10 Life Lessons Investing $2.5 Billion Taught Me

Cut your losses without shame.

If you’ve made a mistake, own it and move on or it will sap your energy, which you can put to better use elsewhere. You will keep making mistakes. Just make better mistakes tomorrow. No biggie.

Your self-worth (process) is not your results (outcomes).

Your big reason for being and values are what define you, not your results. Positive results are never guaranteed. Don’t make results the measure of your self-worth.

Control is an illusion.

The future, like the market, is unknowable and uncontrollable – a range of uncertain outcomes created by ever-changing probabilities. You’re not in charge of the universe, and it WILL bitch slap you from time to time.

Don’t take things personally.

A stock doesn’t care if you own it. When it tanks, it’s not personal. When it goes up, it doesn’t mean you’re a genius. Your identity belongs to you, not your circumstances. Same with your fantasy football team results. Just saying.

Avoid a crowded trade.

If everyone is long or short a stock, there aren’t any marginal buyers or sellers left, and the stock will mean revert. In life, when everyone around you is zigging, it’s probably a good time to zag.

If it’s too “complicated” stay away.

If someone can’t explain or says it’s too complex for you to understand, they could be conning you. And if you don’t understand something, but pretending to, you’re working your own con. Get educated or pass.

"Free lunches" are expensive.

See 20% guaranteed returns on crypto deposits. When you feel greed tugging at you, double down on your common sense. Greed makes us do things we will regret. So does desperation, but that’s another story.

Don’t fight the tide.

Companies make more money when they have a great product, a good business model and a rising tide of demand. Seek ease, not obstacles to overcome in life as in business. Go where you’re wanted and valued.

Bet on good people.

Trustworthy and competent management teams mean investors can sleep well at night. When the inevitable shitstorm happens, you know they’re paying attention, can figure it out, and won’t rob you in the process. Surround yourself with competent and ethical people. You won’t have to squander energy watching your back or clutching your wallet.

Play the long game.

A buy and hold strategy over a long investment horizon will make bank. Bear markets become opportunities to back up the truck. In life, small incremental progress over a long time leads to outsized breakthroughs. Don’t let short-term setbacks rattle you and give yourself the gift of time.