Research firm eMarketer estimates that Google will account for 40.7 percent of percent of U.S. digital ad revenues in 2017. Facebook, eMarketer predicts, will capture 39.1 percent of the display ad market.
"If you look at Google, they have just an amazing monopoly when it comes to search advertising," said Calacanis, a media entrepreneur and early Uber investor. "And they know exactly how to avoid triggering what would look like a monopoly. So they've always kept an anemic, incompetent competitor alive. So Google had Yahoo. They could have bought it, they could have taken over their advertising revenue. Suspiciously, they didn't."
Google has what Calacanis referred to as "moats," borrowing from a phrase used by famed investor Warren Buffett: Well-known brand names that make it difficult for them to succumb to competitive forces.
"Google's moats are transcendent now: Chrome, Android," Calacanis said. "It's amazing the monopoly they've built that doesn't look like a monopoly."
The market power behind the tech giants has caught the eye of regulators abroad. In Europe, Google's aggregation of content, WhatsApp's encryption, Apple's low taxes and Amazon's payments to publishers are just a few of the issues that have sparked a regulatory crackdown.
"Facebook, they've always had, or [CEO Mark] Zuckerberg's referred to it as, 'the clown car:' the incompetent Twitter, which can't seem to get out of its own way," Calacanis said. "These are perfect little companies to keep on the side. Don't buy them. Let them be independent. So when the anti-trust people come, you can say, 'Look, no, there's options here.'"
U.S. regulators have their fair share of spats with technology companies, but the debate wages on as to whether these companies cause any economic losses or harm to consumers since they lower prices for some services.
Calacanis said it's a warning for newer tech companies, like Snap, which reports earnings for the first time after the bell on Wednesday.
"They're not going to try to compete with the global user base in the same way Facebook is obsessed with having everybody," Calacanis said. "Snapchat is going to really get themselves into trouble if they get into Yahoo's big problem, which was a constant comparison to .... Google. Snapchat has to establish they are something different."