Asked what he's trying to do, Weiss say: "I'm trying to level the playing field."
Last fall, Weiss gathered the parents of 400 Harlem kindergartners and made them the same promise he's been making for the past 18 years in Philadelphia, Hartford and Cambridge.
As CBS News Correspondent Jim Axelrod reports, Weiss promised the children he'd pay for them to got to college.
You get that?
"He's gonna give us money so we can go to college?" asked one kid.
Yes, Britney, there is a Santa Claus. It turns out he's a Jewish guy from Connecticut.
"There are so many kids just falling off the cliff, and it's really a shame that society doesn't step up and make a difference," he says.
Now, the idea of a gazillionaire swooping in to pay for a group of underprivileged kids to go to college isn't brand new. Philanthropists have been doing this for 25 years. What makes Weiss different is well, Weiss.
"Our parents thought he was a little crazy – a good crazy," says Joelena Fuller, who was among his first group of beneficiaries in 1987. "You know, if we're sick he's there. If we get in trouble he's there. Even if we just need to talk he's there for us."
Fuller was among 112 Philadelphia 6th graders who were the first to receive Weiss' assistance. Twenty went on to college. Fuller did not, but, still, she says Weiss changed her life.
She calls him "pops."
Pregnant at 15, she could've been a statistic. Now she runs her own catering business. Guess who paid for cooking school?
"Whatever it took for him to get us to the next point in our lives, he has done it for us," says Fuller.
Over the years, Weiss has sent well over 100 kids to college and spent $20 million of his own money, and still he felt like it wasn't enough.
"My goal is to help thousands of kids," he says.
Hoping to get more of his kids into college, he's now starting earlier, in kindergarten instead of 6th grade. He's offering tuition for his kids' siblings, even their parents. He's also offering medical care and legal help.
"It's just incredible," says Maria Morales.
Morales, single mother of two, including one of the lucky 5-year-olds, used the legal help to fight eviction and hopes to use tuition help to train for a better job.
"He's an angel, he really is," she says. And she really means it. Weiss, she says, was "sent from heaven."
Weiss is some people's idea of an angel just trying to do a little good here on Earth.