Elon vs. the Libs & Media Asset Moneyball

Elon Musk
Photo: Patrick Pleul/Getty
Theodore Schleifer
December 28, 2021

It’s been a quiet few weeks over the Christmas season, which makes it the perfect time to take stock of some of the biggest storylines in Silicon Valley politics and philanthropy. Today I’m chatting with my boss, Puck co-founder and editor-in-chief Jon Kelly, about what is to come. 


Jon Kelly: Teddy, a big story of the holiday season has been the hyper-aggressive and absurdist back-and-forth between Elon Musk and a couple of America’s most prominent liberals, Bernie Sanders and Elizabeth Warren, about everything from taxation to some more prurient elements. What’s your view on their holiday cheer?

Teddy Schleifer: It felt awfully unbecoming, Jon. Look, these are all big boys and girls—progressive politicians should have free rein to whack whatever rich guy they want, and the rich guys, in turn, are under no obligation to shush their lips and take it. But we’re not exactly getting a high-minded defense of capitalism and wealth accumulation from the world’s richest man. We’ve got Elon telling Bernie that he keeps “forgetting that you’re still alive”; calling Warren “Senator Karen”; and, in some ancient history from November that you probably forgot, reply-guying to Ron Wyden about whether he had just … ejaculated.

Does some of the lefty rhetoric about the evils of the ultra-wealthy veer into histrionics from time to time? Sure. Elon told none other than the satirical Babylon Bee the other day that his Karen tweet was essentially because, well, Warren started it. She and Bernie and Wyden have been raging about his lack of tax payments, casting him as a tax cheat. And that made him mad. I’m sure it did, but that’s a remarkable display of thin skin for a 50-year-old entrepreneur who has been in the public eye for two decades. Elon has at times made the more sophisticated defense of his tax record: That he is set to pay $11 billion in taxes this year, what he claims to be the largest single-year payment in American history (he elides the $0 he paid in 2018); and that he is a better capital allocator than the American bureaucracy (perhaps!). That terra firma is what makes the tweets so childish. I know trolling is a part of his identity, but I wonder if Elon has come to terms with the symbolic significance of his wealth. When you become the single wealthiest person in the world, el numero uno, you fairly or not become almost a spokesperson for and defender of capitalism. Bill Gates’ defense was fundamentally humanitarian, unfailingly polite, and almost ecumenical. I suppose it’s within Elon’s rights to defend it in his own way, but we’ve come a long way from Davos.

A final irony of the story, to me, is that Elon used to be precisely the tech billionaire that the libs, or at least liberal elites, loved. You could totally forget from Bernie and Warren’s rhetoric that Musk’s wealth comes from companies that are genuinely motivated by a social mission to lower carbon emissions and extend life to Mars. In February, when I was back at Recode, we did a poll on the public perception of everyone from Jeff Bezos to Elon—and the results might surprise our dear Democratic senators. Elon had a +30 favorability rating among Democratic voters. (The gnarly gender split is worth observing too.) I wonder if those numbers would hold today, after ten months of tweets.

Teddy, one of the more astonishing elements of our tech-based economy is the speed at which mega-successful founders evolve from innovators to mega-billionaires to influential benefactors and political kingmakers. Who do you see as the millennial or Gen Z Kochs, Adelsons, and Bloombergs of tomorrow?

I’ll give you a few names I’ve talked about before and a few names I haven’t. As to the former, the two most interesting figures to me among the under-40 set have been Dustin Moskovitz, the Facebook co-founder, effective altruist, and newfound and reluctant Democratic mega-donor; and Patrick Collison, the Stripe C.E.O. whose philanthropic and political ambitions are eclectic, earnest and sure to be very, very generously funded.

I’ve written about both of them a good bit this year, though, so let me drop two more names here that I think have real kingmaking potential if they want to grab it: Republican fundraisers are closely watching David Sacks, the PayPal Mafia emeritus and venture-capital provocateur who has made a splash over the last year with a number of G.O.P. events at his mansion in Pacific Heights—obviously there are not many heavy-hitting conservative fundraisers in Silicon Valley, so there is a hill for the taking if Sacks wants it. And also watch for Gretchen Sisson, a UCSF sociologist and Democratic fundraiser who is assembling her own impressive donor network focused on supporting female candidates. Sisson is the type of person whose name comes up all the time in private meetings when you ask insiders about the rising generation.

You wrote recently about Jeff Bezos’ $100 million contribution to the Obama Foundation, facilitated by former Obama aide-turned-Amazon executive Jay Carney. Bezos owns the Post and has a swanky place in Kalorama. You think he’s playing around with getting more deeply involved in politics?

No, I actually do not. I know the man has had a transformative midlife crisis, but let’s accurately take his political temperature here: Bezos has been very wealthy for more than 20 years now, and he has made almost no political donations during that entire time. There was a glimmer of a more Bloombergian Bezos in 2018 when he donated $10 million to a super PAC backing Democratic and Republican veterans running for Congress, but it was telling, to me at least, that he didn’t follow that up with any (disclosed) donations to that group in 2020. Bezos obviously has a professional obligation to pay attention to politics—and, sure, I’d buy that the Bezos gift to the Obama Foundation reflects at least some turning of the weathervane—but there’s no sign to me that it is where his passions lie. (For a sense of his true life passions, if you’re not following Lauren Sanchez’s relatively new Jeff-heavy Instagram over the holidays, you’re missing out.)

For a time, the West Coast elite began gobbling up a series of legacy media products: Benioff bought Time, Laurene Powell Jobs bought most of The Atlantic. And before that Pierre Omidyar launched his own collection of assets. Has this trend subsided?

I’ll take the bet that it hasn’t. But I share your head-scratching that we haven’t seen more of it. Despite the occasional story about a media mogul’s cost-cutting or passion-project-gone-awry, the politics of buying a media brand are pretty incredible. The economics might suck, but who cares? These nine-figure deals aren’t exactly making a dent in their owners’ checking accounts, and the potential, if immeasurable, financial upside that comes with ingratiating yourself to the media elite by appearing at Committee to Protect Journalist galas and the like can be enormous. I know owning Time isn’t as much fun as Ballmer seems to be having courtside during a Clippers playoff run, but I’d proffer that the brand equity gained with a marquee media buy outstrips that of a legacy sports franchise (Also, why not both?)

Speaking of goodwill bought with loose change in the couch, I’ve been amazed that the tech set hasn’t made a run on local media in particular, especially in cities full of elites who are skeptical of the moral codes of their overlords. Can you imagine the fanfare that would greet Jack Dorsey if he plucked The San Francisco Chronicle out of the clutches of Hearst? Or better yet, if he spared a nickel or two for, say, a real homespun, down-on-its-luck brand, like The East Bay Times? Make a small purchase, don’t Alden Capital it, and bask in the headlines declaring you a savior of local journalism.

You reported earlier this month on Mackenzie Scott’s latest end-of-year gift. She’s obviously been showered in adulation for the last 18 months—Forbes just named her the world’s most powerful woman. So let’s end this with maybe a contrarian note: Tell me what red flags we might see with MacKenzie, or at least any reason why the received wisdom might not bear out.

I am as intrigued by the MacKenzie model of philanthropy as the next guy, but let’s be clear about what this is: an experiment. Not a guarantee—and I think the press has been a bit quick to surround her in hoopla without any evidence that she has indeed successfully hacked philanthropy.

So piggybacking on that point, two red flags, Jon: The first should be obvious. This could blow up fantastically. Is there maybe a reason that, say, the Gates Foundation has 1,500 people—program officers, lawyers, even executive assistants—running the world’s most venerated philanthropic machine? Is MacKenzie indeed correct that the bureaucracy isn’t necessary, and that she can essentially make an enormous impact with her consultants at Bridgespan and the few staffers at her family office, who seem to not be conducting the traditional vetting and application process that is S.O.P. in mega-gifts? Maybe she is, but the jury is definitely still out on that one… and I’m baffled why so many scholars and journalists are ready to give her an A+ immediately.

Secondly, the lack of a commitment to transparency that MacKenzie displayed in her last letter should be alarming to anyone who cares about the power of big donors in society. It has been quite evident since her earliest utterances that she feels she should not be the story, and now she is clearly bothered by media coverage that has made her into a thing. So now she has pulled back on the disclosure of actual gifts, wagering that without a headline figure, journalists will not have as much to write about. (A smart wager if you look at the paucity of coverage of her last Medium post.) A few days after her announcement came out in early December, Scott seemed to backtrack a bit and promised some additional information. But she is clearly still wrestling, in real time and in public view, with her inability to be simultaneously transparent while also controlling the narrative about herself. I understand, and can even appreciate, not wanting to be a figure of public fascination—or at least wanting to maintain some privacy. But when you’re donating billions of dollars a year, faster than anyone has before, into the nonprofit sector—and who knows, maybe into political, pseudo-philanthropic causes—there’s a very valid argument to be made that the public interest demands tremendous disclosure, even if you have to suffer through a few Forbes honorifics.

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