He's done his share of crazy will-never-work things too.
I think a lot of the reason it works out is the existence of an external feedback loop, a group of people that are willing to say "Larry, you're insane." Larry is actually pretty good at listening to other people - even now, in the New Google that sometimes does very unpopular things, he's committed to at least hearing out objections and weighing them. When Eric was CEO he also provided a very useful countervailing force to Larry & Sergey's more idiotic ideas, while still letting crazy ones like "Let's build a webmail client!" or "Let's build a browser!" or "Let's buy a mobile phone OS!" go through.
I think a lot of the reason it works out is the existence of an external feedback loop, a group of people that are willing to say "Larry, you're insane." Larry is actually pretty good at listening to other people - even now, in the New Google that sometimes does very unpopular things, he's committed to at least hearing out objections and weighing them. When Eric was CEO he also provided a very useful countervailing force to Larry & Sergey's more idiotic ideas, while still letting crazy ones like "Let's build a webmail client!" or "Let's build a browser!" or "Let's buy a mobile phone OS!" go through.