Kiyosaki?

I think that Robert Kiyosaki probably fits what you're asking for.... He made a lot of money by starting a company which makes those velcro "surf wallets". Then he lost it all again.... But it does seem he DID make it the first time.

I think the next time he made a lot of money was through real estate investments....

He says he's making more from his books than he has from anything else, but it doesn't discount that he has apparently already made a lot (millions, I think) from his previous activities, before he started to write about them....

I'll see if I can think of any more authors who also fit this description.... :)

- Dien Rice