The Real Estate Investor’s Guide To Never Giving Up

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Failure is a loaded word.

Throughout school as young men and women, we’re taught that if you don’t make a certain grade, you have failed.  In the real world, however, failure has a different face.

In most cases, there are allowances for mistakes and setbacks, but none of these are necessarily failures.  You learn from each of these missteps and push yourself a little further toward your goal.

In the real world, failure does not have to be as permanent as a grade that follows you around and a judgement from others each time you try to push forward.

Failure does not have to be a label that follows you forever.  Just ask almost any successful real estate investor what failure has done for them and most will tell you  that failure can be a great teaching moment.

Failure can be a great learning lesson in real estate investing.  The reality of failure is that it does not have to define you in any endeavor…especially real estate!

As the saying goes, “failure only happens when we stop trying”!

Real estate investment is not an easy road.  Yes, there are dozens of cable network shows that chop up 30 minute segments of instant success full of drama and decision.

Do they show the real world?

Not one that I am intimately familiar with.  But they do tell a story that all real estate investors should remember.  When you take out the dramatic cuts and the obvious acting and pay attention to the messaging, most are gilled with a message that you push through mistakes (failure) and learn to work with and motivate your team (to avoid failure) and cut your losses early on problem houses (limiting your failure).

For most investors, their real estate investing projects do not start off with instant success and if they do, most are not followed by continued success – at least not success only!

We’re seeing now, as the number of foreclosed homes decreases and the market becomes less of an easy win for real estate investors, that many are starting to leave what was once a crowded field.

It’s getting “too hard” for some folks.  But this just leaves more room for serious and dedicated investors.  Real estate investors who have been seasoned by failures big and small and have learned the secrets to finding success.

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Real Estate Investors: Redefine Failure

As a newbie real estate investor, you’re going to make mistakes.

You’ll probably lose deals, waste money and think at least a few times that you aren’t any good at this and should throw in the towel.  You will over pay…for everything.  You will over pay for the investment property.

You will overpay for the materials, the insurance, one or more of your contractors etc…  Remember, though, that there is a learning curve to investing in real estate – just as there is in any serious pursuit.

No amount of mentoring, hand-holding, program buying or life altering programs can eliminate the learning curve entirely.  As with anything in life worth doing, there is a process that you have to go through.

A growth pattern that every successful real estate investor has to go through regardless of active or passive investing.  Failure is part of that process.  For some it will be small failures and others it will be large failures, but they will exist in the path that every investor takes.

Related: 3 Reasons Why You MUST Fail At Real Estate Investing

Determination will take you a long way. Even in face of naysayers, believe that you can learn and you can do this.  Be your own best cheerleader.  You haven’t failed at investing until you give up on it.  If you never give up and can avoid making the same mistakes over and over, you will learn and grow.

Deals will come and go, and you can learn from every interaction until you’re a seasoned veteran with your investments.  See “failures” not as dead ends, but as opportunities for growth.

While there will always be other real estate investors who are more experienced, better connected and better funded than you are, it doesn’t mean that you can’t find success in your investments.

Surround Yourself with Positive Influences

If you can, make connections with people in your life that will be encouraging and offer sage advice.

They will not all act as mentors so do not expect them to.  But listen when they speak and ask questions that matter.  Do not waste time with how much they make or how great their last deal was.

Those things do not matter.

Ask how they did it.  How they found the deal and what steps they took to get it under contract and finalized.  Ask how they saved dollars on the renovation and any tips they have for saving a few dollars while still having great quality.  Ask how they rented or sold a property so quickly and if they held out for the highest price or believe in taking the best price as fast as possible.

Related: How Life Coaching has Helped Improve My Business and Life

You will glean little secrets to philosophy from the best in the business and those philosophies will be where the success is made.  Maybe it’s another investor who you have a rapport with, or a family member who believes in what you’re doing.

It could be an investor who always sits off to the side at investor meetings or possibly the one surrounded by everyone.  While you may find yourself in moments where no one seems to think you can do it, it’s always good to have someone who does.

I know from experience that most successful real estate investors want nothing more than for you to be successful too.  They operate with an open mind and openly share advice and tips.  They understand that there are no secrets nor are there any shortcuts.

There are, however, things you can do and things you can avoid that will make your life easier and your investments more successful.  It does not matter if you are actively looking to fix-n-flip a single-family house, buy a multi-family property or passively invest in long-term buy & holds.

Many investors have gone before you and the more you can listen and learn from those that are successful the better off you will be.  Most will share their mistakes (failures) and openly tell you that they have not been 100% right every time.  Those are the ones you listen to the most…

Let Others Pick You Up

Learn from other investors and allow friends and family to offer a pick-me-up when you’re feeling low about investing.

One of the best investment strategies is to surround yourself with a good network of support.  Having a good support team is sometimes as important as the working team.  Now, you can’t get all caught up with the niceties and pick-me-ups and forget that you have to learn when you are struggling.

Surrounding yourself with support will not replace learning.  Pick-me-ups are important, but if you find yourself needing a pick-me-up at every stage of a deal….and on every deal, then you may need some re-evaluation as well!

No one starts off with instant success. Be patient with yourself and with the process of real estate investing. Dedicate time and energy to learning the most you can and surround yourself with great influences.  Your best tool is going to be a closed mouth and open ears with a pad in front of you and pen in hand.  Take notes and learn!

If this sounds like a bunch of business book mumbo-jumbo, well, I read a lot of business books.  I am a firm believer in the basics that so many business books espouse and when I look back at my own business and investing experience, I know that the above tips were crucial in my own growth.

My family has built 10 businesses that have reached $10 million in annual sales and have placed hundreds of properties in our personal and combined portfolios.  We have also all had our share of failure and learning curve experiences.  I tell you there is a process to becoming successful, I speak as someone who has traveled the road.

Be open and honest and always aware of where you are as an investor, and you can over-come any failures, big and small.   How do you keep enthusiasm for investing when circumstances aren’t going your way?

Tell us your investment strategies in the comments section!

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About Author

Chris Clothier

In 2005, Chris Clothier (G+) began working with passive real estate investors and has since helped more than 1,100 investors purchase over 3,400 investment properties in Memphis, Dallas and Houston through the Memphis Invest family of companies.


  1. Gregory Roman on

    Good article. The statement, “Failure only happens when you stop trying” is true. It was put another way by Winston Churchill, the Prime Minister of Great Britain during World War Two,
    When he was asked for the definition of success he said:
    “Success is moving from failure to failure without losing any enthusiasm”

    Keep up the good work!

    Greg Roman

    • Chris Clothier

      Hey Greg –

      Thanks for leaving your comments on the article. I love the quote you shared from Winston Churchill. That is so true and as we all know – or at least anyone who has been in real estate for a while – failure happens. We make bad buys, approve bad tenants, sell things too cheap, hire the wrong contractor, etc., etc…

      These things happen and the key to success – the key to growing and learning – is getting over mistakes quickly and deciding not to make the same mistake/failure twice! It may happen, but if your mindset is correct – you can go from one to the next and keep right on trucking.

      Thanks again for the comments – Chris

  2. Chris I am a big fan of yours and of your brother.

    My simplest advice to struggling real estate investors is understand:
    1. You are what you read
    2. You are what you say
    3. You are what you hear
    4. You are what your “little voice” in your head says.

    I read this every day yo psyche myself up.

    Our Credo as Real Estate Investors:

    I am a Real Estate Investor.

    Of all of the occupations I have tried, researched, pondered, and read about over the years, there is none which compares to mine. My work is fun. I take ugly houses and make them beautiful. I help people out of difficult situations.

    I am a Real Estate Investor. I am my own boss. I often work in my pajamas from the comfort of my home. I have no employees to baby sit, no perishable inventory to move, no franchise fees to pay, and no store to maintain. Still, I am in the top 5% of all income earners.

    I am a Real Estate Investor. I now enjoy freedoms I’ve never had before. I am the master of my day. I choose who to work with. I choose my hours, and I decide if I will work 20 hours or 40 hours this week. I can also choose to take the day off, without obtaining anyone’s permission. I can take a month-long vacation. I can sleep in, or take a power nap after lunch if I want. I can review my notes and return my calls while lounging in my jacuzzi. I no longer have to commute during rush hour.

    I have the freedom to spend lots of time with my wife and children. I do not have the stress and pressure of needing to close my next deal by the end of the week, by the end of this month, or even by the end of this year.

    I live in one of the nicest neighborhoods, in one of the most beautiful states, in the best country that has ever existed on this Earth.

    I am a Real Estate Investor. There are many who ‘want’ to be like me; many who are ‘studying’ to be like me; and many more who would be like me, but are just waiting for ‘this opportunity to appear’ or ‘that circumstance to change’… At the end of the day, very few actually are like me.

    I have been very fortunate and blessed. I am finally living my dream. I love doing what I do, and I would not trade places with anyone, nor trade my life experiences for anyone else’s.

    I am driven by the belief that life is short, and we need to ‘make a difference’ in the short time that we’re here, because after all is said and done, it’s really not about ‘us.’

    I am a Real Estate Investor.

      • Chris Clothier

        Brian –

        This is awesome! Some will scoff at what you wrote and say that it is hokey and the real key to success is just to go to work.

        Reality is – how hard you are willing and able to work and your ability to persevere when times are tough – is a direct relation to how you see yourself and how much you believe in yourself. The key to not quitting when times are tough is simply believing.

        I’m not sure if Josh Dorkin is going to read all of these comments, but he is one of those people whose opinion I really value. Over the years of talking and sharing different ideas and philosophies about business, he is a great example in my opinion of believing in YOUR vision and not compromising as you grow. I don’t know how much struggle or failure Josh has experienced with, but I do know that he could have taken short cuts and instead decided to do it his way. That took some time, but he is a great example – and this awesome site is the result – of believing in yourself and surrounding yourself with people who believe in you.

        Thank you so much for such a long and detailed response. Hopefully people who read this will understand that you have to see yourself as a success and believe long before it can happen!

        All the best – Chris

  3. Jamie Montpellier on

    Failure… it’s a deafening word for many of my high school students.

    I wholeheartedly agree with the post and will use it to fuel my passion for this new adventure. Now if only I can find myself affordable properties and get the wheels turning. 🙂


    Jamie Montpellier

    • Chris Clothier

      Hey Jamie –

      As a teacher you are in such a unique position to mold your students. I love that you are reading and commenting on here. If you really want to get started, make sure you are on a path to learn and keep surrounding yourself with people who want to help you. The ability to afford properties is a direct result of who you are surrounding yourself with and the actions you are taking. They are out there, but you may have to be creative in how you find them and creative in how you get started. It may not look or be exactly the way you think it will be today.

      Just believe in yourself and diligently make your plan and work your plan!

      I sincerely wish you all the best! Thanks for what you do as a teacher! – Chris

    • Chris Clothier

      Jonna – Thanks for reading the article and taking the time to respond! I like that you used the word “critical” in your comments. You are so correct and that is a powerful word. Very few people have climbed to their goals on their own or alone. We have to do the heavy lifting, but having others around you to help encourage us is a big, “critical” piece.

      Thanks again – Chris

  4. Great article Chris.

    Failure is part of taking risks, and taking risks are part of finding success. But with REI, there are so many opportunities and so many places you can learn it’s possible for new investors to sidestep a lot of the mistakes others have made. Being a lifelong learner pays big dividends down the road.


    • Chris Clothier

      I agree Sharon. Thanks for taking some time to read and write your comments on the article. Great points about taking risks and learning from others. It is important to balance those for sure to mitigate how painful mistakes can be!

      All the best to you. Hope things are going well for you – Chris

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