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The Making of an Entrepreneurial Leader Who People Actually Want to Follow


You do not need to be an entrepreneur to be successful. Far from it.

But what that said, the reality is that with the internet leveling every playing field imaginable, it has never been more attainable to monetize your skills as your own boss.

Because of that, many have jumped at the opportunity. 30 million people in America are now following their entrepreneurial spirit and taking business matters into their own hands.

Stories of financial triumph, world-wide reach, and glorious crash-and-burns have given the rise to shows Shark Tank, Silicon Valley, and Girlboss while making entrepreneurism as sexy as anything going down in our modern day culture.shark tank

And, it is sexy. Nothing is more tempting than risking it all on yourself and your ability to build your empire. For success, for fame, for money – it is sexy.

What happens before you roll out your product/innovation/service, once the launch has come and gone, and after the market has decided the fate of your baby – is another story.

In fact, this story is far less sexy. That’s because it probably failed. In fact, the odds are overwhelmingly likely that you failed. To the tune of an 85% percent chance.risk

The reasons start-ups fail are endless, but all failures start at the personal (human-to-human) level -- not having a north star, building a product without market feedback, and mismanaged teams all crush businesses.

Successful leadership is a long series’ of tiny moments done incredibly well at the individual and team level. Inspiring the desired affect or action, leadership is not viewed as sexy because it’s not a new product. Not a wad of cash from an angel. Nor a pitch deck that you slaved over.

Leadership is the way in which people remember you, trust you, and ultimately follow (and literally BUY) you.

The drive you had to sacrifice yourself, your personal feelings, and biases before the dream or the team. It’s the influence you have to set a vision and charge for glory.

It’s growing your team and providing value to at least one person that desires it.

Businesses are people and markets are dialogues. You must be able to lead them, both.

How to make Entrepreneurs into Leaders

First, understand that leaders are direct, specific, and articulate(storytell!) their desired message with purpose to both their team and clients.

Stop beating around the bush. Speak with energy and say what you mean. The ability to articulate your vision, build the APPROPRIATE(note: not flashy) team to propel the vision forward, and create open and honest dialogue on all levels is what sets great businesses apart from the masses -- Work on it!

Here’s how:

Uncover how people best receive your message and product 

Are you charismatic? Are you strong and bold? Do you prefer to speak softly and after you have heard all ideas? What makes YOU unique is how people will truly understand  you best to ensure you are a transformative and supportive leader rather than just becoming noise or just "boss".

And know your message -- IT SHOULD BE A MESSAGE THAT HELPS POTENTIAL CUSTOMERS, NOT SOMETHING THAT HELPS YOU. Product/Market Fit is a reciprocal relationship that your product develops with your users. Your product/service/concept adds value to their lives, while users find enough value to continue to utilize your product in exchange for $$$.

Become comfortable making decisions 

Make every decision with two things in mind: 1. You must be ready and willing to sacrifice yourself before your team or your dream. That means the hours you put in, the compensation you receive, and the credit you take. Give it as much as you can away before you take some for yourself.

2. Be ready to put your name on your decisions. If you can’t make a decision and take FULL ownership for the consequences of the decision, save us the time and defer to someone else. Caution: Deferring decision-making is most likely compromising your responsibility to take lead YOUR team.

Embrace dialogue

This is so much easier said than done. Because oftentimes, the feedback we receive is negative, deconstructive, and discouraging. That’s okay. LISTEN TO IT!

It may hurt in the moment, but it’s better to correct your charted course now than months or years down the road when it wasn’t working well anyway. Be ready to compromise on your methods, but never on your North star.

And the same goes for you to your team. Leaders understand that standards are not what we preach, they are what we tolerate.

Do you tolerate people showing up late? People that give less than 100%? People that knowingly undermine your authority? Nip that shit in the butt immediately, tactfully, and preferably in private.

So how is this applicable, you ask?

Because this is how you’re going to get ahead as a leader and entrepreneur. Ideas are cheap and everywhere. But, execution through leadership is what dials you in as a success.

I know that every leader is not an entrepreneur. But every successful entrepreneur must be a leader.

About the author, Tim

US Navy Surface Warfare Officer.
Lacrosse Player.

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