On the billionaire beat with Teddy Schleifer

A song to read by: "What a Difference a Day Makes," by Dinah Washington

What I’m reading: "Debt: The First 5,000 Years," by David Graeber

More money, more coverage

Back when I was at Business Insider, when friends would ask me what I wrote about, after a long day of profiling people whose primary claim to fame was their uncanny ability to make gobs of money in novel ways, sometimes I would just say, "Rich people."

Had I known of Teddy Schleifer at the time, I might have answered otherwise.

Schleifer, one of the eight staff writers at the newly launched Puck, covers the obscenely wealthy in a way that has, frankly, never been done before — mostly because this level of wealth has never existed before.

The former CNN and Recode journalist has taken up the philanthropy and billionaire beat at Puck, where he covers the gray areas and soft power of the richest people on Earth.

Although Puck only launched officially on Monday, Schleifer started working a few months ago, writing a newsletter called The Stratosphere. During that time, he has written about the tech billionaires pulling the strings behind the California recall election, the philanthropic fall-out caused by the Gates' divorce and the shadowy political machinations of people like Peter Thiel and Dustin Moskovitz.

We live in an era where a growing cohort of billionaires have personal fortunes greater than those of nation-states, and whose whims and worldviews increasingly shape domestic and economic policy. Schleifer, in covering these tycoons as political forces rather than simply the ultra-wealthy, is pioneering a beat whose ultimate aim is exploring what equity looks like under modern economics.

"I think that the rise of the centibillionaire class demands a new kind of coverage," Schleifer said. "To me, the beat is another way of covering inequality—the flip side of covering poverty."

The following has been edited for clarity.

Mark: In a recent newsletter titled “Why I’m Joining Puck,” you wrote that “some people on the internet think [you're] a billionaire bootlicker, while others insist that [you're] some raging pitchfork-wielding class warrior.”

When it comes to coverage of billionaires, we are so often distracted by the moral question of their wealth that its actual impact goes under-examined. How do you cover the subject without getting caught up in the complex emotions surrounding it?

Teddy: I think it's totally reasonable for people to have extremely charged opinions about this stuff, but what should undergird those charged opinions should be basic facts.

Whether you want to be outraged by billionaires’ philanthropy, political spending or tax avoidance, or whether you think that billionaires are God’s gift to the green earth, you need the facts. And I think that too often, we're deprived of them.

So I don't really approach the beat as a critic or defender of the system. I just think that there's an alarming lack of fact-based reporting about it, and that's a damn shame.

Maybe that's an old fashioned point of view — I’m sure there are critics who think I'm too soft on these people or too hard on people — but I just want to pull back the curtain.

In reporting that relies on access, reporters have to toe a line — be too critical and your texts will go unread, be too soft and you lose credibility. How do you strike that balance, especially when, from a communications perspective, billionaires don’t really need you to exert their influence?

These people don’t think they need traditional media, and in some ways that's true. Billionaires have access to Twitter accounts with more followers than I do, and they can publish self-help leadership books that will sell more copies at airport terminals than anything I write.

But I think savvy sources and savvy billionaires know that there's value in credible, independent reporting that can either validate them or critique them in reasonable ways, and that it's in their self-interest to try to engage with rather than circumvent the system.

Unfortunately, not all of them get that. I agree that much of the tech billionaire set is very thin-skinned about some of the questions that I ask. I don't say that necessarily as a criticism, but I think that lots of them think that the billionaire beat itself puts them inherently on the defensive.

Take the topic of philanthropy, which is something I write about a lot. I think a lot of wealthy people are not used to serious philanthropy journalism, as a concept. So the very idea that someone could be asking questions like, “How is your charitable enterprise structured?” Or, “How much money did you give away to this cause?” Or, “What is your net worth, and how is that reflected or not reflected in the amount of money you give away?”

They see those questions as a fundamental threat, not because they believe that they're unfair questions, but because the entire premise of the question is something that's foreign to them. They think about philanthropy as almost above criticism, above journalism. Like, “Yeah you can critique my business record, but don't critique what I'm doing for the kids.”

I think that misses the forest for the trees to some extent, when there's obviously a raging debate in this country about inequality and about whether the wealthy should be as wealthy as they are. I see philanthropy journalism as essential to answering those questions. They might disagree, but I don't work for them.

Which billionaires are your favorite to cover?

Every writer has their favorite characters. There is obviously a set of people who are extremely well covered — folks like Bill Gates, Zuckerberg and Bezos.

But I often find myself drawn to the … B-list, I guess you could say, though I'm sure someone with a net worth of $25 billion is not on any regular person’s B-list. I'm often amazed by how little these folks are covered, even though they could be doing incredibly interesting, controversial, provocative, amazing things.

I've written recently about Dustin Moskovitz, one of the founders of Facebook, and Moskovitz’s ideology, which is called effective altruism, and how he might marry effective altruism with his newfound political power. Moskovitz is now something like the third-biggest donor to Biden, even though he's still an anonymous figure to a lot of people. He’s a good example of a B-lister who still has enormous power that should be understood and analyzed.

What do you think are the defining political issues for the billionaire class at this moment?

The obvious one is taxes, right? What the ProPublica stories have shown is that at least some of these people pay very little money in taxes.

One way to view the tax debate is the very boring question of whether a certain rate should be 35.6% or 35.5%. Another way to view it is really a question about whether or not the economy works, and whether or not the entire capitalist system is working.

How the billionaires try to seed that debate is very interesting. Right now, Biden is proposing a series of tax increases, and a lot of wealthy people have historically claimed that they support rate hikes, at least when they’re on the set of CNBC when they’re asked.

But I think one of the big questions I have is: Will these people actually spend any of their muscle, any of their political capital, or even any of their real capital, to do anything about it?

So really the only common denominator is preserving their cash flow, and then everybody's secondary goal is what they want to do with that.

I don’t know if preserving the cash flow is the primary thing, but these people didn’t get rich by being dumb. One of the critiques from the left of billionaires, however, that I don’t think scans in practice, is the idea that these are all Scrooge McDucks, hoarding cash.

If you’re worth $70 billion versus $100 billion dollars, is your life really any different? No. I don't think wealthy folks are clenching their cash out of greed, Gordon Gekko style. I think most of it is due to boring reasons, such as the quantitative easing program from the Fed that pumps up the stock market. That's a real reason why wealthy people get wealthier. It's not because they're refusing to give money away to poor people.

What do you think the next few years hold for the billionaire class, especially considering the growing push against them from the left and their growing politicization on the right?

I think, sadly, lots of these folks feel on the defensive, because of the trend you just described. I think more and more of them will seek to disengage from public life, or at least appear to disengage from public life.

Wealthy people can feel the heat coming and would rather remain out of the headlines by any means possible, rather than try to defend their wealth against the pitchfork brigade.

To some extent that’s always been true — folks historically try to get off the Forbes 400 list — but to some extent it’s different. It wasn't that long ago that being a billionaire was an unquestionably good thing. It was the embodiment of the American dream, to some degree. People sang songs about wanting to be a billionaire. It was a positive word, generally.

Now, “billionaire” is sometimes an epithet. And lots of them are now somewhat sheepish about their fortunes, which is understandable. Billionaires’ feelings being hurt is not a reason to not pursue certain public policies or pursue certain stories, of course, but that is how a lot of these wealthy people feel.

So one natural thing they can do is to try to aggressively shape the public debate, like Leon Cooperman crying on CNBC about the Warren wealth tax proposal. But most will just disengage entirely and pull a Larry Page, receding into a private life.

If you had to pigeonhole your coverage into a single category, what would it be? Politics, business, tech, philanthropy?

It’s hard to pigeonhole. Some of it’s politics; I definitely compete with Washington reporters who cover campaign finance. Some of it’s business, where I’m trying to understand the tech ecosystem and the winners it produces. There's a tax component to my beat that intersects with traditional business reporting.

And then there's the whole philanthropy side, which is fruitful for me because it's the least covered. Not to toot my own horn here, but I am trying to help create a new type of coverage. I'm not the first person to come up with this, to be sure. But I think that the rise of the centibillionaire class demands a new kind of coverage. To me, the beat is another way of covering inequality—the flip side of covering poverty.

After just reading your reporting for a few weeks, I’ve started to realize that these people are moving billions of dollars around and very few people are paying attention to it.

I'll be toying around through public filings, and I'll find some foundation that sits on $5 billion in assets. And I’ll google it and discover that absolutely nothing has ever been written about it. Zero website, zero public staff. And it makes me wonder what else we don't know.

Have you ever gotten the sense that you uncovered something that a billionaire was hiding in plain sight?

Savvy folks know that some of the stuff is going to become public eventually, but last fall I wrote a story about Eric Schmidt, the early CEO of Google, who applied to become a citizen of Cyprus. And Cyprus, at the time, had a controversial passport-for-sale program.

Did Schmidt expect that to be public? Probably not. But he’s one of the wealthiest people in the world, has tons of interests before the U.S. government and has enormous influence in the Valley, so I think that it’s in the public interest for that to be reported.

That's why I do see this beat as public-service reporting. It's not like, “Here's a rich person who bought a $30 million mansion.” To me, these are people with enormous power — sometimes on on the level of nation states — and understanding what they're doing with their money is something that like voters and citizens should know about.

You’ve been propositioned to join a few new media ventures. What was different about Jon Kelly’s pitch to you?

It had a clear point of view on the world. Puck understood that there was an opportunity to write about the characters of this world in a personality-focused way. It also understood that this is all one world — that the elites of Hollywood were on vacation with the elites of Wall Street and the elites of Silicon Valley — and so Puck was very well suited to cover the white spaces in between these beats. A lot of my colleagues are people who write about the intersections here, whether between politics and media, or media and tech, or whatever it is.

Puck also understood that journalists have unique insights, because we do the work and we do the reporting, and that we should be treated as talent, as folks who see the world in interesting ways. Lots of media companies see the talent as an expense, rather than something that can create revenue on their own. At Puck, as one of my colleagues put it, we're not the window dressing for the advertising machine; we’re the business.

Some good readin’

— I wrote my first really interesting piece on a new cause of ad fraud: dark pool sales houses. (Adweek)

— "Against the commodification of community." (Longreads)

— The final word on the supposed merits of the metaverse. (The Convivial Society)

— Further evidence of a theory I heard last Thursday night: That Defector Media is the new Gawker. (House of Straus)

— A wonderful essay from Haley Nahman whose only fault was that I wished it was longer. (Maybe Baby)

— Easily one of the smartest, funniest sources of media commentary. (On Posting)