[nostrademons]

Many of them are actually pretty good at succession planning: Gates, Page, and Jobs all hand-picked their successor, and had a long apprenticeship period where the successor served in a COO role and basically ran the business while the previous CEO oversaw.

The problem is that the tech business is fundamentally innovation-based, and this means that anyone capable of running the business as #2 is probably unsuitable to be #1. There's a classic a16z essay about this:

https://a16z.com/2010/12/16/ones-and-twos/

Basically, the personality traits to be a successful functional executive and those needed to be a successful tech CEO are often diametrically opposed. So if you pull from the existing exec team, your best case is that you get a caretaker (like Ballmer, Pichai, or Cook) who runs the business, optimizes earnings, keeps people happy, but misses the next tech cycle and eventually mortgages the company's future. Your worst case is that everyone quits and the company implodes because it can't service its existing commitments.

This is why you want to be a financier. Sell the companies at the top of their growth curve and fund the up-and-comers that will eat their lunch.