Entrepreneurs Are Crazy

Becoming an entrepreneur is illogical.  If you were to calculate the expected value (i.e., the probability-weighted average of all possible outcomes) of being an entrepreneur as compared to living the safe life of a traditional executive, it wouldn't even be close.  On a purely rational, probablistic basis, the math for entrepreneurship doesn't add up.

Despite this, entrepreneurship is on the rise.  For those of us who live in that world, we know that entrepreneurship is about passion more than rational thinking.  It inspires those who are crazy enough to believe that they can change beat the odds and succeed in changing the world, or at least their little corner of it.

That's why I love Linda Rottenberg's new book, Crazy is a Compliment.  First, I should admit a bias.  I deeply admire Linda and her non-profit organization dedicated to global entrepreneurship, Endeavor.  We first met in college when we volunteered together in an inner-city high school in Roxbury.  Although I don't get to see her as often as I would like, I've had such respect for Endeavor that I decided to donate the proceeds from my book to it.  Thus, I was positively inclined when I cracked open the binder.

But I still loved it.  It gives entrepreneurs a roadmap, plenty of fun war stories and (in typical Linda fashion) a very human angle.  For example, perhaps the most powerful part of the book is when she shares how her husband's bone cancer diagnosis forced her to be more vulnerable at work and let go of her perfectionist zeal.  She even dedicates a section of the book – "Go Home" – to addressing the importance of trying to "Go Big AND Go Home", i.e., pursue an ambitious career with passion AND at the same time live a balanced life (charmingly, she writes this section directly to her daughters – as if the reader is a bystander in the dialog).

Here were a few of my other favorite sections/lessons:

  • Esta chica esta loca.  As an entrepreneur, there are many times when you need to do crazy things.  In fact, if you're not doing a few things that conventional wisdow would refer to as crazy, you're not thinking big enough.
  • Fire your mother-in-law.  Sometimes, when you are growing and evolving the business, you have the courage to kill "sacred cows" (pun intended – but not all related to my mother-in-law, who is lovely)…
  • Flawsome.  Effective leaders are very human – flawed AND awesome at the same time.
  • Upside down mentoring.  I've written about Reverse Mentors and Linda's concept is similar – senior people should seek out junior ones to learn from them, not just mentor them.

The book is chock-full of funny, engaging stories and case studies as well – some familiar, but most unfamiliar and not your typical entrepreneur yarns (e.g., I never knew the story behind Maidenform Brands).  

If you're looking for a good read this fall, I highly recommend it.

3 thoughts on “Entrepreneurs Are Crazy

  1. Agreed. I find the safe job more stressful because I am making money for someone else (and they don’t appreciate it enough). And the people that work for safe jobs are…well…safe.


  2. I know I’ve heard it said that being an executive or working in a job is a higher expected value than being an entrepreneur, but I find that hard to believe based on my experience and that of all of my friends and contacts.
    From my friends and contacts the ONLY ones that are wealthy with over $1 million in assets are entrepreneurs. In fact most (not all) but the majority are wealthy and far more wealthy than any of those that have worked a 9-5 job all of their lives.
    I guess it depends on a lot of different things but in my experience you are far more likely to be wealthy by choosing an entrepreneurial path.
    A job is safer, definitely could agree with that, and potentially a lot easier, less stressful and less work, absolutely, but not a path to more money.


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