Why I’m an Entrepreneur Who Is Afraid To Fail, and You Should Be Too

Success isn’t about risk tolerance, it’s about risk mitigation

Joe Procopio
4 min readDec 7, 2021
Photo by Fionn Claydon on Unsplash

I’d like to debunk some conventional wisdom about success and failure in business. Namely, this broken circle of logic:

A. Entrepreneurs and business leaders have to take risks in order to succeed.

B. Younger people are more likely to take risks than older people.

C. When taking on a new challenge or starting a new business, older entrepreneurs and business leaders are more likely to be successful than their younger counterparts.

A plus B does not equal C. Why?

Conventional advice about risk and failure is usually poetic garbage

Most of the platitudes associated with risk and failure are often just a bunch of word salad — phrasing that sounds profound when you first hear it, but on reflection doesn’t make a whole lot of sense.

Take your pick from these Successory-style mantras that I know you’ve heard before:

  • Fortune favors the bold.
  • Go big or go home.
  • Fail nine times and get up 10.



Joe Procopio

I'm a multi-exit, multi-failure entrepreneur. NLG pioneer. Building TeachingStartup.com & GROWERS. Write at Inc.com and BuiltIn.com. More at joeprocopio.com