Let's examine the inside story of the dropout billionaire:
World-changing technology is in embryonic stage, but nobody sees it. Bare-feet dude says to Hapless friend "should we go to college?" Hapless friend replies "nah, I'm gonna do my own thing." Bare-feet dude: "I think I'll go to college though."
Three years later, new technology suddenly comes out of embryonic stage and enters the lab. Bare-feet dude is the first person to see it. He jumps up and says "holy smokes, this is the future! I better quit college and get in on this!" He drops out and starts using the new technology thing to improve an existing process, like talking to grandma across the country.
Hapless friend also believes in constant contact with grandma and thinks it's going to be big, so he also starts a side-project to connect all people to their grandmas through two cans and a long string.
Two years later the bare-feet dude wows everyone with the thing he invented using new technology that just became possible in college. You can just think about grandma, and she appears on the wall looking at you in all three dimensions.
Phone companies, fax companies, chat companies, cell carriers, pager providers and the post office all show up to the trade show and in unison drop their jaws like OMFG, that's not possible! Bare-feet dude smiles, "it's buggy and grandma might disappear any second now, but yes, it is possible."
Eight million dollars of funding checks later, Bare-feet dude has hired all of his peers out of college that actually graduated. Together they call the company "Grandma Inc.". They create English, Japanese, French and Spanish manuals, and partner with media publishers to launch it in every channel across the globe.
Hapless friend shows up the next day crying "it was my idea! I knew Grandma was gonna be huge! In fact I told him about the Grandma idea!" -- several lawsuits settled later, Grandma Inc. files for IPO and Bare-feet dude becomes a billionaire.
Bare-feet dude knows the next embryonic technology is right around the corner. So he throws some of his money into a new entity called Bare-feet Family Trust, and the rest in Bare-feet Holdings. The latter starts a startup fund, encouraging young entrepreneurs to walk away from college and work on their "holy smokes, this is the future!" insights.
Everyone else gets it in their head that college is actually not worth the time, because people can drop out and still become billionaires; and that the world is an unjust place, especially to Hapless friend and his kind.
And the billionaire club continues to grow.
Steve Jobs dropped out of Reeds College in 1972, the same year he sold the game Pong to ATARI. In future speeches, he said "If I had never dropped in on that single calligraphy course in college, the Mac would have never had multiple typefaces or proportionally spaced fonts."
Bill Gates dropped out of Harvard University in 1974, the same year he and Paul Allen saw the opportunity to start their own company (Microsoft) in the release of the MITS Altair 8800 CPU, which he learned about while using the school's computers. Harvard later awarded Gates an honorary doctorate degree.
Elon Musk dropped out of Stanford University's Physics program in 1995, the same year the Internet was going to clearly change the world starting from Silicon Valley. He started several companies, including X .com, which later merged with PayPal and made him a millionaire. He later invested in other embryonic technologies related to Physics, like the Electric Engine (Tesla Motors) and the Rocket Engine (SpaceX). He has achieved several honorary doctorates since dropping out.
The Grandma idea is a reference to lawsuits against Facebook by individuals who claimed they were the first ones to think of friendship online.
Peter Thiel, former CEO of PayPal, and a proponent of dropping out of college, invested his money after the PayPal IPO into several embryonic companies. One of these companies was Mark Zuckerberg's Facebook. Mark dropped out of Harvard University, where he learned how to build Facebook, and grew the company to $100 Billion. Peter Thiel's 10% stake for his $500K investment is worth $10 Billion today.
Peter Thiel, after Facebook's IPO liquidity event, started "The Thiel Fellowship", which invests in entrepreneurs with a clear new technological insight from college, who would choose to drop out. This confuses many people who think the message is college is not worth the time. College, in fact, is the catalyst to finding the billion dollar insight.