3 Must-Have Traits of Successful Entrepreneurs

3 Must-Have Traits of Successful Entrepreneurs

5 min read
Dan Sheeks

Dan Sheeks is a high school Business/Marketing teacher, real estate investor, and personal finance advocate in Denver, Colo. In his 16-plus years of teaching high school, he has taught a variety of business subjects including financial literacy, entrepreneurship, and marketing.

Dan’s passions include working with teenagers, advocating for personal finance education, investing in real estate, and promoting the FIRE movement. Embedded in his classes is the co-curricular DECA club in which students travel, compete, acquire leadership skills, do community service, and have fun! His students have competed at the national level in entrepreneurship, personal finance, marketing, and hospitality services with much success over the years.

Dan volunteers in the MoneyWi$er initiative out of the Colorado Attorney General’s Office with a few other hand-picked experts from around the state. The program strives to advance financial literacy in Colorado secondary education. Dan has also taken his high school students into local middle and elementary schools, where his students have taught the importance of personal finance to younger children.

Launched in late 2019, SheeksFreaks is a blog and Instagram page that are dedicated to helping young people learn money management skills, start investing in real estate, and pursue financial independence. The SheeksFreaks blog aims to help teens use specific methods of saving, earning extra income, and investing to set them on a track to purchase real estate investment properties in their early 20s and achieve financial independence at a young age.

Dan and his wife have a variety of real estate investments including multifamily, single family, Airbnb, and out-of-state BRRRRs. They currently have 14 units in the Denver metro area, Colorado Springs, and Detroit.

SheeksFreaks Blog
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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.

meetups group

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

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.