The Gospel of Wealth According to Marc Benioff

Maybe every period seems dark from a certain angle; maybe the autumn of 2018 was extra murky. Mark Zuckerberg was answering for Facebook’s latest security breach, CBS chief Les Moonves had recently resigned amid sexual misconduct allegations, Google CEO Sundar Pichai had been disputing the EU’s record $5 billion fine for antitrust violations. The righteousness of powerful businessmen had been looking extra iffy, but in San Francisco change was coming.

A municipal election approached. Amid an unremarkable assortment of ballot initiatives was one that, on its face, also looked unremarkable. The Homelessness Gross Receipts Tax Ordinance, or Proposition C, sought to stem the city’s spiraling homelessness problem by raising taxes by an average of half a percent on big companies—tech ones, most prominently. Doing so would bring in up to an estimated $300 million a year for various initiatives, from new beds in shelters to expanded mental health services. In the way certain votes do, Prop. C struck many as a referendum on good versus evil: not just a means of addressing San Francisco’s housing emergency but a shot across the bow of the booming industry that was partly responsible for it, and perhaps across capitalism-as-usual.

Enter Marc Benioff, founder and co-CEO of Salesforce, the city’s largest employer. Declaring that “our city is in a crisis,” he threw his full support behind the measure that promised to take his company’s money. He publicly outflanked the city’s ostensibly liberal mayor, London Breed—who opposed it on grounds that the measure didn’t allow for enough accountability—and pledged upward of $2 million to the Prop. C campaign. But it was on Twitter that Benioff truly went to town. “As SF’s largest employer we recognize we are part of the solution,” he declared on October 9.

Jack Dorsey, cofounder and CEO of Twitter and founder and CEO of Square, surely still smarts from what followed.

“I want to help fix the homeless problem in SF and California. I don’t believe this (Prop C) is the best way to do it,” Dorsey replied. “Mayor Breed was elected to fix this. I trust her.”

Maybe Dorsey hadn’t spent much time on Twitter. In 279 characters Benioff calmly eviscerated him.

“Hi Jack. Thanks for the feedback. Which homeless programs in our city are you supporting? Can you tell me what Twitter and Square & you are in for & at what financial levels? How much have you given to heading home our $37M initiative to get every homeless child off the streets?”

In his response, Dorsey claimed he was simply following his mayor’s strategy for dealing with the crisis; indeed, people who work on homelessness issues have told me the question was hardly open and shut. But this was no time for nuance. The spectacle of two billionaires virtue-squabbling lit up the internet, and the Twitter mob came for Dorsey, hoisting atop its shoulders a triumphant Benioff. Publications around the world heralded a rare instance of C-suite selflessness. One headline read, “Marc Benioff is 2018’s Most Woke.”

I’d been curious about the 55-year-old software entrepreneur for some time. In addition to his Prop. C efforts, Benioff had spent the previous year running a powerful company (the bulk of Salesforce’s revenue comes from its cloud-based customer relationship management software); he’d overseen annual revenue growth of more than 25 percent; and he’d written his fourth book, Trailblazer. For San Franciscans, the 61-story Salesforce Tower visually dominates the city, as does Benioff’s name—there it is on buildings, in headlines, and now on the masthead of Time magazine, the world’s biggest newsweekly, which he purchased in 2018 with his wife, Lynne. But these are the kinds of adrenalized and quasi-random achievements we expect of our tech billionaires. What piqued my curiosity about Benioff was his upending of the genre altogether.

On the surface were superficial departures. Where the modern tech-billionaire template reflects a certain nerdy abstemiousness—slender Paleo physique, biohacked sleep program, the whiff of a cryo appointment earlier that day—Benioff, 6’5″, playful and feisty, calls to mind a big old bear. (Metallica’s Lars Ulrich told me he longs for a milk crate when his large friend comes in for a hug.) Chief among Benioff’s distinguishing characteristics, though, is his incessant public munificence, emphasis on incessant, emphasis on public.

Scarcely a month goes by without another grant, another ribbon-cutting, another broadside against complacent CEOs. He and Lynne gave $250 million to build UCSF Benioff Children’s Hospitals in San Francisco and Oakland. Between 2017 and 2019, Salesforce and the Salesforce Foundation gave away about $130 million, and the Benioffs personally donated nearly $200 million in roughly the same time period. Via large individual and company donations, a philanthropy-centric business model, and a general irrepressibility on social issues, Benioff has set his sights over the years on homelessness, oceans, public schools, local hospitals, LGBTQ+ rights, the gender pay gap, and the country’s gun crisis. Forbes referred to him as “San Francisco’s Giant of Generosity.” To The Silicon Review he’s “the intrepid tech visionary who pioneered a groundbreaking philanthropic model.” Pando went so far as to call him “a people’s billionaire.”

Integral to Benioff’s reputation for goodness is the insistent badness regularly displayed by his ultrarich brethren. Benioff does not offer the Russians a handy platform for derailing our democracy or erode civil discourse 280 characters at a time. He doesn’t use his wealth to undermine public education or fund climate change denial. He does not accuse British rescue divers of pedophilia. At a moment when his plutocrat peers seem increasingly hell-bent on mucking everything up, Benioff has carved out a different brand altogether: the good billionaire.

The particulars of the brand can be dissected, but the point is a feeling, a man-sized dollop of hope that powerful interests might start working for us rather than against. On November 6, 2018, San Francisco residents passed Prop. C. But in a sense the biggest victor was the magnanimous billionaire behind it.

Anyway, that’s one way of telling it.

As Bay Area childhoods go, Marc Russell Benioff’s was solitary and geeky. He was shy, favoring the company of his golden retriever or, better yet, circuit boards. A streak of defiance ran through him. Once, in kindergarten, his teacher asked him to draw a circle. He looked her in the eye and drew a straight line.

In 1966, when Benioff was 2, his father, the son of an immigrant from Kyiv, took the helm at a local dress shop chain. The job ruled him. Most nights he’d be at the kitchen table until 11, going over the books. On Sundays, Marc would climb into his father’s 1970 Buick station wagon. His “most formative business classroom wasn’t a classroom at all,” he writes in Trailblazer. It was delivering bolts of wool, poplin, and polyester in that hot Buick. Among the lessons he absorbed: work ethic, integrity, I hate retail.

Electronics beckoned. At 12 he relocated to the family basement, where he could geek out unimpeded. At 14 he bought his first computer, a TRS-80, and wrote a program called How to Juggle, which he sold to a computer magazine for $75. At 15 he founded Liberty Software, which made games for the Atari 800. Soon he was bringing in $1,500 a month, which he used later to enroll at USC.

At college, Benioff rushed Tau Kappa Epsilon and did the normal frat boy thing of buying two Macintosh computers and hooking them together. The plan was to start writing code—all he needed was the company’s developer software to arrive in the mail. When months passed with no sign of it, he phoned Guy Kawasaki, Apple’s head of developer relations. It would be the first of many conversations. “Why don’t you spend the summer of 1984 at Apple?” Kawasaki eventually asked the insistent kid on the other end of the line. A summer at Apple led to a job answering the sales line at Oracle soon after graduation.

With apologies to Benioff completists, I’m about to fast-forward through some of his most noteworthy career turns. His time as the youngest vice president in Oracle’s history. His complex relationship with Larry Ellison. His Ferrari, reportedly a more expensive version of Ellison’s. I’m even skimming over the pivotal moment when he came up with his software-as-service idea and his father cautioned against leaving a stable job, but he did it anyway, and the company that started in a rented apartment on card tables and folding chairs now has a market cap dwarfing the GDP of many countries.

More interesting to me is the sabbatical he took before starting Salesforce, after more than a decade at Oracle. For five months he swam with dolphins in Hawaii and traveled throughout India, where he had “an incredible awakening.” He met with the humanitarian leader Sri Sri Ravi Shankar, as well as the Dalai Lama, who “talked about finding one’s calling and the importance of community service.” But most profound, he says, were the words of the Hindu guru Mata Amritanandamayi, known as the hugging saint or Amma.

“It was she who introduced me to the idea, and possibility, of giving back to the world while pursuing my career ambitions,” Benioff wrote. “I realized that I didn’t have to make a choice between doing business and doing good.”

This was the birth of both a generous mindset and a savvy personal narrative. Over the course of four books, countless speeches, and 25,000 tweets, Benioff has created a public persona that marries audacious business acumen with ambiguously spiritual beneficence, all inextricable from Salesforce. Over the years, he would proselytize Salesforce’s 1–1-1 model, in which the company donates 1 percent of its revenue, 1 percent of its product, and 1 percent of its employees’ time to the community. He would install meditation rooms on every floor of Salesforce Tower. He would be periodically subject to epiphanies of rectitude, like “I am not gonna have any more meetings that aren’t at least a third women.” And in the nation’s most influential publication, The New York Times, he would call on “my fellow business leaders and billionaires” to create a “more fair, equal and sustainable capitalism that actually works for everyone.”

San Francisco’s mayor proclaimed May 22, 2018, as Salesforce Tower Day to mark the completion of the city’s tallest building. Benioff used his office’s opening ceremonies to address the city’s less fortunate:

“Kids in schools across the Bay Area, families walking down the sidewalk, families and children in shelters, sleeping in cars—they’re all looking up at this tower. I want to say to them, ‘When you look up and see this tower, I want you to know you are not alone. We are thinking of you, and I hope you see this tower as a beacon, a symbol of hope.’ ”

But times change, even for the affluent, and just two years later those words have a different ring.

By happenstance I’ve worked for two billionaires in my life. From those experiences I concluded that one of civilization’s great challenges stems from millionaire rhyming with billionaire. In holding them in the same linguistic corner of our minds, we conflate them, yet they’re so mathematically distinct as to be unrelated. A millionaire can, with some dedicated carelessness, lose those millions. Billionaires can be as profligate and eccentric as they wish, can acquire, without making a dent, all the homes and jets and islands and causes and thoroughbreds and Van Goghs and submarines and weird Beatles memorabilia they please. Unless they’re engaging in fraud or making extremely large and risky investments, they’re simply no match for the mathematical and economic forces—the compounding of interest, the long-term imperatives of markets—that make money beget more money. They can do pretty much whatever they want in this life, and therein lies the distinction. A millionaire enjoys a profoundly lucky economic condition. A billionaire is an existential state.

This helps explain the cosmic reverence draped over so many billionaires, their most banal notions about innovation and vision repackaged as inspirational memes, their insights on markets and customers spun into best sellers. Their extravagances are so over the top as to inspire legend more often than revolution. Benioff has rented out the entire San Francisco Giants stadium for a corporate event, and he once got David Bowie to perform at a Salesforce Foundation soiree at Carnegie Hall. He owns an estate in Hawaii and multiple homes in the Bay Area. When a hotel room shortage threatened to leave out in the cold some of the 160,000 attendees of the 2015 Dreamforce conference—“four days of innovation, fun, and giving back”—the company brought in a cruise ship.

He is regularly invited to spread the gospel of Benioff, as he did in April at NationSwell Summit West, a conference designed to “feature creative, cutting-edge solutions and the problem-solvers behind them.” From the back of a small hall, I watched him deliver a rollicking stream of thoughts on his family roots, negativity, writing down intentions, his friend Stevie Wonder, and radical trust. (“Can you even hold fear in your mind if you truly have radical trust?”) But the heart of his remarks, delivered to this room full of business, tech, VC, nonprofit, and philanthropy types, was clear: From immigration to plastic in the ocean, enlightened leaders have no shortage of opportunities to make a better world. This led him to recall his role in Prop. C.

“What I was not expecting was a huge surge against me by many, many, many business leaders, who are friends of mine, close friends of mine, who are completely opposed to paying any kind of taxes … We’re in a world where we have to look at taxes as a key part of the solution,” he said. Mentioning corporate tax rates, individual tax rates, and city tax rates, he added that “we’ve got to look at that as part of the solution.”

The room broke out in applause. Just 16 months earlier, in 2017, Congress had passed President Trump’s Tax Cuts and Jobs Act, the largest tax overhaul in more than three decades. The law lowered the top marginal tax rate for individuals from 39.6 percent to 37 percent and reduced corporate rates from 35 percent to 21 percent. It was a love letter to the very wealthiest, written hastily behind closed doors. Those new cuts, atop years of tax avoidance, cuts to estate taxes, and rising payroll taxes, meant that, for the first time ever recorded, the 400 richest Americans are now paying a lower overall tax rate than almost anyone else, according to a study by two UC Berkeley economists.

Benioff possesses an acute awareness of this reality. He has called for increasing taxes “on high-income individuals like myself” to “generate the trillions of dollars that we desperately need to improve education and health care and fight climate change.”

But it’s worth noting a few asterisks in his call to arms. For one, Prop. C taxes certain sectors differently than others, making it more burdensome to, say, a fintech company like Square, which would have to pay twice as much tax as Salesforce, despite bringing in a fraction of its revenue. But more important is the part Benioff never mentions: the zero dollars his company paid in federal income tax that year, according to the Institute on Taxation and Economic Policy.

“This is a company that had $7.8 billion in gross profit in 2018 and didn’t pay a dime in federal income tax,” Frank Clemente, executive director of Americans for Tax Fairness, told me, before running through the assorted mechanisms used by the country’s corporations to avoid contributions to the federal treasury: patents held by foreign subsidiaries. The so-called stock options loophole, which allows companies to lower their taxable income by paying executives in stock options. Offshore accounts. (As of 2017, Salesforce had 14 tax haven subsidiaries, in Hong Kong, Luxembourg, Singapore, the Netherlands, Switzerland, and Ireland, according to a report from the advocacy group US PIRG and ITEP.)

To put it in further perspective, the tax burden Salesforce stood to face under Prop. C amounted to roughly $10 million a year—a fraction of what a multibillion-dollar company’s federal income tax would be without those loopholes.

Benioff was whisked away after the NationSwell event; asking him questions was proving difficult. It wasn’t that Benioff owed me anything. He’s a private citizen. But at the same time, he’s not a private citizen. Without running for office, he’s attained a phenomenal level of influence; the San Francisco Business Times called him “the most influential man in San Francisco.” If a local elected official had as much power and sway as Benioff, they’d feel some responsibility to answer to the press.

So I went back to watching him from afar and talking to those who know him. His friends and even Mayor Breed described his genuine love for his city and fellow citizens; I also heard accounts of an oversize ego, a superficial wokeness rooted in vanity or optics. But parsing the personality of a billionaire seemed to be missing the broader significance of his existence. How he wielded those billions seemed more to the point.

Benioff can’t make laws. But as a billionaire and corporate titan, he can influence them. According to public records, Salesforce increased its lobbying expenditures in 2017 and lobbied directly on the Trump tax bill. Was it one of the many companies that had pushed for a lower corporate tax rate, despite Benioff’s public appeals for more taxes? The records shed no light. Salesforce wouldn’t comment on specifics, and the members of Congress and lobbyists I contacted couldn’t or wouldn’t help.

It was starting to look as if I might never know what happened that year in Washington.

Illustration: JOHANNA GOODMAN

Andrew Carnegie was around Benioff’s age when he published The Gospel of Wealth, and in so doing all but invented modern philanthropy. Describing the moral necessity of distributing “the millionaire’s hoard” in one’s lifetime, the steel magnate advocated a “true antidote for the temporary unequal distribution of wealth.” Carnegie’s money—and that of other philanthropists he inspired—created remarkable institutions, from public libraries to Carnegie Mellon University. But this is also true: The temporary unequal distribution of wealth persists.

This partly explains the critique of philanthropy that’s gathered steam in recent years. In a 2013 New York Times op-ed, Peter Buffett, son of Warren, described the “conscience laundering” that’s rampant in that world—giving that “just keeps the existing structure of inequality in place. The rich sleep better at night, while others get just enough to keep the pot from boiling over.” More recently, in his influential book Winners Take All, Anand Giridharadas zeroed in on the righteous do-gooderism of tech elites, whose beneficence merely papers over deeper ills—the “lube of corporate profiteering,” as he has put it.

Skepticism swirled even during Carnegie’s time. Was he selfless or a heartless union crusher? Was such accumulation of wealth natural, as he argued, or the contrivance of unfair laws and regulations? By the end of the Gilded Age, philanthropy had assumed an explicitly legitimizing purpose, according to Ben Soskis, a historian and research associate at the Urban Institute’s Center on Nonprofits and Philanthropy. “The pitchforks were directly invoked at the time,” Soskis said. “It was understood that if you want to be able to maintain this kind of wealth, you have to give back.”

From here, Soskis says, the ideas behind what we now call philanthro-capitalism gradually took root: The people who make the most money are also the best equipped to address the world’s problems. The belief has proven remarkably resilient, given its regular brushes with reality. The passage of the 16th Amendment and the creation of a progressive federal income tax in 1913 arguably did far more for national welfare than all of philanthropy combined. The big, consequential crises—the Great Depression, the millions of people without health insurance that led to Medicare, the 2008 financial crisis—have been marked by a sobering recognition of the limits of voluntary giving and an understanding of the unique power of the state. Meanwhile, though philanthropists traffic in the idea that they’re engaging root causes, a focus on actual structural reform is rare. As Soskis put it, philanthropy “has stayed far away, for the most part, from the systems of economic distribution that it gets its money from.”

At the same time, the tax obligations for the country’s wealthiest that could address the larger issues have been steadily diminished. Under Ronald Reagan, the top marginal tax rates were slashed from 70 percent to 50 percent. And the top rates have fallen further over time. As the richest accumulated more wealth, as unions lost power and wages stagnated, the nation’s wealth disparity has only grown. Today the country’s three richest billionaires hold the same wealth as more than half the nation’s population. As the collective wealth of the world’s poorest 3.8 billion people fell by 11 percent in 2018, billionaire fortunes increased by 12 percent, according to Oxfam. Consider Benioff: Between 2017 and 2018, his net worth rose by $2.47 million a day, according to Business Insider. Meanwhile, recent Federal Reserve data revealed that tens of millions of Americans would be unable to cover a $400 emergency expense.

The 1 percent have entered a new period of interrogation. That inspiring tale of success: At whose expense did it come? These philanthropic gestures: Are they distracting from, and delaying a reckoning with, deeper problems they themselves exacerbate? Towering accumulations of capital start to seem less like symbols of hope than monuments to dysfunction. In Benioff’s case, a penchant for good deeds coincides with a shifting public conversation about good itself—a waning tolerance for symptomatic fixes, a growing appetite for structural change. A simple but persistent question hovers around even a generous, well-intentioned billionaire, in some ways hovers more, because of those intentions. Is extreme wealth part of the solution or part of the problem? As Rob Reich, codirector of Stanford University’s Center on Philanthropy and Civil Society and author of Just Giving, told me, major philanthropy “is an exercise of power by the wealthy that deserves our scrutiny, not our automatic gratitude.”

If this scrutiny results in less munificence from Benioff—if he takes his philanthropy ball and goes home—that would be a great shame. As nonprofits and foundations shoulder more and more of the civic burden, their reliance on charitable giving only grows. Nor can government solve all problems; a vibrant and varied civic sector has been indispensable to the country from the beginning. Still, throwing money at symptoms of inequality without addressing its underlying causes presumably seems foolhardy to big-picture, see-around-the-corner guys like Benioff. “I’m somebody who can see things that other people can’t see,” he has said. Indeed, his company’s success rests on its ability to sell a whole system, rather than bite-size solutions. If anyone can see structural problems—defects in the operating system itself—it should be him.

In a sense, Benioff has painted himself into a corner of good intentions, one avoided by the many CEOs who don’t purport to care in the first place. To speak so much about disrupting the status quo and improving the rapidly deteriorating world—and to increase one’s profile in so doing—is, eventually, to court a response: OK, let’s see then.

The grounds of San Francisco’s Presidio Middle School were swarming when I arrived on a hot September afternoon to witness Benioff’s latest good deed: TV crews, the mayors and superintendents from two cities, and roughly 1,000 amped-up middle schoolers well into a daylong Salesforce-themed fair, complete with Salesforce employees, Salesforce mascots, a Salesforce virtual reality experience, and Salesforce T-shirts for everyone. Benioff’s philosophy on discreet, low-key giving can best be described as: nah.

The occasion was the announcement of an $18.2 million grant from Salesforce to the San Francisco and Oakland Unified School Districts and two education nonprofits. At 1 o’clock, inside a large white tent erected on the school blacktop, Benioff approached the lectern, a phalanx of mayors and other VIPs behind him. Massive in a stylish navy suit, hair swept back as though by sheer existential momentum, he was a picture of swaggering largesse.

To the assembled kids he issued a warning: They were about to get seriously bored.

“It’s going to get worse before it gets better,” he said with a sly grin.

But in truth it was only ever good. His is a frisky charisma that simultaneously commands attention and diffuses it, and when your defenses are weakened, he hits you with some unimpeachable compassion for whatever global problem he’s currently addressing. At the middle school, he told a story of simple civic duty.

“This is my neighborhood,” he declared, for indeed he lives nearby. That was how he’d come to walk through the school’s front door a few years ago and ask the principal how he could help.

Soon Benioff was meeting with faculty and students, asking what needed fixing. Before long there were new computers arriving in classrooms and plans in place for an overhaul of their joyless schoolyard. Gesturing out at the beautifully remade blacktop, Benioff took a moment to crow.

“Did you like the prison yard you had before?” he asked the kids.

The speech culminated in an account of Salesforce’s sustained commitment to public education in the Bay Area. “We’ve now given more than $67 million to these schools, so congratulations to you,” he said, turning to the superintendents behind him. Those donations have led to computer science education at all grade levels, a dramatic rise in the number of students in AP computer science classes, and improved technology in schools, says Chris Armentrout, an official with the San Francisco school district. He even attributed the money to helping improve math scores.

Afterward, I followed Benioff and his entourage into the school for a private event. Inside the library, with its inspirational posters and droning box fans, sat three dozen Bay Area middle school principals. On the agenda was a check-in about a component of Salesforce’s public school grant, called the Principal’s Innovation Fund, in which every middle school principal in the two districts is awarded $100,000 to do with as they see fit. For the next hour Benioff listened as each principal thanked him and explained how the money would hire another teacher or facilitate extra planning time.

By far, though, the biggest issue for some of the principals was teacher retention, a challenge made virtually unsolvable by the Bay Area’s astronomical housing costs. Increasingly, San Francisco schools see members of their staffs spending two or three hours a day commuting from less expensive exurbs, as rents continue to skyrocket. The high cost of housing in the Bay Area is a complex issue, more complicated than well-paid tech workers pricing everyone else out—but that’s part of it, which made the irony hard to miss. The man presenting this enormous gift was also partly responsible for its need.

Beyond that, though, an even deeper truth seemed to be surfacing. Here was a classic use case for the vision of Benioff and other wealthy philanthropists, one in which the private sector steps up to address problems traditionally the province of government. But this was the thing: It wasn’t enough. As immense as Salesforce’s grant was, as profoundly welcome as it was, it was also no match for the deepest challenges faced by two major urban school districts. Clarifying itself there in the library was the simple arithmetic of private versus public, the inescapable difference in scale between what even the most generous corporation or individual can accomplish and what tax-collecting governments can.

The meeting went on, Benioff listening patiently until each educator had weighed in. He was at last bringing things to a close when a thought appeared to occur to him. He cocked his head. How would everyone feel, he wondered, if he doubled the amount in the principal’s grant this year?

In the days that followed, I replayed the moment several times. If any of the principals felt a little queasy—if they deeply appreciated the grant but less so the Apprentice-like theatrics that it came with, or the spectacle of public educators relying on the whims of a wealthy individual—they didn’t let on. Nobody stood and said, This isn’t how the system should work, because that just doesn’t happen. The room erupted in gasps and whoops, and Benioff beamed. “You’ll be leaving the room with a double,” he said.

Benioff is a great salesman and his grasp of optics and spin is unparalleled. He was at Davos last January shortly after Giridharadas tweeted a crack about the surfeit of hollow corporate sanctimony there—phrases like win-win, do well by doing good, and conscious capitalism. Rather than pick up his sword, Benioff, who frequently invokes those very ideas, simply co-opted the critique.

“Anand, there are many companies & CEOs committed to systemic change—yes We need a lot more than to awaken! You are helping—Your message & book are so powerful we need you to be part of Davos discussion.”

Several people I spoke with—in the nonprofit world, in the tech world, in politics—would only criticize Benioff when my recorder was off. Giridharadas, who is now an editor at large for Time, hired by Benioff himself, declined to be interviewed. (His most recent cover story: “Party’s Over: The Fall of America’s Ruling Class.”) When critics do come at him directly, Benioff has proven adept at deflecting them. In the summer of 2018, as border detentions were being widely condemned, more than 650 Salesforce employees signed a letter asking that the company drop its contract with Customs and Border Patrol, which used its software for its operations. When that didn’t work, protesters showed up with a 14-foot cage outside San Francisco’s Moscone Center in September, where the company was hosting its massive Dreamforce conference. Eventually Tony Prophet, the company’s chief equality officer, agreed to meet with some of the activists. Salesforce insisted the conversation be off the record, but someone who attended told me two facts: Prophet had worn a T-shirt emblazoned with the word Feminist, and the company’s CBP contract remained.

Subscribe to WIRED and stay smart with more of your favorite writers.

A few months later, Salesforce created a position ostensibly to handle this very sort of issue. In January, Paula Goldman became the company’s first chief ethical and humane use officer. Six months later we spoke by phone, touching on the various causes Salesforce had championed in recent years: sustainability, gun control, LGBTQ+ rights.

“I will say universally we are a company that does the right thing,” she said.

But as I began drilling into particulars, the conversation swerved. At one point Goldman referred to equality being a core value for the company and quoted Benioff’s frequently stated commitment to “the equality of every human being.” I asked what, exactly, “equality” meant in the Salesforce parlance. She laughed. “I think it’s a self-explanatory statement,” she replied.

I tried a different approach. “Do you feel like it’s possible to have a company as large as Salesforce is, in a city like San Francisco, without exacerbating inequality?”

“I’m not sure how to respond to that question,” Goldman said. “It feels like a little bit of a leading question.”

I conceded that it was, but to no avail. Finally, I asked about the CBP contract, assuming it had been around long enough for a coherent answer to have formed.

“As you can imagine, I think a lot about that,” she replied. “We have a whole set of principles and processes in place to work through a number of questions around how customers use our products and what gets raised.”

But the contract?

“I’d say we’re working on it.”

After months of observing Benioff from a distance, I was granted a half-hour interview with him. It happened after the Presidio Middle School festivities, in an empty office on the first floor of the building. Like many seasoned public speakers, Benioff’s one-on-one persona felt like a quieter version of his stage presence. He told me a much-repeated Salesforce origin story, involving a group of Marines installing a hundred computers in a Washington, DC, middle school. This gave way to a general leadership word salad, best practices and integrated approaches and operationalizing value. Business and government “should be two dance partners,” he told me, more connected than they are currently. When I mentioned rumors of a future political career, he said—convincingly—that it didn’t appeal. When I asked whether he held too much influence as a private citizen, he demurred, then somehow pivoted to the subject of charter schools. But then he found his way back to the need for compassionate capitalism, which brought him to Prop. C and his frequently stated interest in paying more taxes. I’d been waiting nearly a year for this.

Was it true that Salesforce paid nothing in federal income tax, as ITEP had reported? I asked.

He shifted a little in his seat.

“I don’t know exactly what our tax rate is,” he replied, “but it probably wasn’t what we could be paying. We can afford more, which is why we just said we should be taxed higher—”

“But I’m saying zero. What they’re reporting is that there was none paid.”

“We’ll find out. I don’t know,” he replied, and one of his people jumped in, too, assuring me they’d “call our tax people.” Benioff continued: “I’ll tell you, I’ll give you our tax returns, but my point is that we’re not paying enough.”

“OK,” I said. “But Salesforce lobbied for the Trump tax cuts, right? The Tax Cuts and Jobs Act of 2017?”

“No, not to my knowledge.”

“Did they lobby against it?”

“I don’t know. I don’t know if we lobbied against it, but I think … I don’t know. My recollection is that that all happened so fast, which was it all went down in a period of about six months that I don’t think anybody was, I certainly was never solicited to—”

A staff member cut in, then brought things back around to Prop. C, reminding me that in that case he’d supported the idea of higher taxes. I asked what he thought of Elizabeth Warren’s proposed wealth tax for individuals. Given Benioff’s reported net worth of $6.9 billion, he’d pay $373 million in the first year. (“Good news—you’ll still be extraordinarily rich!” notes the calculator page on Warren’s website.)

“I think that those types of taxes are good,” he said slowly. “I think it’s fine, but I think that it should be looked at on the historical levels of what worked in that and what has not worked.”

I asked if that was a yes or a no.

“I don’t want to be on the side of saying that I fully support her,” he said.

Throughout this whole portion of the exchange, the staff member sitting across from him had begun tapping on her phone. There now came a knock at the door. Another staffer entered and informed Benioff of an important doctor’s appointment.

We chatted another few minutes—after the uncomfortable tax conversation, I nudged us back to his outlook for the country’s future. It was a softball and he swung as such, saying what he’d like is for us to be “more united and less divided.” Briefly we discussed his role at Time, but then the doctor’s appointment could be put off no longer.

I spent much of the weeks before and after that interview trying to find out what Salesforce’s lobbyists had argued behind closed doors about the tax bill. Despite many calls around Capitol Hill, I found nothing. Finally, the company agreed to put me in touch with Niki Christoff, senior vice president for strategy and government relations.

Our conversation lasted two minutes. She told me that Salesforce had indeed lobbied on the tax bill, but only for two relatively minor items. Regarding the corporate tax cuts, the company had decided not to take a position. Salesforce walked Benioff’s talk, in other words.

I would’ve dropped the matter after that, had my phone not rung sometime later. It seemed my inquiries had found their way to someone with direct knowledge of Salesforce’s lobbying efforts, and in exchange for not being identified in this piece, this person agreed to talk.

Salesforce had ramped up its lobbying efforts. The tax bill included a number of provisions, some of which would remove tax benefits that corporations had enjoyed. This source told me that the company was interested in how the lower tax rate would work in conjunction with other aspects of the bill. Like other big companies, Salesforce wanted to make sure it wasn’t going to pay more after tax reform. Salesforce expressed a keen interest in the durability of the lower rate, as did many companies. The bill was complex but Salesforce’s ultimate goal, the source said, was straightforward: the best deal possible. (WIRED reached out to Salesforce for comment; the company was emphatic that it had not lobbied for lower tax rates.)

I hung up and, not for the first time, struggled to know how to think about Salesforce and the man behind it. Whatever else is true, Marc Benioff does more good in a day than most of us will muster in our lifetimes. I found myself flashing on a conversation I’d had with Ben Soskis, the philanthropy historian. As he sees it, Benioff’s contradictions and even his existence make him “a clarifying agent” for our times.

His benevolence and its limitations go hand in hand when “the maldistribution itself is the problem,” Soskis said. Regarding his philanthropy and other good deeds, he added, “You don’t have to dismiss it as unimportant to also insist that it’s inadequate … He will do enormous good and he’ll also show its limits.”

After our interview, Benioff and I walked out of the school together, down the front steps. Palpably, he was done with our interaction. It was nearly dusk. We shook hands and then he climbed into the passenger seat of a Bentley SUV, which was either gold or champagne, I couldn’t tell.

Collage and spot photo sources: Getty Images

Updated 12-11-19, 5:45PM ET: An earlier version of this story incorrectly stated Benioff rode in a Rolls-Royce SUV. It was a Bentley.

When you buy something using the retail links in our stories, we may earn a small affiliate commission. Read more about how this works.

CHRIS COLIN (@chriscolin3000) wrote about tech’s relationship to San Francisco’s Tenderloin district in issue 25.02. He’s a contributing writer to California Sunday, and his work has appeared in The New York Times, Outside, and Pop-Up Magazine.

This article appears in the January issue. Subscribe now.

Let us know what you think about this article. Submit a letter to the editor at mail@wired.com.