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

Last year, after pressure from activist investors, Jeff Lawson stepped down from his perch as CEO from Twilio, the cloud communications company he co-founded. But he didn’t spend any time twiddling his thumbs — that same spring, he bought the satirical news organization The Onion, and by the end of the year, they’d tried to buy Alex Jones’ Infowars at a bankruptcy auction. Jeff also stayed busy on the political front, continuing his work on DemocracyFirst, a political action committee he co-founded, in 2022, to support candidates committed to democracy. So there was plenty to chew on when Kara interviewed Jeff last week at Democracy’s Information Dilemma, a symposium hosted by the University of Michigan’s Gerald R. Ford School of Public Policy. They discuss the tech founder mindset; how Jeff is remaking The Onion; why political satire is more necessary than ever; why DEI — which Jeff championed as a CEO — can sometimes do more harm than good; and how to fight for democracy during Trump 2.0. Questions? Comments? Email us at [email protected] or find us on Instagram, TikTok, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:11Kara Swisher?

  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 cofounded in 2022 that donates money to candidates from both parties that are committed to democracy.

• 0:52Kara Swisher?

  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, so stick around.

• 1:29Speaker 01

  Support for the show comes from Engine. Running a small business means every dollar has to work hard, but if your team is still booking travel the old way, it's costing you more than you think. Engine is the fastest-growing travel and spend platform in the country, built specifically for businesses like yours. Book a trip in as little as two and a half minutes, earn up to 10% back on hotels. And in 2025, Engine customers save more than $300 million on travel with zero booking fees, no contracts, and no BS. More than 1,000 businesses join Engine every month. Join them and get $500 when your business signs up and starts traveling at engine.com/vox.

• 2:14Speaker 02

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• 2:57Speaker 03

  I'm Josh Muccio, host of The Pitch, where startup founders raise millions and listeners can invest. For our sweet season 16, we're giving you more of what you love and less of what you don't. Software is out. Actual cool stuff is in. We've got consumer brands, deep tech that changes the weather. Our big vision is to make it rain and snow on demand. We've got hardware that helps blind people see and dairy. I never imagined my life journey would be milk. Season 16 of The Pitch is out now. Listen wherever you get your podcasts. This season is presented by Engine.

• 3:37Kara Swisher?

  Jeff, thanks for joining me in this conversation at the University of Michigan, where you are an alum.

• 3:43Speaker 04

  Indeed.

• 3:43Kara Swisher?

  So let's get into it. So let's talk a little 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.

• 4:06Speaker 04

  Absolutely. Well, I showed up to college undergrad in the fall of 1995, and the internet was brand new, like the commercial internet was really just coming about. And 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 know, 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, FTP'd down a copy of Netscape Navigator 1.0 and started using the web. And you know, a lot, most of the web was like these static webpages about people's, you know, job or their favorite pet or whatever. And then you had these websites where you could do something.

• 4:50Kara Swisher?

  Right. There were few and far between. For people that don't know, the very, one of the very first early internet sites people looked at was people making coffee.

• 4:57Speaker 04

  It was like a webcam on a coffee maker, yeah.

• 4:59Kara Swisher?

  It was a webcam on a coffee maker, and that was...

• 5:01Speaker 04

  Very exciting at the time, right? Like, oh my god, someone's drinking coffee.

• 5:04Kara Swisher?

  It wasn't exciting at the time, but nonetheless. So go ahead. This was important for people to understand.

• 5:09Speaker 04

  But you're like, how do they do these amazing things? Like, how, if I wanted a coffee maker cam, I would... 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, just commit yourself to doing it, and then you have to go do it, right? So tell someone, tell a customer you're gonna go do a thing. And for us, we said, we're starting this company. Great. How do we do this? Or what, 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're 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

• 5:54Speaker 04

  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 this 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 notesnumber4free.com.

• 6:15Kara Swisher?

  Wow.

• 6:16Speaker 04

  Brilliant marketers we were.

• 6:17Kara Swisher?

  No, not at all.

• 6:18Speaker 04

  Notes, we could have had google.com. We could have had like anything was available at that point. Notes number four free, which then later turned into it to versity.com. But it was this excuse to start playing with the internet. So we built this site, and we hired, you know, a lot of our friends to start taking notes in the lectures they were in and posting them on things.

• 6:35Kara Swisher?

  Which you did in analog style, correct, and then uploaded them.

• 6:38Speaker 04

  Well, they, 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... Yes, one 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 the content management system, even though it wasn't called that.

• 6:55Kara Swisher?

  So you were automating, you were automating a process that had been analog.

• 6:58Speaker 04

  Basically, because yeah, in the old way, it was here's my a piece of paper with my notes. And they would 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 from 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, like, 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.

• 7:37Speaker 04

  So we had the classic like dorm room to we were worth 150 million to we're worth nothing again, all in like 18 months. Like the whole story. And in some ways, I I feel very lucky in some ways that I had multiple starts at entrepreneurship before actually Twilio was the one that worked.

• 7:57Kara Swisher?

  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. Let's talk about your history and explain why you left, which is another typical thing. This is not a, things happen like this with entrepreneurs a lot.

• 8:24Speaker 04

  Yeah, you know, I left not by my choosing. The board thought that avoiding a fight with the activists was the right thing to do. And so I was fired. 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.

• 9:01Kara Swisher?

  Right.

• 9:01Speaker 04

  To avoid this outcome. So somehow I screwed up.

• 9:04Kara Swisher?

  Right.

• 9:05Speaker 04

  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 have 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.

• 9:51Speaker 04

  And that took me by surprise. And the fact that that took me by surprise was a very big mistake.

• 9:56Kara Swisher?

  Well, I think 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. Explain for people who don't know what Twilio does.

• 10:09Speaker 04

  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, you know, 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 had 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

• 10:53Speaker 04

  them. I think that's just like, that's the mysteries of the cosmos, how text messages arrive. So started a company to solve that problem. So grew it from that idea in 2008 through about $4 billion in revenue. And you know, at our peak, we had about 10,000 employees. And so really, you know, a wild ride, but you know, unlike the dot com era, building real value, building a real company with real revenue and a, you know, in the B to B space, right? Selling to other companies, but also with this sort of B to C idea of like 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.

• 11:32Kara Swisher?

  That's correct, yeah.

• 11:32Speaker 04

  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 for entrepreneurs in the room, it also goes to show you, like, you work hard and all this. But, you know, 75% of it's luck and timing and all that kind of stuff.

• 11:48Kara Swisher?

  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've been, you haven't founded a new startup. Talk about your relationship with the tech industry now that you have some distance from it.

• 12:13Speaker 04

  You know, it's interesting.

• 12:13Kara Swisher?

  Where do you live?

• 12:14Speaker 04

  San Francisco.

• 12:15Kara Swisher?

  Okay, all right, good.

• 12:16Speaker 04

  That sounded so accusatory.

• 12:18Kara Swisher?

  No, it's not. I'm just like, I, I still have my house in San Francisco. I was just there last week.

• 12:24Speaker 04

  Sorry, what was the question?

• 12:25Kara Swisher?

  What are you doing? What are you doing? What, what are you doing in tech? Why didn't you start a new startup? I suspect you've had money thrown at you, presumably.

• 12:32Speaker 04

  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, 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 going to do is just let myself go do all those things. All the 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 would be a great business or I wanted to run that business. I just was like, can I do this? That was kind of fun.

• 13:17Speaker 04

  And then part of it was, okay, I love mentoring young teams, young founders, management, young management teams. And so I opened up a garage where I do all my building. And I said, 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, so I did that. It's called the Founder's Garage and partnered with Bessemer, a venture capitalist, and Y Combinator, and OpenAI, and a few others

• 14:02Speaker 04

  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.

• 14:37Kara Swisher?

  So we're going to talk about a number of those things. In 2022, you and your wife, Erica, founded a PAC called 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?

• 14:52Speaker 04

  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, and so, you know, we started doing like a typical, we were very apolitical. We, you know, we gave a little bit to 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,

• 15:33Speaker 04

  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 the tenants of democracy. And when that didn't happen, because they would have had to abolish the filibuster to pass it and they didn't.

• 16:20Speaker 04

  We kind of had this, oh shit, we're gonna 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 our 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 gonna bring cases or not of 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 and each of these states that that matter here.

• 17:05Speaker 04

  Are there going to be rational believers in democracy of either party? Or are you gonna crazy people?

• 17:13Speaker 04

  Who don't want to uphold democracy, they just want to see their party in their ideology way.

• 17:17Kara Swisher?

  Right, plot spoiler, go ahead.

• 17:19Speaker 04

  And and so we said, we're gonna work really hard in a bipartisan way. Just to make sure that the the people who believe in rule of law are gonna sit in these seats when the election comes around. And so that's where we started working on the all these things. And, you know, we didn't know about most of these, I mean, nobody knows about half these elections that go on.

• 17:35Kara Swisher?

  And at the time, nobody knew Trump was coming back. He was sort of down in Mar-a-Lago hiding for for a short time.

• 17:41Speaker 04

  Sure, but like, you know, you don't. Play with fire, as I often tell my sons, you know, like, you know, you can light the match for the hundredth time, and that's when you burn yourself.

• 17:48Kara Swisher?

  Right.

• 17:49Speaker 04

  And so.

• 17:50Kara Swisher?

  So how much money did you put into it, and which, how did you decide of 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.

• 18:30Kara Swisher?

  And they did it quietly before, but not quite in this hyper, amplified and hyper way.

• 18:36Speaker 04

  Yeah.

• 18:37Kara Swisher?

  These are sleepy state races, like a judge in Wisconsin that become, I think, Wisconsin's $90 million spent.

• 18:45Speaker 04

  Yeah. It's, um, 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.

• 19:28Speaker 04

  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 Elon's money.

• 19:54Speaker 04

  And what does Elon's money mean? Is it, 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

• 20:10Kara Swisher?

  Right.

• 20:11Speaker 04

  to more people than it is a benefit to the person who, who, who is

• 20:15Kara Swisher?

  Who's getting it, meaning politically toxic, you mean?

• 20:18Speaker 04

  Politically toxic, yes.

• 20:20Kara Swisher?

  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 has, is, because he's standing next to him, when in fact, he's quite a unpleasant person to look at in many ways.

• 20:43Speaker 04

  I won't speak to his physical attributes.

• 20:46Kara Swisher?

  Don't look at that picture, don't take. That cheese head was bad. It was, it reminded me of the Dukakis helmet. I was like, ooh.

• 20:52Speaker 04

  Oh geez, yes.

• 20:53Kara Swisher?

  Ouch. There, I was being bipartisan. That was a bad picture, too.

• 20:57Speaker 04

  Yeah, if you're a politician, just don't put things on your head.

• 20:59Kara Swisher?

  No.

• 21:00Speaker 04

  Yeah.

• 21:01Kara Swisher?

  Unless you're Gavin Newsom, he'd have looked good in the cheese head. But go ahead.

• 21:04Speaker 04

  I just think most people cannot relate to Elon Musk. Therefore, his standing up there trying to lead doesn't necessarily work. And what's interesting is he's used to, I'm sure, leading a bunch of like, tech people.

• 21:22Kara Swisher?

  Who revere him.

• 21:24Speaker 04

  Who revere him and who get their paycheck from him.

• 21:27Kara Swisher?

  Mm-hmm.

• 21:28Speaker 04

  So he's standing up in front of an all hands at Tesla or SpaceX or whatever, and he gets this, you know, certain response from them.

• 21:33Kara Swisher?

  Also on Twitter, same thing.

• 21:35Speaker 04

  And on Twitter, yes, good, good point, right? It's the people who've already opted into liking him that gives them that adoration and therefore has rewarded him for being Elon. But now you go out in front of a, an average group of people in Wisconsin or on the news, everybody, and you see that approach is a turn off 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 Alon 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, he brings this out in a very visceral way, I think, in enough people. And that's what, that's what the big test was. Are there enough people to look at this

• 22:20Speaker 04

  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.

• 22:34Speaker 04

  We'll be back in a minute.

• 22:43Speaker 01

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• 25:38Kara Swisher?

  That's forhers.com/kara. Individual results may vary, and stopping treatment may result in weight regain. 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 Marc Benioff, who was known for his social activism and who you called one of your heroes. I have a long relationship with Marc, and lately I've been sending him kind of irritating texts to him, but I like them.

• 26:18Kara Swisher?

  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.

• 26:28Speaker 04

  Yeah, trophies.

• 26:30Kara Swisher?

  You know, 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 that theory? Because it's sort of, you break down these pillars that you're talking about.

• 26:53Speaker 04

  Well, that's exactly the problem, right? We think that there are all of 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

• 27:32Speaker 04

  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, and January 6th was the best example of it, which was a very extreme event, of an anti-democratic event. And not only were there no consequences for it, the perpetrator was rewarded with another term in office.

• 28:08Kara Swisher?

  Right.

• 28:08Speaker 04

  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, you know, put your responsibility as a citizen arguably ahead of your responsibility

• 28:53Speaker 04

  as a CEO? You have a fiduciary responsibility to your shareholders, yes. Trump has a responsibility to uphold the Constitution.

• 29:00Kara Swisher?

  Right.

• 29:01Speaker 04

  So what do we do about the rule of law? By the way, you don't even have to break the law now to be in trouble with the law, right?

• 29:07Kara Swisher?

  Right.

• 29:08Speaker 04

  Like, when you enter into a lawless world, everything is in question. So can you run a company anymore when, you know, you start to look like a banana republic?

• 29:17Kara Swisher?

  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 US 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.

• 30:01Speaker 04

  A level playing field.

• 30:02Kara Swisher?

  Right.

• 30:03Speaker 04

  Which, by the way, where do level playing fields come from? They come from the rule of law.

• 30:08Kara Swisher?

  Right, right.

• 30:08Speaker 04

  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've... How lucky we are to have a system where in order to get something, you don't 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.

• 30:44Speaker 04

  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.

• 30:53Kara Swisher?

  Right.

• 30:54Speaker 04

  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.

• 31:08Kara Swisher?

  Yeah, I would agree.

• 31:09Speaker 04

  And I, like, I don't know, I remember people asking me, remember there was that tech roundtable when Trump first came to office?

• 31:14Kara Swisher?

  I broke that story. I broke that story.

• 31:17Speaker 04

  You wrote that story? Okay, good.

• 31:19Kara Swisher?

  Yeah.

• 31:20Speaker 04

  So.

• 31:21Kara Swisher?

  I called them sheeple. They didn't like it, but I did.

• 31:24Speaker 04

  I remember people asking me at Twilio, they're like, oh, were you invited?

• 31:26Kara Swisher?

  No.

• 31:27Speaker 04

  Part of it, I was like, well, no, we're not that important. But, uh, but if I was invited, I would not have gone.

• 31:33Kara Swisher?

  Right.

• 31:34Speaker 04

  Because to me, attending and being a part of it is, is an endorsement of like, yes, this process is up, you know, on board, and I want to get me a part of it. And, you know, the excuse people it may cause, well, I'd rather be a part of it than not a part of it.

• 31:47Kara Swisher?

  Right, that's their argument.

• 31:48Speaker 04

  No. We're endorsing what's going on by being a part of it.

• 31:52Kara Swisher?

  One of the, the reason, I broke that story, and the person, 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 gonna, it's not gonna happen. He hates immigrants, and he's racist, and homophobic, etc. And he's like, I can change his mind. But, you know, 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. Um, 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

• 32:34Kara Swisher?

  on immigration, it was built on, 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.

• 33:19Kara Swisher?

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

• 33:22Speaker 04

  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, like, everyone's incentive function in these major institutions that kind of rule our society benefits when we hate each other.

• 34:00Kara Swisher?

  Right.

• 34:00Speaker 04

  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, like, we just create this anxiety and this rage and the, you know, the rush that people get when they're anxious.

• 34:14Kara Swisher?

  There's no what's the solution. The line I had in my book was enragement equals engagement.

• 34:18Speaker 04

  Yes, like, so what's the answer? When, 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 the, whatever, the Rotary Club or church or synagogue or 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 rage-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

• 35:01Speaker 04

  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, 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 win some hearts and minds on the ground.

• 35:19Kara Swisher?

  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.

• 35:31Speaker 04

  I thought Pete should do that. I pitched Pete on that.

• 35:33Kara Swisher?

  Oh, recently unemployed with Pete Buttigieg? Doesn't sound as good.

• 35:36Speaker 04

  Not as good. I was thinking Pete's America.

• 35:38Kara Swisher?

  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, and, and let's talk about the onion now, because I, 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. Washington Post bought by Jeff Bezos, who's a terrible owner right now. Marc Benioff bought Time Magazine. Elon bought X. And you bought the onion. So tell us why the onion

• 36:19Kara Swisher?

  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.

• 36:31Speaker 04

  Well, let me ask you this. If you could own any news source or America's finest news source, which one would you buy?

• 36:40Kara Swisher?

  Well, I'm trying to buy the Washington Post, but he's not calling me back. But, um...

• 36:43Speaker 04

  You know, I remember, because this whole thing started when Bezos bought The Post and Benny Hough bought Time, I started joking with friends, "I'm gonna buy The Onion."

• 36:50Kara Swisher?

  Yeah.

• 36:51Speaker 04

  Because that is, A, proportional to our market caps.

• 36:54Kara Swisher?

  Okay.

• 36:54Speaker 04

  But also, just how the, how the universe should work.

• 36:58Kara Swisher?

  Yeah, okay.

• 36:59Speaker 04

  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, I looked into it a few times over the years.

• 37:05Kara Swisher?

  Yeah.

• 37:05Speaker 04

  And, you know, 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 was 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, you know, really, for three reasons...

• 37:20Kara Swisher?

  You had been calling them. You were like, "I'm interested," yeah.

• 37:22Speaker 04

  Yeah.

• 37:23Kara Swisher?

  I'd like to have it.

• 37:23Speaker 04

  Well, I remember I missed, it got sold from Univision to private equity, and I missed that opportunity.

• 37:27Kara Swisher?

  Yeah.

• 37:27Speaker 04

  I was, oh, when that happened. Why Univision owned it? Again, who knows? Amazing.

• 37:32Kara Swisher?

  Yeah. They owned a lot of things they shouldn't have owned, yeah.

• 37:35Speaker 04

  Uh, and so, uh, the reason for buying, there were basically three reasons. Uh, first was, you know, I started looking into it, because it started as a joke, but I was like, "Actually, that'd be kinda cool. I've been a longtime fan of The Onion." Um, and when I started looking into it, I realized it wasn't buying The Onion, it was saving The Onion.

• 37:53Kara Swisher?

  Mm-hmm.

• 37:53Speaker 04

  Because it was in a death spiral. Um, first of all, I mean, the whole media world has obviously been struggling for the past, you know, ten years.

• 38:00Kara Swisher?

  Some of it.

• 38:01Speaker 04

  Everyone, except for you, Kara.

• 38:03Kara Swisher?

  That's true. There's a lot of very good media entrepreneurs right now, who are doing very well.

• 38:07Speaker 04

  But the last ten years have been tumultuous for the media.

• 38:09Kara Swisher?

  For the big companies, certainly. Yes.

• 38:11Speaker 04

  Yeah. Um, and then, add on top of that, to be owned by private equity, whose goal is to extract cash.

• 38:17Kara Swisher?

  Right.

• 38:18Speaker 04

  From the entity, while it is shrinking. It's just layoff after layoff after layoff. And, and, and so, it was, um, it was basically on life support.

• 38:28Kara Swisher?

  Mm-hmm.

• 38:29Speaker 04

  And so, it became saving it, which I thought was important, because I thought it's an institution the world needs.

• 38:34Kara Swisher?

  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.

• 38:39Speaker 04

  There's a bizarre arbitrage.

• 38:40Kara Swisher?

  And he's since brought it down to $125 million. Um, so...

• 38:43Speaker 04

  Well, there's a bizarre arbitrage, by the way, from tech to media, which is that the, the valuations of tech firms... versus media firms is huge, except the influence of media versus tech is also huge. You can take your tech money and buy influence on the media side, and it's actually a fairly good play.

• 39:00Kara Swisher?

  Yeah, it is interesting. Hence Twitter being pulled into XAI because it 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.

• 39:43Kara Swisher?

  And your CEO, Ben Collins, is a former disinformation reporter. He 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.

• 40:06Speaker 04

  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, 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

• 40:51Speaker 04

  is amazing. We have followership.

• 40:54Kara Swisher?

  Mm-hmm.

• 40:55Speaker 04

  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.

• 41:10Kara Swisher?

  Mm-hmm.

• 41:11Speaker 04

  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, the power of satire is you can float above it all.

• 41:28Kara Swisher?

  Right. You think of Spy Magazine, I just heard Graydon Carter, who created that, and he, they're the ones that coined Trump's famous description, which is "short-fingered vulgarian," which still works today.

• 41:38Speaker 04

  But if you think about it, like, I think our job is actually not, you said it's funny to people on the left.

• 41:44Kara Swisher?

  Right.

• 41:45Speaker 04

  Very specifically, we are not trying to be a leftist satire.

• 41:49Kara Swisher?

  No, you make fun of everybody, you do.

• 41:51Speaker 04

  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.

• 42:00Kara Swisher?

  Mm-hmm.

• 42:01Speaker 04

  And looking at this and being like, how did we get here?

• 42:03Kara Swisher?

  Mm-hmm.

• 42:04Speaker 04

  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, everything. Like, how do we get back to a more civil society?

• 42:17Kara Swisher?

  Where everybody can laugh about something.

• 42:19Speaker 04

  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 you know what, we can see them as human beings.

• 42:26Kara Swisher?

  Right. So, 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.

• 42:34Speaker 04

  Yeah.

• 42:35Kara Swisher?

  The paper has run the headline 38 times.

• 42:37Speaker 04

  Yeah.

• 42:38Kara Swisher?

  Which I think, to me, is much more powerful than any number of editorials. I'm gonna do a lightning round of, of... Because I think it's very serious topics. People don't realize how serious some of this stuff is, you know, 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.

• 42:56Speaker 04

  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.

• 43:26Kara Swisher?

  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 Onion's business. Fast answers, please. How much should you pay for it?

• 43:43Speaker 04

  A few million.

• 43:44Kara Swisher?

  Like, how many?

• 43:46Speaker 04

  It's complicated.

• 43:47Kara Swisher?

  Okay. How big is the staff? I'll let you go.

• 43:50Speaker 04

  Now about 25.

• 43:51Kara Swisher?

  25. What are the different revenue sources and what's the rough breakdown per category?

• 43:54Speaker 04

  Almost entirely now subscription revenue from memberships.

• 43:57Kara Swisher?

  Memberships. What do they cost?

• 43:59Speaker 04

  $99 a year.

• 44:00Kara Swisher?

  Okay, great. I have one myself.

• 44:02Speaker 04

  Thank you, Kara.

• 44:03Kara Swisher?

  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?

• 44:09Speaker 04

  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 four or five million.

• 44:18Kara Swisher?

  Okay. When do you expect to turn a profit, then? You said it's okay not to this year.

• 44:23Speaker 04

  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.

• 44:30Kara Swisher?

  Bad experience.

• 44:31Speaker 04

  The last owner was like, just create things that do clicks. So it was all slide shows. And we just started over. We told the writers, write whatever you want. We can get rid of all these awful ads on the website. It's going to clean website, it loads 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.

• 44:53Kara Swisher?

  Would you mind losing money indefinitely?

• 44:55Speaker 04

  But what I asked them is, I said, let's get, we need to get to break even, and as long as we're 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...

• 45:10Speaker 04

  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 some, we're going to grow it, 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.

• 45:25Kara Swisher?

  Right.

• 45:26Speaker 04

  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'm happy.

• 45:33Kara Swisher?

  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.

• 45:39Speaker 04

  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"

• 45:47Kara Swisher?

  Right.

• 45:47Speaker 04

  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 write a check." 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, like, "Look, we are 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, you know, "Let's, let's do what we need to do."

• 46:08Kara Swisher?

  Yeah, I always say that to media entrepreneurs who are talking. I'm like, "You got to, I say you have to make money." Because then, you know, a lot of time, 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."

• 46:20Speaker 04

  Yeah, right.

• 46:21Kara Swisher?

  And they'd be like, "But..." And I'm like, "Get the fuck away from me," right? And then you can't do that unless you're making money.

• 46:26Speaker 04

  You've got the power then.

• 46:26Kara Swisher?

  I do, that's my favorite power, is saying, "Fuck you" to people. And I'm making money, go away, take your check, now leave me alone.

• 46:33Speaker 04

  Exactly.

• 46:34Kara Swisher?

  Is my favorite part of my job.

• 46:37Kara Swisher?

  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?

• 46:47Speaker 04

  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 their 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. And in exchange, they're going to give us $99 a year.

• 47:03Kara Swisher?

  Right.

• 47:03Speaker 04

  That's how we're going to make a revenue model. Now, there's a younger generation who didn't grow up with that, doesn't know The Onion as a print paper, because they killed the print edition about 10 years ago. And 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?

• 47:27Kara Swisher?

  Oh, I know.

• 47:28Speaker 04

  Actually, well, I'm in a political science program. I don't know. But like, I did this, I asked that question in another student setting, and one person raised their hand, right? 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, right? So we need to develop new properties that will actually satire the media that young people, especially today, are consuming, and that's what leads us to Infowars, actually.

• 47:54Kara Swisher?

  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, it's, it, obviously, there's performative and meminess to it, and, 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.

• 48:20Speaker 04

  I mean, partially, we did it because, as a stunt, it, nothing is funnier than the fake news thing, buying the fake news thing. Like, it, it, it's such a karmic joke that you had to do it.

• 48:32Kara Swisher?

  Right.

• 48:33Speaker 04

  But, second, it, it, 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, you know, 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, blowhard, 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?

• 49:03Kara Swisher?

  Yeah.

• 49:04Speaker 04

  And so, a starting point for that venture would be the Infowars brand.

• 49:06Kara Swisher?

  Yeah.

• 49:07Speaker 04

  Right? Because it stands for exactly, like, the worst of the internet.

• 49:10Kara Swisher?

  Yeah, I've got so many choices for you. I'll help you on that.

• 49:13Speaker 04

  So, stay tuned. We will be launching something soon, regardless of if we end up with Infowars or not.

• 49:18Kara Swisher?

  Yeah.

• 49:19Speaker 04

  And I'm hopeful that we will.

• 49:20Kara Swisher?

  All right.

• 49:21Speaker 04

  We will be launching a satirical product in a matter of months here that is the foundation of that.

• 49:26Kara Swisher?

  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, and you could just parrot it. We'll be back in a minute.

• 49:47Kara Swisher?

  Support for this show comes from Indeed. When the pressure's on and you need to hire the right person for the job, Indeed Sponsored Jobs has got your back. Instead of forcing you to spend tons of time searching, Indeed Sponsored Jobs matches you with quality candidates fast. According to their data, sponsored jobs posted directly on Indeed are 95% more likely to report a hire than non-sponsored jobs. Join the 3.3 million employers worldwide that use Indeed to connect with quality talent that fits their needs. Spend less time searching and more time actually interviewing candidates who check all your boxes. Less stress, less time, more results. When you need the right person to cut through the chaos, this is the job for Indeed Sponsored Jobs. And listeners to the show will get a $75 sponsored job credit

• 50:32Kara Swisher?

  to help get your job the premium status it deserves at indeed.com/podcast. Just go to indeed.com/podcast right now and support our show by saying you heard about Indeed on this podcast. That's indeed.com/podcast. Terms and conditions apply. Need the right hire fast? Then this is the job for Indeed Sponsored Jobs.

• 50:59Speaker 02

  Support for the show comes from TikTok. There is a scientifically documented correlation between listening to podcasts and curiosity. So since you're here, you probably enjoy discovering new things. One great place to indulge your curiosity is TikTok. Whether it's how to forecast volcanic eruptions, strange phenomena that the James Webb Space Telescope picked up near the beginning of time, or a literal deep dive on the ocean's deepest reefs, TikTok has a wealth of fascinating videos just waiting to be discovered. Your next discovery is waiting on TikTok. Learn more at tiktok.com/discovermore.

• 51:42Speaker 03

  I'm Josh Muccio, host of The Pitch, where startup founders raise millions and listeners can invest. For our sweet season 16, we're giving you more of what you love and less of what you don't.

• 51:53Speaker 05

  I definitely start to blank out when we're talking about like middleware AI wrappers.

• 51:58Speaker 03

  Software is out. Actual cool stuff is in. We've got consumer brands.

• 52:04Speaker 06

  We're building Eight Sleep for daytime.

• 52:06Speaker 03

  Hardware that helps blind people see.

• 52:08Speaker 07

  They kept asking for middle finger. Next thing we knew, we had like 10 students running around flipping each other off.

• 52:13Speaker 03

  We've got deep tech to change the weather.

• 52:16Kara Swisher?

  Our big vision is to make it rain and snow on demand.

• 52:19Speaker 07

  What if you wanted to not make it rain somewhere else? Like one day, we're just like, screw Arizona.

• 52:27Speaker 03

  And dairy? I never imagined my life journey would be milk. Season 16 of The Pitch is out now. Listen wherever you get your podcasts. This season is presented by Engine.

• 52:40Kara Swisher?

  So let's finish up with university politics. It's hard not to being here at Michigan. And now you're not an expert on this. Let me just be clear. But there's huge upheaval at universities. Harvard is being targeted now. Columbia was targeted. Twilio and Michigan 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 universities 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 Michigan President Santo Ono met with Michigan lawmakers in March and told them universities have to wake up

• 53:24Kara Swisher?

  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 restored. 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.

• 53:46Speaker 04

  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, and yes, there are a lot of people who are racist and everything, but like, 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 like, there are wrongs in the history of our country and the world, and like, there's things we can do to like, 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.

• 54:30Speaker 04

  But I saw when you started to bring in like, certain like, 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 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,

• 55:14Speaker 04

  DEI has had many names over the course of the last 10 years. And, you know, first it 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 us 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 is the E is really what we're talking about here. Because, like, I don't control Twilio's website anymore. I have no role at Twilio anymore. But I was curious, so 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?"

• 55:59Speaker 04

  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, it's just no equity. Right? So diversity and inclusion is something a majority of people, 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'll lose people. And I saw it happen.

• 56:33Kara Swisher?

  So what would you do?

• 56:36Speaker 04

  What would I do if I was running Michigan?

• 56:41Speaker 04

  I think it would be okay to admit that equity is really a 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 pitting 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, diversity 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.

• 57:16Kara Swisher?

  Or it was executionally done wrong.

• 57:18Speaker 04

  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 one of the groups of people at Twilio." And it'd be like, like, the Filipino Twilios would do a little short, like, one-minute video about, you know, 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, the run-of-show, and it was like, you know, 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, a 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.

• 58:05Speaker 04

  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, "It's your fault."

• 58:20Speaker 04

  That's not gonna end well. That's not how you're gonna win allies. Right? And, you know, some people may feel that, but you're not gonna do any help, you're not gonna 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

• 59:02Speaker 04

  if the goal, 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.

• 59:14Kara Swisher?

  Right.

• 59:14Speaker 04

  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.

• 59:26Kara Swisher?

  Right. No, I get it. I understand it. The only things I would push back, well, I'd push back a few things, but the one I would push back on is being finger-wagging and irritating, which, believe me, I get plenty of shit on 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

• 1:00:08Kara Swisher?

  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.

• 1:00:18Speaker 04

  Yes. But I think what we really need to do is win hearts and minds. Like, that's how you create change.

• 1:00:21Kara Swisher?

  That's who include people. That's the word of inclusion, and I think it's important even if people...

• 1:00:25Speaker 04

  Interesting. You're applying inclusion to the process of diversity and inclusion.

• 1:00:29Kara Swisher?

  So, last question, and 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...

• 1:00:37Speaker 04

  That is the highest praise that has ever been granted by Kara Swisher.

• 1:00:40Kara 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 Lorene 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?

• 1:00:59Speaker 04

  What I told the team was at first...

• 1:01:01Kara Swisher?

  Plus, you give money, Reid Hoffman's under siege by these people, you know.

• 1:01:05Speaker 04

  What I told The Onion is, like, what I told the leadership there is, we have to do what we have to do. Like, this is, 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. Like, they were brutal on Schumer. And, you know, even just, uh, last week, they had Pelosi and Schumer sat next to each other, you know, Democrats debate how best to blow this opportunity as well. Like, you know, and it was like...

• 1:01:37Speaker 04

  And I said, "We have a job to do."

• 1:01:39Kara Swisher?

  Yeah.

• 1:01:40Speaker 04

  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 them, "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?

• 1:01:59Kara Swisher?

  Sorry.

• 1:02:00Speaker 04

  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.

• 1:02:20Kara Swisher?

  Right.

• 1:02:20Speaker 04

  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 gonna 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 gonna, we're gonna defend this little thing called The Onion because satire is highly protected speech." And The Onion is a beloved brand and a beloved publication.

• 1:02:47Kara Swisher?

  Well, Jeff, thank you so much. And you see why I really like them. Thank you.

• 1:02:51Speaker 04

  Thank you, Kara. Thank you all.

• 1:02:58Kara Swisher?

  On with Kara Swisher is produced by Christian Castor-Russell, Kateri Opum, Dave Shaw, Megan Burney, Megan Cunane, and Kalen Lynch. Nishat Kurwa 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 Track academics. If you're already following the show, we get to keep our democracy. If not, the onion is now banned. Go wherever you listen to podcasts, search for On with Kara Swisher, and hit follow. Thanks for listening to On with Kara Swisher from New York Magazine, the Vox Media Podcast Network, and us. We'll be back on Thursday with more.

• 1:03:40Speaker 01

  Support for the show comes from Engine. Running a small business means every dollar has to work hard. But if your team is still booking travel the old way, it's costing you more than you think. Engine is the fastest-growing travel and spend platform in the country, built specifically for businesses like yours. Book a trip in as little as two and a half minutes, earn up to 10% back on hotels. And in 2025, Engine customers save more than $300 million on travel with zero booking fees, no contracts, and no BS. More than 1,000 businesses join Engine every month. Join them and get $500 when your business signs up and starts traveling at engine.com/vox.

• 1:04:25Speaker 02

  Support for the show comes from TikTok. There is a scientifically documented correlation between listening to podcasts and curiosity. So since you're here, you probably enjoy discovering new things. One great place to indulge your curiosity is TikTok. Whether it's how to forecast volcanic eruptions, strange phenomena that the James Webb Space Telescope picked up near the beginning of time, or a literal deep dive on the ocean's deepest reefs, TikTok has a wealth of fascinating videos just waiting to be discovered. Your next discovery is waiting on TikTok. Learn more at tiktok.com/discovermore.

• 1:05:08Speaker 03

  I'm Josh Mucio, host of The Pitch, where startup founders raise millions and listeners can invest. For our sweet season 16, we're giving you more of what you love and less of what you don't.

• 1:05:19Speaker 05

  I definitely start to blank out when we're talking about like middleware AI wrappers.

• 1:05:25Speaker 03

  Software is out. Actual cool stuff is in. We've got consumer brands.

• 1:05:30Speaker 06

  We're building Eight Sleep for daytime.

• 1:05:32Speaker 03

  Hardware that helps blind people see.

• 1:05:34Speaker 07

  They kept asking for middle finger. Next thing we knew, we had like 10 students running around flipping each other off.

• 1:05:40Speaker 03

  We've got deep tech to change the weather.

• 1:05:42Speaker 07

  Our big vision is to make it rain and snow on demand. What if you wanted to not make it rain somewhere else? Like one day, we're just like, screw Arizona.

• 1:05:53Speaker 03

  And dairy? I never imagined my life journey would be milk. Season 16 of The Pitch is out now. Listen wherever you get your podcasts. This season is presented by Engine.