Managing Partner at Dragonfly. Effective Altruist. Airbnb, Earn.com (acquired by Coinbase) alum. Writer. Former poker pro. Donate 33% of my income to charity.
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Get better at speaking. Do embarrassing stuff like record yourself, Toastmasters, study good speakers and try to emulate them to try out their verbal techniques and see how they fit you. Charisma is the omni-skill.
Drink less, or not at all. It will force you to become a better conversationalist.
Buy art that your friends make and hang it on your walls.
Never lend money to family or close friends. Instead gift it to them, and if they pay you back, consider it a pleasant surprise.
Spend most of your money on experiences, not things.
Make sure your spending scales sublinearly compared to your income, and you will always feel rich.
Take a lot of risks. More risks that you think you should. When you’re young, the downsides are never as big as you think, and other people’s memories are short.
Every man is cobbled together from people they surround themselves with, both physically and mentally. Surround yourself with people you respect. If you never lose friends or never try to acquire better ones, you’re doing it wrong.
Whenever you feel comfortable that you’ve made something of yourself, it’s time to move on. Move to a bigger city. Try for a more prestigious company. Find the biggest games, and try your hand at them.
Say yes to every adventure, at least once. Your 20s are the only time you’ll get to do that.
Originally published on X, November 2025.
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