"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."
Last month Facebook acknowledged its mobile challenge in a regulatory filing. The company stated that the growing number of mobile users using Facebook is hard to monetize and "may negatively affect our revenue and financial results."
Jackson's comments on the future of the social network come at a time when Facebook's stock is down about 27 percent from its IPO price of $38 a share, making it the biggest two-week loss of any IPO since 1995.
"The world is moving faster, it's getting more competitive, not less, and I think those who are dominant in their prior generation are really going to have a hard time moving into this newer generation," he said. "Facebook can buy a bunch of mobile companies, but they are still a big, fat website and that's different from a mobile app."