The Joy of Sacks

Happy Tuesday and DeSantis announcement eve…

Tonight, a deep look at the cultural, political and media force that is David Sacks—who tomorrow will launch Ron DeSantis into The Stratosphere. Sacks is an archetype of a new type of donor who melds their money with their knack for getting attention, and his ascension in the world of politics says a great deal about the media.

I’ve got tons of new details on Sacks’ and DeSantis’s moves in this story—including the people behind the Sacks operation, intel on DeSantis’s upcoming trip to California, and how Sacks thinks DeSantis can beat Trump.

DeSantis-Sacks ’24

David Sacks, the PayPal Mafia scion, has ascended from mere rabble-rouser into a genuine G.O.P. cultural and political force, starting super PACs and dark-money groups, appearing on Tucker, and in his latest media venture, launching DeSantis himself.

TEDDY SCHLEIFER

A few months ago, when Ron DeSantis was still being coy about his obvious ambition for the presidency, the Florida governor made a clandestine pilgrimage to Silicon Valley. DeSantis was a shiny object in the world of G.O.P. donors, and he was in town to lock down the support of some of the wealthiest and most connected people in his party. And during one evening on this particular trip, DeSantis had a powerful ally: David Sacks.

The ex-PayPal billionaire, Elon sidekick, libertarian-ish podcast star and aspiring political maestro had quietly organized a dinner for top Bay Area leaders to hear directly from the governor. It wasn’t a fundraiser, but one subtext at least was clear—when the time came for DeSantis to actually raise money, Sacks would be the guy in his corner.

On Wednesday, Sacks will emcee a Twitter Spaces conversation between DeSantis and Musk, in which the long-time sotto voce Trump rival will formally announce his presidential run. The honor is also a sort of coronation for Sacks: As he ushers DeSantis into the race, he is establishing a new archetype of an influencer-donor—sought-after not just for his phenomenal wealth, but also his media profile in conservative circles. Sacks, after all, is powerful not merely because of the money he directly controls, but because of the people he can activate—whether they are his podcast listeners or his far-richer buddies, Elon Musk and Peter Thiel, among them.

“I think in the grand scheme of things, he’s a pretty minor- or
moderate-level donor. He’s probably a pretty moderate- or mid-level influencer. Maybe what’s different is just that he’s doing both,” a person close to him told me on Monday. “There aren’t many people who have a successful podcast who are also donors and organize fundraisers.”

That’s an understatement, of course, maybe a little billionaire self-effacement. Sacks’ network is sui generis, and DeSantis would never select a “minor-level donor” or a “moderate-level influencer” to headline his announcement. Sure, Sacks has only donated in the low six-figures to DeSantis, but his money is only one facet of his growing political and cultural influence. In the two years, I’ve learned, Sacks has hosted more than a half-dozen fundraisers for his favored candidates, expanded his political team and donation infrastructure, and started multiple outside groups to channel his and his friends’ cash into local, state, and now national campaigns.

The Media Is the Message

When I ask high-level G.O.P. cash-collectors about the key figures on their radar, Sacks’ name comes up constantly. This is partly because he is only 50 years old and ascendant at a time when so many of his elder donor peers are, shall we say, declining. Republican fundraisers are very eager to get in front of him. His strong support for DeSantis, who is effectively kicking off his presidential campaign this week at the Four Seasons Miami, is poised to make the software investor one of the most interesting players this cycle.

It’s impossible to separate the ascendancy of Sacks from Peter Thiel, his fellow rabble-rouser at the conservative Stanford Review and co-author of The Diversity Myth, which included a highly-controversial passage about rape that Sacks would later apologize for. After law school, he joined Thiel and Musk as founding C.O.O. of PayPal, which sold to eBay in 2002 for $1.5 billion—an early, life-altering liquidity event that allowed him to dabble in film production, including the dark comedy Thank You For Smoking. (He has said his production company is exploring turning a recent book about PayPal into a movie). Sacks later co-founded the workplace messaging startup Yammer, which sold to Microsoft in 2012 for $1.2 billion.

Sacks has always had center-right politics, but he now appears willing to be more aggressive in partisan politics than ever before. Back in 2016, he passively supported Hillary Clinton, a decision he connected to his work at Zenefits, where he was brought in as C.E.O. to help clean up various misconduct scandals. “I’ve always tried to not take public partisan political positions for the simple reasons that the country is very polarized by politics,” he said at the time. “[The] last thing you want to do is… bring that polarization into your company.”

Sacks, of course, is now a private investor, and more than eager to offer partisan political positions, polarization be damned. His Twitter feed is an endless stream of provocations that generate tons of heat online. His myriad bête noires include the mainstream media, San Francisco socialists, and neocons that Sacks believes have taken over the G.O.P.; his loves include Elon Musk and his “Twitter Files,” a pseudo-journalistic series that, Sacks believes, demonstrates the corruption of the old Twitter regime under Jack Dorsey and its complicity in government censorship. Sacks has a day job at Craft Ventures, but it is no stretch to say that he is now also a bona fide conservative media sensation, podcasting with the likes of Megyn Kelly, Dave Rubin, Benny Johnson, and Glenn Beck.

Then there is his own podcast, All-In, a banter- and jargon-heavy tech and political talk show (co-starring Jason Calacanis, Chamath Palihapitiya, and David Friedberg) that has vaulted up the charts, gained a foothold on Capitol Hill, and spawned an events business to match. Sacks has accumulated an audience of veritable groupies who hang on his every word, and his co-hosts have recently said that they’re going to bring as many presidential candidates as possible onto the show—they’ve already hosted Democratic spoiler R.F.K. Jr., who I’m told Sacks is mischievously planning to fundraise for—trying to turn All-In into something approaching a must-hit venue, just like the popular Ruthless podcast. Nowadays, the monetary value of the earned media Sacks can offer likely exceeds any six- or even seven-figure checks he cuts anyway.

The Sacks Operation

But the person close to Sacks is right about what makes him unique—he’s got a microphone and a fat checkbook. Over the last year or two, Sacks has quietly established a network of organizations to channel his money into politics. In late 2021, Sacks had his financial adviser Jimmy Kull set up a new super PAC, Purple Good Government PAC, to back moderate candidates across the board. Then, in July 2022, he and Kull filed for a new dark-money nonprofit, Purple Action, Inc. that, according to Delaware incorporation documents I obtained, would seek to influence the world of politics and policy as a 501(c)4 group. Kull, Sacks, and his right-hand man, Chris Massey, serve as Purple Action’s directors, according to the documents. The idea, according to a person close to him, was to create an organization that served as a catch-all political receptacle for his friends’ astronomical wealth, rather than just backing candidates one-at-a-time.

One method I’ve long used for gauging the seriousness of a donors’ operation is to track whether or not they’ve brought on donor-advisers to help with their political spending. And Sacks has recently been building up a team: These days, Republicans who want his cash primarily interface with Massey, whose day job is as a government-affairs fixer in D.C. for Sacks’ portfolio companies. Massey, a big golfer and technically a Democrat, has expanded his role, helping Sacks think through strategic questions and execute his political moves, such as setting up his constellation of dark money groups and organizing a fundraiser for Silicon Valley rep Ro Khanna, which took in some $200,000.

Sacks has also quietly been consulting with a more well-known player in Washington: Kevin McGrann, who was once known as the political eyes and ears for John Boehner during his speakership. McGrann mostly helps Sacks with machinery and compliance, I’m told. But other Republicans view the well-connected McGrann as another entry point for folks looking for Sacks’ cash. (Another Sacks ally is Chris Buskirk, a conservative media entrepreneur who over the last year or so has been standing up a buzzy hard-right fundraising network called the Rockbridge Network, whose biannual conferences Sacks has attended.)

Sacks is an influencer at heart, and this team has helped operationalize the money of several of his friends. Veteran entrepreneurs Sky Dayton and Diego Berdakin made rare political contributions, chipping in $50,000 each to the super PAC, as did Kull and Doug Dohring. Over the next year, Sacks’ super PAC would dispense $500,000 to a super PAC behind Blake Masters in Arizona, a longtime Sacks friend through Thiel; $100,000 to DeSantis’s Florida reelection campaign; and $50,000 in the final weeks of the 2022 midterms to back congressional Republicans. (Sacks also personally put $1 million into the super PAC behind J.D. Vance.)

Sacks has also recently become much interested in hosting events, many of which take place at Broadcliff, his Pacific Heights residence on a block of Broadway sometimes called “Billionaires Row.” (“An incredible facility,” one recent guest remarked.) That’s where he hosted DeSantis, for instance, in November 2021, with tickets ranging from $2,500 for the cocktail reception to $25,000 for the dinner. Sacks has also played host to an eclectic mix of populists and moderates, including Miami mayor Francis Suarez, Vance, Masters, Khanna, Kyrsten Sinema, and last week, for the non-interventionist Quincy Institute. Just before the midterms, Sacks had top billing on a co-hosted blowout event with Keith Rabois in Miami for a dozen Senate Republican candidates. Sacks didn’t even attend, but his bold-faced name on the fundraising invite was enough to turn folks out.

The DeSacksis Test

Despite all of this activity, a person close to Sacks insists, he has not been intentionally building out an operation per se, and doesn’t see himself as a power player. Make of that what you will, but he has indisputably become a major force in the DeSantis orbit.

While he is not in the governor’s inner circle—DeSantis likes Sacks, I’m told, but the governor remains closest to his inner sanctum in Florida—he is widely seen as the de facto leader of his Bay Area operation. Sacks has told the DeSantis team that he is prepared to fundraise and throw events for the candidate, beginning with Wednesday’s kickoff. “DeSantis is very focused on building financial infrastructure in California,” one person familiar with their moves told me. “I think David is a natural leader—one of the natural leaders for California.”

The official DeSantis ’24 fundraising tour kicks off shortly, including a fundraising swing through California next month to meet with some of the party’s wealthiest Republicans. DeSantis is expected to have two events in the Bay Area on June 19, and then a trip to Southern California the following day. Thiel disciple Joe Lonsdale, a Bay Area emigre who maintains a home in Woodside, is likely to be involved with one of the events. DeSantis is also expected to be hosted by Robert Day in Los Angeles and legendary G.O.P. bundler David Horowitz in Orange County. (Meanwhile, Tim Scott is also expected to come to the Bay Area in mid-June for an event that will be hosted by Goldman Sachs executive John Underwood.)

Sacks will unfortunately be out of town during this particular DeSantis tour, but he’s gotten plenty of face time with him as of late. Sacks now spends a not-insignificant amount of time in Miami after recently buying a $17 million mansion on the Venetian Islands (the mortgage was signed by Kull). He attended the governor’s second inauguration in January, including the intimate evening gathering for the top supporters that followed. In mid-February, he visited a DeSantis fundraising weekend retreat in Palm Beach, receiving briefings from his top aides.

Some people in politics sneer that Sacks’ money doesn’t match his mouth: He can only contribute “mice-nuts in relative terms,” as Sacks himself texted Elon when discussing a personal investment in Twitter. Nevertheless, Sacks has a vision for how DeSantis could win, with a little help. He has argued that this is a “Trump-DeSantis race” and that his guy will be the Republican nominee if he gets a “clean shot” at the former president in a one-on-one battle, similar to the Obama-Clinton fight of 2008. He frequently encourages his more liberal podcast colleagues to abandon their fealty to the likes of Tim Scott or Nikki Haley. Sure, he is concerned about a repeat of 2016, but that’s why he’s planning to do all he can to get his wealthy poker buddies and PayPal friends to get behind the Florida governor. “DeSantis is going to be the most well-funded candidate probably in history,” he told Megyn Kelly a few months ago. “He’s going to have huge amounts of money behind him.” Including, unsaid, from Sacks himself.