Book: Crazy is a Compliment

If you are in Boulder and you haven’t heard of Linda Rottenberg, you are in for a treat. She’s the founder / CEO of Endeavor and recently joined the board of Zayo. Dan Caruso, the CEO / co-founder of Zayo is hosting an event tonight at eTown Hall interviewing Linda about her new book Crazy is a Compliment.

I read the book last night. After a long Monday, I realized I had three physical copies on my desk at home (that had come from different friends) and I still hadn’t read it. That didn’t seem right, especially since I’m having dinner with Linda, Dan, and a small group of people tonight. So I gobbled it up last night.

Before I get into the book, there are still a few seats available for the event tonight. If you are into entrepreneurship, I highly recommend you attend the fireside chat between Linda and Dan from 5pm to 7pm (Tuesday, 1/13/15).

I’ve known of Linda for a while through her work at Endeavor and finally met her for the first time in March 2013 in Rio while I was at the Global Entrepreneurship Congress. Among other things, she roped me into giving a Day1 talk, which was extremely fun to do. If you’ve never seen mine, it’s below.

Ok – on to the book. It’s dynamite. Like my upcoming book Startup Opportunities (which you can pre-order now – hint, hint), it’s aimed at first time and aspiring entrepreneurs. Linda is an amazing storyteller and builds the book around stories from her own experience as well as many of the entrepreneurs who have been affiliated with Endeavor programs. Her stories are all in first person and powerful to read – very personal, easily consumed, and full of lessons.

She weaves the stories into three major sections: Get Going, Go Big, and Go Home. Get Going is about getting started. Go Big is about scaling. Go Home is about getting harmony between work and life.

Linda breaks entrepreneurial companies into four categories:

  • Gazelles: super high growth (I use the same word in Startup Opportunities)
  • Skunks: inside corporations – what is tediously referred to in academia as intrapreneurship
  • Dolphins: social entrepreneurship
  • Butterflies: small, local businesses

I loved her taxonomy and will use it going forward. Then, on page 90, I did something I rarely do when reading a hardcover book – I dogeared the page so I’d come back to it. On this page Linda defined four types of entrepreneurs using labels I’d never seen before.

  • Diamond: Visionary dreamers leading disruptive ventures (Mark Zuckerberg, Sergey Brin / Larry Page, Ted Turner, George Lucas, Elon Musk)
  • Star: Charismatic individuals building personality brands (Oprah Winfrey, Martha Stewart, Richard Branson, Estee Lauder, Giorgio Armani, Jay-Z)
  • Transformer: Change makers reenergizing traditional industries (Howard Schultz, Ray Kroc. Ingvar Kamprad, Anita Roddick, Blake Mycoskie)
  • Rocketship: Analytical thinkers making strategic improvements (Jeff Bezos, Bill Gates, Fred Smith, Michael Dell, Mike Bloomberg)

This categorization totally nailed it and she went on to spend a lot of time discussing different entrepreneurial personalities. Throughout, Linda used examples from all over the world, drawing from the broad range that Endeavor has covered over the 17 years it has been around.

As someone who has spent the last six months immersed in writing a book aimed at first time and aspiring entrepreneurs, it’s pretty cool read one from a totally different experience set, with so many different stories, and feel lots of conceptual overlap. If I’m describing you when you see the phrase “first time or aspiring entrepreneur”, grab Crazy is a Compliment and pre-order Startup Opportunities. And, if you are in Boulder tonight, come check out the fireside chat.


  • I love the term “Crazy”, one of the leaders of the startup community here in Western Mass calls all entrepreneurs “crazies” – and does so in the most complimentary way possible. Thanks for the book recommendation, I wish I could attend the event.

    Since I learned about you through Mattermark I’ve watched tons of your videos and read lots of your blog (thanks so much for having so tons of great content out there for folks)

    But this talk filled in some of the backstory of growing up in Dallas and MIT that I hadn’t heard before – I can really see how you were able to learn from those early experiences the power of software and entrepreneurship. Both the good side (those checks showing up every month) and the decline.

    “We knew Boulder was home for the rest of our lives. It’s a very powerful notion of how important it is to choose where you want to live your life rather than having it chosen for you or feel you have to be somewhere.”

    Boulder has been on my list to check out as a possible place to move for over a year. Now I’m “jonesing” to experience Boulder.

  • I’m going to have to weigh in on the title. Being someone living with bipolar disorder, I do not find “crazy” to be a term anyone should use. While I am a high-functioning entrepreneur, I have spent far too much time in the company of the mentally ill who are truly debilitated. To them, and to me, “crazy” is a pejorative. Just like any of the other ones that come to mind. Because I am able and healthy, relatively speaking, I take it upon myself to be an advocate for those who are not, and that includes speaking out to people using “crazy” like it’s a compliment. I know my perspective is unique (1/100 have bipolar; far fewer are as functioning as I am), but it’s because it is unique that I stand by it and stand up for it. Few speak for the truly mentally ill. Few ever really see them. I do. I have. So I speak.

    • I would have to respectfully disagree that nobody should use the word “crazy”. It has so many applications and this particular one doesn’t seem to be of the pejorative nature. I completely agree with you Emily in that nobody should use the word “crazy” in the matter you’re referring to. To me, it seems the author is simply just stating that people who think differently, work manically, and care a ridiculous amount about building awesome products are often referred to as crazy and that its should be a compliment. That being said, I haven’t read the book yet but plan to read it asap.

  • Just ordered it! Sounds awesome. I want to be a gazelle….

  • I have a passion for business books which describe the personalities and dynamic of people and companies, My favorite term is wild duck.
    How cool to do a taxonomy of these terms. I deeply love taxonomy, so I guess this book is next on my reading list. Thanks for posting.

  • Rick

    I just realized something… I’m so bored. I’m going crazy!
    Do you think crazy would still be a compliment in this case?

    • Rick

      Did I ask that question? lol


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  • Gustavo Corral

    Skunk works generally have a hard time getting off the ground : mid-level managers often do not have budgetary authority and so can’t dedicate resources to new ideas even though their work puts them in the best position to come up with those ideas.
    Innovation also takes time : you need to mentally clear your desk and let other dishes drop.
    Apple was saved many a time during the 90s by low level engineers doing unauthorized side projects.