Life Lessons


  • The brevity of your existence is important.
  • Always keep it in mind.
  • Use it to bring urgency and appreciation to your life.


  • Without choosing a direction you will float on the path of least resistance.
  • Our hardships are what forge our character.
  • The combination of these two insights is critical.


  • It is very important to be uncomfortable.
  • It is important to both be hard on yourself and optimistic about what you can do


  • It is difficult and important to give someone your full attention as you talk to them.
  • You should attempt to re-express your opponent’s position so clearly, vividly, and fairly that your target says, “Thanks, I wish I’d thought of putting it that way.”


  • The biggest risk of sobriety is appearing to be boring.
  • The biggest risk of inebriation is everything.
  • Interpersonal relationships are both a way and a reason to live a full life.


  • There is a deep deep joy in simplicity.
  • There is deep deep simplicity around bodies of water.
  • It is important understand the difference between the use-value of an object and the exchange-value of it. The mindless pursuit of exchange-value is extremely hollow and suggests a lack of thoughtful direction and furthermore money has no controlling end without a purpose.


  • Everyone has stress behaviors and normal behaviors. Figure out which is which and who is where.
  • Respond to things rather than reacting to things
  • Take time to figure out what you are aiming for


  • Train at altitude – have passive systems do work for you and acknowledge the phasic nature of work to capture “free energy” when you can
  • Always ask yourself “Does this person think I am trustworthy?” If the answer is no, then it will be very hard to change their mind about anything else
  • Don’t speak for more than 20 seconds at a time unless you are on stage


  • In general, people significantly overvalue money and significantly undervalue time.
  • Only exceptionalism and favoritism help you achieve your goals.
  • To refocus your energy on important goals try these two things:
    • You are a character in a movie and someone is watching. Ask yourself, “In the movie of my life, what is this particular scene about?”
    • Focus on the boundedness of life. How many years left? How many days? At this pace will you get to where you want to go?



  • The main thing is to keep the main thing the main thing.
  • Gather, then reflect, then use your informed intuition. Know which phase you should be in on this cycle.


  • happiness = health + rent and beans + relationships + a goal to chase
  • Put yourself in a position to explore your interests (vs directly chasing your dreams)
  • Make your housing situation an asset and track your net worth.


  • Wu wei — moving but not forcing
  • There are 3 types of problems: important ones you can fix with money, important ones you can’t fix with money, and unimportant ones. Categorize and act accordingly
  • You are only as wealthy as what you can and do say no to

Lessons from my bosses

  • The more uncomfortable a conversation is, the more urgent it is.
  • Find someone going somewhere and ride their wave.
  • The only way ahead is through hard work, relationships, and focused attention.
  • Learn to dial up and down your intensity. Your negativity will radiate 3x.
  • Find an environment where you can be yourself and excel in the culture.
Lessons about business
  • Always have a partner in business (even if it is your spouse)
  • If no one will pay you to do it, you are not yet in business
  • It is easy (and important at times) to fool yourself that people will want what you’re offering at a price you can afford to deliver it
  • The people you work with are what will motivate you and inspire you.
  • To be successful, make them successful. It really is that simple.
  • There are only three aspects of business that matter: sales, delivery, and r&d
  • Sell the thing. Deliver the thing you sold. Make it better.
  • People and tools are what will help you do the 3 above items, nothing else. Get good ones.
  • If you aren’t working on something you feel will make the world better, get out ASAP.
Other miscellaneous lessons, mostly from books
  • The things people most want are the things they have the most self-doubt about.
  • If you get ahead of yourself (too much freedom) you will fail.
    • If you get afraid of yourself (afraid to claim your freedom), you will get stuck.
    • The way to tell the difference between the two situations is to see if people will pay you for “it” – if not; then don’t take the freedom yet.
  • Be careful of “heroic” people who want to sacrifice to get their freedom — they are perhaps too passionate.
  • You need to recognize if you are in a type of career where only 1 skill matters (e.g. writing things people want to read for blogging) or multiple skills matter (e.g. being a venture capitalist).
  • You can only get things done with hard work, relationships, and self-belief
  • It’s important to get immediate feedback on the skills that matter in pursuit of your goal.
  • When only 1 skill matters – you need to be brutally honest with yourself about if you are working on that skill and the relationships required to “not be ignored”
  • Working deeply in a field before becoming “passionate” about it helps you understand the adjacent possible.
  • This adjacent possible is where progress can be made and thus where efforts can be applied.
  • Staying small helps you survive winters and have more flexibility, but in order to thrive you have to find new growth opportunities and expansion opportunities
  • Doing things that are roughly aligned with your business that are fun and remarkable ⇒ press ⇒ the best form of marketing. If the paper won’t write about it, it isn’t interesting.
  • Three Disqualifiers for Applying the Craftsman Mindset
    • 1. The job presents few opportunities to distinguish yourself by developing relevant skills that are rare and valuable.
    • 2. The job focuses on something you think is useless or perhaps even actively bad for the world.
    • 3. The job forces you to work with people you really dislike.
  • People are defined by hierarchies or by geographies. Whenever either one gets too large people lose their sense of identity relative to others. The flipside of this is that they must find their true sense of self.
  • Know when you are facing and embracing “resistance”. Facebook checking, email checking, cleaning your room, any kind of procrastination. It is a devil in disguise, but it is quite easy to see when you are avoiding the pressing matter of “doing your work”
  • Show up every day and do the work, being present is the first key to success.
  • At the end of each workday, write down the six most important things you need to accomplish tomorrow. Do not write down more than six tasks. Then prioritize those six items in order of their true importance.
  • When someone says they want to be an entrepreneur are they really saying they want to be rich? Does just kidding mean the opposite? In what ways are people shading the truth?
  • Skill acquisition is better than passion when you are looking to discover what to do next.
  • For a successful technology, reality must take precedence over public relations, for Nature cannot be fooled.
  • Seven questions for an opportunity
    • The Engineering Question — Can you create breakthrough technology instead of incremental improvements?
    • The Timing Question — Is now the right time to start your particular business?
    • The Monopoly Question — Are you starting with a big share of a small market?
    • The People Question — Do you have the right team?
    • The Distribution Question — Do you have a way to not just create but deliver your product?
    • The Durability Question — Will your market position be defensible 10 and 20 years into the future?
    • The Secret Question — Have you identified a unique opportunity that others don’t see?’
  • The process of getting wealthy is a generational baton passing more often than a sprint
  • Let it be death that takes us, not lack of imagination. – BJ Miller
  • There is such a thing as perfect health, but no such thing as perfect wealth
  • The exquisite detail that takes the ordinary and makes it extraordinary can be taught/learned.
  • The statute of limitations has expired on anything your parents did to you as a kid.
  • Always look to see if people are asking for advice on “how to take a cold bath”
  • Externalize measurements for projects because once you become invested you lose the ability to objectively evaluate them
  • Your goodness must have some edge to it, — else it is none. – Ralph Waldo Emmerson
  • The numbers are important, but read between the numbers. That is where the magic happens.
  • Do not be argumentative for argumentation sake.
  • Get people from lower-level to upper-level, then communicate about the items at hand
  • “The worst enemy of life, freedom and the common decencies is total anarchy; their second worst enemy is total efficiency.” – Aldous Huxley

People who have an interesting, considered, and uncommon point of view

  • Big Think – playlist
  • Nassim Taleb (Antifragile)
  • Peter Theil (CS183)
  • Mike Rowe (
  • Ben Horowitz (The Hard Thing About Hard Things)
  • Keith Rabbois (@rabois)
  • Richard Feyman (Surely you must be joking)
  • Carl Sagan (Cosmos)
  • Richard Branson (Losing my Virginity)
  • Penn Gillette (Big Think)
  • interviews
  • Matt Groening
  • Trey Parker and Matt Stone (Southpark)
  • Rick and Morty 
  • Rory Sutherland