The Hard Thing About Hard Things

Setting your own hours, being your own boss – oh the life of an entrepreneur. You can do what you want when you want because you are the boss. Right?

Financial Glass - The Hard Thing About Hard Things bookshelfNot so fast says Ben Horowitz in his book The Hard Things about Hard Things. Horowitz talks about his time as CEO of Opsware a technology company that eventually sold to HP in 2007 for $1.6 Billion. He is now a venture capitalist and advises startup CEOs about how to run their businesses.

 Horowitz hilariously dethrones the myth of the carefree CEO with a fast growing company experiencing the hockey stick of growth. The stories that he tells in the book highlight how difficult and challenging the role of a startup CEO is. There is no playbook or processes for making hard decisions which is why they are so hard.

Financial Glass - Man Stressing Covering His Eyes on Chair

I learned a lot about what good decision making as a CEO of a technology company looks like versus how a manager operates. The buck stops with the CEO and being able to wade through difficult decisions when there is no good choice is a real challenge. 

Through his time at Opsware Horowitz talks about taking a company public in the midst of the dot-com bubble. Pivoting Loudcloud to an enterprise software company and selling off all of the company’s revenue. How he navigating firing friends and faithful employees. How he ultimately sold Opsware for $1.6 Billion with only having 24hrs to fix an accounting error that would have blown up the entire deal.

Financial Glass - Like A Boss Mug 

This book is fantastic at painting the picture of what being a CEO of a fighting startup is really like. What I find illuminating is that during the time of Horowitz’s tenure as CEO he was ridiculed and not seen as a great leader outside of the company. Yet after the sale to HP for $1.6 Billion and becoming a Venture Capitalist (VC) where he is able to be candid to the CEOs he works with now, he is seen as a great success.

It is easy to create a narrative after the fact and we often forget what it is really like during the actual experience. I really enjoyed Horowitz’s take on the really challenging decisions that most people don’t talk about. Being a CEO is not easy yet we glamorize it today with the stories of Mark Zuckerberg, Jeff Bezos, and Elon Musk. Horowitz brings us back down to Earth and puts things into perspective for current or want to be CEOs.

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3 thoughts on “The Hard Thing About Hard Things

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  1. This sounds like such a good read! I have a 50 books in 52 weeks (taking a week of for Thanksgiving and Christmas), and I’m thinking of theming it with entrepreneurial / lifestyle enhancement book. I might add this one to my list!

    1. That’s an awesome challenge Moriah! It is a good book to add to the list and a pretty quick read as well. The author is a great story teller and keeps things interesting. Good luck on your chellenge!

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