Garry Tan has a YouTube channel through which I have learned a lot of small nuggets of wisdom over the years. He is best known as a venture capitalist and founding Initialized Capital. He is now the CEO of Y Combinator, and had previously co-founded Posterous and Posthaven. His big claim to fame in startup investing was getting in early on Coinbase, and turned $300,000 into $2 billion, a 6000x return, or 600,000%. Regardless of his political views or activities, I have found there is a lot of positives I learned. Here are my favorite notes I’ve taken over the years.

-There are five levels people can ascribe to. Most people are stuck at level 2, which is still caring about what others think about them. Get to level 5, transcendence. This involves thinking about the future, legacy, and taking yourself out of the equation. Transcendent individuals move the balance of humanity.

-No conflict leads to resentment. Don’t keep up the image of good relationships, and instead focus on having good relationships

-too little conflict is not good. Don’t let things remain unresolved in disagreement, work to get a resolution of some sort. Agreeing to disagree is not smart. Feedback is key, give more feedback rather than less

-embrace conflict, don’t avoid it. Conflicts delayed are conflicts multiplied.

-don’t sacrifice what is right for what is wrong just for some temporary harmony

-make your point heard

-if you try to keep your interactions at a minimum, that’s a tell that something isn’t working

-the four horsemen of the apocalypse, per John Gottman:

1; defensiveness

2; criticism

3; contempt

4; stonewalling

-delegate roles and responsibilities to one person only

-know yourself; be really great at one or two things and dangerous at the rest. That will leave you prepared and able to seize opportunities as they present themselves

-life is an infinite game; each experience better prepared you for the next one, so it’s not a wasted experience

-Getting to where you want to be involves:

-1; pick an audacious goal

-2; know yourself

-3; the myth doesn’t make itself

-4; embrace the infinite game

-if you’re great at what you do, it turns out the only risk is not taking any risk at all

-in life, choose the decision that will lead to the least regret; regret minimization. Jeff Bezos

-when I’m 80, how will I feel about my decision, or indecision? Not taking the chance vs opportunity cost

-Most people are optimistic in the short-term, pessimistic in the long term

-To succeed in life, you must be pessimistic in the short-term, optimistic in the long term, especially for founders or CEOs to invest in

-short-term optimists get killed

-optimistic employees make more than pessimistic employees, pessimistic founders/entrepreneurs make more than optimistic founders (by more than 30% average)

-in power vs patience, patience wins

-Postel’s Law; be lenient in what you accept, be strict in what you put out

-Ideas work due to technology, regulation, macro (in business). Good ideas that work is very rare. Most ideas are mediocre or bad ideas.

-Timeboxing; don’t spend too little or too much time to know when something doesn’t work. Set aside a specific amount of time, and then quit if it hasn’t worked. Otherwise too much time spent is a waste and not enough time leads to not knowing

-we can choose our instincts or our elevated self in decision making

-desire for control comes from insecurity

-desire for fame comes from vanity

-greed and insecurity beget failure

-most damaging shadow trait; aversion to criticism

-one does not become enlightened by imagining figures of light, but by making the darkness conscious; Carl Jung

-no one can become conscious of the shadow without considerable moral effort. To become conscious of it involves recognizing the dark aspects of the personality as present and real. This act is the essential condition for any kind of self-knowledge. Carl Jung

-Accept reality, test your theories, listen to opposing beliefs

-Key to wealth: Solve problems and produce, not consume

-curiosity, empathy and serenity lead to first principles thinking

-shame; pay attention to it, what went wrong, what process change can we make to prevent it from happening again?

-don’t get one-itus

-We want what other people want (envy). We are repetitive, memetic. However, new ideas are thus going to be weird as most don’t know what it is. Thus, embrace what’s weird as that is what will work for innovation

-Zoom out and view things from a bird’s eye perspective. To be innovative, do different things from others and have different experiences, it will make you different and stand out, especially as you get older. Good founders teach you a new way to view the world and life itself

-Don’t have to copy others or be novel. History doesn’t repeat but it rhymes

-better, faster, cheaper, and definitely if you aren’t the first mover

-competition is not your friend

-the first startup doesn’t have to be perfect; one can pivot within it and take what works and bring it to the second version of the company or product

-cheaper: cut margins for market share like amazon and robin hood

-faster: speed like Uber

-better: technical excellence like google and Dropbox. Page rank and first introduction of the cloud. Discord low CPU requirements for gamers first

Airbnb cheaper and better service from direct homeowners

5 steps to winning competitive tournaments (I.e. life) where something people are looking for is finite

-gatekeepers are imperfect, don’t get discouraged

-know you’re in one (you and your coworkers are actually competitors for bonuses, not getting laid off first, getting promoted first)

-know the criteria

-apply to many

-get advice from the previously successful

-door closed? Try the window

-competition is not zero sum, it’s for us to be better

-the whole goal is to get so good to no longer need to be in tournaments and create your own tournament for others to participate in.

-great founders: good at adapting and pivoting quickly with new information, strong leaders, good at systematic rational thinking (not emotional), visionary

-better to have a company and product loved by 100 people than liked by 1 million people

-Garry’s favorite advice from Hans Tung to young people: be patient, reflect, think, learn, and don’t compare with each other’s where you are. Learn from other people’s mistakes rather than to be envious; this helps you figure out who you are and what you are good at. To make the most impact, have a positive impact to others

-good founders change lives for the better, and start new movements/better ways to live life

-tackle problems head on

-be a better cofounder by knowing others roles and stories by being at least a little multi-versed

-pre-emptive therapy can be a great ounce of medicine