As someone who has always been infatuated with the startup community, tech companies, and entrepreneurship as a whole, I decided it was finally time to give The Hard Thing About Hard Things a serious read.

Years ago, I was first exposed to this world by following Marc Andreessen on Twitter. A single Twitter account might seem like too small of a platform to skyrocket an entire passion, but it did. Reading Andreessen’s constant insights and witticisms on VC culture and tech got me more and more interested in being involved in it myself. Eventually digging down the rabbit whole led me to learn about the wider scope of it all including his business parter, bhorowitz. When I saw Horowitz had written a book on everything I wanted to learn more about, I knew it was a great place to start.

I didn’t really know what to expect from this book; I figured it was going to be a walkthrough of how Horowitz and Andreessen met and eventually created Andreessen Horowitz — and it had some of that. What I wasn’t expecting was a nearly explicit tutorial on how to start and manage a company. It turned out to be a really great goldmine and reference to all the nuances building a business might entail.

Just Win, Baby

The beginning chapters of The Hard Thing About Hard Things explains how Ben Horowitz met Marc Andreessen and takes us through some of the early days of his career when he was running Loudcloud and Opsware. If nothing else, Ben’s story makes you extremely sure he’s more than qualified to be telling us how to run a company since he’s taken failing companies and turned them into success stories with higher stock prices when he’s through.

I’ll refrain from going into too much detail on the biography side of things as I find the core of the text to be in the following chapters, but the ultimate idea is that Opsware IPO’d at $6, fell all the way to $0.35, and rose to $14.25 by the time it was sold to HP. With those numbers alone, it’s clear management was top-notch at the company.


The text quickly gets in to more logistical aspects of companies. Being interested in productivity, systems, and such, the book started really heating up for me here.

There’s a lot of discussion on what makes a good place to work. What draws people to your company? What keeps them there? An important thing to keep in the minds of employees is the big picture. Everyone should know exactly what their roles are and how it impacts the company. The idea is to be sure employees feel accomplished for themselves and that they have made a contribution to the company.

Let me break it down for you. In good organizations, people can focus on their work and have confidence that if they get their work done, good things will happen for both the company and them personally. It is a true pleasure to work in an organization such as this. Every person can wake up knowing that the work they do will be efficient, effective, and make a difference for the organization and themselves. These things make their jobs both motivating and fulfilling.

Keeping employees is more directed toward the trajectory of the actual company. People are much more likely to stay at company that is booming and all their friends are using than one that is actively laying people off and making headlines about shrinking stock prices. Being sure the company isn’t failing and doesn’t meet these negative criteria is the #1 method to keeping a quality staff.

Training plays a large part in your business as well. Defining the role, organizing tasks, and being certain everyone knows exactly what they’re doing will make or break the productivity of the office. Horowitz even expresses frustration when employees at Netscape were unsure of their jobs due to lack of training — specifically the product managers. There are many guidelines set out for product managers in the text as well. Good product managers value discipline, are not told what to do, ask quality questions, decompose problems properly, and ultimately know good products.

Big Company Execs vs. Small Company Execs

The time will eventually come when the board of a company suggests hiring some high-level executive with outstanding résumés to really kick the business into high-gear. The problem is that a Marketing Director from, say, Coca-Cola, has a very different role than the Marketing Director at your 2-year old tech startup. One of the key differences is simply behavioral. The Big Company Exec will be conditioned to wait for emails, phone calls, and make important decisions. These are valuable skills that require experience and will help immensely in a large company, but building a company is very different than running an already established company — this is also why, for example, Steve Jobs was a fine CEO at Apple, Inc. only after a few more CEO-like people took care of the role before him.

Anyone motivated by equity looking to get in on a small company is someone you do not want on your team. Any percent of zero is still zero. The biggest reason to get in on a small and growing company is to wear different hats, be creative, and build something from nothing with a great team.

Bad Employees

The Hard Thing About Hard Things has some great scenarios regarding bad employees. Firstly, it is said hiring is one of the most important and difficult jobs while building a company. Deciding who is a good cultural fit and who exhibits the right (or wrong) characteristics is impossible to decipher in just a few interviews. It is recommended to jot down exactly which skills are necessary for the role, and which weaknesses can be tolerated; this will make for a fine guideline on who can assume the roles.

The text gives three examples of poor employees: The Heretic, The Flake, and The Jerk. The Heretic is usually very smart and has a way of making people listen to them. Their primary goal is to convince everyone the company is doomed and run poorly. The Flake can come in different shapes and sizes. The text’s example has a prodigy genius programmer who learned an entire codebase in half the time they would’ve expected and churned out some of the cleanest code they have ever seen. The prodigy soon changed and missed days at a time, then weeks without calling in. Long story short, he was addicted to cocaine. The Jerk is more harmful than the former two. This employee (or executive) will take opportunities to shoot down ideas, give snarky remarks, and just be unpleasant. More than being a poor cultural fit, the danger lies in ideas being suppressed in fear of The Jerk retaliating with a morale-killing remark.

NFL Coach John Madden once stated that he would hold the bus for a player like Terrell Owens. Owens was an exceptional player in that he was extremely good and a jerk.

Keeping Calm

Focus on the road, not the wall. The text explains the old driving adage applies to life and running companies as well. When you look at the wall which represents death, crash, and failure, you’re focusing on the wrong thing. Look ahead at the road to where you’re going and what you’re going to accomplish and the wall may as well not even be there.

The text says a CEO being born is as wild an idea as a Jolly Rancher being grown from a plant. CEO is an unnatural job that can only come with experience and doing it. A quality CEO’s job is to actually master the unnatural. It’s part of the process to feel incompetent and that you won’t be able to run your company in one year, or even fifty years.