Sitting in the elegant sunroom of her Pacific Heights mansion with a view of the Golden Gate Bridge, the San Francisco socialite and philanthropist Dede Wilsey might seem an unlikely person to criticize the world of extraordinary wealth.
“No civilization has survived where there is only rich and poor,” Ms. Wilsey said.
She is being outspoken because she is worried about her city, where a booming economy, largely fueled by the tech industry, has flooded the region with thousands of overnight millionaires. Ms. Wilsey said too many are not sharing their riches with the community that helped incubate their billion-dollar start-ups.
“Why don’t you do something? Why don’t you give back?” Ms. Wilsey said, imploring the area’s newly wealthy. “In a city like this, you’ve got homelessness, AIDS, feces in the streets. It would be nice to give back something.”
As a member of one of the nation’s wealthiest families, Ms. Wilsey is a rare example of someone who speaks relatively openly about money. She said she does not seek the attention, but it comes with public-facing roles, like a controversial run as president of the Fine Arts Museums of San Francisco.
Her history of being candid has sometimes come at a cost — her stepson, a writer for The New Yorker, wrote a scathing depiction of her in his memoir. Her decision now to admonish the area’s nouveau riche might gain her new stripes as a polarizing figure.
But Ms. Wilsey is in a position to personally witness the lack of generosity.
As one of the city’s highest profile philanthropists, she has served on local nonprofit boards for decades, often soliciting potential donors. Convincing the latest crop of tech millionaires has been difficult.
“I hope sooner or later these kids will realize that they were lucky,” Ms. Wilsey said.
As a product of old money, as well as newer fortunes in food and real estate, Ms. Wilsey, 75, wondered if part of the problem was too little conversation about the responsibilities that come with wealth, a lesson she received during her gilded upbringing.
Her mother was an heir to the Dow Chemical fortune, and her father was the chief of protocol under President Dwight D. Eisenhower and served as ambassador to Luxembourg and Austria.
In Washington, the family lived near an orphanage. “I was very aware, and made very aware, that I was much more fortunate than those children,” Ms. Wilsey said.
“You have to teach philanthropy,” she said. “You train people to be grateful and give back.”
Ms. Wilsey’s concerns about the lack of local giving by the newly minted rich are backed up by area leaders and research — the influx of so much wealth has altered the Bay Area’s fabric, aggravating income inequality and driving up costs, especially housing.
In San Francisco homelessness has increased and evidence of desperation abounds: A study showed the city has the worst package theft rate in the nation, police say car break-ins occur every 22 minutes, and daytime open-air needle drug use is common in some neighborhoods.
At the same time, many with new fortunes have largely not been donating locally when giving to charity.
There are many reasons for this disconnect, according to experts, including a lack of awareness, an unwillingness to plant local roots, a generation gap and skepticism about charities.
Those issues came into sharp focus in 2016 with “The Giving Code: Silicon Valley and Philanthropy,” a research project that compiled data from foundations, the I.R.S. and other sources.
The report estimated that there were 76,000 millionaires and billionaires in the Silicon Valley counties of Santa Clara and San Mateo, and twice as many more “millionaires and billionaires, if you add San Francisco,” said Alexa Cortés Culwell, the study’s co-author.
“Silicon Valley is actually quite generous,” Ms. Culwell said, noting that billions of dollars have been committed to charity.
But “most of the money leaves the region,” Ms. Culwell said, “a small fraction is used for local community causes” — sometimes less than 10 percent, according to her study.
Some say they believe the new tech rich don’t see local problems because they live in a bubble, “literally gated and then virtually gated,” said Kyra Kazantzis, chief executive of the Silicon Valley Council of Nonprofits, an advocacy group.
Employees work long hours on isolated campuses where meals and other needs are provided, then take private buses home.
“It might be that if you drive on the freeway you’re going to see encampments from time to time,” Ms. Kazantzis said. “But you may very well live in a neighborhood that has really no visibility into what the most needy folks are experiencing.”
“There’s also technology that has allowed people to be more disconnected,” said Evan Owski, founder of a tech start-up and a former LinkedIn employee. “Things like Uber and Lyft and meal delivery services, you can pretty much live in San Francisco and avoid contact with anyone in a different social strata.”
After observing the despair of some city residents, Mr. Owski campaigned for and donated $40,000 toward passing a proposition to increase spending on homelessness, but he sees why others might not get so involved.
“The cost of living here is so high. People don’t imagine a future for themselves in the city, and so they feel disconnected,” Mr. Owski said.
A devotion to data-driven thinking might also hurt local giving, experts said.
In an industry dominated by math, many donors demand quantifiable results from charities — a proven dollar of results for every dollar donated.
An analysis of one local foundation revealed how this thinking can play out. The database for the Silicon Valley Community Foundation, a repository for tech wealth with about $10 billion of assets, showed that $1.4 billion in grants were awarded last year. About a third of those grants stayed in the Bay Area, with $250 million to San Francisco nonprofits.
But a closer look at those donations revealed that more than half went to nonprofits that might have a San Francisco address, but the charities are not focused on the city. Tens of millions actually went to medical research or to provide vaccinations in Africa, where it is relatively simple to demonstrate that a donation equaled a quantifiable number of inoculations.
The benefits provided by many local charities, such as the fine arts organizations that Ms. Wilsey champions, don’t easily fit into mathematical equations.
There is also a generation gap because many of the newly wealthy tend to be millennials. Most charities rely on checks for donations, and “not many millennials write checks,” said Nick Fitz, co-founder and chief executive of Momentum, a company that connects donors and nonprofits.
Mr. Fitz cited studies that said millennials are intrinsically generous, but charities must connect on their turf. Momentum has created an app that facilitates donating based on lifestyle and interests. Users automatically donate to a food bank when they eat out, or give money to the A.C.L.U. for every Donald Trump tweet. “You can cap it, of course,” Mr. Fitz said.
Other innovative outreach ideas include The Board Match, which is like speed dating for charities seeking board members. And in June the San Francisco Foundation and partners started the Bay Area Equity Atlas, a database explaining local needs designed to appeal to wonky minds.
There are signs the tech world is responding. Apple, Google and the Facebook founder Mark Zuckerberg recently announced plans to spend more than a billion dollars to address the area’s housing shortage.
However, it can also be difficult to step forward as a transparent, high-profile donor like Ms. Wilsey.
When asked what she received for her public generosity, she said, “Criticism, harassment, bad press and false stories.”
That happened last month when Ms. Wilsey received an honor for her donations to the Shanti Project, which supports people with H.I.V./AIDS and other needs.
David Campos, the Democratic County Central Committee chairman, threatened a boycott if the honor was not rescinded, arguing that Ms. Wilsey, a Republican, is a financial supporter of Donald Trump, which she denied. A review of campaign records found no Trump donations, although her son, Trevor D. Traina, works for the administration.
“I’m not buying it,” Mr. Campos told The San Francisco Chronicle. “Her son was appointed Trump’s ambassador to Hitler’s Austria. If you believe that happened without her raising any money for Trump, I have a bridge I can sell you.”
The boycott never materialized, but receiving a Nazi slur in conjunction with charitable giving is unlikely to encourage others to become high-profile donors.
Ms. Wilsey seems undaunted. Giving anonymously, she said, is not as effective as seeing names endorse a cause.
“It attracts people. I know it does. I’ve seen it happen,” Ms. Wilsey said. “I don’t want people to stop using their names, but I don’t want to see them get hurt.”