Never sell what you got for free (or cheap)

Tom is a good friend of mine, he used to work for Apple back in the very old days of the first iPod (Hint: it is the one on the left).

Tom was holding on to some AAPL shares he got after exercising his options.

Believe it or not, Apple was not doing well. Almost nobody thought the company will survive, employees were selling their stock while it was still worthing something.

Tom decided to sell all of his 50,000 shares. The value of those shares today? 7,500,000 USD. Not many companies give 7.5 million for free to their employees.

Blame human nature. We think we are smart, we think we know the future, we think we know what the right choice is. We think…

We are not as smart as we think we are.

I also thought I was smart, I sold my Ethereum. Read how I bought it initially. But why did I sell?

I invested around 10,000 EUR and once my Ethereum was worth 20,000 EUR, I sold. Maybe it was a wise decision, it is still a good 100% profit.

But later on, with Ethereum going higher and higher, this is what I realized:

It is easier to lose 10,000 than to look back and see a lost “out of this world” opportunity.

What if Ethereum goes to 1,000 EUR / ETH, that would be a 2.5mil unrealized loss. It could go higher, who knows. Or it might crash down to zero, then the loss would still be the same, 10K.

So I gave up something with insane upwards potential to avoid a 10,000 loss. That does not feel wise. You have to take your risks and stay the course.

If you have been given something for free or you got it cheap, hold it. Never sell it, unless it feels like you won the lottery.

Sleep well Tom.