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The Mythical Entrepreneur Mindset

5 Mental Qualities that Make Founders Legendary

This article originally appears in The Startup Forum Newsletter published by Jason Bennick on Substack and LinkedIn

Hey everyone, welcome to the first issue of The Startup Forum newsletter!

I want you to know that my goal with you as the reader is to provide a routine publication of informative and authentic insights that break down the world of startups, all of which you can put to practical use in your entrepreneurial journey.

Whether you’re a first-time entrepreneur, seasoned founder, any range of startup investors (high net worth, Angel, or VC), or an industry professional servicing or providing help to startups, this forum serves all interests.

Also, if you’d like to know a bit more about myself as the Editor behind this illustrious newsletter, feel free to click below and read more.

With that said, let’s get down to business, and see how I can make this first issue memorable and add some value to your life.

The Mythical Entrepreneur Mindset

You may have seen the subhead “5 Mental Qualities that Make Founders Legendary.”

While there are plenty of schools of thought on this topic from renowned teachers, many of whom I have had the fortune to meet and chat with, I will speak from my own experience in sharing these irrefutable qualities.

After speaking with billionaires, millionaires, winners, and losers; reading well over 100 books on this topic; working in, at, or with some of the largest companies in the world; as well as with many startups and companies you may never hear of, entrepreneurship comes in every imaginable shape, color, gender, and size.

In collectively analyzing all of this over many years, one definable character is common to every entrepreneur that becomes the hallmark of one.

A character that every brand new or even highly-seasoned founder will demonstrate, manifest, or otherwise embody in their daily life.

A character so observable, blatant, and natural that it is irrefutably factual in rating how serious that entrepreneur is.

The degree to which any entrepreneur leverages this character separates the “successful” from the “insanely successful” entrepreneur.


Entrepreneurship, at its core, is about your purpose.

Your purpose is factually your “why” for being an entrepreneur. Your purpose is what drives you. It’s why you get up in the morning. It’s what makes you solve the impossible. And it’s your daily reminder of why giving up can become far more complicated than remaining steadfast on your path to bringing the Big Win with your startup, regardless of whatever it takes. Simon Sinek’s “Start With Why” tells us that the leaders who’ve had the greatest influence in the world all think, act, and communicate the same way—yet it’s the opposite of what everyone else does.

However, rolling back any characteristic of decisive leadership means examining where every startup begins: with yourself.

Becoming an entrepreneur, much less an insanely successful one, means realizing the success of your startup journey depends 100% not only on a great product, team, or business but on your mindset starting from Day 0, combined with how much life you are willing to inject into your purpose.

So, long before any entrepreneur or founder begins discussing the attributes of being a great startup leader, one must start where it all begins.

If you can’t successfully lead yourself, you will never succeed in leading others.

Becoming a successful entrepreneur begins with your mindset and tackling the very foundation you must breathe through as an entrepreneur.

As an entrepreneur, your mindset for success is equivalent to the intrinsic value of your heart in operating your body. A weak heart will yield a weak body that cannot withstand stress or physical challenges. Likewise, a weak mindset will bring about a weak “you” that cannot withstand the challenges of building a winning startup.

With that said, knowing your entrepreneur foundation begins with your purpose; let us examine the 5 Mental Qualities that Make Founders Legendary and how the most insanely successful entrepreneurs leverage their purpose to crush the odds to achieve success.


I have never met an insanely successful entrepreneur who was not unmistakably passionate about their purpose.

True, every entrepreneur desires to achieve what they have set out to do.

But it is that unmistakable passion in their voice that echoes sniper-level focus when describing their objectives, explaining how they’re building, or what they’re doing to solve and overcome XYZ challenges.

Genuine passion is pretty tough to fake, but it is possible. However, any experienced investor or real entrepreneur can spot the wannabes strictly in it for the status or money a mile away and tend to avoid them like the plague. After all, who would want to be struck with their collision debris when they finally hit the brick wall they’re already heading straight into?

I will admit it took me a little while to spot these characteristics, but they genuinely are unmistakable.

  • They have a burning desire in their eyes to win, not a dull, lifeless glare, and their eye contact is searing to the point you can see their fire within.

  • Their voice tonality reflects a reserved emotion behind their drive, which comes across as confident as Kobe Bryant talking about game discipline.

  • Their stories sound genuine because they are. You can ask for any detail about it, watch their reaction, and see that this is the real thing.

  • Their energy fills the entire room. I mean the whole room. They seem to “run the table” at essential discussions. Not because they are great at talking, presenting, arrogant, or even a great storyteller. They have more energy from within than nearly anyone in the room, and it would take a corpse not to see and feel it when they talk about their purpose.

  • Their responses to challenges come with ease, confidence, and clarity. This is one characteristic that is a somewhat observable difference. Passion will drive any response, and in doing so, genuine passion breeds a level of confidence that can be scary to observers. That’s the difference.

Passion is not acting excited. Passion is what gets others excited to be around you.

Entrepreneurs who demonstrate an unmistakable passion for their purpose can never be mistaken for those who do not.


This is one of the most utterly remarkable traits of the wildly successful entrepreneur you will ever observe.

This trait has publicly defined Jeff Bezos, Elon Musk, and many others who have changed the world simply because of their ruthless determination to do so.

Hold up — does this mean ruthless with no compassion for others? Not necessarily. Hear me before you think I’m an advocate of fascist managers. That is not the case at all.

What I am talking about is an utterly ruthless, pitiless, unsympathetic, unforgiving, callous, insensitive, merciless, compassionless, unsparing, and cold-blooded determination with oneself to accomplish one’s purpose.

A determination that is observable in the life patterns of the incredibly successful entrepreneur:

  • Never relenting on arriving at your destination.

  • Never giving in to stops, blocks, or barriers.

  • Knowing that every “No” means “Yes.”

  • Laughing in the face of adversity and what anyone will tell you is impossible.

  • Not stopping at the 1st or especially 1,000th slammed door.

  • Never accept going significantly backward, even if it means kicking, scratching, and clawing to move everything one inch forward.

How exactly one chooses to go about executing one’s purpose and treating others with respect is what openly defines leadership style, personality, and ability to inspire (which will be an upcoming topic in future articles).

But please, make no mistake.

Finding yourself on the path of an entrepreneur with ruthless determination will be equivalent to pushing directly against the forward progression of a bulldozer––with your bare hands.

From what I know, it will typically be the bulldozer that wins.


This is the one black-and-white quality any entrepreneur can immediately gauge themselves against to rate just how successful they think they can be.

Have you ever met someone that can just “get sh#t done” no matter what?

Discipline is either a strength or a weakness.

Fortunately, it is not a DNA-attributable quality; it can be entirely overcome psychologically.

This is why the military can be so successful in changing people. It is because they teach discipline as the one life-saving quality that every soldier must learn if they want to stay alive.

As I carry the highest respect for our country’s military, as an entrepreneur, we can learn something from even the entry-level Private.

Discipline is Boss

If you want to make it as an entrepreneur, you must have a military-like discipline to get up every day and do what it takes, as long as it takes, and win your battles.

But the insanely successful entrepreneur pushes discipline to a much higher level.

  • Up at 0500 for months and years on end, eating the frog every morning, and working at near madman levels consistently to finish (no matter what) the mission-critical daily tasks at hand.

  • Door-knocking, cold-calling, road shows, or whatever it repeatedly takes, over and over, for days, weeks, months, and years to obtain and onboard the customers, partnerships, or investors needed to make their startup win.

  • Persistently and patiently having the same conversations as needed with their teams over and over and over on the same topics, on the same products, and on the same tasks until things are built, deployed, and delivered as Big Wins.

  • Refusing the parties, drugs, promiscuity, cop-outs, and excuses. Disciplined focus. Like a sniper through hours of a sandstorm. Unmoving. Unwavering.

Near insane levels of disciplined commitment and focus on executing, a trait that mere business and working mortals have difficulty grasping how such a human can exist.

And they get the job done.


This quality is one most people can’t seem to put their finger on when seeing a monstrously successful entrepreneur, but it is one characteristic that almost all of us can truly call the stuff of magic.

This quality alone separates the wheat from the chaff.

Hunters from the hunted.

Lions from the lambs.

And legends from everyone else.

Let’s define the word “grit.”

Or, more succinctly, from within our world of entrepreneurship:

This is where the rubber meets the road for most entrepreneurs. It’s where the magic happens.

More importantly, it’s where you either succeed or fail with your startup.

The mountainous barriers so many entrepreneurs have had to overcome would be enough to scare off anyone wanting to try and launch their first startup.

But we should also keep sight of one critically significant factor: nearly every successful billionaire, millionaire, or small business entrepreneur had to start once.

At some point, they had nothing behind them to fall back on for experience. They faced the same barriers you have, but of their own business nature.

Hard decisions must be made in situations, whether on the first day or the 1,000th day. Tough challenges must be overcome. And impossible odds must constantly be won.

Insanely successful entrepreneurs not only have the courage to take on the impossible but do so like a boss.

In fact, they do it with such confidence and grit that one may even question their sanity.


I saved this one for last because if you’ve made it this far in my newsletter, you likely have sufficient energy (and interest) to build from and move things to the next level.

Have you ever met or known someone who seems to have an endless supply of energy to work or do things?

Take that and multiply it by 100X, and you might finally reach the endless energy level of the highly successful entrepreneur.

Legendary entrepreneurs are notorious for their work ethic, long schedules, performance output, and pure drive to execute.

While I have never been, nor ever will be, an advocate for repeated all-nighters to solve problems, working insanely long hours for weeks on end to get self-imposed deadlines met, or even persevering through pain, illness, or bodily injuries to still show up and get sh#t done, I will confess that I have been guilty of doing all of this on more than one occasion.

Yet my energetic sacrifices pale compared to the long list of stories I have heard of what other entrepreneurs have gone through to bring a Big Win.

While one must sleep and eat reasonably well to remain coherent, healthy, and focused, the uncommon energy some entrepreneurs can muster out of nowhere can be mind-boggling.

Yet those levels of seemingly endless energy that can be sustained for weeks, months, or even years define the highly successful entrepreneur.

After all, with the unbreakable mentality of “why stop or even slow down until I’ve arrived,” when such a destination is 3, 5, 10, or even 15 years up the road, it would only seem fitting that such a human anomaly would have to have endless energy even to stay alive.


Let’s recap. We have 5 Mental Qualities that Make Founders Legendary which comprise what many call the “Mythical Entrepreneur Mindset”:

  1. Unmistakable Passion

  2. Ruthless Determination

  3. Military-like Discipline

  4. Unyielding Grit

  5. Endless Energy

Looking stable, focused, and sound-of-mind, when everything around them is going over a cliff spectacularly, may seem borderline spin-bin to some. Especially when you hear such a founder respond with maniacally calm comments such as “I think this is a great time to make a pivot” (with a genuine look of amazement) or “there seems to be a problem — give me a minute, and I’ll tell you how we can probably salvage this,” as the house is burning down.

At those moments, you can recognize the signs of a hard-core entrepreneur and one that makes sense to commit yourself to support and work with.

1 in 10 startups succeed. While the reasons are many, I genuinely believe that number could be bumped to 2 in 10 by every founder simply eating, drinking, and breathing these five qualities.

No one ever said entrepreneurship would be easy, and it is certainly not for everyone.

But the rewards of achievement go well beyond financial wealth.

In almost every instance, the greatest risk can bring the greatest rewards. For entrepreneurs, that comes in the form of consuming the fruits of your labor and toils with your teams, fulfilling the very reason you set out to become an entrepreneur in the first place.

Achieving your purpose.

And for me, there is no more extraordinary game to be played.

Best of luck in your own entrepreneurial journey, and I can’t wait to see you in my next newsletter with more startup insights!

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