Personal Development

3 Must-Have Traits of Successful Entrepreneurs

Expertise: Personal Finance
15 Articles Written

As my wife and I continue to grow our investment property portfolio, I often find myself wondering why everyone else isn't doing the same thing. I look around my circle of friends, all of whom know about our real estate investment ambitions, and am puzzled why they aren't taking action to grow their net worth through REI.

Almost every time we are with our friends, they will ask us, “How are things going with your real estate?” We make a point not to bring up the subject ourselves, because once someone does, we usually have a hard time talking about anything else. But when asked about what the latest news is regarding our properties, we are happy to converse and answer any questions they have.

And we obviously give a pretty optimistic picture of why we think REI is a great way to grow our wealth.

But I sometimes wonder if our friends’ inquiries are more embedded in a secret desire for us to fail than rooted in a genuine inquisition for an update. I sometimes feel they are mostly asking because they want to hear about a tenant horror story or how a property has gone terribly wrong.

Related: Dirt, Dead Mice & Cobwebs, Oh My: What I Learned From My Latest Tenant Horror Story

Now, I honestly don’t think our friends are rooting for our failure. It has nothing to do with us and is all about them. I think the reason they are waiting for the bottom to drop out of our real estate endeavors is that it would justify the fact that they are choosing not to do it themselves.

It’s more about FOMO. See, if my wife and I succeed (and we are) in our real estate investments, it proves to them that it’s a viable way to grow wealth quickly—or at least more quickly than the traditional investment strategies those friends are using. And if that’s true, then they would likely feel they have made a mistake by ignoring the opportunity, especially since they had friends (us) who offered to help them get started.

I often ask myself, “Why don’t they do it, too?” My wife and I are no more intelligent than our friends. We don’t have more financial resources than they do, as we are both public school teachers. We aren’t privy to a secret, bulletproof doctrine that guarantees success in real estate investing.

So, why don’t they join us on board this tried-and-true train chugging steadily towards Wealthville?

There’s probably more than one reason. But as I ponder them all, the one I always come back to is that not everyone is cut out to be an entrepreneur.

What is it exactly that allows us real estate investors to pull the trigger of the property investment gun while others sit back, watch, and covertly hope for us to struggle?

3 Traits Vital to Succeeding as an Entrepreneur

Here are three traits I feel are vital to the entrepreneur’s journey. How my wife and I have come to embody these traits and others have not is a mystery to me. I’m just grateful we have them.

  1. An insatiable thirst for knowledge

Once we leave the secondary school system, additional education is a choice. Many choose to continue their education with a degree or certification, then stop. For entrepreneurs, that’s not an option. Continued learning is as necessary as oxygen and nourishment. Knowledge is nourishment for our brain that we naturally seek.

It’s not a secret that an entrepreneur needs to have wisdom and knowledge to be successful in their endeavors. Pursuing an investment opportunity without knowing and understanding the details is not the best strategy. The more we know, the more likely we are to succeed. (But only to a point—see No. 2 below.)

If someone wanted to start a restaurant but knew very little about food, business, accounting, cooking, customer service, managing people, or the market area, it would likely be a quick and disastrous attempt. We need to know before we go.

There are numerous ways to seek out knowledge. But no matter what options are available, entrepreneurs will find at least one to satisfy their hunger for knowledge until another option is available—they’re always learning.

I’m sure this will look familiar to you, but here is a shortlist of ways to gain knowledge:

  • Attend a class
  • Attend a seminar
  • Find a mentor
  • Read books
  • Listen to podcasts
  • Read blogs
  • Converse with others

top real estate books

Related: 4 Influential Business Books Every Entrepreneur Should Be Reading

  1. The ability to pull the trigger at the right time

We will never know everything about real estate investing, but there comes a point where we know enough. Therein lies the real test of the entrepreneur: Can they pull the trigger at the right time?

There is a spectrum of decision making. The left extreme is making decisions without any information. The other end is the extreme of always needing more information, resulting in no decision whatsoever. Either extreme is rarely the case, as most of us make decisions somewhere in between.

But entrepreneurs can actually make a decision. Too many fall on the right side of the spectrum and always feel they need more knowledge.

The left side of the spectrum is for fools. They are the quick-draws, who jump in without any prudence. They often fall victim to scams and are broke without knowing what happened. A fool and his money are soon parted.

Those who find their home on the right side of the spectrum are the “paralysis by analysis” types. They want to have every detail figured out. They are continually seeking that additional piece of insight or always waiting for the perfect opportunity. Neither ever comes, and in the end, they do nothing.

An entrepreneur knows when they know enough. They recognize that point in time, which is key. Because once they are confident in their knowledge, they act. They are able to know when they know what they need to know.

  1. An unusually low fear of failure

Success does not come without failure. Period.

“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.” —Michael Jordan

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We’ve all heard the story about how Thomas Edison tried a thousand materials before he found the one that made the light bulb work. Or how Stephen King submitted his first book, Carrie, 30 times, while would-be publishers rejected it each time. Or how George Lucas took his idea of Star Wars to Disney, United Artists, and Universal and was sent walking on each occasion—until finally FOX decided to roll the dice.

Entrepreneurs don’t fear failure; they thrive in it. An entrepreneur inherently realizes that failure brings education, knowledge, growth, confidence, and opportunity. They recognize that failure is the key. It’s about trying; it’s about putting yourself out there; it’s about breaking the norms; it’s about exploring beyond the box; it’s about ignoring the hoops and jumping through walls; it’s about challenging the status quo. And this approach will inescapably come with massive failure at times, but those failures are the needed steps to be taken on the path to success.

Unfortunately, most people are too concerned about what others may think if they fail. Or too worried about the consequences of a failure. Entrepreneurs are more concerned with the consequences if they don’t fail.


What crucial entrepreneurial trait have I missed?

Let me know by commenting below.

Dan is a high school Business/Marketing teacher, real estate investor, and personal finance advocate in Denver, Colorado. He and his wife have a variety of real estate investments including multifa...
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    Wenda Kennedy JD from Nikiski, Alaska
    Replied 7 months ago
    I totally agree with your analysis. I too don't talk about my real estate and other business interests with those around me -- except for a select few. And you're right. I'm always educating myself and I expect to fail on a regular basis -- so I'm willing to put my toe in the water when others won't.
    Dan Sheeks Rental Property Investor from Denver, CO
    Replied 7 months ago
    Thanks for your comment, Wenda.
    Turner Wright Investor from Houston, TX
    Replied 7 months ago
    Good read! And, I agree with your three vital traits. I began pondering the idea of REI this last summer when a career I wanted didn't go through. I decided I wanted something more stable, where I'm in control, and I don't have high overhead--like many businesses have. My wife and I did very well selling our two previous properties ($397k in profit), but we were committed to our careers and didn't think about doing real estate. But, things have changed for me and I am itching to get at it! I decided in October to change my career to REI. I'm currently refinancing my home to help lower my monthly mortgage bill and then I'm going to open a HELOC to help purchase my first property. In the meantime, I'm learning everything I can about REI, financing, foreclosures, pre-foreclosures, lists, going to auctions, meeting other REInvestors, brainstorming the name for my LLC, securing a domain name for it, etc. I'm just itching to get started! I'm hoping to have everything in order by mid January to be ready for my first purchase before the end of February. Thanks for posting your article!
    Dan Sheeks Rental Property Investor from Denver, CO
    Replied 7 months ago
    Hey Turner. Best of luck to you in your REI endeavors!
    Michael P. Lindekugel Real Estate Broker from Seattle, WA
    Replied 7 months ago
    be skeptical of what you read on the internet. dont take it as gospel. turn your bullshit detector to high when anyone says they are a guru.
    Dave Rav from Summerville, SC
    Replied 7 months ago
    Great article! What reasonated with me especially was you're forenote about non-REIs inquiring about your investments. I recently posted a similar post about this "feeling" I get when people ask "how many properties do you own?" For me, I don't feel they are hoping I fail, but rather they are trying to "figure me out" and inquire about my financial house. Sometimes, after I answer, they respond with jealousy, reservation, or merely just viewing me in a different (unequal) light. They see a younger working-age person with multiple properties bringing income affording him the ability to only work part-time. --------- Anyways, yes two of your points I strongly agree with - 1 Lifelong education and 2 Atypical lack of fearing failure. Continued education is paramount
    Dan Sheeks Rental Property Investor from Denver, CO
    Replied 7 months ago
    Hey Dave. Thanks for your comment. Glad the article resonated with you.
    Jeremy Ruff
    Replied 7 months ago
    Oh my lord! Where is this community of ppl Dan? I want to do this have been around ppl who build 4 million dollar homes in Bonnie Brea and cherry creek as investments.. how do I break into this investing? I know a guy named Steve who owns half of the hylands... I’ve done work for these ppl for years as a contractor and can never quite get there.. please help!!
    Dan Sheeks Rental Property Investor from Denver, CO
    Replied 7 months ago
    Hey Jeremy. Step 1 for you - go to a meetup in the Denver area. You can find them on the BP website under "Network" and then "Events". Or go to and join a group of RE investors and go to one of their meetups. Then talk to people. If you do this, your whole world will open up and opportunities will come out of nowhere.
    Anthony Jeffers from Jersey City, New Jersey
    Replied 7 months ago
    It would be interesting if, the next time someone inquires about your REI, you told them the bottom fell out, so you’re done with REI. Then after seeing how they respond, laugh and say, I was just joking with you, it’s going great! Some will react in a way that shows their true feelings. I agree 100% with your statement, “not everyone is cut out to be an entrepreneur”. Entrepreneurs are willing to do what others won’t and thus ultimately achieve what others don’t.
    Dan Sheeks Rental Property Investor from Denver, CO
    Replied 7 months ago
    Hey Anthony. I love your idea! I will play that trick on my friends next time REI comes up just to see what their reaction is. :-)
    Pat Tobin Investor from Salt Lake City
    Replied 7 months ago
    I cried tears in fear after I bought my first home to house hack. I mean, talk about buyers regret, but I DONT regret it one bit. Holy smokes the pressure to succeed was high but I did what I had to do day by day until each of the rooms was filled and Im now I'm not paying a mortgage. I call that a success. I wish you all the best of luck in your aspirations!
    Barry A. Rach
    Replied 7 months ago
    "Nothing will ever be attempted if all possible objections must first be overcome". Great quote by Samuel Jackson, English Author (1709 - 1784)