7 Real Estate Investing Lessons We Can Learn from Steve Jobs

by | BiggerPockets.com

I recently read the book “Steve Jobs” by Walter Isaacson. As brilliant as Steve Jobs was, I came away from the book not with a sense of awe about the man who Steve Jobs was, but how despite his incredible success, how idiosyncratic and deeply flawed a human being he really was.

Yes, he was a certifiable genius, although in some ways “certifiable” as well.

Yes, we’ll never see anyone else exactly like him, although Apple’s stock price has done quite well since his death

Yes, in American business, he will live in the pantheon of Edison, Einstein, and Ford, and he really thought he belonged there.

Yes, he did leave an indelible mark on our society – in fact, totally revolutionizing five separate industries nearly simultaneously…but he deeply hurt many people on the way in his rise to near mythic status.

Despite his greatness, he made tons of mistakes, cruelly alienated lots of people including his own daughter, and did some curiously unethical things in his relatively brief time on this earth. No doubt, the further you probe into the true personal lives of your “heroes” oftentimes the more you find, the less you like.

I came away from reading the book in a word — exhausted, but exhilarated at the same time. In fact, it was refreshing in a way to know that although Jobs was “Steve Jobs the icon”, he’s just a guy like you and me. I realized that you don’t have to be perfect to be great. And although there are many traits of Jobs I would never emulate in my own life, I felt like there were so many brilliant lessons that can be learned from him not only as a businessman and real estate investor, but as many lessons in what not to do as a father, a husband and a human being.

The bottom line is this: you, I and anyone can be great. There are multiple paths to ultimate success in life and in real estate investing, and there are multiple lessons Steve Jobs can teach the real estate investor and which can be learned by you.

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The Top Seven Real Estate Investing Lessons Steve Jobs Taught Us

1. Fear Not

Jobs was plagued by strange idiosyncrasies. His diet, his odd personal habits, his driving without a license plate, his parking in handicapped zones just to name a few. But one thing he was blessed with was a total and utter lack of fear. Lack of fear comes from many things; self-confidence, optimism, even delusions of grandeur (checkmarks on all three for Jobs here). One thing’s for sure, he had enormous amounts of self-confidence. He felt he was special and that he was put on this earth to do great things by creating the technical marvels which ultimately influenced and bettered the lives of millions of people. Those innovations still affect us all each and every day.

Even in the face of terminal pancreatic cancer, he seemed to have an almost irrational sense of self-confidence and lack of fear. His self-confidence was so great; he actually thought that he could cure himself with oddball diets and rituals, while shunning traditional medicine – medicine that just may have saved his life. Incredibly, he seemed to have a complete absence of fear of the one thing that most of us are deathly afraid of…death itself.

It’s terrifying to buy your first house flip, for sure. But is it as fearful as death? Keep things in perspective in order to control fear. Think of the worst case scenario if you do what you’re fearful of. If you can handle the worst case pain and aggravation, then do it. If Steve Jobs could fearlessly stare down death, you can do the same.

If you’re just starting, then make your first real estate purchase. If you’ve been around the block a few times, try a new investment strategy you’ve never done before. When you face your fears and do what you fear most, you end up controlling your fears.

2. Pick Yourself Up Even After Your Failures

Can you imagine the humiliation of being fired by the guy you picked to run your company? In one of the most public firings in corporate history, Steve Jobs was fired. This was big news when it happened, sending shockwaves throughout Silicon Valley and the rest of the corporate world. Jobs did wallow for a short period of time, sure. But he picked himself up and created a new company that was ultimate bought by the company and the successor he was fired by.

If you are new to real estate investing and you lose a few thousand on your first deal because you overestimate your ARV, didn’t stick by the 70% Rule or failed to tightly manage your general contractors, then provided the few thousand didn’t bankrupt you, pick yourself up and try again.

It’s not how many times we fail; it’s how many times we get back up after failure that counts most.

3. Marry Art and Functionality

Many of us have iPhones. If you have one nearby while reading this or on the desktop beside you, pick it up. Feel the weight, notice the elegant stainless steel wrapping, the Gorilla glass screen, the smooth back. Swipe a few apps from side to side, browse the Internet, touch an app and see how they all gently jiggle to be deleted or modified. If you think all these enhancements and subtle artistic nuances of the device (since copied by the Google platform) are random, think again.

Jobs dissected each of these features and weighed them for weeks and months prior to being introduced by Apple. And each feature indelibly bears his thumbprint — his signature. He married art and functionality to create everlasting products and innovation that will affect generations to come.

There are lots of posts on this website that discuss the “steps” to real estate investing, house flipping, wholesaling, you name it. Follow these steps here and learn as much as you can. But then, put your own thumbprint on each of them – just like Steve Jobs did with each of his creations.

Is there only one way to rehab a house for maximum resale? No way.

Is there only one way to round up funding for your next apartment building? Not a chance.

Virtually anyone can become a real estate investor as long as they have the desire and the ambition, but to become a massive success, it’s going to take more than just what you learn from others. Its going to require you to put your own indelible stamp on every deal you do. Think like Steve jobs in how you can make your flip or rental a little bit different, enhanced or beautiful…marry art with functionality.

4. Listen to Your Inner Voice

When you are new to real estate investing, you have no voice in your head. If you do have one, that voice is usually screaming to you “don’t do it!”

However, the more deals you do, a different inner voice starts to appear. This is the voice of experience.

Maybe you are thinking about becoming a real estate investor and there’s something that has stopped you from doing it. You went to school, you got a good job in finance or sales or maybe you’re a doctor or a dentist — but there’s something missing. When we don’t listen to our inner voice, we mail it in, we do what we do on autopilot.

You’re reading this blog most likely because you want something more. You want to create the life you’ve always wanted. THAT is the inner voice calling you.

Ignore it at your own peril.

Jobs’ inner voice screamed “change the world” — a pretty dramatic vision and a pretty big voice. He built computers to do it. That was his plan.

What’s yours?

One thing that’s abundantly clear with Jobs is that despite his many imperfections, he lived his life with very few regrets. He followed his inner voice. Whatever that voice is telling you, it would be smart to listen to it.  Even if it tells you to quit your job, become a full-time real estate investor, move to Tibet or become a gourmet sushi chef, listen to it.

Live life with no regrets.

5. Expect More from Yourself and From Others

Jobs was a real prick sometimes. He would berate people. He would yell at people. He would throw little temper tantrums. He was a totally obsessive control freak.

And of course, he was an absolute perfectionist.

He demanded this from himself and he demanded the same from everyone who worked for him. I am not saying that the WAY Jobs did it was right, far from it. He seemed like a real jerk to work for.

But one thing’s for sure, he pushed people to places where they never thought they were capable of going. He expected this of himself and he expected it from everyone who worked for him.

Do it in your own way and do the same thing in your real estate investment career. If you need to get upset, do it. Don’t overdo it or you will find nobody will want to work with you, so be careful. But shoot for perfection and settle for excellence at the very least.

Jobs built products that revolutionized the world using this philosophy and he did it in his own way…so you do it in your own way. But don’t try to be him. Be yourself and expect a lot from everyone and most importantly expect the absolute most from yourself.

6. Surround Yourself with the Most Talented People You Can Find

Steve Jobs gets all the credit when you think of the legacy of greatness at Apple. Sounds good, but it’s simply not true.

Yes, Jobs made the ultimate decisions in all matters Apple from the type of sandstone used in Apple stores to the kind of glass used on iPhone screens. But what’s less known is that he surrounded himself with some brilliant minds that simply made him and Apple better.

Jobs surrounded himself with serious talent: the true mastermind behind the iPhone and iPad design Jony Ive, now CEO Steve Cook, Apple co-founder Steve Wozniak, Toy Story creator John Lesseter, just to name a few. These super-talented people (not the faceless minions kowtowing to Jobs every whim as we may want to believe) don’t get the credit they rightfully deserve.

In real estate investing, surrounding yourself with an incredibly talented and knowledgeable team, including lawyers, real estate agents, general contractors, etc. – people in many cases who know far more than you – is just as important in real estate investing as it was in building one of the great companies of our generation. Steve Jobs realized that he couldn’t do anything without great talent around him.

How about you?

7. Stay Hungry. Stay Foolish

Success in anything in life is consistently looking to improve, to grow, to build and also to have fun. If you’re going to do it for the majority of the time you have in any given day, shouldn’t it be fun too? Jobs summed up this philosophy of innovation, creativity and fun in his memorable 2005 Stanford commencement address (check it out on YouTube if you haven’t):

When I was young, there was an amazing publication called The Whole Earth Catalog, which was one of the bibles of my generation. It was created by a fellow named Stewart Brand not far from here in Menlo Park, and he brought it to life with his poetic touch. This was in the late 1960?s, before personal computers and desktop publishing, so it was all made with typewriters, scissors, and Polaroid cameras. It was sort of like Google in paperback form, 35 years before Google came along: it was idealistic, and overflowing with neat tools and great notions.

Stewart and his team put out several issues of The Whole Earth Catalog, and then when it had run its course, they put out a final issue. It was the mid-1970s, and I was your age. On the back cover of their final issue was a photograph of an early morning country road, the kind you might find yourself hitchhiking on if you were so adventurous. Beneath it were the words: “Stay Hungry. Stay Foolish.” It was their farewell message as they signed off. Stay Hungry. Stay Foolish. And I have always wished that for myself. And now, as you graduate to begin anew, I wish that for you.

Stay Hungry. Stay Foolish.

We can be just as special as he was and although we may not all build the next Apple; we can build excellence in what we do every day as real estate investors. As was previously reported on this blog, we as real estate investors not only enrich the lives of thousands of people every year with quality housing, but we create jobs and opportunities to the tune of $9.2 billion per year as well.

What we do as real estate investors matters. Jobs would agree that is a worthy dream to pursue. And we all can learn much from him – both the good and the bad. But best of all, you don’t have to be perfect in to be wildly successful like Steve Jobs.

In fact, anything’s possible in life if you continue to follow the simple lessons laid out above.

What do you think? If you made it this far, please leave me a comment below! I’d love to hear about what you think of Steve Jobs or questions about anything at all relating to real estate!

Photo: Nopphan Bunnag

About Author

Mike LaCava

Michael LaCava is a full time real estate investor, house flipping coach and the President of Hold Em Realty located in Wareham, MA. He runs the website House Flipping School to teach new real estate investors how to flip houses and is the author of "How to Flip a House in 5 Simple Steps".


  1. Bryan Jaskolka on

    I love this post! Thank you so much for sharing it. I have not read the book and to be honest, I probably won’t, although I agree that the contributions Jobs made were numerous, and the world simply would not be the same today had he not made them. I love the points you make though, about what we can learn, and I’m happy you posted them. This way I sort of get to take away what I want from the book, without actually having to read it.

    Thanks again!

  2. I’m sure that if Steve Jobs would look back over all the things he accomplished in his lifetime, he would feel pretty proud of all that got completed or off to a good start. It is the same for investors or just regular people. Everyone has the basic need of feeling appreciated. For investors looking back at all the people they have helped to get into a home or achieve the dream of home ownership, they too can feel a grand sense of accomplishment and pride. Small accomplishments build up into rather large successes – keep on investing and supporting the recovery of the local economy.


    • Good point Dale. I think we all can relate. We tend to focus on what went wrong more often
      than all the great things that are going right. You make a good point! All should take that advice no matter where they are in their careers.

  3. I guess I never realized how much of a total jerk Steve Jobs was. Hes a bit glorified since his death and this tells me alot about him I didnt know – I am a bit disappointed to say the least. It’s inspiring to think that someone that great and so flawed can still have the vision and leadership to succeed. I need to read the book. Good lessons nonetheless for all newbie real estate investors to learn from though. Well written.

  4. Mike,
    Well-thought out post. Thank you. I especially like your encouragement to “put your own indelible stamp on everything.” Those are some wise words. You extracted some good insight from the book – thanks again for sharing.

  5. STAY HUNGRY AND STAY FOOLISH. The first part is easy, the second, stay foolish, is the difficult part. As adults we loose the foolish part of ourselves we had as children. The inner voice always wants us to be FOOLISH! All our lives people tell us to be careful, how many times did dad, mom or grandparents drill this into our heads. Foolish people go where angels fear to tread.

    • So true, isn’t it? Staying foolish is a bit more difficult the older you get and more “responsible” you get. Every now and then its good to just go do something completely foolish…I just wouldn’t do it when you’re investing in real estate though. I think that comment can also mean to take some chances, put yourself out there and get out of your comfort zone and see where it takes you. Thanks for the comment!

  6. Thanks for writing this article.
    I’ve learn to marry art & functionally in my rehab and it working very well for me. Everyone that enter my rehab wants to live in the house.

  7. Mike,

    The Issacson biography is on my reading list. I’ve known about the dark side of Steve Jobs’ personality for some time, now. Human beings are complex creatures; perfect in our imperfections.

    That this imperfectly brilliant man was able to wrangle and guide such talented associates, while driving himself to surpass whatever creative endeavor he’d previously achieved, speaks volumes about his leadership. While the style of his stewardship may have been off-putting to most, the substance of what he offered mattered to those who chose to enable his vision of creating beautifully elegant products.

    Thank you, Mike, for a very nice post.

    • Thanks for your kind words Anthony. He was brilliant and flawed at the same time, his drive and ambition were absolutely amazing. He really did feel like he was destined to do what he does. My issue was the price he paid by hurting lots of other people close to him in the process, but we all benefit from that single minded focus today, so its a difficult paradox.

    • Thanks for the comment, Karen. It really seemed like the thought of giving up never even crossed his mind. It was just destiny to him to do what he did and create the legacy he created. Its like it wasnt even a choice, he just had to do it. Mike

  8. Sharon Vornholt

    Mike –

    Excellent post! I haven’t read the book yet, but I plan to. Steve was a visionary that managed to bring those dreams to reality. Often times those folks that are so brilliant,are very “odd” in some ways at the same time.

  9. Sharon, so true. I think many of the geniuses of our time were a bit odd. Its rare that geniuses are normal in the classic sense, he definitely had the normalcy in his personality, but many quirks and idiosyncrasies to counter balance. Some of the other geniuses mentioned above in the post were deeply flawed just like jobs was as well, so maybe it comes with the territory? Thanks for your comment.

  10. Mike, you could totally write a book with these seven lessons! (I would buy it, for sure). I think those lessons pertain to life in general, and I think the most successful people in multiple industries exercise, or have exercised, these lessons to the max. Carry these into real estate investing, absolutely, the ticket to success.

    Thanks for putting this one out! Great read.

    (I got your email last week but when I tried to respond, it kicked back. Try again?)

  11. Hey Ali, hopefully you got my response on email. I really appreciate the nice comments.

    We do have a book we do put out for free and although it does talk about house flipping and the success mindset, it doesn’t mention Steve Jobs — but thanks for the excellent idea! BTW, email me ny time with any questions you have. All the best, Mike.

    • Hi Mike!

      I did re-email you after you said your emails were down. Did you get that one? It didn’t kick back but I didn’t hear back either. I’d definitely love to talk to you more. Let me know if my email came through.

      And, yes, I’d love to read that book. Is it on your site? (I suppose I could go look there myself before I ask but I’m already here 🙂 )


      • Hi Ali,
        Yes I did get your email and sorry for not getting back to you last week. I was ko for 3 days with the flu. I don’t get sick much but when I do I get hit hard. Better than being dragged out for 3 weeks though. I will email you directly next week & if you have some time we can talk.
        Let me know how you make out with my ebook. Just put in your name and email & you will get it by email. I would love your feedback.
        Have a great Sunday!

  12. Cool take on Jobs btw. How can you stay hungry and stay foolish in realestate investing though? I’ve had issues with getting partners and investors to buy in on my deals. Thanks for a cool post.

      • I had a partner when I first started but it didn’t work out. Now I’m just looking to find money from others for 90 or even 100% of the finance on my flips. Is there such a thing as 100% finance in your experience or do the hard money lenders always need a percent from you?

        • Terry: All of our flips are financed 100% by investors.

          However, they have been with us for years. Their investments in our deals did not start out at 100%. You need a track record for investors to trust your success.

        • after a number of successful flips, I can get hard money at 100% of the purchase price, albeit at 11-12%, I turn the flip in 90 days. My profit is 20%, I pay for the rehab and make good money. You need a track record. I used to buy at the TD sale auction, but now I’m buying, back on the market short sales and normal short sales, I have to make 35 offer on standard shorts to get one. The amatures are taking the profit out of the TD auctions. The key on short sales it your relationship with the listing agent. I let them take both sides, even though I’m a licensed agent. I’m also an REO agent and have listed and sold over 200 REO properties and made a point to establish a good working relationship with agents.

        • Thats a good point David. I apply that same strategy for agents when we can. They work hard for their money as you know and we want them to benefit as best as they can as well.
          I am also getting 100% funding but in Terry’s case it might be more difficult on his first deal.
          not impossible but more unlikely but it shouldn’t stop him or anyone as there are many more options to make the deal work.

          Thanks for you great points!

  13. Karen is correct Terry. It may be tough to get 100%
    Financing at first. After you build up some credibility you will be able to get 100%.
    You can always find a partner if you don’t have the money for your costs to do a deal.
    Real estate investing allows you to creative to get in.
    Just be careful and do your due dillagence.

    • I figure I can use a credit card or a little cash to get the other percent to make it 100%. I have the deal, have most if the financing, what do you think I’d sulemeting with a credit card too? Ever done that? If both of you could weigh in that’s be cool.

      • I never mind using a credit card to supplement the funds I need (especially when I get air miles!).
        However, I am always aware that money will be paid back with interest, so I like to pay off credit cards every 30 days.
        If you’re fairly new to investing, don’t get in over your head. If you’re having trouble funding the deal, it could be too big for you.

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