“Self-esteem is just the reputation that you have with yourself. You’ll always know.”

NAVAL RAVIKANT is the CEO and co-founder of AngelList. He previously co-founded Vast.com and Epinions.com, which went public as part of Shopping.com. He is an active angel investor and has invested in more than 100 companies, including many “unicorn” mega-successes. His deals include Twitter, Uber, Yammer, Postmates, Wish, Thumbtack, and OpenDNS. In recent years, he is the person I call most for startup-related advice.

What is the book (or books) you’ve given most as a gift, and why? Or what are one to three books that have greatly influenced your life?
Total Freedom by Jiddu Krishnamurti. A rationalist’s guide to the perils of the human mind. The “spiritual” book that I keep returning to.

Sapiens by Yuval Noah Harari. A history of the human species, with observations, frameworks, and mental models that will have you looking at history and your fellow humans differently.

Everything by Matt Ridley. Matt is a scientist, optimist, and forward thinker. Genome, The Red Queen, The Origins of Virtue, The Rational Optimist—they’re all great.

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?
Suffering is a moment of clarity, when you can no longer deny the truth of a situation and are forced into uncomfortable change. I’m lucky that I didn’t get everything I wanted in my life, or I’d be happy with my first good job, my college sweetheart, my college town. Being poor when young led to making money when old. Losing faith in my bosses and elders made me independent and an adult. Almost getting into the wrong marriage helped me recognize and enter the right one. Falling sick made me focus on my health. It goes on and on. Inside suffering is the seed of change.

If you could have a gigantic billboard anywhere with anything on it, what would it say and why?
“Desire is a contract that you make with yourself to be unhappy until you get what you want.”

Desire is a driver, a motivator. In fact, a sincere and uncompromising desire, placed above everything else, is nearly always fulfilled. But every judgment, every preference, every setback spawns its own desire and soon we drown in them. Each one a problem to be solved, and we suffer until it’s fulfilled.

Happiness, or at least peace, is the sense that nothing is missing in this moment. No desires running amok. It’s okay to have a desire. But pick a big one and pick it carefully. Drop the small ones.

What is one of the best or most worthwhile investments you’ve ever made?
Every book I read that wasn’t assigned to me or that I didn’t read with a purpose in mind.

The genuine love for reading itself, when cultivated, is a superpower. We live in the age of Alexandria, when every book and every piece of knowledge ever written down is a fingertip away. The means of learning are abundant—it’s the desire to learn that’s scarce. Cultivate that desire by reading what you want, not what you’re “supposed to.”

In the last five years, what new belief, behavior, or habit has most improved your life?

Happiness is a choice you make and a skill you develop.
The mind is just as malleable as the body. We spend so much time and effort

trying to change the external world, other people, and our own bodies, all the while accepting ourselves the way we were programmed in our youths. We accept the voice that talks to us in our head all the time as the source of all truth. But all of it is malleable, every day is new, and memory and identity are burdens from the past that prevent us from living freely in the present.

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore? Advice: Follow your intellectual curiosity over whatever is “hot” right now. If your curiosity ever leads you to a place where society eventually wants to go, you’ll get paid extremely well.

Do everything you were going to do, but with less angst, less suffering, less emotion. Everything takes time.

Ignore: The news. Complainers, angry people, high-conflict people. Anyone trying to scare you about a danger that isn’t clear and present.

Don’t do things that you know are morally wrong. Not because someone is watching, but because you are. Self-esteem is just the reputation that you have with yourself. You’ll always know.

Ignore the unfairness—there is no fair. Play the hand that you’re dealt to the best of your ability. People are highly consistent, so you will eventually get what you deserve and so will they. In the end, everyone gets the same judgment: death.

What are bad recommendations you hear in your profession or area of expertise?
“You’re too young.” Most of history was built by young people. They just got credit when they were older. The only way to truly learn something is by doing it. Yes, listen to guidance. But don’t wait.

In the last five years, what have you become better at saying no to?

I say no to nearly everything. I make a lot fewer short-term compromises. I aspire to only work with people who I can work with forever, to invest my time in activities that are a joy unto themselves, and to focus on the extremely long term.

So I have no time for short-term things: dinners with people I won’t see again, tedious ceremonies to please tedious people, traveling to places that I wouldn’t go to on vacation.

When you feel overwhelmed or unfocused, what do you do?

Memento mori—“remember that you have to die.” All of this will go to nothing. Remember before you were born? Just like that.

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