I have absolutely no clue if this actually played any role, but pg is also one of the people credited with creating what's considered the first web app, and it seems plausible a vision of a future giant world of web apps could've influenced the startups he picked and the advice he gave. For example, the reddit co-founders say the site was his idea:

>The next morning, on the train back to Virginia, hung over, somewhere in the middle of Connecticut, I get a call from Paul. He says, "I'm sorry, we made a mistake. We don't like your idea, but we like you guys." We got off the train, and I was able to sweet-talk the Amtrak lady into not charging us to turn around. In our conversation, Paul said, "You guys need to build the front page of the Internet." That was all Paul, and that became Reddit.

(https://www.inc.com/magazine/201206/christine-lagorio/alexis...)