Jackson said there have been three generations of web companies. The first generation was big web portals, such as Yahoo, where content was aggregated in one place. The second was the social web with Facebook and the third generation is companies focused entirely on monetizing the mobile platform, something Facebook will continue to struggle with, Jackson said.

“When you look over these three generations, no matter how successful you are in one generation, you don’t seem to be able to translate that into success in the second generation, no matter how much money you have in the bank, no matter how many smart PhDs you have working for you,” Jackson said. “Look at how Google has struggled moving into social, and I think Facebook is going to have the same kind of challenges moving into mobile.”