In this series you and I will look at the pivotal steps the founder of Barstool Sports, Dave Portnoy, took to transform a free local sports newspaper… into a website that Penn National Gaming purchased a 36% stake in for $163 Million, giving the company a valuation of $450 Million in January 2020.

Thinking back on all the remarkable entrepreneur documentaries I’ve listened to, watched, and read I recognize that almost all of them serve as cautionary tales for anyone who has been sheltered from the realities of what it takes to start and build your own business.

When I started watching the Barstool Documentary series it didn’t take long at all for me to see that there were some brilliant lessons to be had here for BOTH… people who prefer to work with/for entrepreneurs AND… for anyone who might be on the fence about starting their own business.

The allure of owning your own business has something in common with this comedic approach to an transparent Tinder proposition…

—>All the cool delusional assumptions people have in their heads surrounding the idea of “Be Your Own Boss” are quickly dispelled once they see everything that comes with the package

—>The emotional and financial roller coaster ride that owning a business can take you on is literally balls to the wall insane and will almost indefinitely make you cry

—>Swimming in the riches from an amazing opportunity paired with hard work and immaculately executed tactics can be otherworldly

This is why , when it comes to professions, being an entrepreneur most definitely fits into the “high risk, high reward” category.

And since there is money to be made in convincing people to hang out their own shingle as an entrepreneur… if you’re on any kind of internet marketer’s list you’ve very likely come across a pitch which flows something along the lines of…

“Stop being someone else’s secret weapon.”

“Stop letting inferior colleagues get all the peer respect, publicity, and wealth that you deserve.”

“Stop letting someone else get rich off of your sweat and your unmatched supremacy.”

“It’s never the right time to take the leap into your destiny! You’ll never be 100% prepared for any new solo entrepreneurial venture you go into but my system for taking yourself from invisible zero to hero will have you starting off in the fast lane.”

Etc. etc. etc.

In these pitches you might hear the Henry Ford origin story, the Richard Branson origin story, the Steve Jobs origin story.

If the marketer is sharp they will adapt the pitch and make sure every example they cite now is from a famous company that was birthed in a dumpster fire economy.

And of course, you’ll hear the hand-picked testimonials of “people just like you” who followed the marketer’s advice and still have a viable business in the midst of this Covid-19 shit show we’re all dog-paddling in right now.

There will be those who hear this pitch and say, “YOU’RE RIGHT! I’ve been hidden in the shadows for too long. I’m going to dare to step into the spot light and start offering my own service/product business.”

Many a founder who end up being the face of their own company got their start as the result of coming to this conclusion.

When I hear this pitch, it bounces right off of me.

Why?

Because I liken it to the options of having a child or a brood of children to raise and… having zero kids and only having yourself to be responsible for.

One option puts the weight of the world on your shoulders.

The other option only puts your weight on your shoulders.

For me, if I have the choice, I would rather be the “fun uncle or Granddaddy” who gets to hand the kids back at the end of the day.

When it comes to earning an income, I personally prefer the option of a partnering arrangement to share in a piece of the upside I create for a business owner or two, who I exclusively pledge my sword to and let the owner take on the brain-bleeding responsibilities of firing, hiring, managing staff, making payroll, securing financing, etc.

While I deeply admire entrepreneurs and want to work exclusively with them, I have not interest in switching seats with them.

If you’re reading this and saying, “That’s me! I feel the same way” and you want to either… work for an entrepreneur as an employee or… work as a contractor/freelancer and find the right handful of people to create long-lasting and profitable partnership arrangements with clients… I trust you will get tremendous value out of what I’m sharing with you in this series.

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