The Hard Thing About Hard Things

A lot of people talk about how great it is to start a business, but only Ben Horowitz is brutally honest about how hard it is to run one.

In The Hard Thing About Hard Things, Ben Horowitz, cofounder of Andreessen Horowitz and one of Silicon Valley's most respected and experienced entrepreneurs, draws on his own story of founding, running, selling, buying, managing, and investing in technology companies to offer essential advice and practical wisdom for navigating the toughest problems business schools don't cover. His blog has garnered a devoted following of millions of readers who have come to rely on him to help them run their businesses. A lifelong rap fan, Horowitz amplifies business lessons with lyrics from his favorite songs and tells it straight about everything from firing friends to poaching competitors, from cultivating and sustaining a CEO mentality to knowing the right time to cash in.

His advice is grounded in anecdotes from his own hard-earned rise-from cofounding the early cloud service provider Loudcloud to building the phenomenally successful Andreessen Horowitz venture capital firm, both with fellow tech superstar Marc Andreessen (inventor of Mosaic, the Internet's first popular Web browser). This is no polished victory lap; he analyzes issues with no easy answers through his trials, including

• demoting (or firing) a loyal friend;
• whether you should incorporate titles and promotions, and how to handle them;
• if it's OK to hire people from your friend's company;
• how to manage your own psychology, while the whole company is relying on you;
• what to do when smart people are bad employees;
• why Andreessen Horowitz prefers founder CEOs, and how to become one;
• whether you should sell your company, and how to do it.

Filled with Horowitz's trademark humor and straight talk, and drawing from his personal and often humbling experiences, The Hard Thing About Hard Things is invaluable for veteran entrepreneurs as well as those aspiring to their own new ventures.

1. From communist to venture capitalist
2. "I will survive"
3. This time with feeling
4. When things fall apart
• The struggle
• CEOs should tell it like it is
• The right way to lay people off
• Preparing to fire an executive
• Demoting a loyal friend
• Lies that losers tell
• Lead bullets
• Nobody cares
5. Take care of the people, the products, and the profits: in that order
• A good place to work
• Why startups should train their people
• Is it okay to hire people from your friend's company
• Why it's hard to bring big company execs into little companies
• Hiring executives: if you've never done the job, how do you hire somebody good?
• When employees misinterpret managers
• Management debt
• Management quality assurance
6. Concerning the going concern
• How to minimize politics in your company
• The right kind of ambition
• Titles and promotions
• When smart people are bad employees
• Old people
• One-on-one
• Programming your culture
• Taking the mystery out of scaling a company
• The scale anticipation fallacy
7. How to lead even when you don't know where you are going
• The most difficult CEO skill
• The fine line between fear and courage
• Ones and twos
• Follow the leader
• Peacetime CEO/wartime CEO
• Making yourself a CEO
• How to evaluate CEOs
8. First rule of entrepreneurship: there are no rules
• Solving the accountability vs. creativity paradox
• The freaky Friday management technique
• Staying great
• Should you sell your company?
9. The end of the beginning
10. Appendix : Questions for head of enterprise sale force

After getting over the authors obvious self-esteem issues and frequent namedropping, I discovered a book that I may not always agree on but that explained an experienced entrepreneurs learnings from creating successful companies and the choices that he had to do along the way.

Not exactly a classic, but well worth reading, as there are some interesting thoughts and wisdom in there, that is not always self-evident or explained in detail in other books.