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I Don’t Know What I’m Doing · Sep 28, 2023

The Books Every Startup CEO & Founder Should Read

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David Thielen · I Don’t Know What I’m Doing

Not only is the job of CEO incredibly difficult, but there’s almost no training or resources for the job. A large part of that comes from the fact that most of what is out there is written by people who have never been a CEO and therefore, don’t know what they’re talking about. It’s like virgins writing about sex - no true understanding.

Here are the few books that, in my opinion, are accurate, helpful, and well written. Each is well worth your time.

While many people talk about how great it is to start a business, very few are honest about how difficult it is to run one. Ben Horowitz analyzes the problems that confront leaders every day, sharing the insights he’s gained developing, managing, selling, buying, investing in, and supervising technology companies.

The book lays out what is involved when you are a CEO, which is radically different from any other management job. It does this in large part by talking through how I navigated the challenges and opportunities growing Windward. And rare in a business book, it is brutally honest about the mistakes I made. Giant mistake after giant mistake – which occurs at every company, but is rarely talked about.

Back in 1999, he started a company called Return Path, which later became the driving force behind the creation of his blog, OnlyOnce―because "you're only a first time CEO once."

START WITH WHY asks (and answers) the questions: why are some people and organizations more innovative, more influential, and more profitable than others? Why do some command greater loyalty from customers and employees alike? Even among the successful, why are so few able to repeat their success over and over?

Note: While Simon is not a CEO and this is focused on a particular component of being a CEO, it is an incredibly important part of being a successful CEO. You absolutely must lead your company starting with why.

From the visionary head of Google's innovative People Operations comes a groundbreaking inquiry into the philosophy of work -- and a blueprint for attracting the most spectacular talent to your business and ensuring that they succeed.

Note: Again, not written by a CEO. But the most important decisions you will make is who you hire… and who you fire. This is the best guide to success in this endeavor.

Gallup presents the remarkable findings of its revolutionary study of more than 80,000 managers in First, Break All the Rules, revealing what the world’s greatest managers do differently. With vital performance and career lessons and ideas for how to apply them, it is a must-read for managers at every level.

Note: This is the one “Management” book on the list, but it’s not here because of that. It also is a great book on what matters in culture, training, and building a cohesive organization. By all means make use of the management ideas in the book. But the giant value is using it to build a powerful culture and amazing employees.

And that’s it. Yes there’s a lot of other quality books out there. But a list of 20 books is of no help as it’s too much. 6 is manageable. These are the 6 best. What are your top 6? Please let me know in the comments.

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