[RickJWagner]

Retired Red Hatter here.

When IBM bought Red Hat in the late twenty teens, they offered us a 10% discount on the stock as an ESPP. At the going price, the stock already had a 5% dividend. It seemed like a great deal.

Our internal mailing list ( the late great Memo List ) had a lively discussion. The majority didn’t see the raging bargain ahead of them. Most seemed to like the safe path— buy the stock, then immediately sell it and invest the proceeds in an index fund. It’s not bad advice, but it deconcentrated your bet.

The index has had some fantastic years since. But I think IBM did even better. The stock went from low one hundreds to over 300 for a while. Even after this big drop, you’d still be far, far ahead. You still get the dividend, too.

In this case the only way to lose was to not play.