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How To Avoid Losing Investments Before They Cost You Money

Key Ideas

  1. Learn how to profit from the “business common-sense test.”
  2. Discover the most important question you should always ask first… before anything else.
  3. Get 5 extra bonus due diligence questions to protect your money.

Ignorance about investing isn’t bliss… it’s expensive.

What you don’t know about investing will cost you money.

But the cure is simple – due diligence.

Due diligence is the critical skill that separates professional investors from amateurs.

Amateur investors act irresponsibly by risking their hard earned dollars on hunches, articles they read, brokerage investment advice, or hot tips without first performing due diligence. This invites unnecessary and avoidable risk resulting in catastrophic losses.

Professional investors do the opposite by investigating all investments first before ever putting a dime of capital at risk.

Sure, it’s a pain and sometimes takes hard work, but getting answers to the tough questions up front can save you from expensive losses down the road.

There’s simply no substitute for investment due diligence because it’s what you don’t know about investing that will cost you.

Below are the five due diligence questions you must ask yourself before making any investment.

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Due Diligence Question #1: How Can I Lose Money With This Investment?

This question is so important I’m tempted to throw away the remaining four questions and just repeat it over and over again until you get it in your bones.

You don’t know an investment until you understand all the ways you can lose money with it.

“Rule No. 1: Never lose money. Rule No. 2: Never forget rule No. 1.” -Warren Buffett

I can’t overemphasize the importance of this question. You must first focus on the return of your capital, and only second concern yourself with the return on your capital.

The first question in my mind when analyzing any investment is to find all the ways I can lose money by identifying in advance all the major risks that can lead to losses.

Once these risks are fully identified, the second step is to pro-actively manage away whatever risks are manageable. I explain this two-step due diligence process in greater detail below:

The First Step in Risk Management is to Identify the Risk Profile

Your first job is to identify all the ways you can lose money with a particular investment. You do this by identifying and grouping the risks associated with that investment.

You may be surprised just how much risk is manageable.

With proper portfolio design and investment strategy, you can usually manage away every significant risk (except one or two) to acceptable proportions.

These one or two remaining risks define the specific, uncontrolled risk profile for that investment. It’s the leftover risk you must live with.

In order to manage away the risks of loss, you must first know what risks are inherent to the investment you’re considering.

Using the stock market as an example, there are almost a limitless number of risks, but for practical purposes, they can be profiled down to a few major categories:

  1. “Company specific” risks include things like accounting scandals, lawsuits, and mismanagement – anything unique to the company that’s not part of the industry. These risks are managed away by diversifying among multiple companies. Mutual funds and exchange traded funds (ETF) are great examples of simple, cost effective tools to diversify away company specific risk.
  2. “Industry specific” risks include a downturn in demand for widgets, changes in consumer tastes, disruptive technology changes, and industry law changes. This risk is controlled by not concentrating your portfolio in a single industry.
  3. A closely related risk is “investment style” risk such as value vs. growth, or large cap vs. micro cap. The market will vary how it rewards or punishes different investment styles over time. For this reason, you should manage this risk by not concentrating too heavily in any one specific investment style like micro cap, value, or growth.
  4. “Market” risk is associated with a general downturn in investor’s appetite for stocks, causing an overall reduction in the valuation level of equities. This risk is manageable through a sell discipline, hedging, or by diversifying into non-correlated markets such as real estate, commodities, cash, or international equities rather than solely domestic equities.

Again, the above risk profiles are designed to illustrate stock investing. However, the same principles can (and should be) applied to every asset class in your portfolio.

“All of life is the exercise of risk.” -William Sloane Coffin, Jr.

For example, if you invest in real estate, you wouldn’t want over-concentrate in one property, or one city, or one type of property. It’s wiser to diversify away those risks that can be managed, rather than concentrate them.

The Second Step in Risk Management is to Create a Controlled Risk Profile

Once the risk profile for an investment is fully understood, your job as risk manager is two-fold:

  • First, you must design ways to manage away whatever risks can be eliminated.
  • Second, you must accept only investments where the remaining uncontrolled risk profile doesn’t overlap with other investments in your portfolio.

The end result is a minimization of the total risk for the entire portfolio, because it’s composed of mostly uncorrelated, managed-risk investments.

Why bother with all this? Because lower risk means losing less money when you’re wrong. That’s important because losing less when you’re wrong results in making more when you’re right.

“Often the difference between a successful person and a failure is not one has better abilities or ideas, but the courage that one has to bet on one’s ideas, to take a calculated risk – and to act.” -Andre Malraux

Your ability to manage risk is limited only by your knowledge and creativity.

The critical point to understand is that each investment has unique risk management tools available that are directly related to the unique characteristics of the investment and the market it trades in.

For example, one of the largest risks to income producing real estate is a change in interest rates, since mortgage interest is one of your biggest expenses. This risk can be managed by locking down long term, fixed rate, fully amortizing financing.

You can also limit your loss in real estate to the amount of your down payment through the use of non-recourse financing, thus controlling the risk of widespread capital losses impacting your entire portfolio should one property turn into a loser.

Notice that these two financing tools for managing risk are unique to real estate and aren’t available to investors in business or paper assets (the other two primary paths to wealth).

Each market has its own unique characteristics for managing risk, and the paper asset markets are no different.

For example, most securities markets offer high liquidity and low transaction costs, making them a natural candidate for cost effectively managing many risks through a sell discipline.

In fact, many mutual funds have zero transaction costs and daily liquidity through their commission free exchange privilege.

However, using a sell strategy in real estate to control downside capital risk doesn’t make sense compared to paper assets because of the prohibitively high transactions costs, and possible low liquidity during tough market conditions when you would want to sell.

In short, each market has unique characteristics that can be exploited to effectively manage the risk inherent in that market. What works in one market to lower risk may not apply in another market.

Doing your own due diligence and not relying on others is critical when choosing what to invest in. Ask yourself these 5 questions before you make any investment so you can avoid an expensive mistake.

In summary, your first due diligence question is to uncover all the ways you can lose money with an investment.

  • The first step in this process is to profile what the risks are inherent in that investment.
  • The second step is to develop strategies to control losses that match the unique character of that asset should the worst come to pass.

This is the essence of active risk management.

“And the day came when the risk to remain tight in the bud was more painful than the risk it took to blossom.” -Anais Nin

After you have managed away all risks that can be eliminated, you’re left with a specific, uncontrolled risk profile for that investment. This leads to your final risk management step, which is to make sure the remaining risk profile doesn’t correlate with other investments in your portfolio.

For example, when I purchase apartment buildings, they are financed with long-term, non-recourse debt to control both interest rate risk and to minimize total risk of loss should Murphy’s Law prevail.

In addition, each building is located in a different geographic market to assure the uncontrollable risk profile associated with location doesn’t correlate to other assets in my portfolio.

The risk of loss on each apartment building similarly has no correlation to the risk inherent in my paper asset portfolio or my business. Each risk profile is unique to the asset.

This excessive focus on risk might seem pessimistic to many, but my experience is quite the opposite. All it really does is bring balance because investing is by definition a game of greed.

The objective is to make money so the game is naturally played offensively by looking for the profit. By disciplining yourself to look for the loss, you’ll balance offense with an equally strong defense to create a winning team.

Stated another way, the hallmark of great investors isn’t just strong positive returns, but consistent returns through all market conditions.

This can only be achieved by focusing on controlling losses through disciplined risk management.

Due Diligence Question #2: How Will This Investment Help Me Achieve My Personal and Portfolio Objectives?

The portfolio objective for most investors is to maximize profit with minimum risk.

You achieve this goal by building a diversified portfolio of non-correlated, risk managed, high mathematical expectation investment strategies that capitalize on a competitive advantage in business, real estate, and/or paper asset investing. (Sorry, I know it’s a mouthful. Read it twice. There is a lot of meat in that sentence.)

But it’s not enough to just have a portfolio objective – you must also have a personal objective.

Your personal objective for investing is to achieve your portfolio objective in a way that honors your personal values, skills, and interests.

You’re a unique human being who must travel his own path to success. After all, there’s no point in climbing the ladder to success if it’s leaning against the wrong wall.

“Success with money, family, relationships, health, and careers is the ability to reach your personal objectives in the shortest time, with the least effort and with the fewest mistakes. The goals you set for yourself and the strategies you choose become your blueprint or plan. Strategies are like recipes: choose the right ingredients, mix them in the correct proportions, and you’ll always produce the same predictable results: in this case financial success.” -Charles J. Givens

Investment success is a lifelong process, and humans aren’t robots. The only way you’ll stay the course long enough to succeed is when your investment strategy fits your interests, skills, goals and resources, thus providing emotional satisfaction.

Stated another way, one of the biggest obstacles to success is getting distracted by the endless opportunities that will cross your path.

There are many ways to make money investing, but I recommend you find the one or two that are going to work for you, and not get diverted by all the rest. You must stay the course long-term until you succeed.

For example, I’ve worked with successful real estate investors in single family homes, commercial real estate, mini-storage, office parks, mobile home parks, notes, apartments, and more. Yet, seldom do I meet successful investors who are actively working more than one of these investment niches at any one time.

The smorgasbord approach to investing doesn’t work because each investment specialty has its own twists and turns that require specialized expertise.

Each niche has its own network that you must plug into for success. Each niche requires its own specialized skills and competitive advantage.

Nobody can (or should) be a master of all investment strategies because any one offers more than enough opportunity to reach financial freedom.

For that reason, you must determine which niche has the inherent characteristics that best fits your interests, investment goals, and risk tolerance because that’s where you’ll discover wealth, happiness and fulfillment.

Not every investment alternative is suitable for every investor. Your job is to find the one uniquely suitable for you.

For example, every investment has an “active” and “passive” component to it. If you don’t want to be a “hands on” real estate investor, then professionally managed apartment complexes make more sense than single family homes.

Even greater passivity can be obtained through paper asset investing if that fits your objective.

“Success is the progressive realization of worthwhile, predetermined, personal goals.” -Paul J. Meyer

However, if you’re age 55 and just starting to build for retirement, then beware of investment advice pushing you toward passive investments like paper assets. Your situation may require the leverage only available in business and real estate to allow you to make up for the late start and still achieve your financial goals.

In summary, if you want to succeed with investing, you must make sure Step 2 of your due diligence process analyzes each investment for congruence with your personal and portfolio objectives.

Below is a summary of the key points in the second due diligence question:

  1. Each paper asset investment strategy must have a positive mathematical expectation, and each business or real estate investment strategy must have a competitive advantage or exploitable market edge to place the odds for profit in your favor. This is the source of your investment return.
  2. The source of investment return must persist long enough into the future to be reliably exploited (adequate sample size).
  3. The investment strategy must be consistent with your personal skills, interests, values and abilities.
  4. The investment strategy must be consistent with your portfolio objectives.
  5. You must follow the investment strategy long enough to benefit from the competitive advantage without being distracted by other investment alternatives.

When your investment passes these tests, then it’s worth putting your hard-earned capital at risk to try and reach your personal and portfolio objectives.

Your financial coach can be particularly valuable in clarifying these principles and how to apply them because he has no conflict of interest biasing his investment advice since he sells no investment products.

Due Diligence Question #3: What’s My Exit Strategy?


You should always have your exit planned before acquiring any investment.

Why? No investment is appropriate forever.

Times change, market conditions change, and your objectives change.

You have a reason for acquiring an investment, and when those reasons are violated, it’s time to exit without delay. By knowing your reasons in advance, there’s no confusion or hesitation with the sell decision.

The reason it’s important to sell is because your portfolio is a living entity. Selling is to your portfolio what pruning deadwood is to a tree – it makes room for new growth to occur. It’s healthy.

You should never marry your investments.

Polaroid was once a darling blue chip stock that got decimated by technology changes. The rust belt was a real estate boom at one point, and the railroads were the king of transportation … but not anymore.

Everything changes, and you must change your portfolio to be congruent with the times.

There’s no such thing as a “permanent investment”. I’ve never met an investment I wouldn’t sell given the right circumstances. My job as the manager of my portfolio is to understand what those circumstances are, so that I’m ready to take action when conditions warrant it.

“Affairs are easier of entrance than of exit; and it is but common prudence to see our way out before we venture in.” -Aesop

I must know the assumptions and premises under which I enter an investment so that I can exit as soon as they are violated. Wherever possible, I must pre-define exit points in terms of price to control losses when things go wrong.

For example, I was a partner in a company that invested in real estate tax liens. We developed an entire business model to acquire valuable real estate for little more than back taxes. Yes, we actually purchased valuable real estate free and clear for pennies on the dollar of what it was really worth.

However, despite it being profitable, we exited the business because we learned how a legal assumption critical to the success of our model was simply wrong.

Once we uncovered the false premise of our model, we exited with our profit and moved on to greener pastures. We knew the reasons behind our model, and we knew when that model was invalidated.

Some would question our logic because the model had previously been profitable, but we knew it was just a question of time until the invalid assumption would bite us in the rear.

Similarly, when I enter equity positions, I pre-define the point at which I’ll exit based on price behavior that would prove my decision was incorrect.

In summary, you must always pre-define your exit strategy because the first loss is usually the best loss.

You must conserve capital when the inevitable mistake arises so that you’re prepared to invest in the next opportunity. By consistently pruning your portfolio of troubled investments, you’re making room for new growth to occur.

“A prudent question is one half of wisdom.” -Francis Bacon, Sr.

Due Diligence Question #4: How Does This Investment Make Business Sense?

Investing is ultimately about business, so every investment must make business sense.

What that means is the earnings, valuation, and return on investment must be congruent with the competitive advantage and barriers to entry possessed by the underlying business.

Let me clarify this idea with a little bit of Economics 101.

The world of business and finance is competitive. Above market returns and excessive valuations can only be supported if a significant competitive advantage coupled with barriers to entry for future competitors exists.

Otherwise, the high valuations and returns will attract competition until returns and valuations are forced down to market level. In plain language, that means your investment loses money – which is a bad thing.

For example, when the NASDAQ indexes were selling at over 200 times earnings in 2000, it didn’t take a genius to figure out this made no sense. How could a broad equity index representing a claim on the earning power of many companies in competition with each other be worth 200 years of earnings?

The truth is it wasn’t, and prices declined accordingly.

Similarly, when looking at various Southern California apartment deals in 2005, it didn’t take a genius to figure out they made no business sense when they were selling at prices so high you couldn’t service the debt with zero vacancy, no operating costs, zero taxes or insurance, and the lowest interest rates in the last 40 years.

There isn’t a valuation model in existence that can make business sense out of such inflated prices except the greater fool theory.

In summary, you can use the business common sense test to help you avoid dangerous investment manias and speculative bubbles that can lead to losses.

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Investment Advice: How To Avoid Fraud With The Business Common Sense Test

But the business common sense test isn’t just limited to avoiding investment manias and speculative bubbles, because you can also use this same test to sniff out potential frauds.

For example, a common fraud I see is the classic “Ponzi” scheme where someone is offering you outrageous interest rates on your money and “guaranteeing” your principle to invest.

The business idea supporting the investment usually sounds plausible on the surface, but is often laced with techno-babble terminology to intimidate the novice from asking the following necessary and obvious questions:

  1. How does it make business sense for the promoter to go through all the headaches of soliciting many small investors, when a legitimate business could attract all the capital needed from professionals with one phone call and at lower interest rates? (Answer: It probably isn’t legitimate, and a professional would figure that out with due diligence – amateurs don’t do their due diligence.)
  2. How are the exorbitant returns being promised adequately earned by the underlying business, and what are the barriers to entry that will keep those returns from being competed away (assuming the business is legitimate)?
  3. What’s really behind the “guarantee” and what’s really being guaranteed anyway? (Investment advice: the more somebody “guarantees”, the closer you should look at the guarantee and what you’re being guaranteed from.)

Knowledge is the nemesis of the con man, and an informed investor who’s willing to ask questions is his worst enemy.

The way you learn is by asking questions and listening – that’s what due diligence is all about.

Amateurs want to hope and believe they found an easy road to wealth so they don’t ask questions and don’t want to know the truth. The result is usually expensive.

I see investment fraud cross my desk with remarkable regularity. They’re out there, and if you invest, you must apply business common sense and do your due diligence to flush this stuff out.

I’ve saved many clients hundreds of thousands of dollars just by coaching them on how to ask the right questions … and I can help you, too.

“Just wanted to thank you for your advice about the (name withheld for legal reasons) investment. I recently cashed $220K out of his deals making over 20%. The money was over a month late but it arrived. A real estate lawyer thought it was the worst contract he had ever seen; from the first sentence he knew it was bogus. Working with you really helped. I got an education and learned to do my due diligence and let the numbers be the basis for my decision.” -Name Withheld For Legal Reasons

(This scam was later uncovered by the S.E.C. – investors who didn’t get out early lost everything.)

Always remember that your investment represents a claim on either the assets or earning power of the underlying business. Whether it’s debt, equity, or real estate, you must ultimately be able to make business sense of the return you’re being promised.

If it doesn’t make business sense, then it probably isn’t real.

Remember, if it sounds too good to be true, then it probably is. That’s just common sense investment advice for a competitive business world.

Due Diligence Question #5: How Does This Investment Affect The Risk Profile And Mathematical Expectancy Of My Portfolio?

For the statistically or financially trained, what we are talking about here is efficient frontiers and modern portfolio theory. For the rest of us, I’ll try to translate into plain English.

You should never add an investment to your portfolio unless it either lowers your portfolio’s risk, or raises its return. Preferably, you should get both.

How do you do this?

Let’s say you have an investment strategy in stocks that returns 8% compounded over multiple cycles in the market, but loses money during bear markets. If you add an inversely correlated asset (something that zigs when the other asset zags) with a return expectancy of 12%, you’ll lower the risk of the whole portfolio while increasing the return.

Examples of assets with low or negative correlation to domestic stocks include commodities, gold stocks, real estate, and certain alternative investment classes like hedge funds.

All investments should first be analyzed for their risk profile (under what conditions they will zag), and their mathematical expectation (how much they should return over time).

In Summary …

In summary, the game of investing is won or lost on the due diligence battlefield.

You must ask questions until you have the answers you need to make an intelligent decision. A quick review of the five “must ask” due diligence questions follows:

  1. How can I lose money with this investment?
  2. How will this investment help me achieve my personal and portfolio objectives?
  3. What’s my exit strategy?
  4. Does this investment pass the business common sense test?
  5. How does this investment affect the risk profile and mathematical expectancy of my portfolio?

My intention is for the above list of due diligence questions to serve as a basic starting point for your own due diligence process.

I don’t pretend this list is exhaustive because a whole book could be written on the subject. Other due diligence questions to consider include:

“The key to wisdom is knowing all the right questions.” – John A. Simone, Sr.

  1. How realistic is the expected return?
  2. What are the assumptions and drivers behind the expected return?
  3. How dependent is the historical return on the time period analyzed?
  4. What are the tax consequences of this investment?
  5. What’s the background and history of each principal involved?
  6. And many, many more.

My goal with this article was to arm you with some of the more important due diligence questions that can help you avoid the most obvious and expensive errors on the road to retire early and wealthy.

I hope it helps you.




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