πŸ“ˆ How the rich use debt to avoid taxes and get richer

An insider’s guide to borrowing your way to wealth

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How the rich use debt to avoid taxes and get richer

Ever wonder how Insiders and Elites use debt to build huge fortunes in record time?

And more importantly, how can you use these same strategies and tactics to your own personal life to build generational wealth?

Here’s the good news: if you want to build wealth the way the rich do, the β€œsecret” is to have a basic understanding of corporate finance.

The main difference between personal finance and corporate finance is understanding how to use other people’s money to buy (or build) cash flow producing assets…

And of course, how the tax code works, so you can maximize your potential profit margin on all income you earn.

In today’s issue of Private Capital Insider, we’re going to talk about how private equity firms have mastered this process through their trademark leveraged buyouts.

-Jake Hoffberg




The Difference Between Good Debt and Bad Debt

While I generally appreciate why financial gurus like Dave Ramsey are so anti-debt, and why plenty of people get themselves into trouble by acquiring too much debt…

When you look at all the richest people in the world, they typically have one thing in common: they borrow a LOT of money.

More specifically, they understand that we exist in a debt-driven financial system, and how to use debt to acquire assets that build wealth (β€œgood debt”)… not acquire liabilities that destroy wealth (β€œbad debt”).

Some examples include:

  • Business Loans: Debt taken to expand a business by purchasing equipment, real estate, hiring more staff, etc. The expanded operations generate additional income that can cover the loan payments
  • Mortgages: Borrowed money used to purchase real estate that will generate rental income. As long as the rental income exceeds mortgage payments and expenses, the debt is considered “good”
  • Student Loans: Loans taken to pay for education that allows acquiring skills and credentials that result in higher lifetime earnings. The increased income makes the debt productive

    [publishers note: I personally think higher education – and the student loan racket – is one of the biggest scams in America today. But otherwise, I am a big believer that investing in yourself to increase your lifetime earning potential is one of the best investments you can make in terms of raw ROI – especially as it relates to corporate finance and investing]

The key features of good debt are that it is used to acquire income-producing assets and has a reasonable cost structure compared to the expected returns.

If this is the case, that is how debt leads to greater wealth creation.

Bad debt does not help generate income or acquire appreciating assets. Instead, it is used for consumption.

Some examples include,

  • Credit Card Debt: Money borrowed on credit cards to finance consumer purchases like electronics, clothes, vacations etc. These expenditures do not help produce future income, so the debt is unproductive
  • Payday Loans: Predatory short-term loans with exorbitant interest rates that trap borrowers in cycles of debt. The high interest makes paying off the principal difficult
  • Car Loans: Vehicle loans are considered bad debt if the interest rate is high and the vehicle loses value rapidly. There is no asset to show for the borrowing

The key distinction is that good debt has a clear productive purpose while bad debt is taken on to fund consumption and lifestyle inflation. Avoiding bad debt and using strategic good debt helps magnify wealth.

But hey, I know you don’t read Private Capital Insider to get some cookie cutter answer you could google yourself…

You want to know about those juicy β€œInsider” secrets that you’re not going to find anywhere else.

And even though you might be happy living an all-cash lifestyle…

If you want to build true generational wealth, the #1 skill you’re going to need to develop is allocating capital towards productive investments.

Why? Because money is a commodity that can be bought and sold at a variety of prices (β€œcost of capital”).

And once you understand that the secret to building wealth is to play the Game of Money the way bankers do, you’ll see why debt is such a powerful tool.

With that in mind, let’s talk about how Private Equity firms have traditionally used debt to unlock one of the craziest money-making opportunities in finance: the Leveraged Buyout.

How Private Equity Gets Rich with Debt-Fueled Leveraged Buyouts

As a quick refresher – generally speaking, there are two main reasons people invest:

  • Money Now: the investor is looking to increase short-term cash flow to cover living expenses and lifestyle
  • Money Later: the investor is looking to increase net worth, which, in reality, is just cash flow at a future date

Bankers (i.e., β€œInsiders”) want their Money Now. But the general public (i.e., β€œOutsiders”) has been conditioned by financial institutions to buy, hold, and otherwise hope for Money Later.

So how do Bankers create Money Now, more commonly called cash flow?

In one word: Arbitrage

To create an arbitrage opportunity, you need to have the following criteria in place:

  1. An income-producing asset (such as an operating business, real estate, insurance policy, and bonds)
  2. A lender that is willing to lend against the asset as collateral, in order to obtain leverage (i.e., debt)
  3. Income that is larger than the loan payments and expenses related to the asset

This, in a nutshell, is the secret to passive income.

But the devil is always in the details. Namely, collateral and leverage.

More specifically, whose collateral is being used, and who is responsible for paying back the debt borrowed against it?

It is this devil that non-bank lenders (like Private Equity firms) are exceptionally well-experienced at using to their own advantage.

Enter: The Leveraged Buyout

Private equity firms are financial actors that sponsor investment funds that raise billions of dollars each year.

The hallmark deal structure of a Private Equity firm (or β€œsponsor”) is something called a Leveraged Buyout (LBO)...

A strategy for buying established companies using a large amount of debt – as much as 90% of the purchase price – with the plan to resell that company 3-5 years later for a profit.

How an LBO works

Some of the most iconic LBOs occurred in the 1980s, fueled by the availability of junk bonds and loose lending standards.

  • In 1989, KKR acquired RJR Nabisco for $25 billion, the largest LBO at the time.
  • Other famous LBOs in the ’80s included TWA, Beatrice Foods, and Safeway.

The LBO process is similar to buying a house with regards to how the collateral and leverage works.

For example, in many cases, an individual can buy a house by putting down 5-10% of the purchase price (equity), and borrowing the rest of the money from the bank (debt).

As a condition of that loan, the bank requires you to pledge the asset as collateral. However, that debt needs to be serviced – which refers to the money required to cover the interest payments on that loan.

The ability to service debt is a key factor when borrowing money – which makes sense, because the lender wants to know if the borrower is going to be able to make their monthly payments.

The same logic applies to buying a multi-billion dollar company using a LOT of debt.

The sponsor is going to borrow as much money as they possibly can, and then use the revenues of the business they are buying to service the debt.

The logic behind an LBO is simple:

  • Find companies you believe you can make significant operational improvements to, and drive meaningful growth (collateral),
  • Buy it with as much debt as possible, to minimize dilution of your equity (leverage), and then
  • Sell it in the future, for a multiple of what you paid, and cash out with a tidy profit.

For those who’ve read our article on the Buy, Borrow, Die strategy – which takes advantage of the fact that borrowed money is not counted as taxable income.

This is more like Borrow, Buy, Sell.

Actually, to be more accurate, it’s more like Borrow, Buy, Plunder, Sell, or Bankrupt (whichever is more profitable).

And here’s where those devilish details come into play.

After loading a company up with debt through an LBO, PE firms can then strip assets, sell off divisions, and cut costs aggressively to rapidly pay themselves back.

To make things even sweeter, PE firms often structure deals with “payment-in-kind” features that allow the company to pay interest on the debt, by issuing even more debt.

As a reward for loading the company up with even more debt, the PE firm can then use that money to pay their management fees, and issue special dividends to themselves…

Even if the company is struggling to service its debt and could go bankrupt.

But a company going bankrupt isn’t necessarily a bad thing.

In fact, the sponsor could actually stand to make more money by bankrupting the company than it would stand to gain by doing a pure β€œfix and flip.”

Here’s why…

A key advantage for private equity firms is that the debt used to fund LBOs is taken on by the acquired company, not the private equity fund itself.

This means if the deal goes south, the PE firm is not directly liable for the debts – only the company that borrowed the money is.

In fact, this is arguably a feature of the LBO model.

Why? If the overloaded company does go bankrupt, the PE firm can then take advantage of tax credits for canceled debt, which can then be used to offset the tax they would otherwise pay from the profits they just made plundering the company!

If that isn’t the definition of β€œheads I win, tails you lose” I don’t know what is.

As a matter of disclaimer, I don’t think all Private Equity firms are evil, bloodsucking capitalists who are a blight on society, and do far more harm than good…

But it’s hard to ignore the rather concerning examples of how these firms make huge sums of money through no actual value creation, but rather, through financial engineering and extraction.

For example:

Yet, private equity and its leaders continue to prosper, and executives of the top firms are billionaires many times over.

Even crazier? Because of the way these deals are structured, these sponsors are basically immune to any legal liability, and wind up getting massive tax benefits from their prolific use of debt (not to mention the lower tax rate they pay on the β€œcarried interest” they earn).

Consider the case of the Carlyle Group and the nursing home chain HCR ManorCare.

In 2007, Carlyle β€” a private equity firm now with $373 billion in assets under management β€” bought HCR ManorCare for a little over $6 billion, most of which was borrowed money that ManorCare, not Carlyle, would have to pay back.

As the new owner, Carlyle sold nearly all of ManorCare’s real estate and quickly recovered its initial investment.

This meant, however, that ManorCare was forced to pay nearly half a billion dollars a year in rent to occupy buildings it once owned.

Carlyle also extracted over $80 million in transaction and advisory fees from the company it had just bought, draining ManorCare of money.

ManorCare soon instituted various cost-cutting programs and laid off hundreds of workers. Health code violations spiked. People suffered.

In 2018, ManorCare filed for bankruptcy, with over $7 billion in debt. But that was, in a sense, immaterial to Carlyle, which had already recovered the money it invested and made millions more in fees.

The family of one ManorCare resident, Annie Salley, sued Carlyle after she died in a facility that the family said was understaffed.

Yet when Ms. Salley’s family sued for wrongful death, Carlyle managed to get the case against it dismissed.

As a private equity firm Carlyle claimed, it did not technically own ManorCare. Rather, Carlyle merely advised a series of investment funds with obscure names that did. In essence, Carlyle performed a legal disappearing act.

We can see similar stories to this one happen over and over again, across every industry that Private Equity touches.

And even though this is a well-known problem, there is no shortage of lobbying done on behalf of the industry to protect their favored tax treatments and limited liability.

Ironically, these PE funds came to prominence because pension funds – who, thanks to decades of poor management – need substantial, above-market returns to make up their funding shortfalls…

They seek to obtain those gains through a predatory practice that often results in stripping employees of their livelihood, and destroying their pension plans.

Final Thoughts: Be Careful Using Leverage

As much as I’d love to see some huge, fast gains in the β€œprivate equity” portion of my portfolio that would presumably come from a private sale…

As a co-founder at Equifund, and someone who considers himself a decent human being, I believe that better outcomes are produced when you invest in management teams focused on building an enduring, and eventually publicly traded, company that provides true value to the market…

Not a thinly veiled scheme that eventually leaves retail investors holding the bag.

Now, to be clear, I’m not saying that using leverage – in itself – is a bad idea.

But without proper governance – and a management team who believes in doing the right thing – it’s all too easy to go broke by acting irresponsibly with debt.

As Charlie Munger reportedly said, there are only three ways a smart person goes broke – liquor, ladies, and leverage.

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All information contained in this communication should not be considered investment advice, but education and entertainment only.Investing in private or early stage offerings (such as Reg A, Reg S, Reg D, or Reg CF) involves a high degree of risk. Securities sold through these offerings are not publicly traded and, therefore, are illiquid. Additionally, investors will receive restricted stock that is subject to holding period requirements. Companies seeking capital through these offerings tend to be in earlier stages of development and have not yet been fully tested in the public marketplace. Investing in private or early stage offerings requires a tolerance for high risk, low liquidity, and a long-term commitment. Investors must be able to afford to lose their entire investment. Such investment products are not FDIC insured, may lose value, and have no bank guarantee.

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