The Awful Truth About Real Estate Everyone Is Too Afraid To Talk About

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Guys – I’ve been writing this particular article for about four months; writing and deleting, writing and deleting, and on, and on, and on…  I don’t know what it is about this one.

I seem to feel innately what I want to say, but I just can’t seem to get it out!

I could, of course, emulate my dear friend Brandon Turner and write about How You Can Buy a Small Multiplex and how you can do it in the next 90 days, or something to that effect, but I’d be crossing into Brandon’s territory which is severely punishable at BiggerPockets; so – I can’t do that.

Related: How to Buy a Rental Property in the Next 90 Days (With Bonus PDF!)

And to tell you the truth, I’d loose my mind from boredom…

No – there’s more to writing but this one is just so tough for some reason.  So, today I sat down in my glider with the intention to finally get this article out of my system.

I’ve been thinking about this for a long time, and I am finally gaining some clarity on what I want to say and why.  This will not take long, so bear with me please!

How I Bought, Rehabbed, Rented, Refinanced, and Repeated for 14 Rental Properties

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Click Here For Your Free eBook

Is America Over-Medicated?

I know – what a segue…  But the answer is abso-freaking-lutely!

I see people reaching for their favorite flavor of antibiotics over so little as a sneeze! We, as a nation, flat out consume too many drugs…

In short, there are two types of people in this world relative to medication.  Most people believe in pills, which is easy to understand since pills alleviate the symptoms and discomfort in the short term.

Pills may even expedite the recovery process (this time around anyhow), but what about later…

But then there are those of us who believe that the symptoms, as annoying, uncomfortable, or even painful as they may be, are indicative of the body’s immune system putting up a fight, and that the process of defeating the illness a lot of time, simply entails us getting worse before we get better.

Naturally, there are situations which warrant medication but do you see what I am saying..?

Personally, I tend to be all about allowing the body to fight – it may be a little more painful and take a little longer but what doesn’t kill us, will make us stronger!

What Does Any Of This Have To Do With Real Estate?

Nothing – except for the fact that Real Estate works exactly the same way!

It usually gets worse in the immediate in order to get better in the long-term.  Every new acquisition usually stretches us, at times to the point of breaking, before it gets better and contributes to the strength of our over-all business.

Seriously, did anyone out there imagine for a second that all those wonderful triplexes and 6-plexes that my friend Brandon writes about in his articles, really happen without pain?  Seriously…?

There is pain, my friends.  The process is painful for his wallet, for his psyche, for his time and even for his whole family to a certain extent.  How do I know this? Brandon is my friend and he’s got my number – that’s how!

Or, what about that 10-plex that I bought because it looked like $1,500 of monthly cash flow at 100% financing on paper, but having filed my taxes I realized that I’ve only barely broke even in the first year?

You think it wasn’t painful to spend $30,000 in the first 12 months, or to go through the process of evicting a bunch of people?  I am sure that over time this 10-plex will prove to be an excellent asset to own, but in the mean time – it’s a lot of pain my friends…

Related: One “Painful” Tip You Can Start Using Today to Get More Deals

But – Brandon And I Still Do It!

That’s right – we still get ourselves in the middle of situations akin to physical ailments and we take the pain as big boys do, and allow our investment immune system (otherwise known as skill) to fight and defeat the virus that we knowingly inject into our businesses via deferred maintenance and a bad tenant base.

We do this with eyes wide open, knowing and feeling comfortable with the philosophy that we must to go through pain in order to come out smelling like the couple of pretty roses that we are (well – may be Brandon isn’t pretty enough to be a rose; what’s another flower that better suits him? Be sure to share your thoughts in the comment section below!)

What’s Another Way?

Well – we could take the pill and make all of the aches and discomforts disappear.  We could buy A Class managed property at 4% CAP, and perhaps in a different time and place that will be something to consider, but for now we take the pain and benefit from the gain.

So, is buying real estate poison or cure?

Well it depends on how you answer the following question:

Question: Are you willing to set yourself back in order to propel ahead?

Incidentally, if your answer is “no”, are you sure that real estate is the best choice of investment vehicle for you?

About Author

Ben Leybovich

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


  1. Go ahead and write about buying small multiplexes, it’ll give Brandon something to write in retaliation. LOL

    Even the best property will eventually cause one pain sooner or later. Case in point- $6,000 heat pump in one of my best rental this month. If my rentals weren’t so large I would rent only to seniors, never had a problem with one.

    RX: take two seniors and call me next month.

  2. Dawn Anastasi on

    There is always the “rehab period” for me. I buy a property, have to fix it up, then get tenants. I think I get everything but I’m not actually living there so sometimes, something comes up that one would know by living there (e.g. showering, etc.) I’ve never had a major issue and the rehab period is something I always look forward to being DONE! But I like the “before” and “after” and reflecting on that.

    • Agreed – there’s always the “courting period”, but as I get older I am getting more and more tired of it. Now-days, it better be 100 units and really make a windfall impact on my bottom line when complete if I am going to go through it – just not worth it to me for the small stuff; I’ve got enough…

      Thanks so much for your comment Dawn!

  3. “did anyone out there imagine for a second that all those wonderful triplexes and 6-plexes that my friend Brandon writes about in his articles, really happen without pain? ”

    I am glad you have pain too (not really). Every purchase I make, I wonder if I am going to go broke. I analyze the numbers 100x over, and am very conservative, and I have been blessed tremendously for it. But it is still a bit nervous on EVERY one. Am I going to lose on this one? goes through my head on every one.

    Thanks for the confirmation!

    • Hey Eric!

      We spend so much time on BIggerPOckets motivating people by way of writing articles around “how good it can be”. Sure – we believe it can be good; that’s why we are all still in the game. However, pain is a reality of REI. This is as much a full contact sport as anything, and I think it’s important that we open up about that side of things…

      Thanks so much for commenting Eric!

  4. Those REITS are looking better and better after reading these past few articles. I am so looking forward to building my rental portfolio to hedge against corporate downsizing and create my own parachute. Realestate to me is a business. Im just creating a job for msyelf that can pay my bills without having to work 200 hours a month. Is that even possible…….?

  5. When I first started reading your article, I thought it would be a tenant story! I’ve had my share of medicated tenants as well as those who should be medicated. I was lucky and experienced the most pain my first year in business. I got it out of the way quickly and learned and grew from it.
    If you keep telling the truth about pain in real estate investing, you’ll never become a guru!

    • Haha – that’s funny all the way around Amy!

      You even brought the “guru” into the mix – lol… People sometimes think that I love Real Estate; that I live and breath Real Estate. Not at all. RE represents solutions to very real problems in my life. So, I take the bad with the good and hang on for dear life. To suggest that there is no pain is at the very least disingenuous.

      Thank you son much for recognizing that being popular is less important to me than being honest!

  6. Travis Fisher on

    This one really hit the spot Ben.

    We’ve been getting our financial house in order to finally buy our first investment property and the closer I get the more I start thinking “do I really want to get in to this?”

    It’s nice to hear about the hard times as well as the good times. Then I won’t feel so lonely when it’s my to slog through the hard to get to the good.


    • Travis – the irrevocable fact is that in order to get to the good, you must go through the bad. Sure, once in a while someone gets really lucky in their “bad” is rather underplayed – this doesn’t happen often. Most of the time, the name of the game is – where do I get the strength to hang on…?

      The thing is, BiggerPockets happens to be home to the absolute best of the best; this is why the content here is so much better than anywhere else. But, this is also why it’s a mistake to judge this game based upon the successes of folks that are at home on BP – in a lot of ways we are the exception that proves to rule, as Jeff the bold guy likes to say.

      I tend to think that you guys need to see the other side of the equation, and there’s definitely another side! I am glad you enjoyed the article Travis – make your bed wisely because you’ll need to sleep in it my friend…

  7. Ilhan Dahir on

    Great article, really enjoyed reading. I think if people want something really bad, then they must go through the pain in order to mold. No pain no gain.

  8. There’s few other businesses out there where if a person applies themselves, and learns the ropes, they can make as much money as you can in real estate.

    This is a great blog post Ben, because everyday I read posts on BP of people that have heard the pitches, and think there’s no work involved, or that you can start with nothing and within a few months you’ll be making money hand over fist. If you want to be successful in real estate, plan on putting in the time, being laser focused, and making whatever sacrifices need to be made to get a deal going. You can’t give up! If that’s not you, then this business isn’t for you.

    Believe me, being developer/builders we have been stretched to the limits, pounced on, kicked around and one thing I know, you have to be tenacious, and willing to do what it takes to get a deal done, and yes, sometimes it’s PAINFUL! But, as they say, what doesn’t kill you makes you stronger!

  9. Sharon Tzib on

    I’ve undertaken many entrepreneurial endeavors in my life, not just in the real estate genre, and I can tell you that it was never easy, especially in the beginning. Where does one get the strength? I’m not sure, but when you’ve “burned your boats” and failure isn’t an option, that sure can be motivating. I will say that one thing that can ease the pain, that I’ve unfortunately learned the hard way over the years, is making sure you have enough reserves when you go into any new venture. Having a supportive partner is very helpful too.

    In terms of what kind of flower is Brandon, that’s a tough one. Since he’s such a rurrrrral guy, I’ll go with a sunflower 🙂 Take care, Ben.

  10. Karin DiMauro on

    Oh man, this is SO timely for me! We are in the throes of dealing w/an agent who I suspect self-medicates a bit too much, then throws temper tantrums and attempts to bully us w/idle threats about the deal blowing up (we’ve done everything they’ve asked, but the moment we push back even a little, watch out – The Boy Who Cried Wolf (and drinks too much) appears!). Throw in a buyer w/an FHA mortgage that has gone through several iterations and delayed the closing by at least 4-5 weeks … and OUCH. Pain and frustration.

    But are we learning? Yeah. We’ve had a number of “We’re not doing THAT again” moments. And when all is said and done – next week, knock on wood – it will still have been a pretty excellent rehab project w/excellent profit.

    So thank you! I’ve been attempting to step back, take deep breaths and focus on the big picture, and this blog helps remind me that this pain is all part of the growing process. We will be better and more savvy for it in the end.

  11. Ben,

    Another great read, it’s frightening during the acquisition period of buying a rental. I do not have experience in multiple units only SFRs but similar as it pertains to the beginning stages. I am looking forward to possibly buying my 1st 4plex this year and you and Brandon’s post really keeps me looking for my deal.

    Thx for the great read

    • Hey Marcus – thanks a lot for your comment.

      There is virtually no difference going from SFR to duplex or triplex, but there is a management going to 4-plex. It would be too long of a discussion for this post as to why, but I have an e-Book on Amazon in which I go into all of that.

      Friendly piece of advice – when you hear Brandon say something or see him write something, just ask yourself – would the Professor agree? 🙂

      Thanks Marcus!

  12. I am grinning! Partly because I enjoy this discussion and partly because I am in pain myself. After months of self educating, I jumped right in and bought a 56 unit complex. The figures made sense, I had the capital for the down payment, all the ducks in a row. Then came the closing…. Sigh! And the pain. The figures and due diligence, all positive, but then we needed to take over from a seller that did not want to let go. Didn’t want to hand over keys, collected rent when we were not looking. The list goes on…and on. My husband and I have been running a very successful business for over 15 years, and not one of those were without pain, some with severe pain. So I can rightly say, no business comes without pain. Success does not come without pain. Some deals come with a lot of pain others don’t.

    • Lani –

      Getting knocked down is indicative of progress; we can agree on that. So is getting up once knocked down; we can agree on that too.

      Where this gets interesting is defining the line of what is too big of a piece to bite off. There is a balance that exists, and it is a function of always remembering that:

      We don’t know what we don’t know! This, as much as anything, defines the boundaries of what is too much to take on and could bring us down. We live our lives on that edge…

      (Thank you for giving me a topic for an upcoming post 🙂

  13. Ben:
    Great article. I have made mistakes on each of the 6 apartments I’ve bought so far. Each, however, have been different mistakes so I guess I’m learning to not make the same ones. As long as they are not fatal you can persevere and get better. This business is not for the faint of heart or of fragile ego. Most successful people insist they learn the most from their mistakes.

  14. I really like this fresh angle of your column, Ben.

    Most of my past real estate deals have incurred short-term pain for the expected benefit of long-term gain.

    At times, that has meant “stretching” to buy all that I absolutely could, then hoping nothing goes wrong so that I can hold onto it all. Some would call it “overleveraging”.

    If one is going to do this, it will rarely be more rewarding than the past few years: where fixed interest rates are so low that our arbitrage over the life of the investment will almost surely swell ever-larger.

  15. Sara Cunningham on

    Ben you always come up with a topic that is near and dear to my heart lol. Yes there is a lot of pain. It’s bad when you don’t even want to check email any more because you wonder what the next problem is going to be. While working on getting my last two deals into shape with numerous cosmetic and capital expense items which are growing by the day, I wake up to an email from one of my Property Management companies that starts with the comment. Sara I wish I had some good news! Yes another major expense at a property that I’ve had for some years. What’s the saying ” when it rains it pours” well I just have to tell myself there is a rainbow at the end of it, grit my teeth and keep moving. Lol

    Thanks for the reality check Ben.

  16. Sara Cunningham on

    In this case there is a rainbow! Capex right now but I knew that going into the last two deals. Turnover hasn’t been a problem to date.

    However the one smart thing I have done is made sure that I have the resources and funds to cover all those rainy day scenarios, or at least so far. I like to think that all the money I am putting in now on HVAC new plumbing etc will pay off down the road.

    Look forward to your next article as always.

  17. Ken Huston II on

    Thanks Ben. The truth hurts sometimes. And medicine can taste like the worst stuff in the world. So we may as well suffer through. By the way, have you noticed that coming out of an illness you feel better than when you have been well for awhile?

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