Ask George A. Weiss what drives his decades-long commitment to philanthropy and he will tell you about a pledge he made when he was as a sophomore studying at the Wharton School.

“My fraternity was asked to host a Christmas party as a community service project for a dozen kids from South Philly,” he explains. “The kids were only a few years younger than me.” They came from disadvantaged neighborhoods, and they had little reason to believe that even their most humble aspirations might come true. Weiss could relate.

“I grew up very poor outside of Boston,” he says, adding that he understood the obstacles the youngsters faced. “Those kids and I became friends. We would play basketball together. I would bring them to Penn football games. We talked about everything, and we stayed in touch.”

When Weiss reached his mid-20s, he invited the 12 friends to lunch and during the meal they spoke about their lives. “They talked about how some of their siblings had dropped out of school, how some had gone to jail, how some of their sisters had gotten pregnant,” Weiss recalls. “And yet, all of them had managed to graduate.”

Weiss asked his friends why their paths had differed from those of their peers, “and one of the kids said to me, ‘George, we couldn’t look you in the eye if we’d dropped out.’”

That, Weiss says, is when he made a pact with God.

“I said, ‘If You ever give me the financial wherewithal to make a difference, I will do what I can to help the poor through education, I will help my university and I will help my religion.’”

After college, Weiss rose to become a highly successful businessman, first as a stockbroker, and then as president of George Weiss Associates Inc., a money-management firm with offices in Hartford, Conn., and New York. He became a wealthy man, and he kept his pledge.

Over the past two decades, Weiss has given more than $80 million to Penn to fund endowed professorships, a deanship, endowed scholarships, the Weiss Tech House, the Weiss Center for International Financial Research at Wharton and the George A. Weiss Pavilion at Franklin Field. In January, he donated another $20 million to endow four PIK professorships as part of the Penn Integrates Knowledge initiative.

But Penn isn’t the only target of Weiss’ philanthropy. He is the founder of Say Yes to Education, a program that he started in 1987 by promising to pay college tuition for 112 sixth graders from Philadelphia’s Belmont Elementary School if they graduated from high school.

Like the youngsters Weiss befriended so many years ago, the Belmont students faced tremendous odds, coming from one of the most troubled neighborhoods in the city, so Weiss coupled his financial gift with hands-on involvement in each of the student’s lives. He provided the Belmont 112 with tutors, counselors, summer programs and even his home telephone number with instructions to simply reach out to him whenever they felt the need.

Weiss established such strong connections with the Belmont students that he referred to them as family. By 2007, 20 of the students had earned undergraduate degrees; 10 had earned associate degrees; 14 had vocational degrees and 65 had high school diplomas or GEDs.

The Say Yes to Education program has now expanded to include 22,000 students in Philadelphia; Hartford, Conn.; Cambridge, Mass. and Harlem, N.Y. Weiss says the program has taught him a lot about the importance of early intervention. As a result, he has changed the mentoring program over the years to intervene in the lives of students as early as kindergarten and to provide comprehensive academic and social support for the selected students’ family members, including scholarships for parents who choose to further their own education.

Weiss became a trustee of the University in 1988 and as chairman of the current $3.5 billion Making History campaign, Weiss calls his recent $20 million donation to Penn a leadership gift that he hopes will “catapult our faculty to even greater heights.”

The Making History campaign recently reached a significant milestone, having raised 75 percent of its overall $3.5 billion goal. Weiss’ gift brings the amount raised for faculty support to more than $386 million.

“We have a once-in-a-lifetime opportunity here, establishing these amazing faculty positions with Nobel Prize potential,” Weiss says of the PIK professorships. “There’s a buzz out there about these professorships. I was talking to an associate professor at another school recently, and she said the PIK professorships are the most sought-after positions in academia.” The University has, so far, hired 10 endowed PIK professors, each holding joint appointments in Penn schools.

When Weiss announced the $20 million gift in January, Penn President Amy Gutmann called it transformative. “True to form, George Weiss has demonstrated a profound love for Penn, a consummate sense of our mission and impeccable timing,” she said. “Faculty support is a key campaign priority, and the George A. Weiss University Professorships will help us to catapult our academic community to a new level of eminence. We are grateful for George’s vision and unwavering support.”

Among students, Weiss has built a reputation for being a caring and attentive mentor (he is the former chairman of the University Committee for Undergraduate Financial Aid). Weiss says he gets personally involved in the academic aspirations of students because he knows firsthand how profoundly a Penn education can change lives.

“I was too poor to fully enjoy a lot of the aspects of Penn,” he explains. “But, I felt it was a second home to me, and Wharton afforded me the opportunity to be successful.”

Weiss returns to Penn often, for Board meetings, athletic events (he is a member of the Athletic Board of Overseers) and sometimes just to take students out for a meal. He makes a point of noting that his two daughters, Deborah and Allison, also graduated from the University, and, he adds only half jokingly: “I have three grandkids that will be going to Penn. Of course, the oldest is only two and a half right now.”

Despite his affinity for his alma mater, Weiss says he has not always been comfortable asking others to give money to the University. But when he agreed to serve as chairman of the Making History campaign, he knew he would have to get over his reluctance to sell the school to donors.

“I never raised a dime for anything until my 25th reunion,” he says. “It was a little hard at first, but I’ve gotten used to it. Now, I’m not only comfortable with it, I’m enthusiastic. You certainly can’t be anonymous and raise money, and you have to be generous yourself because giving begets giving.”