The Ultimate Oprah Moment

Imagine a reality TV show with no housewives or bachelorettes, no tribal councils or rose ceremonies. Imagine a show that rewards the winner with a million dollars, not because he outfoxes his opponents, but because he out-philanthropies them. Meet Greenwich resident Stephen Paletta, the man Oprah crowned the biggest giver

One of the hardest things Stephen Paletta has ever done is donate $100,000. And it wasn’t even his money. He received it on Oprah’s Big Give in 2008 and was the only contestant who succeeded in giving away all of the money in accordance with the rules of that particular challenge. The feat reduced him to tears on camera.

In his utilitarian office at his nascent company, GiveBack, Paletta does not come across as a particularly sappy guy. “The show in which we each had to give away $100,000 was strange,” he says. He and his opponents had only a few days to disperse the chunk of money in the form of goods or services—no cash—with no more than a value of $500 going to any one person. “You would think it would be a really special treat. But, after it was over, I started crying. I said, ‘That wasn’t much fun.’ In previous weeks, we really got to know the people we were serving. In Denver, we helped a woman running a children’s home. We built a relationship with her and the kids. But handing out things randomly, we didn’t build a relationship with one single person. We had no idea who they were and what they needed.”


The forty-six-year-old comes from a construction background and has the wide neck and thick upper body of the All-American lacrosse player he was in college. Born in Port Chester to parents who hailed from the Bronx, Paletta spent most of his childhood in Bedford. Philanthropy was not part of his family culture. However, aside from proving himself a natural Big Giver—with big ideas and a big heart—on Oprah’s show, Paletta has been giving in little and large ways since a church trip to Rwanda in 2004.

“As I get older, I get a whole lot more emotional,” offers Paletta. “My kids would say I’m an overly emotional dad sometimes.” But it’s not a cry-at-Hallmark-commercials sentimentality; it’s more the deep well of emotion that runs through people who are incredibly giving and caring.

The Big Give Big Break

Paletta claims “pure luck” landed him on reality TV, but really his actions made him a much more likely candidate than your Average Joe for this out-of-the-ordinary show. First, during college, the reluctant Catholic went in search of God (more on that later). Second, in 2004 Paletta volunteered to go to Africa with a group from Trinity Church in Greenwich—something that a husband with three little girls at the time could easily sidestep. Third, in 2005 he started the International Education Exchange, a nonprofit providing aid to schools in Rwanda, and visited numerous times to give hands-on help.

The next part could be called luck, or divine intervention. An email about a casting call for Oprah’s Big Give, hit Ian Cron’s inbox at Trinity Church, where he was senior pastor at the time. The reality series sought to discover “America’s best unknown philanthropist.” Cron already knew him.

“The woman who called me said they were having trouble finding men for the show,” recounts Cron. “I asked what they were looking for and she said, ‘Guys who are interested in social justice, who are good looking, intelligent, well-educated.’ I replied, ‘Not only do I have the guy you are looking for, you may as well write him a check right now. I don’t know anyone more competitive or ingenious than this guy.” Cron, founder of Trinity Church and now its spiritual director and a celebrated author, had known Paletta for ten years and watched him pioneer educational programs in Rwanda. “He’s a rocket,” says Cron, “all energy and ideas.”

Cron contacted Paletta and urged him to attend the casting the next day in New York. Paletta resisted, saying, “Ian, I really don’t want to do this and I won’t get chosen anyway.” Cron replied, “Not only are you going to get chosen, you’re going to win this thing.”

After several callbacks, including a week of interviews in L.A., Paletta proved the first part of Cron’s prediction true. Four days after arriving home from California, Paletta got the call telling him to pack his bags. He was going back to L.A.

“I was thrilled because I loved what the show was about,” says Paletta, whose frat-boy good looks (he was a Chi Psi at Cornell) and on-camera ease combined with his philanthropy résumé must have bowled over the producers. “Oprah had a vision. She wanted to change the face of reality TV, to not have it be about the backstabbing, negative things that go on in the world, but to make it about giving and caring. She wanted to start a movement of giving.”

Oprah Winfrey
(c) 2011 Harpo Productions, Inc/All Rights Reserved/photographer George Burns

Stephen with Oprah after his appearance on her show in April 2011

For Paletta, the hard part of the next eight weeks was being away from his family. “He’s an incredible, hands-on dad,” says his wife, Christine. For the most part, the challenges—being dropped in a different city each week and asked to do various charitable acts—came easy.

In L.A., the contestants helped a young widow facing the prospect of losing her house. “We rallied the whole community and did a big street fair. We raised $280,000 in goods and services for her in eight days,” explains Paletta. “In Houston, we provided low-income kids with their first Christmas ever. We turned their school gymnasium into a winter wonderland, with fake snow. Toys R Us donated presents, and Santa came in on a helicopter. It was a truly spectacular event. To see these kids who had never opened a Christmas present, and Santa arriving—it was one of the best moments.”

Paletta proved himself a resourceful, quick thinker. For example, one way he whittled down the $100,000 wad in Miami was to buy $10,000 worth of Florida Marlin tickets and distribute them to the families at the Boys and Girls Club. Paletta attributes his success with the Big Give tasks to his construction experience: “In construction there are always different things happening on the street and you have to figure out how to make things work.” He continues, “The show just fit me. It ended up being the most natural and easy thing for me to do. I also put no pressure on myself to win. It was not about me; it was about serving other people.”

Of course, this is just the sort of attitude that triumphs in Oprah’s world. The second part of Cron’s prediction came true: Paletta won and took home a million dollars—half for him and half to donate. “I don’t remember it well,” says Paletta of the moment when he opened the winning envelope. “But I get to watch the video of it happening.” He relaxes back in his chair, hands behind his head—body language that could read as cocky, but on Paletta says Isn’t life great? I still can hardly believe it.

Bad Luck Turns Good

Stephen Paletta’s life started out ordinary: He grew up in a big Italian family, with a stay-at-home mom and a dad who worked for the family construction business. He spent his teenage summers installing water and sewer lines under New York City. In 1982, he graduated from Fox Lane High School in Bedford and headed to Cornell to study engineering and play lacrosse.

A reluctant Catholic, he quit going to church until junior year, when a religious roommate sparked his curiosity about God. “I was supposed to be one of the best defensemen in the country that year,” says Stephen. “I started going to church and learned that I should be playing for God, not me. If I did that, God would make me even better. On my first day of practice, I blew out my ACL. I cursed God and asked the priest, ‘Who is this God who destroyed my knee?’ He told me, ‘You have no idea what God has planned for your life. It’s so much bigger than a lacrosse season.’”

Paletta didn’t go back to church. As a fifth-year senior, he returned to lacrosse after a year off. His coach asked him to talk to a freshman gymnast, Christine Kaiser, who had blown out her ACL. “She became my wife,” says Paletta. “Things like that continued to happen. By 1992, I said, ‘OK, I believe. I’m all in.’”

After college, Paletta joined the family construction business and then branched out, establishing his own company, built around technology he developed and patented for pipeline rehabilitation. “Our first major project was in New Orleans. But when Hurricane Katrina hit, it wiped out our business.”

By this time, Paletta and his wife had forged a strong faith together and become actively involved in nondenominational Trinity Church. The forced lull in work gave Paletta time to start the International Education Exchange. Inspired by his 2004 trip, this nonprofit organization, which aids schools in Rwanda, still exists (Paletta is chairman of the board). “That trip started to change my life in a pretty significant way. I became interested in the nonprofit world and the developing world but couldn’t support my family that way. My company was in the early stages then. I had hoped it would make me a lot of money, so I could retire and focus on nonprofit work.”

Enter Oprah, in 2007, with perfect timing, and as tends to be the case when Ms. Winfrey is involved, a life-changing experience unfolded. “The show solidified in me that I wanted to be in the nonprofit world,” explains Paletta. “I also saw the power of media, especially if used to highlight the good in the world, and I developed a relationship with Oprah Winfrey. I’ve had the opportunity to stay in contact with her and discuss what we are doing here.”

Journey of 1,000 Miles

Paletta put his winnings toward launching a foundation called Stephen’s Journey. “It was set up as a nonprofit that would promote small grassroots organizations that I knew were doing great work, in an attempt to inspire more people to give to those causes,” explains Paletta. “Ultimately, that’s what led to GiveBack. When I talked to people about what I was doing, at the end of my story, typically the person would say, ‘Now can I tell you what I care about?’ They’d tell me about their favorite organization. Their next question was, ‘Would you tell Oprah about this?’ I realized the business shouldn’t be about my causes, but how I could support people and the causes they care about.”

Stephen’s Journey morphed into GiveBack. On, launched last fall, anyone can create a free account or “foundation,” make deposits that are immediately tax-deductible and give the money whenever they want to whatever causes they want. All charities in the United States are in the site’s database. “The wealthy have access to donor-advised funds; we do that for the other 98 percent of the world,” says Paletta. No more writing out multiple checks to various charities, mailing them and filing paperwork. Individual foundations serve as savings accounts for charitable giving, and all the accounts together form an endowment management account, held at Merrill Lynch. Members receive one end-of-the-year receipt for the IRS. They also have the option of a payroll deduction plan.

That’s all great, but Paletta had a bigger vision for Giveback: “I wanted to take Oprah’s idea and do it for people across the country.” His quest to give people more money to give led to a system that is similar to the Red Campaign. “With that, you buy a product and part of the proceeds goes to fight AIDS in Africa,” explains Paletta. “That’s a good cause, but what if you’re more passionate about something else?”

Answer: Go to’s shopping portal. When members spend money at any of the 500 stores, including Apple, Nike and Walmart, between 2 and 40 percent goes back to their GiveBack accounts to be distributed to the charities they choose. Or, sign up for a GiveBack Visa card, and 1 percent of charges reverts back. “This way, you can give back every day of your life,” says Paletta.

Greenwich resident Chuck Royce, a financial investor in GiveBack, comments, “I think it’s potentially game changing for how people think about giving away money. GiveBack puts an ease of operation in front of every person—the average person who wants to organize his giving in a more intentional way.”

More than 3,000 people have set up accounts on GiveBack. Paletta envisions 10 million users, each with $500 to give, making GiveBack a five-billion-dollar foundation—the biggest in the country. Speaking to the average person, not the super rich, Paletta says, “It’s your foundation with $500, but also the whole foundation, with $5 billion, would be your foundation. People like Bill Gates and Warren Buffett get a lot of credit and they deserve it, but the guy giving $300—the last $300 he can give—needs to be celebrated as well.

In April, Oprah invited Paletta back on her show to share what he did with his winnings. She described GiveBack as “one of the best ideas we’ve heard to get everyone involved in their own Big Give.” During that show Paletta launched a campaign called 100 Days of Giving. With Visa as a corporate partner, he gave audience members $1,000 each to set up GiveBack accounts. “The money has to go to a charity; it can’t go to your cousin Bo Bo,” Oprah joked with the audience.

All GiveBack members can benefit. Paletta explains that every day between April 8 and July 17, a randomly selected winner from all GiveBack accounts will receive a $1,000 infusion. Referring friends during the campaign earns members Impact Points, and the person with the most points tallied during the 100 days will get a foundation boost of $50,000. Also, the GiveBack mall will offer a Daily Deal, with select retailers doubling, tripling or quadrupling the percent of purchase allocated to the buyer’s foundation. Clearly, now is the time to GiveBack (“GiveBack” is as worthy of morphing into a verb as Google is!).

“You can set up accounts for your kids,” suggests Paletta. “They may want to give to an animal shelter. They choose where it will go; you get the tax deduction. It’s an opportunity for a teaching moment.”

Behind the Scenes

Paletta’s work life blends nicely into his home life here in Greenwich. The family relocated from Bedford to the Glenville area a year ago, after, as Paletta says, “living in Greenwich and sleeping in Bedford for the last ten years.” His three daughters attend Sacred Heart and the older two will go to Greenwich High in the fall. Paletta enjoys coaching his youngest girl’s lacrosse team, and spending time with his children and wife. Giving is a dominant theme in their family culture.

“My kids inspire me through their giving more than I inspire them,” claims Paletta. “My eleven-year-old came up with an idea for books that are sent to Africa. The kids there don’t know how to read English, so she proposed recordable books, with American kids reading to them, so they can learn to understand English.”

The Palettas sponsor ten kids in Rwanda, and the family made a trip there several years ago. “It was life changing for all of us,” says Christine. “Our children were able to meet those kids. Even though they didn’t share the same language, they were able to connect in so many other ways—playing Frisbee, playing with bouncy balls.” She also noticed, upon their return, that the kids ceased being picky about things like which shower they used.

The changes Christine has seen in her husband in his journey from Rwanda to reality TV have only been positive—and she hadn’t thought he had much room for improvement. Attracted by “his smiling eyes and beautiful smile” when they met at Cornell, Christine says, “He was a charismatic, great guy. I thought he was too good to be true!” Over two decades later, she only has more praise to pile on: “He’s authentic, generous, kind, thoughtful, fun, entrepreneurial; he has integrity; he’s a visionary, a risk-taker, a family man and a great friend.” She adds, “He leaves his socks on the floor, though.”

Paletta almost appeared human, until Christine recounted another story about her husband. “I came downstairs this morning, and he had completely cleaned the kitchen and lit two candles. I told my girls, ‘Most guys don’t do this! You have to appreciate this.’” You’re not kidding. Thanks, Stephen. Husbands, ya paying attention?

With the world paying attention to Oprah—and, in turn, GiveBack’s mission—there just may be a chance for reality TV redemption. After Oprah’s Big Give, even in a small city in Italy, Stephen Paletta got recognized. “You’re that Oprah guy, aren’t you?” asked the fan in broken English. Expect to hear a lot more about this Oprah guy.



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