By Chloe Aiello

As Cheddar reflects on 2018, we are profiling the most innovative, flamboyant, and often-controversial entrepreneurs and corporate leaders who delivered the year's most memorable moments in business. Of the CEO Class of 2018, who was crowned Biggest Flirt? Class Clown? Look here for all the Cheddar Awards and more year-end coverage.

On May 22, 2018, the tallest building west of Chicago opened for business. Fog and spattering of rain obscured a breathtaking view from the not-yet-completed 61st floor, as employees reported to work there for the first time. But for Salesforce CEO Marc Benioff, who will pay an estimated $774 million over 15.5 years to lease much of the building and brand it with Salesforce’s name, the opening of Salesforce Tower was the culmination of years of hard work ー and just the start of what would be one heck of a year for Benioff.

As CEO of San Francisco’s largest employer, resident of the city’s tallest building, and one of its most generous and outspoken philanthropists, Benioff’s influence across San Francisco ー and the nation ー is hard to miss. And although Benioff and Salesforce may not be household names in the way that Facebook ($FB) and Zuckerberg are, Benioff is hugely influential in the tech industry.

But he’s not there to make friends ー he's here to make the world a better place.

From Benioff’s $190 million purchase of Time magazine, and his penchant for pouring millions into local philanthropy, to his support of taxes that lean more heavily on tech and outspoken endorsement of regulation, his beliefs are antithetical to the libertarian, free-market ones typically embraced by Silicon Valley.

Benioff's unusually populist perspective was on display on May 22, when the who’s who of San Francisco united to celebrate the tower’s grand opening. There was no shortage of declarations about the symbolism of the tower, but when it came time for Benioff, then 54, to speak, he brought things back down to Earth.

He steered the day’s conversation away from the building’s cloud-grazing girders toward what he described as the “grinding poverty that exists in the shadow of this very building,” the San Francisco Chronicle reported. Benioff pledged to raise $200 million for the homeless, urging others to do the same. And that same day, Benioff, his wife Lynne, and Salesforce announced they had donated a combined $3 million to end long-term family homelessness in San Francisco.

The move is not a radical departure for Benioff, who donated an estimated $31.6 million in the first 11 months of 2018 to causes in and around San Francisco, the San Francisco Business Journal estimated. Some donations went to support wildfire relief and research at University of California San Francisco, but homelessness is Benioff’s passion project.

His positions don't come without controversy. Benioff raised eyebrows during the midterms when he went all in on Proposition C or the “Our City, Our Home” initiative. Easily the most divisive issue on the city's ballot, it proposed a tax on revenue over $50 million to help mitigate San Francisco's homeless problem. The tax disproportionately hit tech companies, including Salesforce, which dominate the business landscape in San Francisco, but Benioff was all for it, putting him at odds with his fellow C-suite techies.

Benioff and Jack Dorsey even engaged in a back-and-forth about the issue on Twitter ($TWTR), the platform Dorsey co-founded. “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 wrote in response to an exuberant tweet by Benioff, championing the proposition.

It’s not the first time Benioff’s interests have run afoul of those of his colleagues and, occasionally, even of those of his own company. Alongside Apple ($APPL) CEO Tim Cook, Benioff has made a name for himself as a proponent of tech regulation and decried the malignant effects of social media on society.

In January, he compared social media companies, like Facebook, to cigarette companies, because “they’re addictive, they’re not good for you,” and called for them to be regulated as such, the Guardian reported. He’s also positioned himself as a champion for user privacy ー as well as for the free press. On Sept. 16, Benioff and his wife purchased the nearly 100-year-old publication Time from Meredith ($MDP), saying in a statement that he would not seek to influence the publication's "day-to-day operations or journalistic decisions."

Owning media organizations has become something of a trend among the wealthy tech elites. Benioff’s purchase follows similar ones by Jeff Bezos, who bought The Washington Post in 2013, Laurene Powell Jobs, whose foundation acquired a major stake in the Atlantic in July 2017, and biotech billionaire Patrick Soon-Shiong, who bought the LA Times in June.

In an interview via text message with The New York Times, Benioff said Time fits with his and his wife’s values as investors, but ultimately he seemed to suggest the purchase was a bit off-the-cuff.

“I live with a beginner’s mind. I didn’t realize two weeks ago I was going to buy Time,” he texted, referencing a zen concept.

In Salesforce matters, Benioff takes a similar zen-like approach. The CEO loves Hawaii and has infused much of Salesforce’s company culture with what he calls “Aloha” spirit, or being “genuine, inclusive, caring, and compassionate, enjoying a healthy dose of fun and treating those around you like family,” according to a Salesforce blog post on company culture. In September, Bloomberg reported that not all employees were happy with the statement, after one employee wrote on an internal forum that the company was “justifiably open to charges of cultural appropriation.”

Benioff's efforts to be woke don't always go over well with everyone. But if 2018 was any indication of what's to come for the Salesforce CEO, we can expect he will continue to champion his causes ー homelessness, data privacy, and media ownership ー and speak his mind into the new year.