How Robert F. Smith, the Wealthiest Black American, Is Making Change

Photo credit: The Washington Post – Getty Images From Town & Country The software titan Robert F. Smith and his wife Hope were supposed to be in Malibu in late March. They own two properties there, an $18 million beach house and a $19 million blufftop mansion, more than enough […]

Photo credit: The Washington Post - Getty Images
Photo credit: The Washington Post – Getty Images

From Town & Country

The software titan Robert F. Smith and his wife Hope were supposed to be in Malibu in late March. They own two properties there, an $18 million beach house and a $19 million blufftop mansion, more than enough room for their family, which just expanded by two: Identical twin girls Zuri and Zya were born, by surrogate, in December, joining brothers Legend, 4, and Hendrix, 5.

Instead the Smiths, their children, Robert’s and Hope’s mothers, and multiple staffers have decamped to the family’s ranch in the mountains outside Denver to ride out the pandemic. Hope isn’t sleeping much, partly because the baby nurse got altitude sickness and bolted. And Robert is spending marathon days in his study coordinating a philanthropic response to the health crisis.

With a self-made fortune of roughly $5 billion, Smith is the United States’ wealthiest African American. (Oprah Winfrey ranks fifth on the Forbes global list of black billionaires.)

“In times like this you have to think about the assets that you can truly leverage,” he says during a Zoom interview. “I have the great fortune of having relationships with very smart people. I’ve been on calls since five this morning.”

Photo credit: Allie Holloway
Photo credit: Allie Holloway

One conversation—it is now late afternoon in the Rockies—was with Randall Stephenson, the chief executive of AT&T. Another was with Tim Cook of Apple. The portfolio Smith oversees owns 50 percent of PowerSchool, an educational software provider, and he wanted their help in getting internet access and smartphones to children from low-income families so they could participate in remote learning.

“We’ve already extended for free the licenses that schools need,” Robert says, before rattling off a daunting list of additional relief efforts from his Vista Equity Partners portfolio, which includes 64 companies. Companies like TIBCO, a technology company that Smith has now deployed to create county-level maps showing real-time visualizations of Covid-19 cases, which will then help predict the availability of hospital resources (mainly ventilators) across states and regions.

“I want to help at scale,” he says.

Robert, 57, is also the chairman of Carnegie Hall, which he has been pushing to organize online concerts. “We’ve got to stay connected and alive and excited about who we are,” he says.

At this moment Legend arrives with a question. Can he watch Venom, a PG-13 superhero movie? Robert squints behind his red glasses (one of numerous pairs in various hues). “Why don’t you go ask your mom if we can watch something else,” Dad says.

Robert swivels back to Zoom. “Home schooling!” he says with a laugh. “Man, we’re all having fun with that.”

Until a few years ago Robert Smith would almost certainly have refused this peek into his home life. He actively avoided media attention as he climbed from humble roots in Denver to the pinnacle of the 1990s dot-com boom as a Goldman Sachs banker in San Francisco; he went on to found Vista in 2000 in Austin, Texas. During that time, he was married to Suzanne McFayden (they met while attending Cornell) and had three children.

Photo credit: Allie Holloway
Photo credit: Allie Holloway

The national spotlight found him in 2014. Vista had grown into an impossible-to-overlook force, delivering a 31 percent average annual return since its founding. “Vista Equity Partners Emerges from ­Private-Equity Shadows” read a Wall Street Journal headline from that year, which also marked the end of his first marriage. In 2015 he generated tabloid headlines by marrying Hope Dworaczyk in epic style at the Hotel Villa Cimbrone on the Amalfi Coast. The New York Post’s Page Six noted that the couple and Hendrix, who was seven months old, “floated down the aisle on a cloud” made by Cirque du Soleil designers.

Mr. and Mrs. Smith had arrived.

Around the same time, the Fund II charitable foundation—of which Smith is the founding director and president—began to make humongous grants. In 2016 alone it pledged $27 million to the Susan G. Komen organization to reduce the racial disparity in breast cancer deaths (mortality rates are 40 percent higher for black women than white women), $39 million to preserve such African-­American heritage sites as Harriet Tubman National Historical Park, and $48 million to the United Negro College Fund to support students studying science, technology, engineering, and math.

But it took a grand gesture at Morehouse University last year to cement Smith’s status as one of the world’s most interesting philanthropists. To the shock of Morehouse officials, Smith went off-script during his commencement speech and told the 396 graduating students that he would pay off their student loans. Poof. Gone. It cost him about $40 million.

“I was looking at 400 students 400 years after 1619,” he says, referring to the beginning of American slavery. “And they were burdened. And their families were burdened. They had taken on a tremendous amount of debt to get that education. And liberating them was the right thing for me to do. Honestly, I didn’t think it was going to be that big of a deal,” he continued. “I mean, globally. I didn’t realize how many people understood the pain and debilitating effect that student debt has for decades—not just on that individual but on families.”

On another afternoon at the ranch, Hope, 35, sits on a white sofa in a fuzzy green sweater. It’s starting to snow outside. “I’m here in this quarantine bubble with four kids and my mom and… This whole thing is just so unbelievable,” she says. “I don’t even know what day, what time it is anymore.” On top of everything, Hope recently started a skincare company: Mutha, described in a press release as offering products that allow women to “take the MUTHA f*ing reins.” She personally formulated the signature product, a stretch mark–preventing body butter that sells for $95.

Photo credit: Allie Holloway
Photo credit: Allie Holloway

Hope’s straightforwardness is invigorating. What message does she most want to impart in a philanthropy-focused article? “How the people with the deepest pockets too often turn away from the hard things,” she says.

Okay, she has my attention. Like what?

Hope points to Unlikely Heroes, a nonprofit focused on child sex trafficking. The Smiths are patrons. They also host survivors at their ranch for a week every summer. Hope takes them rafting.

“The stories are hard to hear—awful, awful stuff,” she says. “And a lot of people that I rub elbows with, that I sit at tables with in New York, don’t want to hear about it. They will only do the ballets of the world or the Metropolitan Museum of Art.

Those things are great, but it’s hard for me to sit with these people—to look them in the eye and know those are the only things they are giving to. We can’t turn away from the hard things and be too guarded and safe, behind our, you know, our castles.”

Get it said, Mutha!

Hope grew up in tiny Port Lavaca, Texas, with her mother, a nurse, and graduated high school at 16, around the time she was crowned Miss Teen Texas. That title led to a modeling contract with Wilhelmina in New York. Suddenly she was walking runways in Paris and Tokyo for brands like Versace. Between modeling jobs she became a licensed esthetician.

Playboy made her a star. She posed for the cover and centerfold in 2009 and was named Playmate of the Year in 2010. That notoriety led her to reality TV, notably as a contestant on Celebrity Apprentice, where she won $20,000 for Best Buddies, a charity that finds mentors for people with intellectual and developmental disabilities. “It wasn’t a lot of money,” Hope says, “but it did raise a lot of awareness for the cause.”

Photo credit: Marcus Ingram - Getty Images
Photo credit: Marcus Ingram – Getty Images

These days, along with Unlikely Heroes, Hope focuses most intently on two nonprofits: Together We Rise, which supports foster children (in particular those who have aged out of the system and want to attend college), and the global disaster relief organization International Medical Corps, which gave the Smiths its humanitarian award in 2018. Currently 10 percent of Mutha sales go to IMC to help battle the coronavirus pandemic and promote maternal health.

“My charities are always tied to women and children,” she says. “I grew up watching children who were underserved, and single mothers, like what I had, who were struggling.”

As a child in Denver, where his parents were high school principals, money was tight, and racism was rampant. Looking out the window of his study at the spitting snow, Robert recalls how their neighborhood always got plowed last. The trucks showed up only after the wealthier, whiter areas had been tended to. To demand better treatment from the city, his father started the North City Park Civic Association.

“I also saw my dad make sure that all the little kids who looked like me had a local YMCA to go to,” Robert says. “Sometimes we think it’s just the Giving Pledge-kind of people making a difference, but it’s also individuals who may not have great wealth but who give generously of their time and resources.”

Photo credit: Kevin Mazur - Getty Images
Photo credit: Kevin Mazur – Getty Images

Robert signed the Giving Pledge in 2017, committing to give at least half of his wealth to charitable causes during his lifetime. The Smiths are working hard to pass similar values on to their children. Hendrix and Legend started to participate as toddlers, Hope says, pointing to holiday shopping trips that have become a tradition.

A couple of years ago Hope took the boys to Walmart and Target and told them to buy whatever they wanted. Excited, they filled basket after basket. On the way home she stopped at a collection site for needy families and told her sons—to their shock—to unload everything, even a toy shark to which Hendrix had become particularly attached.

“He was begging to keep it,” she says, “but the lesson was that he had to give it away.”

“It’s our duty.”

Photo credit: RICKY CARIOTI/WASHINGTON POST/GETTY IMAGES
Photo credit: RICKY CARIOTI/WASHINGTON POST/GETTY IMAGES

This story appears in the Summer 2020 issue of Town & Country.

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