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Kara Swisher
It's on. 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 tact. So stick around.
Jeff Lawson
Foreign.
Kara Swisher
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Jeff Lawson
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Kara Swisher
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Jeff Lawson
It is on.
Kara Swisher
Jeff, thanks for joining me in this conversation at the University of Michigan, where you are an alum.
Jeff Lawson
Indeed.
Kara 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, people who don't know it absolutely well.
Jeff Lawson
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'd have dial up and all this back then, which none of you know what that is. But you, 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 I ftped down a copy of Netscape Navigator 1.0 and started using the web. And most of the 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?
Kara Swisher
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.
Jeff Lawson
It was like a webcam on a coffee.
Kara Swisher
It was a webcam on a coffee maker. And that was very exciting at the time, right?
Jeff Lawson
Like, oh my God, someone's drinking water.
Kara Swisher
It wasn't exciting at the time, but nonetheless. So go ahead. This is important for people.
Jeff Lawson
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 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? 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 cement. 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 notes number four free dot com. Wow, brilliant marketers. We went to.
Kara Swisher
No, not at all.
Jeff Lawson
We could have had google.com we could have had like anything was available at that point. No noes. Number four free. Which then later turned into versity.com, but it was this excuse to start playing with the Internet. And so we built this site and we h a lot of our friends to start taking notes in the lectures they were in and posting them on Twitter.
Kara Swisher
Which you did in an analog style. Correct. And then uploaded them.
Jeff Lawson
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 someone wrote a Java applet to 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.
Kara Swisher
So you were automating. You were automating a process that had.
Jeff Lawson
Been analog, basically, because, yeah, in the old way it was, here's 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 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, 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, very 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.
Kara 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. Cause 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.
Jeff Lawson
Yeah, 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 something that never in a million years did I expect would happen in terms of I being fired from the company that I started and ran. And the interesting thing that happened, look, I was mad, I was. 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 as I look back, I kind of realized, 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 gonna go. And that took me by surprise. And the fact that that took me by surprise was a very big mistake for me. Right.
Kara Swisher
Well, you grow up 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.
Jeff Lawson
Yeah. So Twilio is infrastructure that software developers use to embed communications ins, 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 throughout the course of my prior, 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 just like, that's the mysteries of the cosmos, how text messages arrive. So 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.
Kara Swisher
That's correct. Yeah.
Jeff Lawson
And therefore there was a huge now surging demand for apps for developers and for all the infrastructure needed to build those. And we happened to be right there at the right time. And so for entrepreneurs in the room, it also goes to show you, you work hard and all this, but 75% of it's luck and timing and all that kind of stuff.
Kara 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 haven't founded a new startup. Talk about your relationship with the tech industry now that you have some distance from it.
Jeff Lawson
You know what's interesting?
Kara Swisher
Where do you live?
Jeff Lawson
San Francisco.
Kara Swisher
Okay. All right, good.
Jeff Lawson
That sounded so accusatory.
Kara Swisher
No, it's not. I'm just like, I still have my house in San. I love San Francisco. I was just there last week.
Jeff Lawson
Sorry, what was the question?
Kara Swisher
What are you doing? What are you doing? What are you doing here? Why didn't you start a new startup? I suspect you have had money thrown at you, presumably.
Jeff Lawson
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 are 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 going to do is just let myself go do all those things. All these stupid ideas I've had in the back of my head, like building a car or like building. 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. And then part of it was, okay, I love mentoring young teams, young founders management, young management teams. And so I, I open 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 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 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. 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.
Kara Swisher
So we're talking 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?
Jeff Lawson
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 we started doing typical. We were very apolitical. We gave a little bit to the candidates that made sense, but not really involved. 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, whether it was Supreme Court seats that weren't granted when the norm said they should have been, or. 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 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, we'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 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 going to bring cases or not of the right kind. And all the way down to 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 you're gonna get crazy people who don't wanna uphold democracy, they just wanna see their party and their ideology way.
Kara Swisher
Right, plot, spoiler, go ahead.
Jeff Lawson
And so we said we're gonna work really hard in a bipartisan way just to make sure that the people who believe in rule of law are gonna sit in these seats when the election comes around. And so that's when 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.
Kara Swisher
And at the time, nobody knew Trump was coming back. He was mar a lago, hiding for a short time, sure.
Jeff Lawson
But like, you know, you don't play with fire, as I often tell my sons, you know, like you can light the match for the hundredth time and that's when you burn yourself.
Kara Swisher
Right. And so, 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, cuz 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.
Jeff Lawson
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 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. That's ideally how democracy should work, in the same way that we should decide who our president is without maybe the Russians helping us to decide that. 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 the judgment upon Alon's money. And what does Alonz money mean? Is it toxic or not? And what I think we've shown is that, 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.
Kara Swisher
Who's getting it.
Jeff Lawson
Who's getting that money.
Kara Swisher
Politically toxic, you mean?
Jeff Lawson
Politically toxic, yes.
Kara Swisher
What do you think happened there? Personally, when I saw the cheesehead, 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.
Jeff Lawson
I won't speak to his physical attributes.
Kara Swisher
Don't take that. Cheese Head was bad. It reminded me of the Dukakis helmet. I was like, oh, geez, yes, ouch. There I was being bipartisan. That was a bad picture, too.
Jeff Lawson
Yeah. If you're a politician, just don't put things on your head.
Kara Swisher
No.
Jeff Lawson
Yeah.
Kara Swisher
Unless you're Gavin Newsom. He'd have looked good in the book Cheese Head, but go ahead.
Jeff Lawson
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 an all hands at Tesla or SpaceX or whatever and he gets this certain.
Kara Swisher
Response from them also on Twitter.
Jeff Lawson
Same thing on Amazon 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 in 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 are 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.
Kara Swisher
We'll be back in a minute. Support for this show comes from NetSuite. Running your business would be a lot easier if you knew exactly what was going to happen tomorrow. You'd sleep well at night knowing when the next bull market or bear market was on the horizon or where interest rates would be in a year. Unfortunately, you can't predict the future, but you can Prepare for it. NetSuite by Oracle has helped over 40,000 businesses future proof their operations. NetSuite is a top rated Cloud ERP, bringing accounting, financial management, inventory, HR into one platform. Having one unified business management suite gives you the visibility and control you need to make quick decisions. Real time data gives you actionable insights. And closing the books in days, not weeks means you're spending less time looking backwards and more time on what's ahead. No matter how big your company is, NetSuite helps you respond to your most pressing challenges and seize your biggest opportunities. Speaking of opportunity, download the CFO's Guide to AI and Machine Learning at netsuite.com on the guide is free for you at netsuite.com on netsuite.com on PayPal lets you pay all your pals like your graduation gifters.
Jeff Lawson
Who's paying for the mattress topper?
Kara Swisher
You mean the beanbag chair? Aren't we getting a mini fridge? Can we create a pool on PayPal?
Jeff Lawson
It lets us collect the money before we buy.
Kara Swisher
Oh yes, that's smart.
Jeff Lawson
Glad can agree on something easily.
Kara Swisher
Pool split and Send Money with PayPal. Get started in the PayPal app. A PayPal account is required to send and receive money. A balance account is required to create a pool. Support for today's show comes from Chevrolet. Whether it's a quick jaunt or a long journey, no matter where you're going, the all electric Equinox EV allows you to travel with confidence, comfort and connectivity. Equinox EV comes equipped with a standard 17.7 inch diagonal color display touchscreen, making it the largest center screen among EVs in its class. Its sleek lines and a commanding stance define the exterior of Equinox ev, while the no Compromises interior has a cargo room and storage that let you do you at a starting price of around $34,995. Equinox EV a vehicle you know, value you'd expect and a dealer right down the street. You can go EV without changing a thing. Learn more@chevy.com Equinox EV based on latest competitive data, the manufacturer's suggested retail price excludes tax, title, license, dealer fees and optional equipment dealer sets final price. A lot of tech CEOs in the interim have embraced President Trump. 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 and advantage. That includes Marc Benioff, who was known for his social activism and who you call 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. 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 that theory? Because it's sort of you break down these pillars that you're talking about.
Jeff Lawson
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 paper. 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.
Kara Swisher
Right.
Jeff Lawson
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. 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. 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.
Kara Swisher
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, 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, a level playing field.
Jeff Lawson
Which by the way, where do level playing fields come from? They come from the rule of law. 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 how lucky we are to have a system where in order to get something, you don't have to bribe people. 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 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 in a way that I find disgraceful.
Kara Swisher
Yeah, I would agree.
Jeff Lawson
And I like, I don't know. I remember people asking me, remember there was that tech roundtable when Trump first came into office.
Kara Swisher
I broke that story. I broke that story. Yes, I did.
Jeff Lawson
You wrote that story. Okay, great.
Kara Swisher
Yeah. So I remember, I called them sheeple. They didn't like it, but I did.
Jeff Lawson
I remember people asking me at Twilio, they're like, oh, were you invited? And I'm like, no partively. I was like, well, no, we're not that Important. 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 up. You know, I'm bored and I want to be a part of it. And you know, the excuse people make is, well, I'd rather be a part of it than not a part of it. Right?
Kara Swisher
That's their argument.
Jeff Lawson
I can change endorsing what's going on by being a part of it.
Kara Swisher
One of the reasons I broke 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 gonna. It's not gonna 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. 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. 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 or especially social media. But to me, if I had to pick three things, I would say social media gerrymandering and Rupert Murdoch have killed our country in a lot of ways. In a combination created the polarization. What do you point to if you had to pick three things?
Jeff Lawson
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.
Kara Swisher
Right.
Jeff Lawson
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.
Kara Swisher
Anxious to know what's the solution. The line I had in my book was, enragement equals engagement.
Jeff Lawson
Yes. So what's the answer? And I literally don't know what is gonna 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 having a barbecue with your friends. Whatever it is, people are the answer to it. Real people that live near you and whose values you share with them are because you live in the same area, not because you've rage. Click 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 I think it would be a great agenda item 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 community groups to bolster local picnics, the ice cream social at a church. For 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.
Kara Swisher
You can 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.
Jeff Lawson
Yes. I thought Pete should do that. I pitched Pete on that.
Kara Swisher
Oh, Recently Unemployed with Pete Buttigieg. Doesn't sound as good.
Jeff Lawson
Not as good. I was thinking Pete's America, stick to your guns.
Kara Swisher
I'll do the podcast. 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 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.
Jeff Lawson
Well, let me ask you this. If you could own any news source or America's finest news source, which one would you buy?
Kara Swisher
Well, I'm trying to buy the Washington Post, but he's not calling me back.
Jeff Lawson
But, 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 gonna buy the Onion.
Kara Swisher
Yeah.
Jeff Lawson
Because that is a proportional to our market caps, but also just how the universe should work.
Kara Swisher
Yeah. Okay.
Jeff Lawson
Like, oh, that's me. The universe is in sync, if that's what I did. And then I looked into it a few times over the years, and it's 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 going to 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 years, you had been calling them.
Kara Swisher
You're like, I'm interested. Yeah.
Jeff Lawson
Yeah.
Kara Swisher
I'd like to remember.
Jeff Lawson
I missed it got sold from Univision to private equity, and I missed that opportunity when that happened. Why Univision owned it again, who knows? Amazing.
Kara Swisher
Yeah, they owned a lot of things they shouldn't have owned. Yeah.
Jeff Lawson
And so the reason for buying. There are basically three reasons. First was 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 10 years. Some of it, everyone except for you, Kara.
Kara Swisher
That's true. There's a lot of very good media entrepreneurs right now doing very well.
Jeff Lawson
But the last 10 years have been.
Kara Swisher
Tumultuous for the big companies, certainly. Yes.
Jeff Lawson
And then add on top of that, to be owned by private equity whose goal is to extract cash from the entity while it is shrinking. It's just layoff after layoff after layoff. And so it was, 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.
Kara Swisher
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 down to 125 million.
Jeff Lawson
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 play.
Kara Swisher
Yeah, it is interesting. Hence Twitter being pulled into Xai. Yes, I 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 Pam 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.
Jeff Lawson
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 this, you know, like, if you have a dog and you need to give them medicine, you 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, 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 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 true no matter who it 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.
Kara Swisher
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 vulgarian, which still works today.
Jeff Lawson
But if you think about it, I think our job is actually not you. You said it's funny to people on the left, very specifically. We are not trying to be a leftist satire.
Kara Swisher
We make fun of everybody.
Jeff Lawson
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 Zuckerberg makes more money. When we hate each other and looking at this and being like, how did we get here? 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 where everybody could 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 you know what? We can see them as human beings.
Kara Swisher
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 papers run the headline 38 times, which I think to me is much more powerful than any number of editorials. I'm gonna do a lightning round 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.
Jeff Lawson
And by the way, I'll say before Jonathan's book, before you go into it, the Onion. One of the things that's great is at 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.
Kara 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 onions business. Fast answers, please. How much should you pay for it?
Jeff Lawson
A few million.
Kara Swisher
Like how many?
Jeff Lawson
It's complicated.
Kara Swisher
Okay. All right. How big is the staff? I'll let you go now.
Jeff Lawson
About 25.
Kara Swisher
25. What are the different revenue sources and what's the rough breakdown per category?
Jeff Lawson
Almost entirely now. Subscription revenue from memberships.
Kara Swisher
Memberships? What do they cost?
Jeff Lawson
$99 a year.
Kara Swisher
Okay, great. I have one myself, thank you. 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?
Jeff Lawson
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 somewhere there.
Kara Swisher
When do you expect to turn a profit? Then you said, it's okay not to. This year.
Jeff Lawson
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 going to clean website that 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.
Kara Swisher
Would you mind losing money indefinitely?
Jeff Lawson
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 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 great. I'm going to flip it and sell it, make a bunch of money. I was like, that's not why I bought the Onion. I bought the Innings. I want to own it for the rest of my life.
Kara Swisher
Right.
Jeff Lawson
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 break even, I'm happy.
Kara 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.
Jeff Lawson
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 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. 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 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, you know, let's do what we need to do.
Kara Swisher
Yeah. I always say that to media entrepreneurs. You're talking about, like, you got to. I say, you have to make money. Because then, you know, 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.
Jeff Lawson
Yeah, right.
Kara Swisher
But I'm like, get the fuck away from me. Right. And you can't do that unless you're making money.
Jeff Lawson
You've got the power of that.
Kara Swisher
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.
Jeff Lawson
Exactly.
Kara Swisher
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?
Jeff Lawson
Back to basics. Right? So we said we're gonna 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 gonna give it back to them. And in exchange, they're gonna give us $99 a year.
Kara Swisher
Right.
Jeff Lawson
That's how we're gonna 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. 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?
Kara Swisher
A lot, actually.
Jeff Lawson
Spry. Well, they're 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 satirize the media that young people, especially today, are consuming. And that's what leads us to Infowars, actually.
Kara 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. Obviously, there's performative and meminess 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.
Jeff Lawson
I mean, partially. We did it because, as a stunt, nothing is Funnier than the fake newspaper thing, buying the fake news thing. It's such a karmic joke that you had to do it. 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, 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 because it stands for exactly like the worst of the Internet.
Kara Swisher
Yeah, I've got so many choices for you. I'll help you on that one.
Jeff Lawson
There's so many. 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.
Kara Swisher
Yeah, it'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. We'll be back in a minute.
Jeff Lawson
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Kara 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 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 Michigan President Santo Ono met with Michigan lawmakers in March and told them 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.
Jeff Lawson
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 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. Then 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 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 advantage someone who is underrepresented over someone who isn't because of that. Isn't that equally wrong? I saw good people really try to square that. And I think that there is truth that is, 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, Deis had many names over the course of the last 10 years. And first was diversity and inclusion and all this. And then equity came in and that's the E. And 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 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, it's just no equity. So diversity and inclusion is something of 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 unique, comfortable with that idea. I don't know how that works. Unless you have really good answers that put that question to bed. You lose people. And I saw it happen.
Kara Swisher
So what would you do?
Jeff Lawson
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, because it's incredibly complicated. I think everybody wants diversity, everybody can 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.
Kara Swisher
For that ride or was executionally done wrong.
Jeff Lawson
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 give a, you know, we 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, it 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 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 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, 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, 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 were getting increasingly finger pointy and wagging and all this kind of stuff in a way that the backlash was probably inevitable.
Kara Swisher
Right. No, I get it. I understand it. The only things I push back. Well, I push back on 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 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. While 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.
Jeff Lawson
But I think what we really need to do is win hearts and minds. That's how you create change.
Kara Swisher
That's how you include people. That's the word of inclusion. And I think it's important, even if people.
Jeff Lawson
You're applying inclusion to the process of.
Kara Swisher
Yes, including.
Jeff Lawson
Right.
Kara Swisher
So last question, and I'm going a tiny bit long because really interesting. Actually, I wasn't surprised. I'm teasing. In the worst case scenario, that's the.
Jeff Lawson
Highest praise that has ever been granted by Kara Swisher.
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 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?
Jeff Lawson
What I told the team was at.
Kara Swisher
First, plus, you give money. Reid Hoffman's under siege by these people.
Jeff Lawson
You know, 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 even just last week they had pelosi and Schumer standing next to each other, Democrats debate how best to blow this opportunity as well. 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 I asked them, what's the worst thing that can happen? And if the worst thing that can happen is the administration sues the Onion out of existence, well, that's still better than private equity ruining it, right? So if that's the worst thing, but I've got your back, I will defend you. I'm here to make this publication successful. But if for some reason I can't do that, this is the worst thing that would happen. 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 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. 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.
Kara Swisher
Well, Jeff, thank you so much. And you see why I really like them. Thank you.
Jeff Lawson
Thank you, Kara. Thank you all.
Kara Swisher
On With Kara Swisher is produced by Christian Castor, Roselle, Kateri Yocum, Dave Shaw, Megan Burty, Megan Cunane, and Kaitlyn Lynch. Nishat Kurwa is Vox Media's executive producer, producer of audio. Special thanks to Annika Robbins. Our engineers are Rick Kwan and Steve Bone, and our theme music is by Trackademics. 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.
Podcast Summary: "The Onion’s Owner on Satire, Infowars, Defending Democracy & Trump"
Podcast Information:
In this compelling episode of On with Kara Swisher, Kara engages in an in-depth conversation with Jeff Lawson, the owner of The Onion, co-founder and former CEO of Twilio, and co-founder of Democracy First, a political action committee (PAC) dedicated to supporting democratic candidates across party lines. The discussion delves into Lawson's entrepreneurial journey, his motivations behind acquiring The Onion, his efforts in defending democracy, and his perspectives on the current political and media landscape.
Early Ventures and Twilio: Jeff Lawson recounts his early entrepreneurial endeavors, including his first startup, Versity, which aimed to digitize lecture notes—a precursor to modern online note-sharing platforms. Reflecting on this venture, Lawson shares:
"We could have had any domain name we wanted… Number four free. Which then later turned into versity.com, but it was this excuse to start playing with the Internet." (03:45)
Despite initial success and raising venture capital, Versity eventually succumbed to competition and market challenges, teaching Lawson invaluable lessons about the volatile nature of startups.
Transitioning to Twilio in 2008, Lawson describes how the company became a frontrunner in cloud communications, positioning itself as essential infrastructure for developers to integrate communication features into their applications. He credits timing and luck for Twilio's meteoric rise, especially during the mobile boom.
Twilio's Success and Departure: Twilio reached a valuation peak of approximately $70 billion during the pandemic. However, internal conflicts with activist investors led to Lawson stepping down as CEO and board member in January 2024. Reflecting on his departure, Lawson admits:
"It was wartime. You know, when an activist is at the gates, that for a board is wartime… And I wasn't doing that. And as a result, we had this moment where push came to shove…" (08:03)
This experience reshaped his approach to leadership and governance within startups.
Founder's Garage: Post-Twilio, Lawson established Founder's Garage, a mentorship hub for early-stage startups. Partnering with notable entities like Bessemer, Y Combinator, and OpenAI, Founder's Garage provides aspiring entrepreneurs with guidance and resources without the immediate pressure to launch new ventures.
"I just was like, can I do this? That was kind of fun… Surrounding myself with interesting people doing interesting things… that's a much better way to spend my days." (11:12)
Democracy First PAC: In response to growing threats to democratic norms, Lawson co-founded Democracy First in 2022. The PAC focuses on supporting candidates committed to upholding democracy, particularly at the state and local levels where election integrity is most vulnerable. Discussing the PAC’s mission, Lawson emphasizes:
"We're gonna work really hard in a bipartisan way just to make sure that the people who believe in rule of law are gonna sit in these seats when the election comes around." (16:59)
Lawson highlights the challenges posed by external influences and big-money campaigns, advocating for grassroots efforts to preserve democratic institutions.
Big Money and Election Integrity: Lawson critically examines the impact of wealthy individuals like Elon Musk on political races, particularly referencing the Wisconsin Supreme Court case where Musk’s substantial financial support for Susan Crawford was ultimately unsuccessful. He reflects:
"What's happening is people don’t want to be thought of as just pawns that can be bought for a price… enough people believe that this is just, it's not what America's about." (19:56)
He argues that such overt financial interventions are politically toxic and undermine the foundational principles of democracy:
"Politically toxic, yes." (19:55)
Consequences for Business Leaders: Lawson discusses the dilemma faced by tech CEOs who feel pressured to align with political figures, potentially compromising their company's values and integrity. He underscores the tension between fiduciary responsibilities to shareholders and personal civic duties.
Reasons for Buying The Onion: Initially approached as a humorous match in proportional market caps compared to other media acquisitions like Bezos’s Washington Post, Lawson’s acquisition of The Onion evolved into a mission to save the satirical publication from private equity's cash-extraction approach.
"The reason for buying… it's saving the Onion because it was in a death spiral." (37:10)
Shift to a Membership Model: Under Lawson’s ownership, The Onion transitioned from ad-driven revenue to a subscription-based model, focusing on quality content and reader engagement. He notes:
"Almost entirely now… subscription revenue from memberships." (43:01)
This strategic pivot aims to ensure financial sustainability while preserving the publication’s comedic integrity.
Satire as a Truth-Telling Mechanism: Lawson champions satire as a powerful tool for societal reflection and truth-telling. He explains:
"Satire is for the truth. You wrap the truth in this pill, in this pill pack, and now someone can… you get it inside of people’s head." (40:35)
The Onion serves as a satirical mirror, reflecting and critiquing political and social dynamics in a manner that pure journalism often cannot.
Attempt to Acquire Infowars: In a bold move, Lawson attempted to purchase Alex Jones’s Infowars at a bankruptcy auction, intending to transform it into a satirical platform. However, the bid was rejected by a federal bankruptcy judge. Discussing this endeavor, Lawson states:
"We did it because, as a stunt… The Infowars brand because it stands for exactly like the worst of the Internet." (47:27)
This attempt underscores his commitment to countering misinformation through humor and satire.
Challenges with DEI Programs: Lawson addresses the controversies surrounding Diversity, Equity, and Inclusion (DEI) initiatives at universities, particularly the University of Michigan. He reflects on the difficulties in implementing equity-focused programs without alienating allies:
"Equity means someone gets something and I don't get something or vice versa… that's where it gets really complicated." (54:14)
He advocates for a more inclusive approach that emphasizes diversity and inclusion without overcomplicating equity, aiming to maintain broad support across different demographics.
Strategy for Managing DEI During Political Upheaval: In light of political pressures and potential funding cuts threatening DEI programs, Lawson suggests:
"It would be okay to admit that equity is a really hard concept for a society to get right… Diversity, inclusion. Diversity, inclusion. Diversity, inclusion. Diversity." (54:14)
He emphasizes the importance of refining DEI strategies to foster genuine inclusion without triggering backlash.
Protecting Satire in a Polarized Climate: As the conversation wraps up, Lawson expresses commitment to defending The Onion against potential threats, including hypothetical scenarios where the publication might be targeted under authoritarian regimes:
"We have a job to do, which is to cut through and deliver truth as best we can to people… We have to do this… that's our calling." (60:25)
He underscores the essential role of satire in maintaining a resilient and reflective society, committed to upholding democratic values through humor and critical commentary.
Notable Quotes with Timestamps:
Jeff Lawson on Starting a Company:
"I'm gonna start a company in order to just have an excuse to go play with this new thing called the Internet." (04:47)
Lawson Reflecting on Twilio Departure:
"I had every title imaginable to avoid this outcome. So somehow I screwed up." (09:37)
On Twilio's Role:
"Twilio is infrastructure that software developers use to embed communications ins, the apps that you have on your phones and use on the web." (09:48)
On Big Money Influencing Elections:
"If we need to develop new properties that are going to be relevant to today's generation… Infowars… represents that the worst of the Internet." (47:17)
On The Onion's Mission:
"We are not resistance media. We just need to call out bullshit when we see bullshit." (40:58)
Final Thoughts: This episode provides a multifaceted exploration of Jeff Lawson's perspectives on entrepreneurship, media ownership, political influence, and the role of satire in modern democracy. His insights offer valuable reflections on navigating the complexities of maintaining democratic integrity and fostering meaningful societal discourse in an increasingly polarized world.