The coin flip that explains why Buffett's Rule #1 actually matters (Ergodicity & Margin of Safety)

Let me offer you a bet. we flip a coin. heads, i pay you 50% of whatever you put in. tails, you lose 40% of it.

odds look favorable so most people would say yes. you win more than you lose (positive expected value) & if i offered this at a party, i'd have a line out the door

now let's actually play. you put in $100

first flip, heads. you're at $150. feeling smart

second flip, tails. down 40% of $150 is $60 gone. you're at $90… wait. you've won one and lost one on a coin that favors you, and you're below where you started

third flip, heads. $135. fourth flip, tails. $81.

two wins, two losses and you've lost almost a fifth of your money. keep playing and it doesn't get better but play long enough and you go to 0 on a coin that was supposedly rigged in your favor

nothing unlucky happened here. the issue is that the wins and losses are not working with the same amount. the 50% gain is on your $100. the 40% loss is on $150. once you're down 40%, you need to gain 67% just to see your money again and this coin never pays 67. you lose more than you gain back, basically every time

the strange thing is that the bet really is good (for a crowd) if a thousand people each flipped once, the average person walks away up. that average is real. but it just belongs to the crowd not to us. we're not a thousand people flipping once. we're one person flipping a thousand times, and we have to survive every flip in order, carrying every loss into the next one. the crowd's average and our actual path are two different numbers.

that's ergodicity. you don't get to live the average. you live your sequence.

now, investing. you know the famous rules. buffett's rule number one, never lose money. graham hammering on margin of safety for an entire book. and if you're honest, part of you has always found this a little overdone (i did). of course you'll lose money sometimes, that's the game. why the obsession?

the coin is why. i'll admit these rules used to sound like temperament to me i.e. the kind of thing careful people say because they're careful. once you feel the actual math: down 10%, you need 11% back. annoying. down 50%, you need 100% back. down 90%, you need 900%, and realistically you're not coming back. past a certain size, a loss stops being a setback and becomes permanent

margin of safety is the tool that keeps you off that curve. buying with a buffer in the price. keeping any one position small enough that being wrong is a wound and not the death of your portfolio. holding in a way where nobody can force you to sell at the bottom. all of it is the same move: making sure no single flip can put you in the hole the next win can't fill

the people quietly compounding for forty years didn't find better coins/stocks. they understood this…

also this is simpler in theory and harder to practice. that is why you see a lot of smart people blowing up their portfolios… one bad swing to end it all (looking at you leopold aschenbrenner/bill hwang 👀)