Mark might have. I'm pretty sure neither Elon Musk nor Larry Page has.
If we're talking the Larry Page scale, well, Marc Andreessen posts here often enough to have noticed Maciej Ceglowski's Co-Prosperity Cloud; he saw a comment I left about a $50 follow-on investment and matched it.
How successful? Depends on your perspective. I thought I had relatives who I would classify as "extremely successful" and "rich", and they sold their companies for... high 5 figures. :) I must admit, my vision gets a bit blurry when it comes to distinguishing between numbers with 8+ figures...
https://news.ycombinator.com/submitted?id=picnichouse
However they were not well received (as has been discussed in a couple other threads)