The “All In” Entrepreneur

For years, I used to say I was an entrepreneur. I worked in a midsize company and was a rising star, as Kim Scott describes it in her book Radical Candor, Sr. Manager and then executive managing operations of over 3000 employees all over the world. I had an assistant, an office, and margins. But for whatever reason, because I thought innovative and constantly tried to think like a business owner, I considered myself an entrepreneur. For years I thought I was an “All in” leader that took risks. But I aaa wrong. WAY WRONG.

When I left that company to join a flailing startup of five employees, with no cash, no margins, no structure, and no strategy (but we did have three executives including me), I really learned what being an entrepreneur was. When my name became tied to ownership and payroll, when I stayed late making collections calls to unpaid clients because otherwise we weren’t going to make payroll, when I felt the absolute earth shattering pressure that we either close three big clients this week or we have to let go of five people, I realized all of a sudden “I guess this is what it’s like to be an entrepreneur.”

Go “All In”

It’s not the glamorous videos online or the 100 posts a day to multiple feeds. It’s not the coolness of 1.5M followers or more. Celebrity does not make someone an entrepreneur; It’s the constant grind that does, it’s the risk. Grant Cardone describes the “All In” mindset as overcommitment, taking on the ownership and risk, and always figuring it out.

Figure It Out

When people that work with me say they want to be an entrepreneur but are unsure how, I quote Gary Vaynerchuk and say:

You didn’t grow up driving…you figured it out. – Gary Vaynerchuk

Just get your idea and figure it out. Execute your passion.

We are so overloaded with mediocre employees, mediocre podcasts, and mediocre leaders that all it takes is for individuals to fully grasp the idea of risk to be fully baptized into the true gospel of entrepreneurship.

All In On You

You have to go all in:

  • All in on your ideas
  • All in on your passion
  • All in on yourself

I learned this in my time at the startup. In the first four months, our performance was struggling, cashflow was down, and I wasn’t sure we were going to make it. In fact, I had just met with the CEO and discussed how we were completely underwater financially (did I mention it was the holiday season).

That night as I talked to my wife, my spirits were low and I just didn’t think this could happen. Then my partner asked me something that was forever life-changing:

“Do you believe in yourself or not?”

I’m not sure if it was the bullish tone she used, or how right she was, but the question struck a chord. If you are truly an entrepreneur, you have to believe in yourself and go all in.

Take risks.

Go All in.

Be a real entrepreneur and change your life.

Oh and that business? We killed it and set record performance over the next two years.

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