Personal Development

7 Life-Changing Lessons I Wish I Knew as a Real Estate Newbie

Expertise: Flipping Houses, Landlording & Rental Properties, Personal Development, Real Estate Investing Basics
44 Articles Written
baby girl with computer laptop and mobile phone

As can be expected in real estate, I'm often approached by people who see me as a "real estate guy" (sounds better than "slumlord," which cops love to call me—despite owning nothing in the slums). I'm often asked about how I did it, how I do it, what I'm going to do next, etc.

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I’ve come to learn that while every so often someone will actually be interested in my story, the overwhelming amount of people really want to know how they can do it. They want to know the secret—the foolproof way to make lots of money. It’s interesting to hear about how a blue collar worker was able to get into real estate investing without a background in it.

Many people are curious about real estate investing. Some hear the late night infomercials. Some watch too much HGTV. Some know an old man who’s worth millions from buying rental properties. While the curiosity comes from many places, one thing is almost always certain—people want to know how they can do what I did. They seek the comfort that comes from hearing another share their story.

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Overwhelmed? You’re Not Alone

I remember when I was new. EVERYTHING felt scary. Man, it was overwhelming, paralyzing even, to think about all the things I didn’t know. On top of that, I was constantly being told “be careful,” “it’s not for everyone,” “don’t get greedy,” and other ambition-killing comments. When you combined my inherent fear from what I didn’t know with the external fear of those giving me “advice,” it is very easy to see why I started slowly.

I missed out on hundreds of thousands of dollars by not moving on deals that were no-brainers by just about any investing standard.

Now, that was an unprecedented time in recent U.S. history. We aren’t likely to see a perfect storm like that again anytime soon. But if I could go back, I would absolutely gobble up everything I could get my hands on in great neighborhoods with incredible schools, close proximity to freeways, very low crime rates, and access to parks and commercial shopping. I had plenty of disposable income—not to mention, everything cash flowed very healthily.

Why didn't I buy more? I was scared. Paralyzed. It's embarrassing to admit now, but I actually felt like I was the only one doing this—that no individual person had actually tried to buy a bunch of rentals and make money from renting them out. I didn't understand vacancy. I didn't understand property management. I didn't understand repairs. I didn't understand economic cycles. I was just a deputy sheriff with a degree in Psychology and Criminal Justice.

I was alone, isolated, and unnecessarily fearful.

I didn’t have BiggerPockets as a source of support and confirmation. I didn’t have—nor did I know I should have—a mentor. I didn't know books were written on this. I didn't know how to check market rents. I actually thought if the tenant notified me something was broken, it was somehow a reflection of my failure as a landlord—that repairs being needed were an indication I had screwed up with my rehab.

Not gonna lie. I really sucked at investing.

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Sucking a Little Bit Less

But guess what? I've come a long way since then. I don't suck as badly anymore! I actually think I suck much, much less. I now make enough to cover 100% of my living expenses. I have a net worth that allows me to invest in SEC-accredited investment opportunities. Luckily, I've yet to lose money on a real estate deal. I have a website (very fancy). I have a "portfolio" of real estate investments (also very fancy). Soon, I've written my own book (uber-fancy). I've been on podcasts, spoken at conferences, joined elite masterminds, and rubbed elbows with some pretty successful investors. And you know what I’ve learned?

I don’t quite suck as much as when I started.

See, you could write books on what I don't understand about real estate investing. There is so. Much. To. It. God, I can't even begin to explain how much there is to it. There are so many different strategies for how to pick an area to invest in. So many different schools of thought on how to maximize returns and minimize risk. So many rules of thumb to learn and memorize. So many acronyms! Oh my word, it's an alphabet soup of ROI, IRR, ARV, FSBO, IRA, JV, LTV, NNN, REIA, SFR, PITI, MLS, HUD, HOA, and BRRRR!

Related: 3 Underlying Issues That Keep Newbies From Investing Success (& How to Conquer Them)

There are also strategies for how not to overextend, how not to hold back, how much to keep in reserves, when to use partners, when to use wholesalers, when to use turnkey, when to self-manage, and when to 1031 into larger properties.

I could go on and on and on. But I’ll spare you.

The point I’m trying to make is that although I’ve achieved a measure of success by most people’s standards, I still know very little when compared to how much there is to know. I learn literally every single day, and sometimes I’m embarrassed that I didn’t realize some things sooner.

If other investors are honest, they’ll tell you the same thing.

Now, if there can be SO MUCH that I don’t know and if I’ve still experienced “success,” why would you think that you can’t?

Common Misconceptions

I’ll tell you what I think. I think that many of you believe you need to know much more than you really need to in order to get started. I think you’ve read the success stories of people who have done great, realized you can’t do what they did, and counted yourself out. But there is a lot you don’t know about them.

You don’t know they have contacts you don’t that sped up their learning curve or access to deals. You don’t know they started out with a huge trust of money someone left them.

You don’t know all these “deals” they are putting together are actually joint ventures with other investors where they are putting zero money in the deal, have zero risk or liability, and are possibly just gambling that thing works out—with no clue if they’re going to or not.

You don’t know a lot of them are posers. You also don’t know what advantages they had that you didn’t.

If you did know, you would probably feel much, much more confident about your own odds.

Now, in a personal display of transparency, I’m going to share some examples of things I did not know when I got started investing that I now wish I had. Things that would have sped up my learning curve, increased my confidence, and increased my exposure to people who would have benefited my budding RE investing career.

I truly believe RE is the "poor man's" way to build wealth. It's the "everyman's" opportunity to take control of his or her future. It bothers me to see hedge funds, large corporations, and people who are already insanely wealthy buying all the rental property. It also bothers me to see people wasting precious time getting started. Time they can't get back.

I want to help you get started. I hope I can. Without further ado, here is a list of things I wish someone had told me when I got started.

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7 Life-Changing Lessons I Wish I’d Known as a Real Estate Newbie

1. You don’t need the perfect mentality—or the perfect deal.

Remember that school term paper you knew you needed to write but you kept putting off because you wanted to make sure you wrote something amazing and weren’t quite ready?

That paper never got written until the last minute.

Perfection leads to procrastination. Sometimes it’s better to just get it done than to present a flawless product. Sometimes trying to be perfect just ensures you’ll do nothing.

Real estate investing can be this way, too. I remember being embarrassed to tell others what I paid for a house, thinking they would judge me. I remember having no idea what a fair price for a house was, so I would just offer significantly under asking price because I mistakenly believed that meant I got a "good deal." I remember not knowing what a "good" ROI was. I also remember holding out for two months and missing out on $3,000 in rent to get an extra $50 a month because I thought it made my investment appear stronger to others when I shared my numbers.

Pretty foolish in hindsight.

My pursuit of perfection, handled incorrectly, caused me to stand on the sidelines instead of playing because I wasn’t in Olympic shape yet. I didn’t understand that actually playing the game is what gets you in shape! Had I understood that on my first few deals—the real value is in learning, not earning—I would have shortened my learning curve considerably.

My point? You don’t need home runs to win games. Base hits win games. Walks, sacrifice flies, stolen bases, and bunts can win you games.

Heck, even a great at-bat where you don’t reach base but learn about the pitcher can help you for next time, right? Chasing after a deal and learning what motivates sellers, how to negotiate, how to improve the terms of your offer, and how to analyze deals more quickly can have significant impact on boosting your investment career, even if you don’t get the deal. The reality is, most of the value of your first deal is in what you learned, not what you earned.

Related: For Newbies: The Motivation You Need to Take Off the Training Wheels (& Start Down the Road to Investing Success!)

Focus on acquiring good, solid, cash flowing properties in good neighborhoods and school districts at below market value. If you round up enough of these, you’ll find yourself much wealthier, much sooner than you thought.

2. Don’t ever undervalue the importance of relationships.

When I was new, I was a little obnoxious jerk.

I was penny wise and pound foolish. I scrimped and saved on small costs at the expense of hurting the people who could bring me future deals. I actually asked my agent to give up part of her commission sometimes when she was already getting me a screaming deal (and had given up some of her commission to get me a better price). I cringe at these thoughts now. My word, was I ever stupid. I just didn't know any better.

Here’s a fact many of you don’t know yet. People, not your own brilliance, are going to be what bring you the majority of your deals—especially when you’re new.

We all love to talk about strategy because it makes us feel in control of the whole thing. We control our own destiny through our hard work and ingenuity. I’ve been there, too. I thought that’s what it took. Know what I’ve learned? It’s 10 times easier when someone just calls me and says, “Hey David, looking to flip a house right now? I’ve got one you’ll like.”

Sometimes it’s really that easy.

If people like you, they will want to help you. If people know how they can help you, they will. Sure, you can hide in the basement for three months and develop a super-secret algorithm, develop it into a program, and unleash it upon the world to help you locate distressed properties, OR…

You can make people like you and make sure they know that you’re looking to buy good deals.

I, to my shame, did not focus enough on making people like me. I was selfish and short-sighted. God only knows how many deals I missed out on because people brought them to someone else. UGH!

Don’t be that way. Make it a priority to help others. Make sure they get paid. Make sure they get referrals. Make sure they are appreciated. If you do, more often than not, the deals will find you.

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3. It’s probably less scary than you think.

This one’s big. Many people don’t get started because they don’t know what to expect. All they can think about is what they stand to lose. While it’s very important to measure risk (very, very important), one of the risks people fail to measure is what you stand to lose by not investing. In economics, we call this “opportunity cost,” and it’s real.

If you check out a previous post of mine on BiggerPockets, you’ll see the first comment is by BiggerPocket’s very own Scott Trench. He agrees with this sentiment, stating, “A failure to enter the game is a much bigger risk.”

Truth is, you’ll never know everything. I’ll never know everything. I started this article speaking about all the things I didn’t know, all the things I still don’t know. Now, I know there is a bunch of stuff I still don’t know. Why do I have the confidence to keep investing?

Because I know there are very few problems I will come across that someone else hasn’t. I know that the internet makes it pretty darn easy to find info, and it won’t be too hard for me to find someone who has faced this riddle and solved it. I can usually just piggyback off their solution and save myself a lot of time. Shoot, there’s a very high probability I will find the solutions to my problems here on BP, either in the blog or on the forums.

It’s just much easier these days to find stuff.

Let go of thinking you need to know it all. You will find yourself learning at an exponential rate once you get some skin in the game and own a property. So find something small if you’re worried, run it by a few others you trust, and if it sounds good, buy it and rent it out. That’s how you’re going to learn. And you’ll realize this whole thing isn’t as scary as you’ve made it out to be in your mind.

4. Don’t trick yourself into thinking you’re an investor when you’re an analyzer.

This one is weird, but it’s true. So many people love to talk about the game and think that means they play it. They understand all those acronyms I mentioned earlier. They love to play on the calculators to estimate returns. They read all the articles, scour the internet, and know what the experts say. They are totally immersed in real estate.

But don’t own any.

Don’t be that guy. Make no bones about it, we do this to make money. You aren’t going to make money by talking about it, you’re going to make money by being about it. Don’t be fooled into thinking you’re making progress because you’re giving your opinion on the forums or you can recite Robert Kiyosaki verbatim. Knowledge gained without being put to use is useless and a waste of your time.

Real estate isn’t fantasy football. You don’t get points for watching others playing and winning.

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5. Realize not knowing where the market’s going is OK.

This one is tough, I’ll admit. I myself spend a fair amount of time worrying about if I should be buying, selling, waiting, or spending. None of us really knows. It’s easy to see how this can cause a lot of people to hesitate. But let me tell you why it’s ridiculous to constantly use this as an excuse.

When I started buying in 2009, the market was at or near its bottom. When people look back, they often say, “I wish I had bought back then. I would have made a killing. It’s just too late now, prices have already risen.”

The problem with this is, back in 2009, everyone was saying the economy had collapsed and we were fools to buy! Why do you think everything was so cheap? Because no one was buying it, that's why! It felt like a huge risk. Like things were going to get worse or possibly never recover. All the news was saying that America had been struck a death blow, and the great recession was coming.

So everyone clutched their money close and didn’t want to risk it.

Now, I’ll admit, a great recession might be coming again. Or it might not. I don’t know. You don’t know. Nobody knows. It might come and be followed by a huge comeback. It might not come at all, and prices might just creep up forever. None of us knows! So talking about how you would have done something before does you no good now.

Why do I have confidence to keep buying when the market is already “up”?

Because of cash flow. Cash flow is the great equalizer in real estate. If the market goes up, I can make a bunch of money and sell. If the market goes down, I don't lose crap unless I sell. I don't need to. I can just let the cash flow pay for my mortgage until the market turns around again. It's an amazing hedge against bad markets. My renters are assuming a lot of my risk for me. That's one of the reasons I buy real estate instead of other investments.

There is a reason real estate has done so well over long periods of time. Markets go up and markets go down, but if you have a tenant, you can ride it out. I don’t know what the market is going to do, but I know people are likely going to need a place to live.

6. You CAN overcome lack of sufficient reserves.

Honestly, this is the one reason I usually agree is a good reason not to get started. Having healthy reserves is crucial. When I first started, I was hesitant to buy until I had a significant amount of reserves built up. The problem was, I didn’t know what was healthy. I thought I needed to have enough saved up to pay for every single property for two years, with 100% vacancy. Pretty silly.

Looking back, I didn’t need that much—especially with lots of disposable income. However, if you’re not buying because you don’t have enough in reserves, that’s still no excuse.

What good reason can you have for not saving up enough money yet?

Real estate investing is still investing. It is putting your money to work for you and assuming some risk while doing so. If you’re trying to use RE as a vehicle to build wealth but you aren’t actually building wealth with what you already have, you’re not ready for this. RE is not a financial savior for you. In all practical terms, it does take money to make money. If you want to play in this space, you need to be saving money. Not having reserves is not an excuse. Start saving reserves today.

Related: Want to Lose All Your Money & Cry Yourself to Sleep? Make These 4 Newbie Mistakes!

7. Finding a support system is very possible.

I think at one point, this was a legit concern. Today, however, it’s not.

We have BiggerPockets, the internet, REI meetings, books, blogs, articles, paid RE sites, free RE sites, and coaching. You want it? It’s out there.

I agree a support system is necessary, but if you’re reading this, you have access to one. I’m here, BP is here, tons of investors are available on the forums.

Not getting started because you don’t have a support system is just silly. Start reaching out and finding one. I wish I had.

In Conclusion

If you are still unsure what to do to get the ball rolling, send me a message on here. I love to help, and I remember what it was like being new and feeling alone and scared.

If you know someone who feels alone and scared right now, please forward them this article. Sometimes it helps to know that you’re not the only one feeling that way.

If I had known about a site like BiggerPockets when I was getting started, I honestly believe I would have twice as many properties right now. I know it’s hard to believe when you’re new, but real estate isn’t rocket science. You are likely much, much closer than you think to getting started and putting together a portfolio of income property to support you in retirement.

Your future you is dependent on present-day you to put things into action. What you do today matters.

Don’t be like me. Don’t let silly things hold you back from an epic future. There is an answer to whatever questions or objections you have. Go find them!

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If you haven’t started investing yet, what’s holding YOU back?

Let’s talk through it in the comment section below!

David Greene is a former police officer with over nine years of experience investing in real estate that includes single family, multifamily, and house flipping. David has bought, rehabbed, and man...
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    Laura Ludwig
    Replied over 3 years ago
    Great article! Very inspiring. I love the ending part “Your future you is dependent on present-day you to put things into action. What you do today matters.”
    Shaun Mckbight from Cape Coral, Florida
    Replied over 3 years ago
    I’m a total greenhorn. I do have a mentor, his name is Russ, but, you said if I’m feeling “alone or scared” to email you. Yup, that sounds about right. I made an offer on two houses to flip, thank god those fell through. I tried to buy the guys house I was living in that was house hacking, come to find out even though he just got done spending 30 grand on rehab he has more money than he knows what to do with. I tried to put together a deal with getting three property owners together so I could change a pocket of duplexes (4) from a blight into a nice area in Punta Gorda, the listing agent for the first one didn’t ever call me back. I tried to buy a duplex in Cape Coral, but the guy wanted 100k over fare market value. I have tried and tried again to get something going but nothing has worked. I would like to get a tri or quad but have found out they are in short supply. I really want to get into the game but it seems like every time I try I seem to hit a wall. FYI I have ben at it sense last September.
    Evelyn Kop Investor from Pearl City, Hawaii
    Replied over 3 years ago
    This was a great article! I may be a little late to the party but were new investors and excited about getting started. We are totally priced out of our market so we’re looking at different communities but its hard to decider where to buy. I’ve also looked into turnkey companies since we will not be able to manage the property being so far away…but how to decide on a reputable turnkey company. They all have great numbers…. any advice or insight would be greatly appreciated!
    Angela Hagen from Belton , MO
    Replied over 3 years ago
    I do understand this business is about relationships but those take time to build. I am working on that. What paralyzes me is not having any relationship with lenders. I would like to try some wholesaling but I am afraid if I get a property under contract I won’t be able to find an end buyer because I don’t have those relationships.
    Jeff Lisa Investor from Woodland Hills, California
    Replied over 3 years ago
    What a great and inspiring article! I plan on re-reading this often.
    Cristian W. from Miami, Florida
    Replied over 3 years ago
    Great Article David. I am just starting, thank you for the motivation!
    Tom Geiger Real Estate Professional from Exton, Pennsylvania
    Replied about 3 years ago
    “Don’t ever undervalue the importance of relationships.” I read through all the comments and people seemed to have read right past this. The very foundation of successful business is relationships. Having good people who want you to succeed in your corner isn’t just important, it’s imperative! The people who you least expect to help you will be the very ones who will come through for you ! The art of business negotiations is that everyone must be successful if a deal is to come to successful conclusion. Everyone has the common goal to be successful and make a living. You cannot force a vendor into a money losing deal. They have lost the ability to perform that service for you. The people that you nickel and dime will bring the next deal to someone with better business skills! Never focus on the immediate quick win, always plan for the long term. Relationships are key to winning! And a bit of my own advise… treat everyone equally well. I make sure I know the name of every person on the crew. At the end of the day I thank each one of them. An out of work carpenter I knew socially got me out of a jam when I had a construction company go bankrupt and disappear from a project. My very first listing as a realtor was from the cleaning lady at my previous employer! And leave your Mercedes at home when you collect rent! I have an old Dodge Caravan I use as a work van. You don’ t need people thinking you are affluent on their backs. When I was buying my 10 year old Jaguar at a Rolls Royce dealer, I asked the salesman a bit about their customers. I learned that the average Rolls Royce buyer buys the car for personal use, most transactions in cash. A CEO will not bring that car to work, opting for something common like a Ford Explorer as his business image. The age of conspicuous affluence is over!
    Beverly Bowman
    Replied about 1 year ago
    Hello David, My name is Beverly. I just finished reading your article and saw myself. Can't seem to get started. Can't seem to meet prople who are in this business. I lost everything in Hurricane Florence and had to move to a new town where they don't offer nothing much on how to network much less how to network with real estate. I did manage to go to one real estate wholesaling meetup. That turned out to be totally different from what was being advertised. I do feel lost and alone. But I refuse to give up. I have been doing a lot of reading about everything thing realestate. I just wish I had one person I could connect with. I won't let that stop me! Again thanks for the article. Very uplifting!!
    Bill Dean Professional from Bismarck, North Dakota
    Replied about 1 year ago
    As an investor, agent, and deal maker, I totally agree with these statements. It is fun to see new investors get excited and find their first deal. It is painful when new investors spend thousands of dollars on classes then never buy an investment property (meaning they're analyzers instead). I really enjoyed your lines about what actual deals are like versus what they sound like to new investors. I will definitely be more aware of how I discuss deals in the future. Thanks for the article!