Apple was going out of business until Microsoft invested ~190 (or was 90) million in Apple to bail it out. IIRC, it was late 90s.

Actually the real investment for Microsoft wasn't the stock purchase but the commitment to keep Office on the Mac for X number of years. Without that, the Mac probably would have tanked before the iMac ended up saving Apple. Retaining Microsoft at that time was key to retaining legitimacy.

There's an awesome talk with Steve Jobs where he goes into it - it's been posted on Hacker News many times.

Yes - that's why I said it's not quite a fair comparison as that was probably more or less the best time in history to make an investment in Apple. Maybe akin to investing in Amazon in 1994 or in Google in 1998.

The drama "Pirates of Silicon Valley" covers MS & Apple from their founding in the 70s till the late 90s (the movie was made in 1999) and I believe it ends in that scene (I've last seen it when it was new so it may end a bit later but that definitely appears in the movie).

Apple was never close to going out of business, irrelevancy sure, but not bankruptcy.

$10,000 to $5.5M in Apple. Yup, that's absolutely insane.

You could have probably gotten some similar/greater gains investing in some of the dotcom "stars" (even "real" companies like Qualcomm/Broadcom/Sun/etc rather than Pets.com) & exiting before the bubble burst!

Easier to say in hindsight of course. I remember my brother convinced my parents to buy stocks (something like a few thousand $s) in a company making broadband internet modems in the mid 90s (this was high-tech future-like stuff at the time when most people were on dial-up internet - ISDN was considered fast) and they ended up going out of business shortly thereafter.

So even if you have good insight & bet on the right trajectory of technology it's not that easy to get it right without the benefit of a time machine or crystal ball.