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I just finished one of the first books in a long time called The Hard Thing About Hard Things. This one is by VC Ben Horowitz of Andreesen Horowitz. Ben shares the lessons he learned during the tumultuous years of building LoudCloud then Opsware which was later acquired in 2007 by Hewlett-Packard for $1.6B.

The gist of the book is sharing all the hidden experiences entrepreneurs face to create a valuable company—lessons that are rarely, if ever, discussed in other entrepreneurship / CEO books. For example, what is going through an entrepreneur and founder’s mind when having to lay off an entire workforce.

There are many lessons I learned from the book, but the one lesson / theme I came away with was the appreciation for my former CEO, Gregg Freishtat, at SalesWise—the startup I was a part of from 2016 through 2018. In the book, Ben discusses many of the trials and the thrust to push through incredibly difficult circumstances or fail. Some of those stories included running out of money and having to raise capital on the back of little revenue, competing against much larger, well-funded rivals, and even the challenge of hiring a friend / acquaintance. SalesWise was very much an up and down experience that eventually led to the company largely dissolving (though, created another brand that was acquired—Burner Rocket). My former CEO kept looking for “veins of gold”… constantly pushing and prodding looking for new ways to sell and grow. Unfortunately, unlike Ben’s company, things did not work out. But it was the sheer determination and the scrappiness to survive that was such a big appreciation I did not have prior to this book.

Other lessons I took include:

  • The nuances between a peacetime CEO vs. a wartime CEO including adherence to control and procedure (or otherwise), paranoia of competition, focus on execution vs. finer details, etc.
  • How to make decisions with little to no real experience or knowledge and the impact to the company when decisions go against consensus.
  • The lonely road sometimes walked by CEOs and founders during difficult times. This reminded me a lot of Ray Dalio’s journey described early in his book Principles including having to lay everyone off and then having his cofounder leave as well. It’s critical to have a support system with people who have experience.

There are a lot of fine details in the book to which I have less experience to truly appreciate what Ben went through. Instead, what will forever resonate with me is the determination, focus, and grit required by entrepreneurs / CEOs to pull companies to survive. Having been a witness to the gargantuan effort this requires in a startup I was a part of, I better understand now the true commitment I must make to create a valuable company.