Why People Don't Understand Entrepreneurship

I believe there is a huge misunderstanding in society today about entrepreneurship. Most people think entrepreneurship is about coming up with a great business idea and making money. I’ve heard people say “let’s come up with an app and get rich quick.” It’s delusional.

Great entrepreneurs come in every shape, size, and form. And the greatest ideas come in the most unexpected ways at the most unexpected times. 

It was the mid-’90s when I had an aha moment on a crowded train headed into work. I saw a photo of Mark Messier on the back page of every passenger’s newspaper. Messier was holding the Stanley Cup after snapping the New York Rangers title drought. As I looked at the photo, I envisioned a signed photo that my company could sell as a signed item to die-hard Rangers fans, just like me. This marked the official beginning of the next phase for Steiner Sports, one that would make it the country’s leading sports collectible business and it was my most daring leap forward as an entrepreneur. 

As it turned out, with this idea I was right. There weren’t even 20,000 people at the game, but many thousands more now have on their walls a photo of the pinnacle moment with a beautiful, bold autograph from Messier. 

Why is a clever person wise? Because he knows what to do. Why is a stupid person foolish? Because he only thinks he knows.

—Proverbs 14:8

The years that followed the launch of the collectibles end of Steiner Sports (we had been operating as a sports marketing firm for a number of years prior) were a time of tremendous growth. In August of 2000, I sold my company, Steiner Sports, to the Omnicom Group. As part of that process, I accepted a buyout that paid me more money than I ever dreamed I could have. After working nonstop since I was ten, I didn’t have to work another day in my life. I should have been on top of the world, as all my hard work had finally paid off in a huge way.

But after putting in relentless effort and long hours to build a company—and frankly, an industry—for close to two decades, I was emotionally bankrupt after selling my company. After fourteen years of relentless work, I went through a of resetting my life.

I was searching for more clarity and more time to commit to my top priorities. As I examined how I spent my time at work, I found that I was SOS—stuck on stupid. I’d always prided myself on being resilient in the face of possible failure. I embodied all those messages we’re bombarded with every day: Don’t quit! Fight through it! Keep going! Don’t get me wrong, I’m a big fan of those qualities. The problem was that sometimes my ideas sucked, and I was too stubborn to realize it.

As I built my company, I fell into the trap of reading my own clippings. I started to think I could do anything I wanted, that every idea I had was a slam dunk—that everything was going to turn out like the Messier project. As an entrepreneur, don’t let your ego swell to the point that you are SOS. Right after I sold the company, I made more mistakes in one year than I had in my previous fourteen years in the industry combined.

Looking back at that mess, I saw I should have been a better quitter and let go of bad ideas. To help me move forward, I developed a three-step process to test if my ideas were worthwhile: dream big, sample small, fail fast. I like to say that losing gives you the blueprint for winning, and this blueprint has helped me and my team at Steiner Sports decide if we should stay with an idea or let it go.

Great ideas usually start with big dreams. When I dream big, I visualize a goal that I want to achieve. That’s when the path to that achievement begins to take shape. I know the destination. How do I get there from where I am now?

Once I begin to pursue my goal with purpose and commitment, the extraordinary traits we talked about earlier—creativity, clarity, focus, determination, diligence, and thoughtfulness—initiated as a result of my efforts. Purpose is what lights the fire, but it’s my big dreams that are the logs and the kindling that allow it to burn.


This story and more can be found in my new book Living on Purpose: Stories About Faith, Fortune and Fitness that Will Lead You to an Extraordinary Life. The books will be released tomorrow, December 4th.

There's still time to pre-order to assure that yours ships ahead of the pack. Pre-order here.


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