I recommend The Hard Things About Hard Things by Ben Horowitz. It's a book that chronicles experiences and lessons he’s had through the founding and running of an Internet company over many years. It’s written in an easy to read format, in plain terms that I can relate to. Not to mention it quotes rap lyrics which sings to me in particular.

The book is organized but not so processed that the lessons are too abstract. It provides insight into specific difficult times - raising money, laying people off, pivoting a business. It’s up front with the idea that there isn’t necessarily a theme except that these are hard things that any CEO may encounter, most specifically someone leading a start-up.

The examples in the book come from Ben’s specific experience in starting a company during the dot-com days. I also started a small tech company during that time, and I found the stories very relatable. Even if my experience was smaller his experiences mirrored my own. In particular, in the section "when things fall apart." There are hard things you can’t be prepared for, but you must deal with regardless. There are decisions and options you never knew were coming. I found the lessons relatable even for an executive in a leadership role in a larger company, particularly "how lead even when you don't know where you're going."

The book walks through the history of being a CEO through tough times. In particular the stories of how to continue to survive are very real. The chapter on taking care of "the people, the products and the profits" outlines examples. Pushing yourself to see all the options, even those you don’t want to pursue, is at the heard of being a scrappy start-up. And as a leader, you have to make tough choices. He talks about changing the focus of his business, letting people go, hiring the right people and firing the wrong ones.

He also brought some insight into situations such as when to bring on people who have “big-company” experience. His description of what the difference in small-company and big-company leaders helped me understand my own transition from small start-up experience to my recent work experience with a larger company. How you work and prioritize your time is very different, and as someone responsible for taking a company from small to big I can imagine it’s hard to know when you need folks with each kind of experience.

Ben has turned his experience and observation of how tough it is to be an entrepreneur into a style of venture capitalism. VC with sympathy for the entrepreneur. The books describes how he and his partner, Marc Andreessen, manage their relationships with start-up founders. They recognize that although they have the capital, the founder is very much on the hook for results to everyone involved.

There are great key lessons that I took away from this book. On how to execute layoffs. On exploring all your options. On leadership and supporting your staff. On seeing things through and sticking with it. On how hard it is to lead, especially at the top. And the importance of advisors.

In the end, I like that the book talks as much about running a business as it does how to make money. And it avoids the trap of just talking about "how to make an exit" that you might expect from a VC.