The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers

What does Horowitz mean by the title of the book, The Hard Thing About Hard Things? Does he answer this question at any point in the text? If so, how does his response correlate with the book’s central themes?

How is Andreessen Horowitz different from other venture capital firms? Why did they choose to distinguish themselves in this way? In your opinion, is their approach helpful or not?

Explain the dot-com crisis of the late 1990s. How does it relate to Horowitz’s arc as CEO?

Is adapting to change a critical skill in business? To what extent is it specific to the tech industry? Does the ability to successfully adapt to change relate to entrepreneurship in general? Why or why not?

Give some examples of the way communication breakdown can affect a company. Who in the organization is most at risk if this happens?

Discuss the differences between a founder and a company CEO. How do these roles relate to Horowitz’s definition of the management styles he calls Ones and Twos? In your opinion, which one might be most useful in a startup?

What does Horowitz believe regarding the concept of struggle in business? How does this conviction relate to his early years in Silicon Valley? Is struggle specific to his unique experience, or do you think it has wider applicability? If so, where?

What role does venture capital play in the life cycle of a business? How did it affect Horowitz as the CEO of Opsware? Choose another tech startup and analyze the role of venture capital in its success or failure. Are Horowitz’s assertions universally applicable?