Ian Hsiao

Risks

• Ground rule: Only risks that you can afford to fail are worth taking
• To balance your self-belief with self-awareness, you should work hard in your early career to educate yourself on your own capabilities in order to Cultivate self-belief early, by getting more "i can do it"→ "i did it" data points.
• Thinking about risk the right way, you only have to be right once (to make it to the next level of whatever you are progressing).
• Look for small bets you can make where you lose 1x if you're wrong but make 100x if it works. Then make a bigger bet in that direction.
• Anti-fragile describes systems or strategies that will benefit from volatility. For the anti-fragile, shocks bring more benefits (or less harm) as their intensity increases, up to a point. e.g. lifting a 100 lb weight once is more beneficial than lifting a 1 lb weight 100 times.
• Smart, driven, resilient people are the anti-fragile.
• I am willing to take as much time as needed between projects to find my next thing. But I always want it to be a project that, if successful, will make the rest of my career look like a footnote.
• Have confidence in taking risks. Success means a series of well-calculated risks that one took to go from nowhere to somewhere.
• It's impossible to be right all the time—you have to try many things and adapt quickly as you learn more.
• Start with small risks, then you should take bigger risks. You will soon learn that the downside of risk is much smaller than you think, and the upside is much bigger.
• Inexperience makes you fear risk, but it's when you are young that you can afford the most (most = as much as you want).
• "Most people think about risk the wrong way—for example, staying in college seems like a non-risky path. However, getting nothing done for four of your most productive years is actually pretty risky." — Sam Altman
• Regarding future, there is no right path, but you want to do the things that is most likely to get you on a path to do something great.
• Most of the time the no-risk path is priced-out. The expected return is limited (e.g. priced as your salary), you can never get above average return following this path.
• Remember that you are going to die, there is no reason why you shouldn't take big bets to try leaving dents in the universe.
• "Remembering that I'll be dead soon is the most important tool I've ever encountered to help me make the big choices in life. Because almost everything — all external expectations, all pride, all fear of embarrassment or failure - these things just fall away in the face of death, leaving only what is truly important. Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart." — Steve Jobs, June 12th 2005 Stanford commencement speech

Dealing with uncertainty mentally

• When you are popping out of a local maxima (the no-risk path), your first step is definitely a drop.
• Be comfortable about living with uncertainty. One trick to build tolerance is to cold shower in the morning, where you will go through three stages: fuck, fuck, fuck and then you will be comfortable enough to think clearly.
• Decisions you made when you are in panic is almost always bad. You should always try to recognize your feelings and deal with it (verbalizing every thought with ChatGPT could be very helpful at pinpointing hidden worries).
• Besides self-awareness justified self-belief, optimism and faith from the macro could be very helpful when you are living with uncertainty.
• Beware of the effort myth so you don't get stuck: "It's not working because it's I'm not working hard enough" → definition of maniac