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165: Gray Hair, Peacocks and Unicornomics

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We recently had a Wealth Formula Network call in which we talked about an offering some members were participating in that I didn’t care for as much. One thing to remember is that smart people can disagree about things without anyone necessarily being wrong. I pointed out some things I avoid when I invest and the topic seemed to garner a lot of interest. So, I decided to share some of the lessons I have learned over the years. After all, the best way to become a good investor is through age and experience.

The problem is that age and experience are hard to teach. When I did my first face lift, I thought I was good. But looking back after doing 500, I definitely was not. I had the basics down and got lucky with my results, but it was no where near mastery.

When you are a young Turk plowing ahead full of energy, you look at guys a few years older and wonder why they are so cautious until, one day, you learn for yourself—the hard way. When you make a mistake that matters it will stick for ever.

The good news is that while mistakes are critical to learning, they don’t always have to be your mistakes. But in order to learn from others mistakes, you have to be humble and receptive. So, let me give you a few investing pearls that have come along with my graying hair.

1) When it comes to investing, it’s not just about the numbers. It is also an over-simplication to say to “invest with people that you know, like and trust.” Of course I truly believe that is a requirement. The problem is that I know, like and trust a lot of people with whom I would never trust my money. Would you trust your grandmother to choose where to invest your life savings?

Look for people who you know, like and trust, then judge their competence by looking at what they have already achieved. A track record is important and really is the report card that you need to look at. Don’t be part of someone’s resume building exercise or someone’s multimillion dollar lesson if possible. If someone has a full time job as a software engineer and trying to get you to invest in their $20 million dollar real estate acquisition so they can work toward quitting their job, politely decline and say you might be interested in 5-10 years.

2) Avoid “good from far but far from good investments”. Every species has some kind of physical attribute that make it more likely to reproduce. Think of the peacock with colorful patterned plumage fanned out for display purposes to attract a mate. Investments have similar qualities that are irresistible to investors and deal sponsors know it. Cash-on-cash is probably one of the most attractive features to the novice investor because, on the surface, high cash on cash numbers can be pretty seductive. Everyone loves the idea of replacing their income with passive cash flow asap.

Let me ask you this—would you rather get 25 percent cash on cash or 7 percent cash on cash? 25 of course, right? Well, what if the 25 percent depreciated down to zero in 4 years while the 7 percent cash-on-cash investment increased in value by 100 percent? 

All investment proformas must be considered holistically. As investors, we should be looking at the profit we make from our investments rather than being content with monthly checks that represent our own money being given back to us in small increments. I would suggest looking at investments in terms of annualized returns or internal rate of return instead. In the process of making this calculation, you will need to get an idea of how the investment will be exited. In some cases, you may discover that there is NO EXIT! No exit is not a good thing—tough to get a return of any kind on that.

3) Risk should be factored into your expected return as well. Many of the real estate deals we see in investor club project an annualized return of 18-20 percent—approximately doubling your money every 5 years. That’s pretty good right? I think it is. After all, we typically deal with tried and true multifamily real estate. If an apartment building has been around since 1980 in a nice market, that’s essentially a highly stable business that’s been around for 40 years. 

The risk of this business is significantly less than a start-up business that lives only in the imagination of the entrepreneur. Real estate investors really get messed up on this one. Established real estate is pretty low risk in competent hands. That’s why we are happy getting 8-10 percent cash on cash or 18-20 percent IRR. Those are great numbers for real estate. But the level of risk for a small start-up is significantly higher.

If you buy a small business from a mom and pop, you are going to pay 2-3X profit. That means that you should expect 30-50 percent cash on cash on that business. Why so much higher than real estate? Risk! Now, I see people advertising investments in start-ups with returns projected at 8-10 percent. Does that make sense to you? Maybe it does to you, but not to me.

Higher risk should mean higher reward. Make sure you don’t compare your rock solid multifamily real estate to a simple sparkle in an entrepreneur’s eye. There may be value in the start-up, but make sure your return prices in the risk you are taking.

4) Boring is good. The vast majority of my money goes to real estate or Wealth Formula Banking. Why?…because they are relatively boring. I like multifamily real estate because people have to live somewhere. I like some other classes of real estate too but I really like sticking to “roof over your head” kind of real estate. I like Wealth Formula Banking because of its track record dating back to before the civil war and the ability to use mass, velocity and leverage to amplify my real estate investments by investing my money in two places at the same time.

I’m fortunate in that I make enough money to afford investing in some higher risk stuff too. I have my asymmetric risk allocation as well—up to 10 percent in any given year. I call this my Maserati money. This money is what I use to take some big risks that could either go to zero or 10X. For me, it’s cryptocurrency. This kind of investing is really fun but don’t do it if you don’t have the money to lose. I still drive my 2007 Toyota instead of a Maserati or Ferrari because those types of things are guaranteed to lose me money the second I drive them off the lot (if they are new). I take that money and use it to invest in high risk, high reward stuff.

The bottom line is that unless you know what you are doing and have some money to lose, don’t chase shiny objects. Some things sound good but, when you get into the weeds, they are nothing but fool’s gold. Boring is GOOD!

5) It’s not what you make but what you keep. Going back to real estate, I like the fact that real estate tends to appreciate over time rather then depreciate to nothing (please don’t invest in things that depreciate to nothing!) Nevertheless, in the eyes of the IRS, real estate does depreciate and we often leverage it significantly with mortgage interest that is also deductible as a business expense. Therefore, if you get 8-10 percent cash on cash, you typically don’t pay any taxes on it. In fact, depreciation might exceed your income by so much that you can use those losses against other passive income (we see this with bonus depreciation all the time!)

Conversely, if you invest in debt and get 10 percent cash on cash but have to pay ordinary income taxes on it, how much are you actually keeping? Is the risk and lack of appreciation of fixed, high risk debt commensurate with the return you are getting after taxes? It may not be when you crunch the numbers.

Anyway, I could keep going—in Wealth Formula Network we recently talked about the classic great deal that is highly dependent on one guy—that’s another recipe for disaster. There are lots of patterns of bad investments that you recognize after you’ve been around the block a few times—sort of like PTSD.

In fact, I would go as far as to say that the key to becoming a good investor is to quickly identify the bad ones so you can spend time diving deeper on the rest. The good news is that most deals out there are not that great so you should be able to spend an increasing amount of time on good ones as you get better weeding the bad ones out quickly.

Anyway, those are just a few pearls. I could go on for a lot longer but I’m sure what I have presented is more than enough for one sitting. That said, when you are ready for more investment advice, make sure to listen to this week’s Wealth Formula Podcast that is focused on investing in those high risk, high reward start-up businesses. Damion Lupo literally wrote a book on this which he calls Unicornomics and you are going to hear all about it on this week’s episode. 

Damion Lupo

American Sensei. Yokido Founder. 5th Degree Black Belt.

Financial Mentor to Transformation Nation.

Best selling author in personal finance. Rewriting the rules and plan for retirement.


  • What is a unicorn and what was the inspiration behind the book Unicornomics
  • Centaurs versus leeches
  • The China 1% idiot statement
  • How to find “Unicorns”
  • Damion talks about eQRP
  • QRPbook.com