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Looking for a Real Estate Coach? Why Experience Matters

Summary: If you’re new to real estate investing, maybe you’ve thought about hiring a coach to help you get started. But how do you choose? What should you be looking for? In this article, we explain why we believe experience is one of the most important factors when choosing a coach.


[Disclaimer: We are not accountants, lawyers, or financial advisors, so please consult your own team of professionals about the topics covered in this article.]


If you’re reading this, maybe you’re already convinced that you need a coach to help you get started with real estate investing.

But for those who aren’t convinced, you might be wondering how you might benefit from hiring a coach.

I think the easiest way to think about the value of coaching is to look at top athletes.

There isn’t a top athlete who doesn’t have a coach. Some have multiple.

What does a coach bring to an athlete?

They help the athlete see things they are missing. For example, when you’re swinging a golf club, you can’t see your own swing. You need someone to observe your golf swing, identify the problem and offer some suggestions for correcting your swing.

They can help you break through whenever you’re stuck. Oftentimes, people get stuck because they are in their head too much. So it helps to have someone who knows you well and your tendencies to help you get out of your head.

We all have limiting beliefs that hold us back. Coaches can help you identify these beliefs about your own abilities and help you change those beliefs. Coaches know that the first step to achieving your goals is to believe that it’s possible.

So assuming you’re now convinced that you would benefit from a coach to help take your real estate investing to the next level, how do you choose? What should you look for?

In this article I’m going to focus on what I think is one of the most important factors when you choose a real estate coach: experience.

What do we mean by experience?

We break down experience into the following and we’ll go through each one by one: 1) experience investing through major market corrections (recessions, downturns, depressions) 2) years of experience 3) going full cycle 4) number of units.

Experience investing through major market corrections

The last major market correction was back in 2007-2009, also known as The Great Recession.

The beginning of that recession was over 15 years ago. For your coach to have experienced that recession, they would have had to have been investing for several years before that.

For example, I started investing in 2001, so by the time 2007 rolled around, I wasn’t just dabbling, I was actively investing. So when we refer to experience, we mean that someone has been investing for well over 15 years.

So why is this type of experience so important?

Some might pooh-pooh this degree of experience and tell you that they’ve read numerous investor stories and even interviewed dozens of them.

But the main difference between someone who experienced the downturn and someone who only heard about it is: emotion.

Why is emotion so important?

Emotion is vital because you remember the lessons from the downturn down to your core.

Don’t believe me?

Tell me where you were, what you were doing, when you first heard about the events of September 11, 2001.

You probably remember things as clearly as if it happened yesterday.

But what about last year on September 11? Do you remember anything about that day? You probably have no idea. That’s because there is no emotion tied to that date.

Real estate investors who experienced The Great Recession remember what it felt like to be an investor back then. They remember the fear. They remember the confusion. They remember the irrational behavior.

So the experience of investing during The Great Recession stays with you and helps keep you (and others) out of trouble. You not only remember the lessons, you have internalized it to your core.

I can’t tell you how many times we speak to our former students who tell us that they made a mistake because they ignored (or forgot) what we taught them.

They just didn’t have the emotional tie to remember the lessons we tried to teach them.

You can know something intellectually but you are more prone to forget the lessons.

We came across a course instructor who didn’t have experience investing through a downturn and was recommending floating interest loans. What happened when interest rates went up? His students lost their investment properties.

We came across another teaching land flipping. If you invested in land back in 2002-2007, you learned both the highs and lows of land flipping. The high was when the market was on an upswing. The down was when the market for land crashed. Trust me, I have an emotional reaction to land flipping. All I can say is, BEWARE.

The lessons from The Great Recession aren’t just about the negative effects of the downturn.

There were also numerous lessons from the hysteria that prevailed in the years preceding the downturn. So between 2003 and 2007, there was an irrational level of excitement and over-confidence.

So anybody who experienced the boom and bust, tends to be more humble. When things go well, they don’t pat themselves on the back and credit their own abilities. The truth of the matter is, anybody who invested between 2011 and 2022 did well as a real estate investor, whether they were truly talented or not.

Years of experience

Another important aspect of experience is the number of years someone has been investing.

Don’t be surprised if the coach you’re considering has only a year or two of experience. I would venture to say that anything less than 10 years is not enough experience.


The reason I picked 10 years is because it’s enough time for someone to experience the ups and downs of the economy at least a couple of times. This means that they’ve invested long enough to have experienced the beginning, middle and end of a recession. As mentioned before, we believe it’s important to experience all parts of a recession.

For example, while there hasn’t been a major recession in 15 years, we did have a minor recession in 2020 related to COVID that officially lasted just 2 months.

Going through these minor recessions multiple times can be instructive. It may not have the same emotional impact of a major recession, but it gives an investor a taste of what it feels like to invest through a major recession.

For example, during those early months of the COVID pandemic, lenders tightened their lending standards considerably. While it didn’t last, it was a shift in lending that investors hadn’t experienced in over a decade.

While the above experience matters, it wouldn’t be as meaningful if the investor was only involved in a few transactions. In other words, you might have invested for over 20 years but if you’ve only owned a couple of properties over those 20 years, it doesn’t mean much.

Therefore, in addition to the years of experience, what you want in a real estate coach is someone who has done a lot of deals.

This can be measured in two ways. One is the number of properties your coach owns and the second is the number of times your coach has bought and sold properties, also known as “going full cycle.”

We’ll describe each of these experiences below.

Properties owned

Mastery in anything comes from repetition.

So it makes sense that owning a lot of properties will lead to mastery in real estate investing.

Each property and even each apartment unit is an experience in itself. There are so many lessons you learn from owning these units.

These are the lessons that your coach can teach you, so you avoid the mistakes they made.

With all of that accumulated experience, your coach should be able to teach you a unique strategy that helps you grow your real estate portfolio faster and more profitably. This is how we came up with our proprietary strategy called The Fast FIRE System. It’s a strategy that we developed based on the lessons I learned from investing through The Great Recession.

Using this strategy, we built up our portfolio from a single duplex to over 150 apartment units. In addition, we also are general partners on an additional 1000+ apartment units.

And we’re not stopping. We are going to continue to push ourselves to grow, so we can continue to improve ourselves as coaches.

Going full cycle

While you may have bought a handful of properties over the last few years, if you’ve never sold those properties, you are missing out on a huge part of the investing experience.

So a “complete” coach is someone who has bought and sold A LOT of properties over the years. People in the syndication world call this, “going full cycle.”

So a question you want to ask your coach is, “How many properties have you bought and sold? How many times have you gone full cycle?”

While we currently own a lot of properties, we have owned even more properties when you include all of the ones we have sold over my 22 years of investing.

Our one-on-one coaching program

Over the years, we’ve had numerous prospective students ask if we do one-on-one coaching.

For years, we resisted mainly because we felt that there are significant benefits to learning while being part of a community. So our flagship real estate program, Zero to Freedom, is community-based. When you sign up, you join a number of other investors and we support this community along with coaches, volunteer mentors.

But we also know that not everyone learns the same way and some prefer the one-on-one approach. This is why we are formally launching our coaching program. As mentioned above, we have had coaching within our programs for years. So we have years of experience leading coaching programs.

The main difference is that this is the first time we are releasing a formal coaching program outside of our courses.

So now you have a choice of taking one of our courses, doing one-one-one coaching as well as doing both.

The choice is now yours!

Do you want to learn how to creatively fund your real estate portfolio and achieve financial freedom? Join the conversation! Follow our Semi-Retired MD  Facebook page and join our Doctors or Professionals  group!

Semi-Retired M.D. and its owners, presenters, and employees are not in the business of providing personal, financial, tax, legal or investment advice and specifically disclaims any liability, loss or risk, which is incurred as a consequence, either directly or indirectly, by the use of any of the information contained in this blog. Semi-Retired M.D., its website, this blog and any online tools, if any, do NOT provide ANY legal, accounting, securities, investment, tax or other professional services advice and are not intended to be a substitute for meeting with professional advisors. If legal advice or other expert assistance is required, the services of competent, licensed and certified professionals should be sought. In addition, Semi-Retired M.D. does not endorse ANY specific investments, investment strategies, advisors, or financial service firms.


Hi, we’re Kenji and Leti

we provide coaching and mentorship for doctors and high-income earners

Several years ago, we were newlyweds working as full-time hospitalists. On paper, it looked like we had everything: the prestigious careers, the happy marriage, the luxurious rental home, the cars, etc.

But in reality? Despite having worked for several years, we had very little savings. Despite our high income, we had very little freedom in terms of time or money.

One thing was clear: we had to do something.

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