Naval is a serial entrepreneur and angel investor with a long list of credentials:

  • co-author of Venture Hacks
  • co-founder of AngelList
  • co-founder of Genoa Corp (acquired by Finisar) and
  • advised and invested in over 100 companies: Twitter, Uber, Yammer Foursquare, DocVerse (sold to Google), Mixer Labs (sold to Twitter), Jambool (Social Gold), SnapLogic, PlanCast, Stack Overflow, Heyzap, and Disqus
  • he has a fan site!

Given that Naval has a fan site (The Angel Philosopher) and also a fan book (The Alamanack of Naval Ravikant) both dedicated to his musings, it is no surprise that philosophy is a rather major component of Naval's life. Here are the major strands of his philosophy:

“Life is a single player game. You’re born alone. You’ll die alone. All your interpretations are alone. All your memories are alone. And in three generations, you’ll be gone – no one will care. Before you were born – nobody cared.”
"Nobody reaches enlightenment or internal happiness, or does serious internal work, in group settings."
"At any given time when you’re walking down the street, a very small percentage of your brain is focused on the present. The rest is future planning or regretting the past. That’s keeping you from an incredible experience. It’s keeping you from seeing the beauty in everything and being grateful for where you are. It can literally destroy your happiness if you spend all your time living in delusions of the future.”
“There is actually nothing but this moment. No one has ever gone back in time, and no one has been able to predict the future successfully in any way that matters.”
"If all of your beliefs line up into neat little bundles, you should be highly suspicious"

Q&A With Naval Ravikant:

Q) What are the things to look for in a company when they go for funding?

1) Product - everyone thinks their product is great and unique so you need a third party assessment of that.

2) Team and background - what schools did they go to and what products did they work on

3) Social proof - who else is investing in the round and put their money in, who is investing and who is putting their time on it

4) Traction - quantitative evidence of customer demand which can be customer references from B2B customer or customer data from Google analytics.

Sourced from Naval at Startup Grind

Q) You are also quite a professed prolific reader. Do you set time apart in your day to read?

I read when I am bored of everything else and I get bored easily so there is always a book to capture the imagination. Usually at night time before I go to bed, I read but it's not a flawless thing. If I am on vacation, if I am on Uber or a Lyft or sometimes in the morning after I've worked out, I'll read. I'm not a very disciplined person so I don't set these hard rules but I love to read and so when I have time and I am bored - I just do it!

Q) You have said before that you think of books as throwaways, how did you come to think of books like that? What impact does that have on what you read?

That's the impact of the internet. Once the internet came along, it destroyed everyone's attention span. All of humanity's works are available to you at any given time and you are being interrupted constantly. Our attention span and focus goes down. At the same time we become more judicious and want the meat.

The problem with books - to publish a physical one - takes a lot of effort and money so people put a lot of wrapping on simple ideas. This is why I avoid a lot in the business and self help category as you have one good idea but it is surrounded by hundreds of pages and lots of anecdotes. In the late 90s I started reading less books and more blogs. You get incredible smart people digestifying, simplifying great things in a page or two.

I stopped reading books. However a lot of the old wisdom are in books. In books you have the combined knowledge of humanity and I missed that so with Kindle, I came back. I treat books like blogs now and skim through - jump up, down, back and forth, in the middle, viewing it like a blog I read what I need right now. It opens the world of books back to us.

I know a lot of people and friends stuck at books. However a lot of people in reality don't finish books. I don't read as much as people think. I probably read 1 to 2 hours a day and that alone puts me in the top .00001% and accounts for any material success that I’ve had in my life.

Q) What does a typical day for you look like?

I don’t have a typical day nor do I want a typical day. I’m trying to get rid of the concept of having to be at a specific place at a specific time. All I care about is am I doing what I want to do, am I being productive, and am I happy. I really want to break away from this idea of forty hour weeks, or 9 to 5s, or roles, or jobs or identities. It just all feels like a straight jacket.

Q) How are negotiations won? How do you turn a short term game into a long term game?

Negotiations are won by who cares less. Negotiation at the end of the day is not wanting it too badly. If you want it too badly, the other person will be able to extract more value by increasing the price charged to you if they take advantage of you.

If you do care more than the other person and they do take advantage of you, then your best way to deal with that is to turn it from a short term game to a long term game. Try to make it into a repeat game. Try bring in reputation in line, try bring other people into the game who may have a say in the future, people that would want to play games with them in the future.

An example of a very high cost, low information single move game is getting your house renovated. Contractors are notorious for overbooking and being unaccountable. They may have their own side, house owners don't understand. Historically it has been quite hard to find a good contractor and for a contractor it is hard to find a good house owner so you are basically going through reputation. You are trying to convert a single move expensive game into a high probability of cheating on both side into a multi move game. One way to do that is you might say you need 2 projects done. Splitting up your work and assessing based on the first project whether to continue the work. Or that you have 3 friends who might also have work. Or another one is they are in the community and have a reputation or you write them a Yelp review.

Source: Naval  

Q) What are your priorities?

If something is your number one priority, then you will get it. If you've got a fuzzy basket of 10 or 15 different priorities, you're not going to end up getting any of them done.

My number one priority in life, above my happiness, above my family, above my work is my own health. And it starts with my physical health. And then second, it's my mental health. And then third is my spiritual health. And then it's my family's health. Then it's my family wellbeing. With physical health I can take care of all other priorities.

And then after that I can go out and do whatever I need to do to the rest of the world. So there's a series of concentric circles starting out for me. Because I made my physical health my number one priority, I can never say I don't have time. So in the mornings I just work out. And however long it takes is how long it takes.

And I do not start my day and I don't care if the world is imploding and melting down, it can wait another 30 minutes until I'm done working out.

Q) What is happiness to you? What does happiness mean? Can you unpack that?

Happiness is a very evolving thing. I think like all the great questions like:

What happens when we die?

Is there a Santa Clause?

Is there a God?

Should I be happy?

There are no good answers to that because there are no answers that apply to everybody.

These questions, the search for truth, these kinds of questions, they ultimately do have answers, but they have personal answers. So the answer that works for me is going to be nonsense to you and vice versa. But I think it's very important to explore what it is. For some people, I know it's a flow state for some people's satisfaction. For some others it's a feeling of contentment.

My definition keeps evolving but today I believe that happiness is really a default state. It's what's there when you remove the sense that something is missing in your life.

We are highly judgmental, survival and replication machines. We're constantly walking around thinking I need this. I need that trapped in the web of desires and happiness is that state when nothing is missing and when nothing is missing, your mind shuts down. Your mind stops running into the future or running into the past to regret something or to plan something.

Then in that absence for a moment, you have internal silence. When you have internal silence, then you are content and you're happy.

To me, happiness is not about positive thoughts. It's not about negative thoughts. It's about the absence of desire, especially the absence of desire for external things. The fewer desires I can have, the happier I can or more than except. The current state of things, the less my mind is moving because the mind really exists in motion towards the future or the past, the more present I am, the happier and more content I will be.

I think the neutral state is actually a perfection state. One can be very happy as long as one isn't too caught up in their own heads... It doesn't always work, but in the, in the computer programming sense, I try to run my brain and debugging mode as much as possible.

Q) You mentioned before that you have foundational values, can you elaborate on what this means?

Foundational values are a set of things that you will not compromise upon. They are things that I've looked at very, very carefully about myself. And I've deliberately chosen and said, you know what? This is a habit. This is a way of life, and I'm not going to compromise on it. I'm going to stay this way forever. I just don't want to live life any other way.

An example of this is honesty. It is a core value and honesty allows me to be able to just be me. I never want to be in an environment around people where I have to watch what I say, because if I disconnect what I'm thinking from what I'm saying, That creates multiple threads in my mind. That would mean that I'm no longer in the moment. That would mean I now have to work on future planning or password regretting every time I'm talking to somebody. So around anyone whom I can't be fully honest, I don't want to be around

I don't believe in any short-term thinking or dealing.

Let's say I'm doing business with somebody and they think in a short-term manner with somebody else, then I don't want to do business with that person anymore because I think all the benefits in life come from compound interest, whether in money or in relationships or love or health or activities or habits. I only want to be around people that I know I'm going to be around with for the rest of my life.

Q) How do you control your mental state?

Taking long walks in nature, helps you control your mental state. We're used to controlling our mental state by hacking our external circumstances to then come back around and control our mental state.

It's hard for a person to sit by themselves in a room for 30 minutes. It's really hard to do. That's meditation. You are essentially struggling with and controlling your internal state. And the first thing to realise is that you can actually observe your mental state.

The advantage of meditation is not that you're suddenly going to get super power to control your internal state but that you will recognise just how out of control your mind is. It is like a monkey flinging faeces. The mind is running around the room, making trouble, shouting, breaking things. It's completely uncontrollable. It's an out of control person.

You have to see this mad creature in operation before you feel a certain distaste towards it. Then you can start separating yourself from it. And in that separation is liberation. When you realise that, you don't want to be that person, so out of control - that awareness calms you down.

One example that I think a lot of smart people say is if you are angry about something or get an unhappy email and want to respond, wait 24 hours. It calms you down, let your emotions subside and your mental state is in a much better shape 24 hours later. A lot of people know this but we don't act on it because we're not conditioned to act on this socially.

Happiness is internal, it is a single player game

We are told, go workout, go look good because that's a multiplayer competitive game. Other people can see if I'm doing a good job or not, we are told go make money, go buy a big house again, external multiplayer competitive game. But when it comes to learn how to be happy, this is completely internal.
There is no external progress, no external validation, a hundred percent. You competing against yourself, single player game. We're such social creatures. We're more like bees or ants that were externally programmed and driven, that we just don't know how to play and win at the single player games anymore.
We compete purely on multiplayer games, but the reality is life is a single player game. You're born alone. You die alone. All your interpretations are alone. All your memories are alone and you're gone. Three generations. Nobody cares before you showed up. Nobody cared.

All the real scorecards are internal. When I was young, I had a lot of jealousy in me, I learned to get rid of it but it still crops up every now and then. It's such a poisonous emotion because at the end of the day, you're no better off if you are unhappy.

The person you are jealous of is still successful or good-looking or whatever they are.

The real breakthrough was for me was when I realised at a personal fundamental level. You have to discover your own personal answer because your personal answers will be different than mine.

Q) What is your opinion on the current education system?

The education system is a pack dependent outcome, from the need for daycare, from the need for prisons, for college age males, who would otherwise overrun society. The original medieval universities had guard towers facing inwards, for example. You had to put a curfew in there.

They needed to lock up the young 18 year old males before they go out with swords and daggers and create trouble. The schools, the way we think about them, they come from a time period when books were rare. Knowledge was rare. Babysitting was rare. Crime was common. Violence was prevalent.

There was no such thing as self guided learning. I think schools are just byproducts of these kinds of institutions. Now we have the internet, which is the greatest level of knowledge ever created, completely interconnected. It's very, very easy to learn. If you actually have the desire to learn everything is on the internet, you can go on Khan Academy, you can get MIT and Yale lectures online.

You can get all the coursework and get interactivity. You can read blogs by brilliant people. You can read all these great books. The ability to learn, the means of learning, the tools, and learning itself is abundant and infinite.

What is incredibly scarce is a desire to learn.

I don't think schools matter for self motivated students. The schools are for keeping the kids out of the parents' hair while they work. It creates socialisation as kids want to be around their peers and they want to learn how to operate in society with those peers.

Another problem with the current educational system is what do you choose to learn?

The current system has a one size fits all model. It tells you that you have to learn X now, and then you have to learn Y and gives you examples of what is obsolete memorisation.

In a day and age of Google and smartphones, memorisation is obsolete. Why should you be memorising the battle of Trafalgar? Why should you be memorising what the capital of this or that state is, but we still put undue weight on that just because that's the way it's always been done. And we lived in a pre-Google world. The system also moves along at a certain pace, if they fall behind in that pace, they miss it say a concept in mathematics then they miss a rung in the ladder and can't go on to the next one as the teacher has moved on to the next topic - missing the fundamentals and resorting to memorisation rather than actual learning.

We teach all these kids calculus and they walk out not understanding calculus at all, when really they would have been better off served, just doing arithmetic and basic computer programming the entire time. So I think there's a, there's a pace of learning issue.

I think learning should be about learning the basics in all the fields. I'm learning them really well over and over, because life is mostly about applying the basics and only doing the advanced stuff in the things that you truly love and where you understand the basics inside out.

Finally there's the issue of what to learn. There's a whole set of things we don't even bother trying to teach such as nutrition, cooking, how to be happy and have positive relationships. We don't teach how to keep your body healthy and fit. We just say sports.

We don't teach happiness. We don't teach meditation. Maybe we shouldn't teach some of these things because different kids will have different attitudes, but maybe we should. Maybe we should teach practical construction of technology.

Q) How do you as an adult spend time on learning new subjects?

Mostly I just stay on the basics. Even when I'm learning physics or science, I'm sticking to the basics. I'll read concepts for fun but I'm more likely to do something that has arithmetic in it than calculus. I'm not going to be a great physicist this point, maybe in the next lifetime or my children will be. It's too late for me.

I have to stick to what I enjoy and what I love about sciences. Mathematics is the language of nature. Science to me is the study of truth. It is the only true discipline because it makes falsifiable predictions that actually changes the world. Applied science becomes technology and technology is what separates us from the animals. It allows us to have things like cell phones, houses, cars, heat and electricity.

Almost everything that people read these days is designed for social approval. All the best sellers are about social improvements, social conditioning. If you really want to be successful, happy, all those external metrics, you're looking for a non average outcome. So you can't be reading the average thing.

Q) How do you break out of the herd mentality?

If you are reading what every one else is reading, you're doing it for social approval. You're doing it to fit in with the other monkeys. You're fitting to get along with a herd.

The returns in life are bring out of the herd. It takes a level of contrarianism and say I'm just going to do my own thing regardless of the social outcome, to learn anything. I think that's why the smartest and most successful people I know started out as losers. If you view yourself as a loser, as someone who's been cast out by society and has no role in normal society, then you will do your own thing. And you're much more likely to find that winning path. It helps to just start up by saying, 'Oh, I'm never going to be popular'.

Q) As an investor and the CEO of AngelList, you're kind of paid to be right when others are wrong. Do you have a process around how you make decisions?

Decision making is everything. In fact, someone who makes decisions right, 80% of the time, instead of 70% of the time will be valued and compensated hundreds of times more in the market.

People have a hard time understanding that but it's a fundamental factor of leverage if I'm managing a billion dollars and I'm right 10% more of the time than somebody else. That's a hundred million dollars worth of value on a judgment call. With modern technology, larger workforces and capital, our decisions are getting leveraged more and more. If you can be more right, more rational, better at decision making then you're going to get non-linear returns in your life.

I just want to be the most successful version of me. While working the least hard possible. In a thousand parallel universes, I want to be successful in 999 of them. I try and set up good systems so it's not just about individual decisions that matter as I think our ability to make individual decisions aren't actually that great. As an investor, I would rather invest in a system.

Q) How do you determine if you can trust someone?

Through the person's integrity. Which usually comes out in two ways.

1) Long-term - where you've known somebody for a while and you know how they think about things.

2) The short-term. Which is the more interesting one. You observe how that person treats other people. There are lots and lots of people who will do something that is self-dealing or slightly unethical relative to another business partner.

The whole time they'll say to you *nudge* *nudge* *wink* *wink* 'I'm taking advantage of that person because they deserve it. But you are my friend so I would never do that to you'. It is very easy to change your definition of who your friends are, the people who do such a thing can easily change their integrity.

If someone is going around and talking about how honest they are, they're probably dishonest because just like a little telltale indicator, when someone spends too much time talking about their own values or talking themselves up, they're covering for something.

Someone with more integrity, an internal, moral compass wouldn't do these unfair/unethical/bad deals with other people because it would soil their own view of themselves. They wouldn't be able to sleep with themselves at night. Usually I find that people that negotiate with or high integrity deal, they're very easy to negotiate with. They'll give you things that they don't need to give you because they think it's fair and vice versa. So negotiations with high integrity people are usually very easy giving each other things to make sure that the other person's happy enough.

Naval's recommended reading:

The truth is, I don’t read for self-improvement. I read out of curiosity and interest. The best book is the one you’ll devour.

The Beginning of Infinity: Explanations That Transform the World by David Deutsch

Sapiens: A Brief History of Humankind by Yuval Noah Harari

The Rational Optimist: How Prosperity Evolves by Matt Ridley

Genome: The Autobiography of a Species in 23 Chapters by Matt Ridley

The Red Queen: Sex and the Evolution of Human Nature by Matt Ridley

The Origins of Virtue: Human Instincts and the Evolution of Cooperation by Matt Ridley

The Evolution of Everything: How New Ideas Emerge by Matt Ridley

Skin in the Game by Nassim Taleb

The Bed of Procrustes: Philosophical and Practical Aphorisms by Nassim Taleb

Six Easy Pieces: Essentials of Physics Explained by Its Most Brilliant Teacher by Richard Feynman

Thing Explainer: Complicated Stuff in Simple Words by Randall Munroe

Thinking Physics: Understandable Practical Reality by Lewis Carroll Epstein

The Lessons of History by Will and Ariel Durant

The Sovereign Individual: Mastering the Transition to the Information Age by James Dale Davidson and Lord William Rees-Mogg

Poor Charlie’s Almanack: The Wit and Wisdom of Charles T. Munger by Charlie Munger (edited by Peter Kaufman)

Reality Is Not What It Seems: The Journey to Quantum Gravity by Carlo Rovelli

Seven Brief Lessons on Physics by Carlo Rovelli

The Compleat Strategyst: Being a Primer on the Theory of Games of Strategy by J.D. Williams

The Evolution of Cooperation by Robert Axelrod

Naval has a LOT more books to recommend. It is also an evolving list but the above are some of the major ones. As Naval once said:

"Reading was my first love. I’ve always loved to read because I’m actually an anti-social introvert".

SIDE NOTE: Naval also estimates that he spends a lot more money and gets a lot ore books than what he actually finishes. He might only get through 10% of the books he has purchased and that he spends as much time rereading than reading new stuff.

I don’t want to read everything, I just want to read the 100 greatest books over and over again

On habits:

How you make it a habit doesn't matter... The point, the important thing is to do something every day... Human beings are entirely creatures of habit.

Sources: The Angel Philosopher