INTRODUCTION

“This the real world, homie, school finished

They done stole your dreams, you dunno who did it.”

—KANYE WEST, “GORGEOUS”

Every time I read a management or self-help book, I find myself saying, “That’s fine, but that wasn’t really the hard thing about the situation.” The hard thing isn’t setting a big, hairy, audacious goal. The hard thing is laying people off when you miss the big goal. The hard thing isn’t hiring great people. The hard thing is when those “great people” develop a sense of entitlement and start demanding unreasonable things. The hard thing isn’t setting up an organizational chart. The hard thing is getting people to communicate within the organization that you just designed. The hard thing isn’t dreaming big. The hard thing is waking up in the middle of the night in a cold sweat when the dream turns into a nightmare.

The problem with these books is that they attempt to provide a recipe for challenges that have no recipes. There’s no recipe for really complicated, dynamic situations. There’s no recipe for building a high-tech company; there’s no recipe for leading a group of people out of trouble; there’s no recipe for making a series of hit songs; there’s no recipe for playing NFL quarterback; there’s no recipe for running for president; and there’s no recipe for motivating teams when your business has turned to crap. That’s the hard thing about hard things—there is no formula for dealing with them.

Nonetheless, there are many bits of advice and experience that can help with the hard things.

I do not attempt to present a formula in this book. Instead, I present my story and the difficulties that I have faced. As an entrepreneur, a CEO, and now as a venture capitalist, I still find these lessons useful—especially as I work with a new generation of founder-CEOs. Building a company inevitably leads to tough times. I’ve been there; I’ve done that. Circumstances may differ, but the deeper patterns and the lessons keep resonating.

For the past several years, I’ve encapsulated these lessons in a series of blog posts that have been read by millions of people. Many of those have reached out to me wanting to know the backstory to the lessons. This book tells that backstory for the first time and includes the related lessons from the blog. I’ve also been inspired by many friends, advisers, and family members who have helped me throughout my career and also by hip-hop/rap music. Because hip-hop artists aspire to be both great and successful and see themselves as entrepreneurs, many of the themes—competing, making money, being misunderstood—provide insight into the hard things. I share my experiences in the hope of providing clues and inspiration for others who find themselves in the struggle to build something out of nothing.