Every high-level entrepreneur pays this price

“There is nothing wrong with having butterflies as long as you can get them to fly in formation.” – Rob Gilbert

Every year for the past ten years, I’ve given a talk at WLU Business School.


And every year (every. single. year), at some point in the discussion, a student has asked me:


​”How do you deal with fear of failure?”


At which point, I introduce the class to a guy named Mason.


Mason started using my basketball training programs when he was 13 years old.


Five years later, he was an All-State shooting guard, and held 3 point records in the state of Oregon.


Impressive stuff, but not as impressive as what he did next:


Instead of playing college basketball, Mason decided to cut his teeth in the world of entrepreneurship.


This year, Mason’s business will generate $20MM in revenue…


…And he is well on his way to landing a $100MM exit before he turns 30.


At this point, I usually pause to let the weight of that number can sink in.


Then, I continue:


One night at our summer retreat, Mason told the story of how he and his partner launched six failed businesses in the span of two years, before they finally got one to take off.


To paraphrase what Mason said that night:


​”I knew I was going to fail before I succeeded, so I decided from the start to keep on going until it worked. I failed fast, learned from each failure, and used what I learned to make the next venture a little better — until eventually, one of them took off.”


That type of grit is rare in society, but it’s the standard price of admission for high-level entrepreneurship.


Nobody learns to fight without taking some punches, and nobody builds a business without taking some bumps along the way.


The take-home point:


Those who make it in business get over “fear of failure” pretty quickly when they realize:

Failure is a mandatory part of the learning process that leads to success.

So no, failure is not to be feared.

It is to be analyzed, learned from, and transformed into progress.


So that’s what I tell the class.


I hope it’s helpful for you, as well.

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​P.S. Our one on one business coaching program is officially full.​

Big thanks to everyone who applied, and big congrats to the three entrepreneurs (two business owners and one fund manager) in the program.

This is going to be fun 🙂

​P.P.S. If you enjoyed this week’s series on entrepreneurship, I think you’ll enjoy this:

​Compound interest isn’t just a financial strategy, it’s a life strategy.



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