The Real Secret in Real Estate Investing Is …

19 exists as a ground-floor resource center, a “how to” relative to all things real estate investing and, in the opinion of this author, BiggerPockets proves its’ worth every day of the week.  Amazingly enough, not only does BP attract beginners who browse for hours, days, and weeks never running out of stuff to learn, but BiggerPockets also attracts seasoned investors, a lot of whom have forgotten more about REI and deal-making than Ben Leybovich will ever know – and I know a few things.

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We Never Talk About This…

One topic, however, does not seem to get enough play, here or anywhere else for that matter.  This is understandable as this particular subject is difficult to talk about and not very “sexy”; it is a bit more “liberal arts” than what is customary.  In my opinion, however, this particular subheading is one of the most important, and while I do not particularly enjoy the responsibility of breaking this news to you, it has to be done because it’s the God’s honest truth and you should know it. Here’s the secret:

Real state investing really SUCKS from time to time!
Sucks is really not the right word, but for fear of upsetting your sensibilities I can’t use the word that I really want to use.  Just think the opposite of glamorous, fabulous, genteel, pleasant, fun, sensible, and easy, and you’ll begin to get close to what I am thinking.  However you define it, the point is that those of you that have been in this sport for a while have likely wanted to quit on more than one occasion – just admit it.  While those who are just now coming into the game WILL feel like quitting many times before you succeed – I guarantee!  Real estate investing is a full-contact sport.  We get beat up!  So the question is very simple:

When you get knocked down and you want nothing more than to just quit, why is it that you won’t?

Life Happens Whether We are Ready or Not!

To jump-start this conversation, allow me to give you an abbreviated version of my story.  I’ve played the violin from the ripe old age of five.  For as long as I can remember, there was never any question in my mind as to what I was going to do with my life – I am a musician.  But, when I was in the first year of my Master Degree program at the University of Cincinnati College-Conservatory of Music, I discovered that I have Multiple Sclerosis (MS), which is an auto-immune disease that I was told would substantially inhibit my capacity to control my physiology as time went on – the time-frame was – and still is – the big unknown.

When the dust settled and I began thinking rationally again, I realized that not knowing how long I would have full use of my body for meant that my path in life would have to be substantially different from most.  In terms of my financial life, it became apparent that I could not rely on a 9 to 5 job to get me to my retirement as most people do – it would be difficult to provide labor and services without my body’s cooperation.  I did a lot of research, and eventually arrived at real estate as the best chance for me to achieve my objectives.

I’ve done all right, though I’ll be the first to admit that the jury is still out on whether or not I will fully achieve my goals.  But I can tell you this – I get up every morning grateful that my body still works as it should (for the most part), and I try like hell…

I Can’t Afford to Fail.

I’ve made it my goal to earn enough passive cash flow by way of long-term real estate investments so that I wouldn’t have to have a job. I am certainly not alone in wanting to achieve this goal.  The difference, though, is that for most folks failure simply means having to go back to their 9 to 5.  They may not like it, but it is a back-up plan.  On the other hand, while I’ve been lucky thus far and the disease has spared me to a large extent, this may not be the case tomorrow.  I just don’t know, and that’s the point.  And since I can’t responsibly rely on earned income until I am sixty-eight and retired, I must succeed in my REI endeavor.  As they say in poker – I am all in.  There is no plan B for me.  My wife and kids need to be provided for.  I can’t fail!

I consider myself fortunate.  Life, by forcing my hand, has taken the possibility of failure off the table for me.  Succeed I must and succeed I will.  Most people reading this, however, must travel a much more difficult path.  You must make a conscious choice not to accept failure!  This is very difficult indeed, and I am proud of each and every one of you who takes this plunge.

One thing I’ll tell you here and now:  You won’t do it for money.  There must be something else that moves you; something much more important than money!

“Success consists of going from failure to failure without loss of enthusiasm.”

~ Winston Churchill

So, I ask again: Why are YOU going to succeed?  When everything turns to crud and when you feel like a miserable failure, why is it that you will go on without “loss of enthusiasm”?

What is your WHY?

You can learn everything that there is to know about the mechanics of real estate investing, but you will not succeed unless you can find the strength to hang on…

Photo: pedrosimoes7

About Author

Ben Leybovich

Ben Leybovich has been investing in multifamily residential real estate since 2006. His area of expertise is creative finance. Ben works extensively with private as well as institutional financing. Ben is a licensed Realtor with YOCUM Realty in Lima, Ohio. He is also the author of Cash Flow Freedom University and creator of a cash flow analysis software CFFU Cash Flow Analyzer.


  1. Wow! Your “why” is intense and touching. I appreciate that you’ve put it out there for us. On a forum like this people can be somewhat anonymous or known only by their REI knowledge or advice, but motives to avoid failure are personal, and rarely glamorous. My thoughts and prayers for much strength and success to you!

  2. This is definitely one of the most powerful posts I have come across on this forum. I admit wholeheartedly to having spent countless hours here in the past few months accumulating so much useful information to help propel me. Yet, this post seemed to almost shake me out of my often hypnotic state of mental immersion and made me remember my own personal “why” of doing it.

    Thanks for the post. Best to you, Ben.

  3. Ben-

    In this business your “why” has to be crystal clear and it has to be big. Otherwise you will throw in the towel when the going gets rough; and there are always rough patches.

    My daughter faced a similar situation with what was to be a lifelong chronic illness when she was a sophmore in college. These are pivotal moments that change your life. My role was to help her think through her situation much like you did. And like you, she completely changed course. In the end, I think you end up where you were meant to be. Great story.


  4. Thanks for sharing your story. I think one of the trickiest times is that initial plunge, especially with the way the market is. Everyone’s waiting for that golden moment when prices are at rock bottom and the getting is good, but like you said, it’s like a poker game. Sometimes you have to feel it out and just “go all in”, so to speak. Nobody can really accurately measure a time that prices have bottomed out, and sometimes suffering a loss for an incorrect call is just part of the game. Brush it off, and move on!

  5. Ben,
    You are “wise beyond your ears”! This newbie is GRATEFUL for your willingness to be authentic, open and honest about your experience on the REI journey. I truly believe we wind up where we can be MOST helpful. Your post has helped me do some real soul searching around my own “WHY?”. May you continue to enjoy each day with much love & grace.

    Be good to yourself,

    • Well Cheryl,

      I don’t know about wise, but more things tend to scare me now then when I was younger – that’s for sure. Commitment to the “WHY” is what makes it possible to step over ourselves and march on in spite of fear. This is my message…

      Thank you for taking the time to read and respond Cheryl

      • Your post is very inspiring. I’m dealing with my first property and UGHHH sometimes it really does suck! I never wanted to be a construction worker but I’m learning so much. Just have to stay the course and look at the big picture. Thanks for sharing your story and for your courage

  6. Tom Smith

    Ben, You nailed it. I seemed to be the vent for unhappy investors. As long as the job gets done, I take it. I too can not fail. I stay motivated because I’m the sole provider for my family. The ever changing market creates the issues with investors. Hot today, cold tomorrow. We have to stay aggressive. Nice post.

  7. Personally I think real estate investing should be looked at a long term investment
    10 years+

    The history of real estate and the stock market for that matter is it will always go up over
    a 10 year period.

    Home values will continue to increase as inflation rises.

    Personally I think its better to invest in areas that have high potential for growth aside from
    the normal value increase.

    For example areas like Miami Design destrict 5 years ago this was the ghetto and now its one of
    the hottest areas in Miami for both commercial and residential real estate.

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