Is it common at all for people who happen to hit gold with one app to actually come back and have other hit apps? I see it all the time that things are advertised as being the next hit app from this or that person and, as far as I remember, it almost never works.
While it might be (way) less popular, Skype still exists. [1]
Also:
> Microsoft Teams is based on a number of Microsoft-specific protocols.[50] Video conferences are realized over the protocol MNP24, known from the Skype consumer version. [2]
I guess the enormity of the challenge is modulated several factors, including if you are trying to invent an entirely new product category, implementing a solution to known problem for lot of users, or "just" creating a new title in an established genre.
Jack Dorsey with Twitter and Square. Richard Branson has started a bunch of successful Virgin businesses. Elon Musk, even without Tesla, there's still Zip2, PayPal, SpaceX, etc.