties. It is knowing...

In today's market, investors with real capital are facing a difficult problem. They do not want to be reckless. Equities feel expensive, private credit has shown signs of stress, rates remain elevated, and the usual recession signals have been flashing for longer than many expected. But they also do not want to hide in safety so long that they give up years of compounding. That is where the conver...

For many business owners, one of the biggest missed wealth opportunities may already be sitting inside the business. Technology upgrades, software implementation, equipment, and operational improvements. These are the kinds of investments owners are already making to grow, modernize, and stay competitive. But in many cases, they may not just be expenses or deductions. They may create R&D tax credi...

Most investors think real estate performance comes down to the asset. At the high-net-worth level, the more important conversation is often about control. Because a deal is not just a building, a market, or a projected return. It is an operating system. Who manages the property? Who controls leasing, maintenance, marketing, resident communication, and costs at the asset level? Who can make decisio...

Most people think franchising is about income replacement. At the high-net-worth level, the real conversation is about enterprise value. Because the operators who approach franchising seriously are not just trying to buy themselves a business. They are thinking about cash flow, unit economics, operational infrastructure, EBITDA growth, private equity demand, and whether the business can eventually...

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 lif...

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...

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...

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 a...

Most people treat taxes as a cost. Something to minimize, settle, and handle once the year is done. But what if that framing is the problem? What if you start treating your tax burden like a profit center, instead? By making that shift, taxes stop being about what you owe and start becoming a question of where that capital should actually go. In this episode of Money School Elite, I sit down with...

Diversification sounds straightforward in theory, but in practice, portfolios don't behave the way most people expect them to. Exposure is layered, concentration often shows up in places that aren't immediately obvious, and decisions that feel like you're spreading risk can quietly lead to doubling down on the same themes. Once you start looking at portfolios this way, the question shifts. It's no...

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 eval...