📚 5 Books I Wish I’d Read in My First Years as a Founder: Part 3— The Hard Thing About Hard Things

One of the best business books I’ve read in recent years, and the book that triggered me to start this series is “The Hard Thing About Hard Things” by Ben Horowitz.

This book stands out as a collection of practical insights, offering real-life scenarios and solutions encountered by the author in his role as a CEO. Each turn of the page seemed to reflect situations I’ve personally encountered on my journey, accompanied by insights on how they could have been navigated more effectively.

💡 Why I Wish I’d Read It Sooner

• When starting a business, every challenge is unique and solutions don’t come pre-packaged. This book brings a raw and unfiltered perspective, something totally different from the polished success stories we often encounter in business books. I spent my initial years thinking that setbacks were unique to my journey, feeling isolated in the face of difficulties. Horowitz’s book might have provided me relief in knowing that others faced similar, if not worse, trials.
• ‎The book doesn’t offer you easy solutions, but rather, it prepares you for the harsh realities of being a CEO and offers you a way to navigate through them. It’s like a mentor sharing war stories and battle tactics. From hiring to firing, hiring executives when you’ve never done the job, evaluating your own CEO game, delivering bad news to your people, or making hard calls for the team — this book gets straight to the point. It even helped me figure out how much weight I should carry on my shoulders and when to cut myself some slack. This book’s like a collection of insights from a friend who’s been there, done that, and wants to make sure you survive and thrive.

🚀 Key Takeaways and Lessons

This book was the most highlighted one that I’ve read. It stands out as a gold mine of insights.

Let’s dive into some of the gems that resonated most with me, often in the author’s own words:

• “Don’t put it all on your shoulders”: Dispelling the myth that sharing worries will demoralize your team, Horowitz highlights that nobody feels the weight more than the one steering the ship. Encourage problem-sharing, and tackle existential threats collectively.
• “‎My single biggest personal improvement as CEO occurred on the day when I stopped being too positive. As a young CEO, I felt the pressure — the pressure of employees depending on me, the pressure of not really knowing what I was doing […] I thought I should project a positive, sunny demeanour and really the unburdened troops to victory. I was completely wrong. […] In my mind, I was keeping everyone in high spirits by accentuating the positive and ignoring the negative. But my team knew that reality was more nuanced that I was described it. And not only did they see for themselves the world wasn’t as rosy as I was describing it; they still had to listen to me blowing sunshine up their butts at every company meeting.”
• “Build a culture that rewards — not punishes — people for getting problems into the open where they can be solved.” — Create an environment where problems are openly discussed. Covering up issues only leads to frustration and delays solving them.
• “Given this stress, CEOs often make one of the following 2 mistakes:
  – They take thinks too personally.
  – They do not take things personally enough.”
• “‎Perhaps the most important thing that I learned as an entrepreneur was to focus on what I needed to get right and stop worrying about all the things that I wrong or might do wrong.”
• ‎Management Debt — occurs when short-term management choices create long-term expensive repercussions. It can come in many different forms. I’ve chosen to highlight 1 out of the 3 types presented in the book: “No Performance Management or Employee Feedback process”.
  – ”Your company now employs 25 pool and you know that you should formalize the performance management process, but you don’t want to pay the price. You worry that doing so will make it feel like a “big company”. More so, you do not want your employees to be offended by the feedback, because you can’t afford to lose anyone right now. And people are happy, so why rock the boat? Why not take on a little management debt?
  – ‎The first noticeable payments will be due when somebody performs below expectations:
  – — — ‎CEO: “He was good when we hired him, what happened?”
  – — — ‎ Manager: “He’s not doing the things that we need him to do.”
  – — — ‎ CEO: “Did we clearly tell him that?”
  – — — ‎ Manager: “Maybe not clearly . . .”
  – ‎ However, the larger payment will be a silent tax. Companies execute well when everybody is on the same page and everybody is constantly improving. In a vacuum of feedback, there is almost no chance that your company will perform optimally across either dimension. Directions with no corrections will seem fuzzy and obtuse. People rarely improve weakness that they are unaware of. The ultimate price you will pay for not giving feedback: systematically crappy company performance.”

📋 Recommendation to First-Time Founders

• Make sure to read it, no, seriously, read it — you will thank me later! → if you don’t believe me, email me at my personal email addrss and I will personally buy it for you!
• ‎Action over Theory — Dive into the book and keep it close even after you’ve turned the last page. Horowitz’s insights are practical and applicable, providing a toolkit that comes in handy when you’re actually handling a real-world scenario.
• Create your Playbook — Absorb Horowitz’s leadership lessons, but don’t mimic them blindly. Tailor his experiences to your unique leadership style and use this book as a guid to start building your own playbook for managing challenges and making decisions.

“If you are a founder CEO and you feel awkward or incompetent when doing some of these things and believe there is no way that you’ll be able to do it when your company is one hundred or one thousand people, welcome to the club. That’s exactly how I felt. So did every CEO I’ve ever met. This is the process. This is how you get made.”

📚 Stay Tuned

Stay tuned for more books that I found very helpful in recent years as a first-time founder. Check the intro article, 📚 5 Books I Wish I’d Read in My First Years as a Founder, for links to the other books.

If you’ve read this book, I’m curios, how did you find it?

What are some similar books you found most useful?

Let’s learn & grow together!