Personal Development

Confessions of Serial Mistake-Maker: How I’ve Found Real Estate Success Through Failure

Expertise: Mortgages & Creative Financing, Business Management, Landlording & Rental Properties, Commercial Real Estate, Real Estate Deal Analysis & Advice, Real Estate Investing Basics, Personal Development, Real Estate News & Commentary
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Pretty much without exception, every real estate investor or successful individual for that matter, will recount the many mistakes they've made before becoming successful. These anti-nostalgic trips down memory lane do make one feel better about their own mistakes and perhaps help one to realize such blunders are part of the learning curve. However, it is not uncommon for there to be an unstated yet harmful undercurrent. These discussions often come with a vibe that screwing up was a problem in the past and only in the past. Something like, "Yes, before I became successful, I made a lot of mistakes. Then I became successful and voilà!"

Let me let you in on a little secret: There is no point when you become “successful” and stop screwing up, sometimes royally.

Embracing Mistakes & Failure

Mistakes aren’t just part of the learning curve. They are part of life. While errors are more common when getting your footing in a new field, experience can lead to its own unique set of mistakes, like overconfidence and apathy. Yet the fear that many new investors have of screwing up can be the biggest hindrance to jumping in and moving forward. Well, for those who are afraid of such things, let me assure you that you will make plenty of mistakes.

Accept it and embrace it.

Indeed, many mistakes are actually a sign of progress. They show we are trying something new or pushing ahead. And while getting educated is extremely important, sooner rather than later we need to jump in (be it with real estate or otherwise), inevitably screw up and then learn, improve and move on.

It is in that vein that my brother has a sign in his office that reads, “Make more mistakes.” Lucky for me, that has never been a particularly challenging feat to accomplish. I’ve been investing in real estate for eight years, have lived around it for my entire life since my father started the company I now work for and have read a small library of books on the subject. Yet even with all of that, I still take the advice of my brother’s sign plenty.

My Experience Making Mistakes

The first property we ever bought in Kansas City is still the biggest, and we purchased while we were all living out-of-state (I moved to Kansas City three months later and my brother followed shortly after). The price was so low that it had to be good, right? We skimped on due diligence, only walking a portion of the units and relied too heavily on an inspection report and ridiculous appraisal. We also trusted the rent roll without verifying it and learned that the $485 rents some tenants were paying were only being paid on paper. The property was a giant money pit and took almost two years to turn around. Good times.

The worst case was a project manager who, while seasoned in construction, was completely inept at any sort of paperwork or systematized process and thereby left an expensive, disorganized mess in his wake. He was so lazy in this respect that he passed off putting together scopes of work onto other people (including me) and wouldn’t even keep a time card. However, he was my friend and had a lot of experience that I looked at with a sort of mild reverence. I just trusted that he had it under control. It took well over a year to figure this out.

Related: The Top 8 Mistakes Made By Rookie Landlords

Oh and by the way, several months after we let him go, we came to realize he had been taking kickbacks from several subcontractors. Even better times.

More than once I've bought houses with broken sewer lines that I didn't know about. More than once I've missed that a house had galvanized plumbing that was so rusted out it needed to be replaced. More than once I have misjudged the HVAC or windows or roof or missed knob and tube wiring or substantially underestimated the necessary budget of a project or used bad comps when analyzing the LTV of a property. I've hired a receptionist with a severe drinking problem and used a contractor who was uninsured unbeknownst to me. I've passed on deals I regret. I've bought deals I regret.

I hesitate to count the times I’ve sat alone in my office shaking my head thinking, “I know not to do that. Why on Earth did I do that?”

My brother can speak to the same. And my father, who is one of the best businessman I have ever known, can certainly do the same. He sold a house once for $45,000 in the late 1980s that he just learned sold for $950,000 a few years ago. He bought a house in Newport, Oregon (three hours from where he lives in Eugene) based on a lease option that would have guaranteed a sizable profit (spoiler: such guarantees don't actually guarantee anything). A bookkeeper he hired appeared to have had a sort of scorched financial statement policy that left our books in such bad shape that at one point, no bank would even consider lending to us.

In Good Company

Fortunately for our self esteem, we’re not alone in this matter. Lists have accumulated throughout the Internet (such as these) about the many failures of extremely successful people. A brief sampling:

  • Bill Gates’ first business failed miserably
  • Richard Branson did terrible in school
  • The Beatles were rejected by Decca Records
  • Stephen King’s first novel was rejected 30 times
  • Dr. Seuss’ first book was rejected 27 times
  • Emily Dickinson published fewer than a dozen of her 1,800 poems during her lifetime
  • Pete Carroll decided to throw the ball on the one yard line when he had Beast Mode in the backfield

You’ll also find many quotes from such people illustrating the same point. For example former IBM CEO Thomas Watson said, “The fastest way to succeed is to double your rate of failure.” Summer Redstone was even more blunt: “Great success is built on failure, frustration, even catastrophe.” And we all know what Thomas Edison had to say about his first 1,000 attempts at the incandescent light bulb.

Yet my favorite quote comes from Michael Jordan in what is indisputably the greatest sports commercial of all time,

“I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. Twenty-six times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.”

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Related: 7 Steps for Rebounding from Major Real Estate Failures


I remember not so long ago while sulking about a particularly egregious purchase, my friend and colleague noted, “Well, we’re still standing.” And yes, we are. The company my father founded 30 years ago and that I joined eight years ago has grown to own more than 500 rental units in four states while employing more than 20 people despite having made enough mistakes to fill a three-volume novel (a fourth volume should be ready for publication shortly).

So don’t let the fear of making mistakes stop you from starting or pushing ahead. No matter how much you read or listen to, no matter how many seminars or REIA meetings you attend, you will still find a way to epically fail in some righteously, almost indescribably stupid way. Get over it.

What mistakes have you made, either while learning real estate or later in your career? What value has failure brought to your business?

Let’s share our biggest missteps in the comments section!

Andrew Syrios has been investing in real estate for over a decade and is a partner with Stewardship Investments, LLC along with his brother Phillip ...
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    Replied over 5 years ago
    Awesome Article. I believe that the only time you fail in life is when you give up. When someone persists the universe will align…that has always been my believe.
    Chris Severns
    Replied over 5 years ago
    This is a brilliant post! It’s so refreshing to see someone be open about their mistakes and admit that they still make them. Like you said, too often successful people make it seem like mistakes are a thing of their past never to happen again. This is such a brilliant counter to that thinking. Great work and I hope you make many more mistakes in the future 😉
    Matt Aspen Engineer from Pleasanton, California
    Replied over 5 years ago
    Thanks for being so forth-coming & honest about your ‘learning’ process. I’m in the IT field (software) and the main thread is “fail often & fail fast”; the later meaning don’t spend a long time developing something only to find out it doesn’t work. Iterate. As a newbie investor, clutching my little pot of hard-saved gold, the greatest fear is making a catastrophic mistake on the 1st investment deal. Like most say, the 1st one if the toughest; especially when part of this is convincing your spouse to pull the trigger when you’re green behind the ears. I suppose the only remedy is to (a) do your homework (learn, ask, due-diligence) (b) don’t shell out 100% of what you have saved and (c) don’t let the fear paralyze you from taking the 1st step. Anything you can add to this list?
    Andrew Syrios Residential Real Estate Investor from Kansas City, MO
    Replied over 5 years ago
    You should certainly learn as much as possible and get as much feedback as possible about your first deal (many successful investors will look it over for you if you have it under contract, maybe even view it to give you their feedback). But I should also note, we have made money on our mistakes. That apartment we bought that was a money pit is now cash flowing well. Many times, it’s just a matter of face palming because you missed something, even though it doesn’t kill the deal.
    Paul Z. Investor from Schaumburg, IL
    Replied over 5 years ago
    Excellent excellent excellent post!!!!!!
    Kim Tucker from Shawnee Mission, Kansas
    Replied over 5 years ago
    Andrew if we didn’t have any failures in life, then it would probably be pretty sad because we would probably be sitting in our bedroom afraid to leave. Some mornings myself while in the shower I think, lets just stay here because nothing bad can happen in the shower. Can say the wrong thing, can’t send out an email with bad typos, can’t pay too much for a house or . . . what ever. But we keep on getting out of the shower, and heading out to see where life takes us. And with the addition of our son to our office we take a few more educated risks in our real estate investing and we are making some much bigger and better returns because of it. In the past I was too afraid of risk, so let some deals go by. Looking forward to seeing you next week at MAREI.
    Andrew Syrios Residential Real Estate Investor from Kansas City, MO
    Replied over 5 years ago
    Amen. Thanks Kim, I’m looking forward to presenting as well!
    Nasar Elarabi
    Replied over 5 years ago
    lol this is my favorite line “Pete Carroll decided to throw the ball on the one yard line when he had Beast Mode in the backfield” Great article and I have failed many of time and will continue to Fail. Its all part of the Game of Success…
    Replied over 5 years ago
    One of my favorite quote is from Star Trek’s Capt Picard to Data “It is possible to make no mistake and still fail. That is not a shortcoming on you bec that is just life”
    Troy Harbin from Valdosta, Georgia
    Replied over 5 years ago
    Looking forward to failing more! Great post!
    Mindy Jensen BiggerPockets Community Manager from Longmont, CO
    Replied over 5 years ago
    Thank you for writing this! This should be required reading for all new investors. We read time and again about this person’s amazing success, and that person’s astounding profits on their last deal. It is so good to read about failure, to know we aren’t alone, and that the world will still stand.
    Rosendo Gonzales Real Estate Investor from Visalia, California
    Replied over 5 years ago
    Awesome story of perseverance and following thru even when the sky is falling Congrats on your level of stewardship.
    Myra F. from Freeport, New York
    Replied over 5 years ago
    Thanks, your post was amusing and very encouraging. I’m smiling on my way to work now.
    Jim Henderson Rental Property Investor from Salt Lake City, UT
    Replied over 5 years ago
    Wonderful article. The biggest thing that damages a person’s future isn’t their mistakes. It’s their fear. Learning to let go of that fear and embrace the mistakes is the only way to learn anything.
    Jeff Hensel Lender from San Diego, CA
    Replied over 5 years ago
    Failure is a part of life. Just make sure you learn from your mistakes.
    Charlotte Beifuss from Houston, Texas
    Replied over 2 years ago
    Loved this! Looking forward to your fourth volume:)