The Onion’s Owner on Satire, Infowars, Defending Democracy & Trump

Hi, everyone from New York Magazine and the Vox Media Podcast Network. This is On with Kara Swisher, and I'm Kara Swisher.
My guest today is Jeff Lawson, owner of America's finest news source, obviously, The Onion. Lawson is also the co-founder and former CEO of Twilio, a cloud communications platform that's used by brands like Netflix, Uber, Airbnb, Toyota, and Salesforce.
In January of last year, Lawson stepped down as CEO and board member of Twilio in response to pressure from activist investors. Since then, he's continued his work on Democracy First, a political action committee he co-founded in 2022 that donates money to candidates from both parties that are committed to democracy.
He also bought The Onion, tried to buy Alex Jones's Infowars out of bankruptcy, and worked on a kit car. I spoke with Jeff last week at the University of Michigan's Gerald R.
Ford School of Public Policy as part of their ongoing forum on democracy's information dilemma.

Lawson had a lot to say about Twilio, The Onion,

the state of our democracy, and the role of tech.

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Another Simple Favor premieres May 1st only on Prime Video. This podcast is supported by Google.
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Learn more at Sophos.com. Jeff, thanks for joining me in this conversation at the University of Michigan, where you are an alum.
Indeed. So let's get into it.
So let's talk a little bit about you here. You quit the university halfway through your senior year, which is an unusual time, in order to work on your startup, which is Versity.
Talk a little bit about that. There are a lot of entrepreneurial seniors probably sitting here who plan on graduating next month.
Talk a little bit about why you did that and your experience here with people who don't know it. Absolutely.
Well, I showed up to college, undergrad in the fall of 1995, and the internet was brand new. The commercial internet was really just coming about.
I remember I got here, and while a lot of people, like their first day on campus, you say goodbye to your parents, and you're excited about alcohol or parties, whatever. I was excited about the ethernet jack in my dorm room, which had fast internet because you have dial-up and all this back then, which none of you know what that is, but you got here and it was like a whole different world and you could really just, you could see the whole internet.
And I remember, you know, I FTP down a copy of Netscape Navigator 1.0 and started using the web. And, you know web was like these static web pages about people's job or their favorite pet or whatever.
And then you had these websites where you could do something. Right.
And there were few and far between. For people who don't know, one of the very first early internet sites people looked at was people making coffee.
It was like a webcam on a coffee maker. It was a webcam on a coffee maker.
And that was very exciting. Very exciting at the time, right? Very exciting.
Like, oh my God, someone's drinking coffee. It wasn't exciting at the time, but nonetheless.
So go ahead. This was important for people to understand.
But you were like, how do they do these amazing things? If I wanted a coffee maker cam, I would it? And so I just said, you know what? I'm gonna start a company in order to just have an excuse to go play with this new thing called the internet. And I've always found that the best way to do something or to learn something is just commit yourself to doing it.
And then you have to go do it, right? So tell someone, tell a customer you're going to go do a thing. And for us, we said, we're starting this company.
Great. How do we do this? Or first of all, what are we doing? And I remember I was walking down campus one day and they had all these signs on campus for lecture note companies.
So you could walk into a copy shop and buy a copy of the notes from the courses you were in. And they would pay one note taker, usually hopefully a good one, who was sitting near the front of the room taking really good notes.
And the copy shop would buy the rights to the notes. And then you could go in and buy them for like 40 bucks a semester.
And there was a little cottage industry. And we said, you know what, wouldn't that be great to do that online so you don't have to walk through the snow to get a copy of your notes? And so we started this thing.
It was 1996. We could have had any domain name we wanted.
And we went for notes, number four, free.com. Wow.
Brilliant marketers we were. No, not at all.
Notes, we could have had google.com. We could have had had anything was available at that point.
Notes, number four, free, which then later turned into diversity.com. But it was this excuse to start playing with the internet.
So we built this site and we hired a lot of our friends to start taking notes in the lectures they were in and posting them on thing. Which you did in an analog style, correct, and then uploaded them.
Well, literally, they would type them. We figured out, okay, well, they need to type the notes.
And then someone's like, well, I have a diagram from econ. What do I do with that?

We're like, oh, crap. Okay, here's, and we, you know, someone wrote a Java applet to like let you

draw a diagram and insert that into the notes. So we basically, I guess we invented the content

management system, even though it wasn't called that. So you were automating.
You were automating

a process that had been analog. Basically, because yeah, in the old way, it was, here's my

piece of paper with my notes,

and they literally get Xeroxed on usually blue paper.

Why blue? Because you couldn't then subsequently copy it again. And so we put the whole thing online, digitized it, and we ended up as like a side project.
Then we ended up like raising a little money for friends and family. We took it to the Big Ten.
And then we actually ended up raising venture capital in about 1998 and blew it out to 10,000 courses at about 200 campuses nationwide. But the thing is, we had a little

bit of success. We ended up selling to a competitor, an all-stock deal.
The competitor filed to go

public, missed the window, was bankrupt a few months later. So we had the classic dorm room

to we were worth $150 million to we were worth nothing again all in like 18 months, like the whole story. And in some ways, I feel very lucky in some ways that I had multiple starts at entrepreneurship before actually Twilio was the one that worked.
Right, which is in 2008. Let's talk about Twilio.
The valuation rocketed to $70 billion during the pandemic, although it's come back to earth. It didn't fall off a cliff like so many other pandemic success stories.
Talk a little about your experience, because you left Twilio after the battle with activist investors. So let's talk about your history and explain why you left, which is another typical thing.
Things happen like this with entrepreneurs a lot. Yeah.
You know, I left not by my choosing. Um, the board thought that, uh, avoiding a fight with the activists was the right thing to do.
And so I was fired. Um, and that was, you know, something that never in a million years did I expect would happen in terms of like, I being fired from the company that I started and ran.
And the interesting thing that happened, like, look, I was mad. I was, you know, all sorts of emotions you go through in this.
But at the end of the day, what I came to realize was I was the founder, chairman, CEO, and president. I had every title imaginable to avoid this outcome.
So somehow I screwed up. And so, you know, as I look back, you know, I kind of realized like, oh, wow, you've got an activist at the gates.
And my conversations with the board were very normal. It's like, no, we're just going to run the business as usual.
And, you know, I kind of thought, great. I didn't really manage the board.
I always felt like, you know, I'm not there to manage them. But the reality is this was wartime.
You know, when an activist is at the gates, that for a board is wartime. And you know, the whole wartime, peacetime notion, I needed to treat the board like it was war.
And I needed to lead them through that. And I wasn't doing that.
And as a result of it, we had this moment where push came to shove. And it was like, are we going to actually have a public campaign with an activist or not? And the board said, hey, you know, life's better without public activist campaigns against you.
And so that's the direction we're going to go. And that took me by surprise.
And the fact that that took me by surprise was a very big mistake for me, right? You grow up in that idea that you're the founder in there because there's a founder culture in technology where the founders are the be all and end all. And so I think you kind of believe in that idea that you're the founder.
Because there's a founder culture in technology where the founders are the be-all and end-all. And so I think you kind of believe in that idea.
Explain for people who don't know what Twilio does. Yeah, so Twilio is infrastructure that software developers use to embed communications inside of the apps that you have on your phones and use on the web.
So, for example, when Cory Booker texts you asking for $5, that's probably Twilio. But also when you ride an Uber or you stay in an Airbnb or any one of these things where you are interacting with some service over text, over voice, over video, over one of these things, Twilio is powering those kinds of communications in the quantity of trillions a year for hundreds of thousands of companies and all the apps that they build.
And built it from zero. I'm a software developer, so I realized through all the course of my prior companies, I needed communications in all the apps that I was building and didn't have it.
It was inaccessible. I was like, I don't know how to add text messaging to my thing.
That's the mysteries of the cosmos, how text messages arrive. So I started a company to solve that problem.
So I grew up from that idea in 2008 through about $4 billion in revenue. And at our peak, we had about 10,000 employees.
And so really a wild ride. But unlike the dot-com era, building real value, building a real company with real revenue in the B2B space, selling to other companies.
But also with this sort of B2C idea of developers and the software developers being the people who would lead us into companies was kind of a novel idea when we started this in 2008 and ended up working very well because and this is where luck plays in the mobile boom happened right around when we started Twilio and therefore there was a huge now surging demand for apps for developers and for all the infrastructure needed to build those and we were happened to be right there at the right time and so so for entrepreneurs in the room, it also goes to show you work hard and all this, but

75% of it's lock and timing and all that kind of stuff.

But when you think about doing that and moving on, how is that, like one of the things that

entrepreneurs, they get sort of celebrated as success, success, success, but there's failure

after failure after failure. And even though it exhausts me when they're always like, it wasn't

a failure, I'm like, well, that was a failure. But since leaving Twilio, you haven't found an

Thank you. but there's failure after failure after failure.
And even though it exhausts me when they're always like, it wasn't a failure, I'm like, well, that was a failure. But since leaving Twilio, you haven't founded a new startup.
Talk about your relationship with the tech industry now, that you have some distance from it. Where do you live? San Francisco.
Okay, all right, good. That sounded so accusatory.
No, it's not. I still have my house in San Francisco.
I was just there last week. Sorry, what was the question? What are you doing? What are you doing? Why didn't you start a new startup? I suspect you've had money thrown at you, presumably.
Number of, number of reasons. First of all, what I, when I left Twilio, I said, I am going to, for a period of time, just do things that bring me joy.
And I knew there were a lot of days when I was CEO running a public company and You know meeting after meeting and all this kind of stuff What I really wanted to be doing was like soldering a circuit board and like building some IOT idea that some stupid idea I had in the back of my head that is of no commercial value whatever, but I'm like, I wonder if that's possible And so I said the first thing I'm gonna do is just let myself go do all those things All these stupid stupid ideas I've had in the back of my head, like building a car or like building, you know, for a while I was working on an internet powered walkie talkie for children, just because I thought that was a neat thing. Not because I thought it'd be a great business or I wanted to run that business.
I just was like, can I do this? That was kind of fun. Um, and then part of it was, okay, I love mentoring young teams, um, young founders, management, uh, young management teams.
And so I opened up a garage where I do all my building and I said, you know, I could go to this garage and be alone every day, tinkering on a car or whatever, or I could invite, you know, a dozen startups and just work out of here and let them ask me questions and do office hours with them and see if I can help them. And I'm like, yeah, the latter.
Surrounding myself with interesting people doing interesting things, especially in this era of rapidly evolving AI, that sounds like

a much better way to spend my days. And so I did that.
It's called the Founders Garage and

partnered with Bessemer, a venture capitalist and Y Combinator and OpenAI and a few others who send me some of their earliest stage startups who need some mentorship and some help along the way. And so that's how I really enjoy spending my days.
And I think there's a lot of folks who jump straight into their next thing. You know, it's a rebound relationship is basically what it is.
And we all know how those tend to end, right? Except now you've got a company to go deal with and employees and customers and all sorts of obligations. And I thought, well, that sounds like a horrible idea to make some rash decision just because I'm used to being in charge and used to being CEO of something.
So let me go be CEO again. You know, I just said, let me let me do things that purely are for me.
And then eventually something will come to me. So we're going to talk about a number of those things.
In 2022, you and your wife, Erica, founded a Democracy First. Explain how you decide what candidates to back and what happens if you don't succeed? What happens if more pro-democracy candidates lose? Well, we have been in fear of democracy here in the United States for a while, since roughly 2016 for some reason.
I don't remember why. And so, you know,

we started doing,

I'm going, and we were very apolitical. Like, we, you know, we gave a little bit to the candidates that made sense, but, you know, not really involved.
And, you know, so we started by doing some of those things, like, oh, let's give to some obvious candidates. But then, in particular, so we did a lot in the 2020 election because we just wanted to have a change of leadership.

And then there was this hope that in 2021, after we'd won Congress and the presidency, that we would pass legislation to strengthen democracy. And there's a number of norms of democracy that got challenged in the 20 teens.

You know, whether it was Supreme Court seats that weren't granted when the norm said they should have been, or whether it was a lot of the stuff that Trump had done during his first term that challenged democratic norms, but luckily didn't happen because the people surrounding him didn't allow it to happen. And we said, wow, that was really close.
Let's not let those things, you know, happen again. And so we believe that this federal legislation, the Freedom to Vote Act, and then John Lewis Voting Rights Act, that passage of those would really strengthen a lot of the tenets of democracy.
And when that didn't happen, because they would have had to abolish the filibuster to pass it, and they didn't, we kind of had this, oh, shit,'re going to have to do this the hard way. And the hard way means going down to the state level and the local level and really asking what are the pillars way below the federal level that uphold our democracy? And it turns out a lot of it is how are elections run? Are they run in free and fair ways? So you've got secretaries of state, how they administer elections, state Supreme Court elections, where a lot of this stuff gets adjudicated.
You've got attorneys general, whether they're going to bring cases or not of the right kind, and all the way down to like local election commissions. Like Pennsylvania has, each county has a three-person election commission.
And the idea was in each of these races, in each of these states that matter here, are there going to be rational believers in democracy of either party? Or are you going to get crazy people who don't want to uphold democracy? They just want to see their party and their ideology with it. Right.
Plot spoiler. Go ahead.
And so we said, we're going to work really hard in a bipartisan way just to make sure that the people who believe in rule of law are going to sit in these seats when the election comes around. And so that's where we started working on all these things.
And we didn't know about most of these. I mean, nobody knows about half these elections that go on.
And at the time, nobody knew Trump was coming back. He was sort of down in Mar-a-Lago hiding for a short time.
Sure. But like, you know, you don't play with fire, as I often tell my son, you know, like, you know, you can light the match for the hundredth time and that's when you burn yourself.
Right. And so.
So how much money did you put into it and which, how did you decide what to do? For example, you and Elon both spent money on the recent Wisconsin Supreme Court case. Congratulations, by the way.
You backed Susan Crawford, the liberal candidate. And although you probably spent less than $25 million that Elon put up, so sorry, Elon, your candidate still won.
Talk a little bit about this race. When you look at this race, what's your takeaway? And is this the new normal now that the world's richest man or rich people are throwing around money for elections? I mean, because it seems like he can do this all day and night, someone like this.
And so can a lot of people. And they did it quietly before, but not quite in this amplified and hyper way.
These are sleepy state races, like a judge in Wisconsin that become, I think Wisconsin's $90 million spent.

Yeah.

It's, look, I wish we lived in a world where you didn't have to do this. First of all, I'd have a lot more money in my bank account.
But second is like, do I think that people should from like out of state be influencing elections? Like, no, ideally, the people of Wisconsin should decide who their Supreme Court members are, without the help of anyone outside influencing it, right? Like, that's ideally how democracy should work, in the same way that we should decide who our president is without, you know, maybe the Russians helping us to decide that. And, but that's not the world we live in.
And so we have to participate. I do think the new norm is this, but I actually think that on the right, they were doing this for quite a while, and on the left, we ignored it at our peril.
And so now what you see is actual fights occurring, and therefore the stakes are going up, the press is going up, all that kind of stuff. Because it's no longer being done kind of quietly by one side.
It's being done by both sides, and now the numbers are going up. And look, I think we all knew that Wisconsin was going to be not just a judgment upon who the Supreme Court electee would be, but actually a judgment upon Alon's money.
And what does Alon's money mean? Is it toxic or not? And what I think we've shown is that like, yes, hopefully this is a sign that somebody coming in and trying to buy elections in such a transparent way is a turn off to more people than it is a benefit to the person who is getting that money. Politically toxic, you mean? Politically toxic, yes.
What do you think happened there? Personally, when I saw the cheese head, I went, no. He didn't do the cheese.
I did. I was like, you nuisance.
And he didn't have Trump next to him, right? I think with Trump there, he's appealing to his constituency, whether you like him or not. And Elon thinks he is because he's standing next to him, when in fact, he's quite an unpleasant person to look at in many ways.
I won't speak to his physical attributes. Don't take...
That cheese head was bad. It reminded me of the Dukakis helmet.
I was like, ooh. Oh, geez, yes.
Ouch. There, I was being bipartisan.
That was a bad picture, too. Yeah, if you're a politician, just don't put things on your head.
No. Yeah.
Unless you're Gavin Newsom, he'd have looked good in the book G's head.

But go ahead.

I just think most people cannot relate to Elon Musk.

Therefore, his standing up there trying to lead doesn't necessarily work.

What's interesting is he's used to, I'm sure, leading a bunch of tech people. Who revere him.
Who revere him and who get their paycheck from him. So he's standing up in front of him in all hands at Tesla or SpaceX or whatever, and he gets this certain response from them.
Also on Twitter, same thing. And on Twitter, yes, good point, right? It's people who've already opted into liking him that gives him that adoration and therefore has rewarded him for being Elan.
But now you go out in front of an average group of people in Wisconsin or on the news, everybody, and you see that approach is a turnoff to a lot of people. They don't want to be thought of as just pawns that can be bought for a price.
They don't want to go to the Elan show where they might get a check for a million dollars in exchange for their fealty and their vote. Like, aside from being illegal, I think enough people believe that this is just, it's not what America's about.
And he is, and he brings this out in a very visceral way, I think, in enough people. And that's what the big test was.
Are there enough people look at this and say, God, you know what? I don't even, regardless where I stand politically, this doesn't feel like what America stands for. And I'm so happy to see that enough people have said, yeah, this doesn't feel right to me.
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A lot of tech CEOs in the interim have embraced President Trump, but at the very least lavished him with praise.

I happen to know at least most of the people on that dais don't like him, right?

But nonetheless, they're interested in growth,

and they're interested in shareholders and things like that, and advantage.

That includes Mark Benioff, who was known for his social activism and who you called one of your heroes.

I have a long relationship with Mark, and lately I've been sending him kind of irritating. I'm sure they're irritating texts to him, but I like them.
But I get why they do this. The CEO of a public company has a fiduciary to their shareholders, and Trump demands fealty.
That's why he had them all there. Yeah, trophies.
Trophies. But if business leaders are incentivized to play nice with a president who doesn't respect democracy, the rule of law, including law firms this week, this week, the attacks are on law firms to show fealty and a surprising number of them are acquiescing.
What does that say about our economic system and the theory? Because it's sort of, you break down these pillars that you're talking about? Well, that's exactly the problem, right? We think that there are all these systems that are in check and balance and there are all of these defenses that are built into democracy to fight the rise of an authoritarian. But what you see historically and here today is that in practice, so much of it is just norms.
So I'm sure the symposium is talking a lot about democratic norms and things that we thought were just the way it worked. Turns out, not so much.
And even things that are, I don't even think arguably, but should be litigated in front of a court are the law and are the First Amendment or things like that. When you break them, it takes somebody to do something about it.
The law is just a piece of the constitution is a piece of paper. And if nobody does anything about it, then it's just a piece of paper, right? The constitution itself is not going to come out and arrest people or whatever.
Right. And so it takes people.
And that's literally what we're seeing happen right now is in January 6 was the best example of it, which was a very extreme event of anti-democratic event. And not only were there no consequences for it, the perpetrator was rewarded with another term in office.
And that to me says, wow, the norms, you cannot get norms that are any more clear than do not raid your Congress with arms and expect to get away with it than that. And so therefore, what should we expect from this next term? That's the thing that I think is scaring a lot of people.
And that both scares them in terms of, wow, if I'm the CEO of a public company, his retribution can actually do harm because we may not be able to go to a court and fight it. Therefore, what do we do? It is a very hard problem if you're a public company CEO.
Now, here's the thing I would say. Can you put your responsibility as a citizen arguably ahead of your responsibility as a CEO? you have a fiduciary responsibility to your shareholders.
Yes. Trump has a responsibility to uphold the Constitution.
Right. So what do we do about the rule of law? By the way, you don't have to break the law now to be in trouble with the law, right? Like when you enter into a lawless world, everything is in question.
So can you run a company anymore when you start to look like a banana republic? Which gets you the idea of innovation. I was like, now Amazon and Meta and others are getting advantage through access and not innovation.
And that to me is the death knell of innovation, right? That you get it because you're sitting there, you get what TikTok decision's about to come down, and it's all friends of.

And it's not the best scenario at all.

It's just the one that's more convenient.

And that's happened over time. But it sort of underscores access over innovation, which is what has kept the U.S.
ahead, is its ability to innovate and disrupt old industries.

I mean, I won't forget when Elon called me when he had his first space win over Lockheed and Boeing. I was thrilled because who wants them to just run everything, right? You liked innovation and cheaper rockets.
A level playing field. Right.
Which, by the way, where do level playing fields come from? They come from the rule of law. Right, right.
Right. They come from there being a clear sense of rights and wrongs and knowing that contracts will be enforced and ownership is honored and all sorts of things that we have taken for granted for a long time in this country.
Now, if you travel to other places in the world, you realize that we how lucky we are to have a system where in order to get something, you have to bribe people. Right.
It's not who you know. It's not how you were born.
I mean, yes, it is to some extent, obviously, in a lot of ways. However, more than any other place on Earth, America was a place where the rule of law was the most important thing, as opposed to all those other factors.

And now you start to see wow, maybe that's not something we can take for granted because you have to be in the good graces of the elected leader in order to be able to do business

Right. And so, you know, the tech world is worried about being broken up.
They're worried about having retribution. They're worried about the government buying their products.
They're worried about all these things. And so they have lined up to try to make sure that they are in good graces and in a way that I find disgraceful.
Yeah, I would agree. And I like, I don't know.
I remember people asking me, remember there was that tech roundtable when Trump first came to office? I broke that story. I broke that story.
Yes, I do. You wrote that story.
Okay, great would agree. And I like I don't know I remember people asking me remember those that tech roundtable when Trump first came to office I wrote that story.
I wrote that story. Yes, I wrote that story.
Okay, yeah, so I Remember sheeple they didn't like it, but I did I remember people asking me at Twilio They're like, oh, are you invited and I'm like no part of it. I was like, well, no, we're not that important, but But if I was invited I would not have gone.
Right. Because to me, attending and being a part of it is an endorsement of like, yes, this process is on board and I want to be a part of it.
And the excuse people make is, well, I'd rather be a part of it than not a part of it. Right.
That's their argument. I can change.
No. We're endorsing what's going on by being a part of it.
One of the reasons, I wrote that story,

and the only person who called me back was Elon Musk.

And I said, how can you do this?

He goes, well, I can change his mind.

I go, well, Jesus, you're not going to.

It's not going to happen.

He hates immigrants, and he's racist and homophobic, et cetera.

And he's like, I can change his mind.

That was the idea by being there.

And one of the things, what I wrote is they want their tax breaks.

They want their money brought back from abroad. They want these things, and it's over their citizenship.
And that's why I called them sheeple. It was shameful when they did that.
And they didn't bring up immigration. And even though there were four immigrants at that meeting, they didn't bring up his hateful rhetoric around immigration.
And they're always like, oh, we'll say it quietly to him. And I'm like, no, I'd like you to say it publicly because Silicon Valley was built on immigration.
It was built on the ability to bring people in this country and innovate. There's a theory that essentially says the Internet is to blame for the rise of populism, right, around the world, in part because of social media algorithms, reward, rage bait, misinformation, conspiracy theories, destroy trust in institutions.
Plus, we're all trapped in these silos that isolate us from the real world community. I've interviewed lots of people like Yuval Harari and others to, you know, this is where it goes.
I was trying to think what I blame for a lot of this. And I think it's very easy initially to blame just the internet, like, or especially social media.
But to me, if I had to pick in three things, I would say social media gerrymandering and Rupert Murdoch have killed our country, like in a lot of ways, in a combination, created the polarization.

What do you point to if you had to pick three things?

Here's what really worries me, is that what I look at as the major institutions of our society, the media, social media, politicians, government, political parties, like all of these major institutions, every one of them wins when we are angry at each other. Every one of them makes more money or gets more powerful when we are rage clicking and angry and all this kind of stuff.
Ratings go up, clicks go up, advertisers are happy. Everyone's incentive function in these major institutions that kind of rule our society benefits when we hate each other.
And so what's the antidote to that? What's the antidote when everything that we look at and hear from and every message we're getting is like, yeah, yeah, we're cool when we just create this anxiety and this rage and the rush that people get when they're anxious and angry. There's no what's the solution.
The line I had in my book was enragement equals engagement. Yes.
So what's the answer? And I literally don't know what is going to come along other than walking outside and going to the park and looking at your neighbor and going to whatever the rotary club or church or synagogue or the the mosque or you know having a barbecue with your friends whatever it is like people are the answer to it real people that live near you and that whose values you share with them are because you live in the same area not because you've raged clicked on the same link that to me is the best answer and so what i like one of the things that I was pitching last year when we were going to win

the trifecta was,

you know,

I think it would be

a great agenda item.

Like if Biden did

the infrastructure bill,

why don't we do

the social infrastructure bill?

Think about how much money

would it take

from the federal government

to bolster local picnics,

the ice cream social

at a church,

like for, you know,

a tiny amount of money

in the federal budget. We could really build up local institutions.
Oh, by the way, I went some hearts and minds on the ground. You could also do it via online.
I just recently spoke to Kamala Harris, and I want her to do a podcast called Recently Unemployed with Kamala Harris, where I want her to go meet people all over the country and tape it and have discussions with real people. I thought Pete should do that.
I pitched Pete on that. Oh, Recently Unemployed with Pete Buttigieg? Doesn't sound as good.
Not as good. I was thinking Pete's America.
Stick to it. Yes.
And have discussions with real people. I thought Pete should do that.
I pitched Pete on that. Oh, Robisa Unemployed with Pete Buttigieg? Doesn't sound as good.
Not as good. I was thinking Pete's America.
Stick to your guns. I'll do the podcast, okay? But I think one of the solutions I have to tell you is humor.
And let's talk about The Onion now. Because I've been recently interviewing, I'm spending a lot of time interviewing comics.
Because I think they have very trenchant social commentary and political commentary. They're the toughest, tougher than media on politicians.
And I mean all sides. Like they're really good stuff, even if you don't agree with it, this and that.
But I've really spent a lot of time interviewing tons of them. Now you, a lot of billionaires are buying things.
The Washington Post bought by Jeff Bezos, who's a terrible owner right now. Mark Benioff bought Time Magazine.
Elon bought X. And you bought The Onion.
So tell us why The Onion and why you bought a satirical paper instead of, say, starting a newspaper like Mike Moritz is doing, which is a very good one, the San Francisco Standard, for example. What was the—and I do recommend that.
It's quite good. They're doing a great job there.
Well, let me ask you this. If you could own any news source or America's finest news source, which one would you buy? Well, I'm trying to buy the Washington Post, but he's not calling me back.
You know, I remember, because this whole thing started when Bezos bought the Post and Benioff bought Time. I started joking with friends, I'm going to buy the Onion.
Yeah. Because that is a proportional to our market caps.
Okay, but also just how the how the universe should work. Yeah, like, oh, like, that's, that's me, like, the universe is in is in is in sync, if that's what I did.
And then I looked into it a few times over the years. Yeah.
And it was never the right time. It was owned by private equity, they wanted to sell it, they had some great idea for what private equity is gonna do with the onion.
Well, finally, last year, they realized that they did not know what to do with the Onion, and they were ready to sell it. And so the timing worked out to buy it.
And really for three reasons. You had been calling them.
You were like, I'm interested. Yeah.
I remember I missed it. It got sold from Univision to private equity, and I missed that opportunity.
Yeah. Oh, when that happened.
Why Univision owned it? Again, who knows? Amazing. Yeah.
They owned a lot of things they shouldn't have owned, yeah. And so the reason for buying, there are basically three reasons.
First was, you know, I started looking into it because it started as a joke, but I was like, actually, that'd be kind of cool. I've been a longtime fan of The Onion.
And when I started looking into it, I realized it wasn't buying The onion, it was saving the onion. Because it was in a death spiral.

First of all, I mean, the whole media world has obviously been struggling for the past, you know, 10 years. Some of it.
Everyone except for you, Cara. That's true.
There's a lot of very good media entrepreneurs right now are doing very well. But the last 10 years have been tumultuous.
For the big companies, certainly. Yeah.
Yes. and then add on top of that to be owned by private equity, whose goal is to extract cash.
Right. Terrible.
From the entity. While it is shrinking, it's just layoff after layoff after layoff.
And so it was basically on life support. And so it became saving it, which I thought was important because I thought it's an institution the world needs.
And it's not very expensive. It isn't.
It isn't. None of these.
I mean, the Washington Post sold for $250 million, which is nothing to Bezos. There's a bizarre arbitrage.
And he's since brought it down to $125 million. Well, there's a bizarre arbitrage, by the way, from tech to media, which is that the valuations of tech firms versus media firms is huge, except the influence of media versus tech is also huge.
So you can take your tech money and buy influence on the media side, and it's actually a fairly good plan. Yeah, it is interesting.
Hence, Twitter being pulled into XAI. You can hide it in there.
So I want to find out what makes an onion story. I'll read a few recent headlines.
I know you don't do the editorial, but still. Trump says he won't rule out a Third Reich.
Pete Hegseth calls for steep cuts of a number of steps in AA recovery. DOJ designates posting photos of balding Elon Musk as domestic terrorism.
And these could all happen, by the way, if Bondi gets her way. College campus tour ends inside unmarked ice vehicle.
It's not funny, but it's funny. So I love these.
You guys really, it's very in your face. And your CEO, Ben Collins, is a former disinformation reporter who was very good at his job and no experience as CEO.
He left news after receiving death threats over his coverage and became irrevocably depressed and anxious. Talk a little bit about what you're going for here because it's very in your face and actually funny for left-wing people, which isn't usually the case.
So, you know, I said there were three reasons. The second one is because I feel like the onion and satire and comedy is a way to drill down straight to the truth because the reason we find things funny is because someone is saying out loud what we're all thinking that's what makes humor and you don't even know you're thinking it but then when someone says it you're like oh yeah that has been what's in my head and that's why we find things funny and it's like it's like this um you know like if you have a dog and you need to give them medicine you like wrap the pill in a little like pill pouch and you give it to them.
The dog eats it and they don't know. That's what satire is for the truth.
You wrap the truth in this pill and in this pill pack and now someone can, you can eat it. You get it inside of people's head.
And that's what is so interesting about The Onion in particular because the brand is amazing. We have followers followership and what the onion can stand for in terms of a delivery vehicle for the truth, because we're literally satirizing the news is a great vehicle to now start saying, okay, and by the way, this would go, this is, this is, this is true no matter who had won in November, that actually being a vehicle to deliver truth about what's going on in our society right now is critical because the media itself is failing to do that.
The politicians, like every institution is failing to do this. What can actually cut through all of that and deliver the truth? To me, it is satire.
And the power of satire is you can float above it all. Right.
You think of Spy Magazine. I just heard Graydon Carter who created that.
And they're the ones that coined Trump's famous description, which is short-fingered Bulgarian, which still works today. But if you think about it, I think our job is actually not...
You said it's funny to people on the left. Very specifically, we are not trying to be a leftist satire.
No, you make fun of everybody. You do.
We do, but what we really want to be is floating above, looking down at this system that we're all in, where, you know, Zuckerberg makes more money when we hate each other. And looking at this and be like, how did we get here? Like what went wrong at many steps along the way that this is where we are.
We hate our neighbors. We're unwilling to hear opinions we disagree with.
We are rage clicking, rage voting,-voting, everything. How do we get back to a more civil society? Where everybody can laugh about something.
Where we can laugh about things and we can actually see eye to eye with friends and family who don't agree with us on everything, but we can see them as human beings. Right.
And you do do topics, too. When there's a mass shooting, The Onion posts the same headline, No Way to Prevent This says, Only Nation Where This Regularly Happens.
The paper has run the headline 38 times, which I think to me is much more powerful than any number of editorials. I'm going to do a lightning round because I think it's very serious topics.
People don't realize how serious some of this stuff is when you're doing it, but it is hidden in humor, which is often some, you know, Mark Twain.

We have a history of this in this country.

And by the way, I'll say before you go into it,

The Onion, one of the things that's great

is that our office in Chicago,

we've got back archives of all the old papers.

And it's just so amazing to pull out random ones

over like a 30-year history and just read random.

And it's amazing how often The Onion got it right.

You know, on the eve of the Iraqi war in 2003,

they had a point counterpoint.

And the point counterpoint was, point,

invading Iraq will create a generation of terrorists

and chaos in the Middle East versus, no, it won't.

Sounds like the Los Angeles Times today.

So that guy, go buy that, please.

Go buy that billionaire, because that guy's insane.

And he's going to be a good one. Sounds like the Los Angeles Times today.
So that guy. Go buy that, please.
Go buy that billionaire because that guy's insane. Anyway, let's do a lightning round about the onions business.
Fast answers, please. How much did you pay for it? A few million.
Like how many? It's complicated. Okay.
How big is the staff? I'll let you go. Now about 25.
25. What are the different revenue sources and what's the rough breakdown per category? Almost entirely now subscription revenue from memberships.
Memberships. What do they cost? $99 a year.
Okay, great. I have one myself.
Thank you, Carol. What's good? It's a good product.
If it wasn't, I'd totally dump you. What's your revenue goal for this year? We want to break even and I think that's about, no, actually I just gave them permission to lose money because there's more important work we have to do.
Our revenue goal is probably about $4 or $5 million. Okay.
When do you expect to turn a profit then? You said it's okay not to this year. Originally, our goal was this year.
We said, because we took our revenue to zero when I bought it. It was a website with awful ads and bad content.
Bad experience. The last owner was like, just create things that do clicks.
So it was all slideshows. And we just started over.
We told the writers, write whatever you want. We're going to get rid of all these awful ads on the website.
It's a clean website. The load's fast.
Amazing this, it actually works on mobile now. And we said, we're going to replace all that horrible, low-quality revenue with memberships.
When we write things that our readers like, they will pay us. The simplest business model in the world.
Would you mind losing money indefinitely? But what I asked them is I said, let's get, we need to get to break even and as long as we break even we are fine. I don't expect this is ever going to make a ton of money.
I'm not going to get rich. One of the things, oh, sorry.
I already am. But the thing is I said I'm not doing this because I want to flip it.
Because so many owners came through with the onion and said, you know, I'm going to make something, we're going to grow it, grow it, and then we're going to flip it and sell it and make a bunch of money. I was like, that's not why I bought the onion.
I bought the onion because I want to own it for the rest of my life. Right.
And I want it to be amazing. And our ability, whatever we can do here, is limited by how much revenue we bring in because we can spend it.
As long as we're break even, I and it has to it has to at least break even i say that to people all the time it has to make money or break even because then you're a charity and i told it actually to the staff to the leadership i said look you want to be break even because you don't want to be dependent on me right to be like yeah i'll write you another check you don't want to be like oh jeff's having a bad day suddenly he doesn't want to agree you want to you want to own your fate, and therefore, being break-even is the best thing that you can do. But I did tell them, look, we were going to break-even this year.
And I said, I think we've got more important work to do this year based on the politics of what's going on. And so I committed to them a certain amount of money, and I said, let's do what we need to do.
Yeah, I always say that to media entrepreneurs who are talking about. I'm like, I say you have to make money because then a lot of times when I was working for the journal, when I had a thing inside and it made a lot of money, and they'd come to me, and I'd go, go away, I'm making money.
Yeah, right. And they'd be like, but, and I'm like, get the fuck away from me, right? And you can't do that unless you're making money.
You've got the power of that. I do.
That's my favorite power is saying fuck you to people. When I'm making money, go away, take your check.
Now leave me alone. Exactly.
It's my favorite part of my job. Now I own all my stuff, so I say it to myself.
So you recently brought back the print edition of The Onion. That's kind of fun.
It's made headlines. What's the strategy? Back to basics, right? So we said we're going to do two things here.
Number one, there's a lot of people who today are actually older. They're in the 30s, 40s, 50s, who grew up with The Onion, the print edition, and that's the Onion they remember, and we're going to give it back to them.
In exchange, they're going to give us $99 a year. That's what we're going to make a revenue model.
Now, there's a younger generation who didn't grow up with it, doesn't know The Onion as a print paper because they killed the print edition about 10 years ago. For those people, we are going to use the revenues and the profits that we make to reinvest back in other forms of media that will probably resonate more with a younger audience.
Because how many people here who are, let's say, under the age of 30, read the New York Times? Oh, I know. Actually, Sprite, well, they're in a political science program.
I don't know. But like, I did this, I question in another student setting, and one person raised their hand.
So our product is a parody of the New York Times, which young people aren't reading. Our other product is the Onion News Network, a parody of CNN, which young people are not watching.
So we need to develop new properties that will actually satirize the media that young people, especially today, are consuming. And that's what leads us to InfoWars, actually.
All right. So you famously tried to buy InfoWars at a bankruptcy auction, but a federal bankruptcy judge rejected the offer after you'd won.
Explain that. And why did the judge reject your offer? And do you think you'll eventually succeed? And will Alex Jones be your employee? No.
Obviously, there's performative and meme-iness to it. And fun.
It's fun. And it drove him crazy, which is always pleasing to me because he's the worst person on the planet right now.
There is something karmic justice going on here. I mean, partially we did it because as a stunt, nothing is funnier than the fake news thing buying the fake news thing.
It's such a karmic joke that you had to do it. Right.
But second, the way we thought about it from a business standpoint was if we need to develop new properties that are going to be relevant to today's generation of Internet consuming media, media consuming on the Internet people. what that's going to look like to us is something that is satire of the bigger than life blow hard

people who will say and do anything to get a follower and then sell something to make a buck. Like that's the internet.
And so who better represents that than Alex Jones? And so a starting point for that venture would be the Infowars brand. Yeah.
Right? Because it stands for exactly like the worst of the internet. Yeah.
I've got so many choices for you. I'll help you on that one.

So stay tuned.

We will be launching something soon,

regardless of if we end up with InfoWars or not. And I'm hopeful that we will.

We will be launching a satirical product

in a matter of months here

that is the foundation of that.

Yeah, there's a lot of trouble over at The Daily Wire.

There's so much you could go for.

You know, there's a lot of things you could do.

You could just parrot it.

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But there's huge upheaval at universities. Harvard is being targeted now.
Columbia was targeted. Twilio and Michium are both the forefront of DEI.
You committed to making Twilio anti-racist in 2021, and Michigan has roughly spent a quarter billion dollars on DEI since 2016. Now it's scrubbed from your website.
Michigan is eliminating these programs. How do you, if organizations want to stick with these, I think they used to be called values, really, to go about it during this crackdown.
How do you do something? And University of Mission President Santo Ono met with Michigan lawmakers in March and told him universities have to wake up and listen to their most vocal critics. President Trump is probably the most vocal critic of all.
He's threatening to cutting these funding to 45 universities, including this one. Columbia University compromised, as these law firms are doing, to get funding restores.
And a lot of people find that critical. So how should, if you were running this school, they react? You're now the head of University of Michigan.
You know, I was thinking about this a lot because I think DEI is obviously very well intentioned. That's where it started.
And then it started going further and further and further. And somewhere along the way, like, we lost people's hearts and minds in terms of going along with it.
And so the question is why? Because I think even the most ardent people on the right are not like, yes, there are a lot of people who are racist and anything, but there's a lot of people who voted for Trump who would agree in principle with like, yes, I believe people should have opportunities and there are wrongs in the history of our country and the world and there's things we can do to make the world better and all that. But then you lose them.
I saw this happen actually at Twilio at times because we had a company that was very invested in DEI. But I saw when you started to bring in certain hiring practices, you got people who were champions, but they'd start to intellectually, they'd be like, but I don't understand how it's legal or right to like advantage someone who is uh underrepresented over someone who isn't because of that like isn't that equally wrong like i saw good people really try to square that and i think that there is truth like that is like you know you can see how well-intentioned people who can and should be allies of this movement get tripped up in the logic of it.
And so what I think happened to me, which is I remember like, you know, DEIs have many names over the course of the last 10 years. And, you know, first was diversity and inclusion and all this.
And then, you know, equity came in and that's the E. And like, I don't think a lot of noticed when equity came in, and we understood what equity stood for.
And I think that's the thing that has triggered a lot of folks who now are anti-DEI, because they're like, well, wait a minute. That's where we cross the line.
That's where someone else gets something that I don't. And that's the part that I'm really struggling with here.
And so one of the things that I noticed, and I came to this realization that it's the E is really what we're talking about here. Because, look, I don't control Twilio's website anymore.
I have no role at Twilio anymore. But I was curious, what would I do if I was running the company today? So I went to Tesla's website, to the hiring website.
I'm like, what are they saying? And it's interesting. They have a diversity page.
And it's all about how diverse the workforce is. And it's all about how inclusive the workforce is.
All this stuff. But it's just no equity.
Right? So diversity and inclusion is something a vast majority of people, I think, can get behind. It's when you introduce the equity part.
And if you don't do it well and you don't do it thoughtfully, that's where we lose allies that we could have. Because that's where you start to say, oh, but I'm so uncomfortable with that idea.
I don't know how that works. Unless you have like really good answers that put that question to bed, you lose people.
And I saw it happen. So what would you do? What would I do if I was running Michigan? I think it would be okay to admit that equity is really hard concept for a society to get right.

Right?

Because, you know, it's incredibly complicated.

I think everybody wants diversity.

Everybody wants inclusion.

But equity means someone gets something and I don't get something or vice versa.

Like, that's where you start putting each other against each other.

And that's where it gets really complicated.

And so I think it would be okay to say, you know what? We were doing diversity, inclusion, inclusion, diversity inclusion, diversity equity inclusion. And we just kind of kept going.
And we assumed everybody was along for that ride. And I think that was incorrect.
I don't think everybody was necessarily along for that ride. Or it was executionally done wrong.
Here's what I'll say. I'll give you an example from my experience at Twilio.
We started doing these videos during our all hands. And the videos were like, you know, meet groups of people at Twilio.
And it'd be like, the Filipino Twilios would give a, we'd do a little short one minute video about Philippine culture, right? And they were really nice and they took like a minute, it was fantastic. And usually I never even saw them before the all hands.
But we were preparing for an all hands and the day before this all hands, I saw like-up show, and it was like, diversity video, white privilege. And I was like, ooh, I wonder what that's about.
And I watched the video, and it was a very great person who was a great employee of Twilio, very well-intentioned, who had agreed to do a video talking about his privilege as a white man. And I believe this was all very well-intentioned.
but can you but i pulled the plug on it because I think sitting in a company setting in an all hands environment, your company with obviously way too much of a percentage of the company being white men, way too many people in the company being basically told you're, it's your fault. That's not going to end well.
That's not how you're going to win allies. Right.
And you know, some people may feel that, but you're not going to do any help. You're not going to help move this movement along by alienating a huge group of people that you want to be your allies.
And being told in a video, which is like, this was during the pandemic, everyone's sitting at home, so you have no one to talk to. So all you have to do is watch this video, be told that you're the problem.
And then what do I do? Like turn to Slack and go yell on Slack. Like this was not the right way, in my opinion, to try to create allies in this world.
And I just think that's the hardest part. And I don't know.
I'm sure some people may agree. Some people disagree with that.
But if the goal isn't to shame and wag fingers and cancel people, but the goal is actually to make progress in our society, then I think you do have to really moderate about who's my audience. How do I bring them along emotionally and intellectually on this? And I think that's where some parts of the movement failed and we're getting increasingly finger-pointing and wagging and all this kind of stuff in a way that the backlash was probably inevitable.
Right. No, I get it.
I understand it. The only things I push back, well, I tried a few things, but the one I would push back in is being finger-wagging and irritating, which, believe me, I get plenty of shit on that on lots of reasons.
Because as a lesbian from San Francisco, they expect me to have a certain point of view, which I don't all the time. But and especially I get a lot of problems because Scott Galloway makes penis jokes and people think I should be offended, but I'm not.
He can do them all day if he wants. But one of the things that I always push back on is that it's, well, the left may be censorious and irritating.
The right actually bans books. The right actually, you know, and that's really a very big difference.
And I think bad execution is one thing, but directionally correct is how, and including people. If you're for inclusion, then include everybody.
I think that's what you're saying, which I think is 100% right. But I think what we really need to do is win hearts and minds.
Like that's how you create change. That's how you include people.
That's the word of inclusion. And I think it's important even if people...
You're applying inclusion to the process of... Yes, including.
So last question. I'm going a tiny bit long because you're really interesting, actually.
I wasn't surprised. I'm teasing.
In the worst case scenario... That's the highest praise that has ever been granted by Kara Swisher.
Yes, it's true. The Onion gets outlawed by Trump during his third term.
If that happens, how do we keep making fun of authoritarians? Are you ever nervous about that? I was thinking about that with Laureen Powell Jobs in the Atlantic because they've done two very tough articles on Trump. I'm sure they're getting, I know they're getting incoming.
Do you worry about that at all? What I told the team was at first- Plus you give money. Reid Hoffman's under siege by these people.
What I told the onion is, what I told the leadership there is, we have to do what we have to do. Our calling is not to be anti-Trump, by the way.
We're not, like people said, oh, resistance media. We're not resistance media.
We just need to call out bullshit when we see bullshit. Always and forever on any side.
They were brutal on Sch Schumer. And, you know, even just last week,

they had Pelosi and Schumer saying next to each other,

you know, Democrats debate

how best to blow this opportunity as well.

Like, you know, and it was like,

and I said, we have a job to do,

which is to cut through and deliver truth

as best we can to people.

And it's more important than ever. And if what's, and I asked him, what's the worst thing that can happen? And if the worst thing that can happen is, you know, the administration sues the onion out of existence.
Well, that's still better than private equity ruining it. Right.
Like, like if that's the worst thing, but I've got your back. I will defend you.

Like I'm here to make this publication successful.

But if for some reason I can't do that, like this is the worst thing that would happen. Like there's worse things in the world.
Oh, and by the way, I believe and we have worked to create a environment where people will come to defend us. Right.
In a way that they don't necessarily come to defend the New York Times. Because it's believed that New York Times can defend itself.
It's a big organization. The Little Old Onion, when you go after satire and it shows just how small, I'm going to make a penis joke, just how small your penis is when you come after satire, I think people rise up and they say that's enough.
Like we're going to defend this little thing called the Onion because satire is highly protected speech. And the Onion is a beloved brand and a beloved publication.
Well, Jeff, thank you so much. And you see why I really

like them. Thank you.
Thank you, Cara. Thank you all.

On with Cara Swisher is produced by Christian Castor-Russell, Kateri Yopam, Dave Shaw, Megan

Birdie, Megan Kunane, and Kaylin Lynch. Nishat Kirwa is Vox Media's executive producer of audio.

Special thanks to Annika Robbins. Our engineers are Rick Kwan and Steve Bone, and our theme music is by Trackademics.
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