No industry has had more impact than technology over the past few decades. Tech companies have changed the way we live, work, and interact with each other. They’ve helped us in a lot of ways, but they’ve also created some big problems. Kara Swisher is a journalist, entrepreneur, and host of the podcast On with Kara Swisher. She’s had a front row seat to the tech industry’s evolution and interviewed all of its biggest players. She speaks with us about key trends — past, present, and future — and the lessons she’s learned as not just an observer but also a media entrepreneur herself along the way.
ALISON BEARD: Welcome to the HBR IdeaCast from Harvard Business Review. I’m Alison Beard.
No industry has had more impact on society over the past few decades than technology. Tech companies have changed the way we live, work and interact with each other. They’ve helped us a lot of ways, but they’ve also problem created some big problems. The question now is whether they’re going to direct all the brain power they have and wealth they’ve created toward the biggest challenges we face as a society, or just keep selling us more stuff.
My guest today has had a front row seat to this entire evolution, and she no doubt has some thoughts on where it’s going next. As a journalist, she started covering the tech industry, and she has interviewed, some would say grilled, all of its biggest players. She co-founded her own conference and media company, first within the Wall Street Journal and then independent independently. Now she’s a popular podcaster. Her new show just dropped today, the day we’re taping, and she’s here to talk to us about history and future of the tech industry, as well as her own career.
A big welcome to the woman once described as the most liked and feared figure Silicon Valley, journalist, entrepreneur, and host of On with Kara Swisher. Kara Swisher. Kara, welcome.
KARA SWISHER: Hi. Hi. Thanks for having me.
ALISON BEARD: As I just said, you have been covering the tech industry since close to the beginning. What drew you to it back then when you were a young reporter and you could have focused on anything?
KARA SWISHER: I was super intrigued by the idea of a medium, especially the internet, that was a worldwide network of information. I went to Georgetown Foreign Service School, I was very interested in propaganda, and so I was super interested in the next iteration of communications. The minute you saw the world wide web using a Netscape browser, a mosaic browser, you could tell, “Wow, you could download anything across great distances,” and I knew it would change media and commerce and everything else.
ALISON BEARD: And so you wanted to be a part of that?
KARA SWISHER: Yeah. It was like meeting Thomas Edison when he invented the light bulb kind of thing. To me, it was that important, and I got to really know the people who created it instantly. That’s a huge opportunity.
You know, I had covered retail at the Washington Post right before that, and I saw what was happening to the retail sector and classifieds and all their businesses. So, I kept thinking, “Well, if this, then that.” That was my area of specialty at Georgetown was the scenario building. So, if there was going to be a digital classified, that’s the end of newspapers, because that’s one of their big things. Same thing with retail. If everything was delivered, there was a company ever that would be created, and Amazon just didn’t exist at this point, or maybe just did and was just selling books.
But if you could do that and iterate it, you could carry out the business model. Same thing with phones. I was very into cell phones, and I thought, “Wow, what happens to all the industries?” So, I just was one of those people who would say, “If this, then this,” so I think that was why. Most people who are incumbents, they can’t imagine their death, and I could always imagine people’s death, the kind of things, I guess. You know what I mean?
That’s how I do entrepreneurship now. I change. I moved to podcasting eight years ago because I was like, “I’m not done with this print stuff,” even though it was online. I was done with print and then I put print online, and then I was like, “I’m done with this. I think people are going this way.” So, I think about that almost constantly.
ALISON BEARD: Yeah. As these companies, the whole industry evolved, what most impressed you and what most disappointed you? Let’s start with impressed and then we’ll get to the complaints later.
KARA SWISHER: I mean, the very invention of it. I really do appreciate entrepreneurship quite a bit. I’m always impressed by the persistence of entrepreneurs, even despite failures and things like that. I do think a lot of these things have been world changing. The idea of a worldwide network of information, think about that. That’s just an astonishing vision.
What I’m less impressed with is how they conduct themselves while they’re building it, which is to say is they don’t think about consequences, and I spend a lot of time talking about consequences and thinking “What’s the worst case scenario here?” And they never do.
They can’t possibly tolerate the idea of problems. They’re not adult enough to say, “Okay, if I do this, what about this?” I think even Robert Oppenheimer understood what the bomb meant and he said that, “I have become death,” something like that. He understood it. So, I think if you’re an inventor, you should understand the impact of your creation, and they don’t do that. Either it’s because they always have to be optimistic for some reason, or they just want money and they want growth over everything else. So, I think their lack of care is really disappointing.
ALISON BEARD: What are some of the biggest negative outcomes that you worry about?
KARA SWISHER: I started writing about it very early, is the social media misinformation. A diet of really bad information creates a populous… I don’t think the populace was very informed before, but now it had too much information, and so people who are conspiracy theorists now have a buffet of – before they had little bits and pieces. So, it tends to make people even worse than they were.
I think the addictive nature of these technologies and the necessary nature is a problem. You need to use them to survive in the modern work world, and at the same time, the addiction and the isolation that it creates using digital things is really problematic. I think the power of a couple big companies, I’m always worried about big companies. I don’t care if they’re trains or planes or automobiles, it’s the same thing with tech companies. There’s too few of them that wield too much of the power, and it hurts innovation and it hurts the consumer.
ALISON BEARD: In the wrap up show for your last series, Sway, someone asked, “What’s one thing you would change?” And you first said you would shut down the internet, and I think I gasped as I was listening, because that would make your job sort of hard. But then you corrected yourself and you said, actually, you would go back in time and make it better. How could it have been made better?
KARA SWISHER: Well, I was using that phrase because one time when they were worried about Russian involvement on the Facebook platform, I think it was Sheryl Sandberg said, “Well, what do you do?” I said, “Just shut it down for a day and figure it out,” because they were doing stuff in real time and giving answers that weren’t clear and they kept having numbers. I’m like, Where’d you come up with that number? You just made it up. You don’t know. You haven’t looked in every closet of your platform.” So, I was like, “Just shut it down and see where the problem is.” Right? “Just close the house and fumigate it and then we’ll move on.”
Course they were never going to do that because they make too much money. But it would be very hard, because I think one of the things that has happened with these internet companies is they sort of encourage juvenilization of their young entrepreneurs, and so they were never wrong, they never could make a mistake. The money was too good. I don’t know how you could prevent them for being more thoughtful. Grow less, I don’t think that would be a very welcome message, even if you traveled back in time. So, I don’t know how you make someone think about consequences when they’re in a headlong rush to wealth and power, but I don’t quite know what you would do.
ALISON BEARD: What role did you see venture capitalists play in pushing the tech industry to where it is today?
KARA SWISHER: Well, they’re interested in only one thing, which is to make money and onto their next deal. So, I think they completely allowed these tech entrepreneurs to do whatever they want. It’s like raising children on endless amounts of sugar and then wondering why they’re diabetic. They’re not interested in anything but making money. They aren’t. They just aren’t. So, whenever that’s the case, what do they care if it’s unsafe? What do they care if it’s this? What do they care? It just gets in the way of their vibe. They love their vibe. If I had a dime for every time I’ve heard, “I’m a bummer,” I really would be rather wealthy. if I had a Bitcoin for ever… I’d still be wealthy, even if it’s down.
ALISON BEARD: I really love cynics, so it’s all good with me. Of all the tech founders and CEOs you’ve interviewed, you obviously don’t have high opinions of a lot of them because you’re calling them children.
KARA SWISHER: Some of them.
ALISON BEARD: But whose leadership do you think merit’s the most respect?
KARA SWISHER: Well, Apple’s the most powerful company right now, period, and I liked Steve Jobs, even though he was a lot. He was a lot. There was a lot of negative qualities he had, but everybody has negative qualities. But I thought he was very passionate and challenged himself and others. Even when you disagreed, you could have a big argument with him and he actually had one, which he wasn’t scared of defending his ideas. Even when he was wrong, he wasn’t scared of doing it. I had Code Conferences past couple weeks ago where I had all the big names, and I like everyone I invited. I actually picked people, because it was my last Code Conference, of people I like. I like Andy Jassy of Amazon. I think he’s really interesting and smart. I like Sundar Pichai of Alphabet. I like Evan Spiegel of Snapchat. I like Tim Cook. I mean, he’s not my friend. None of these people are my friend, but I think they’re smart, I think they engage, I think they allow you to challenge them and listen.
ALISON BEARD: And do you think that those people are moving the industry in a better direction, a more positive direction?
KARA SWISHER: Yeah. It depends on the company. I think, look, Facebook’s down, it doesn’t work very much right now. I think it’s 300 million, 200 million. It’s down a lot. That’s because Apple’s been the regulator of Facebook with its ad transparency efforts, so that’s not good. I mean, I’m glad they’re doing it, but I wish it was our government that was doing it, not Apple. That means Apple’s really powerful and can make or break companies. That’s not something that’s fair. Even to Facebook, it’s not fair.
ALISON BEARD: Right. I’d love to talk a little bit about that liked, feared thing that I mentioned. How did you-
KARA SWISHER: So ridiculous.
ALISON BEARD: … manage to maintain good relationships with all these people who you were very, very tough on? These are guys with very big egos. Why didn’t more of them just stop giving you access?
KARA SWISHER: I don’t know. I have used this before, but smart people like smart questions. I’m not unfair, right? I’m not mean. I don’t think I’m snarky. Every now and then I get one off, but so do they. I think I know a lot. I think I’ve spent a lot of time understanding them, and I think they appreciate that in the back of their minds. I think nobody likes doing talking points all day, right? Who likes that? You feel so stupid. I think they good discussions. I talk to everybody. I think that’s helpful to them, because they’re surrounded by people who they pay, and therefore they’re not getting great information.
So, if I say something, they’re like, “Huh, where did you hear that?” You know what I mean? So, I think they like that. Tough is okay as long as you’re fair. I think most people or most adults are fine with that. I don’t know an adult who doesn’t appreciate honesty, and when I’m wrong I say it. I’m not that wrong very often, honestly, but I tend to spend a lot of time studying it, and I think they appreciate that. Then sometimes some of them just like to see if they can go around with me, but all the insecure ones never show up. I’ve been trying to get an interview Peter Thiel forever. We’ve had some very good discussions, though, over the years.
ALISON BEARD: And Zuckerberg hasn’t done an interview with you in a long time, right?
KARA SWISHER: Well, now in his case, no, 2019, 2018. I would give him an out. Every time he shows up for an interview with me, it gets worse. The first one was the sweating, which was not his fault, really. He was having a classic panic attack, I think. We were asking him very easy questions about privacy. It wasn’t like we were beating on him. The second one, I was very adamant about what they were doing around Alex Jones, and he himself shifted the conversation to Holocaust deniers. I didn’t do it. He walked himself into a wall on that one and banged his head. I think I unsettle him for some reason, so I can’t imagine… I’m always like, “Third time’s a charm, Mark.” You know? But I don’t think he feels… why should he? He doesn’t care. He doesn’t care.
ALISON BEARD: One thing that I do think comes across in all your interviews, more so in some than others, but just you are very tough and you do ask very direct questions, but there’s also a level of empathy. You do understand where people are coming from, and that’s very clear when you’re talking to someone like Monica Lewinsky or Maria Ressa, but you also seem to have it for the people for whom most of us don’t feel a lot of empathy. I did say guys before when I was talking about-
KARA SWISHER: It’s mostly guys.
ALISON BEARD: … most of the people you talk to. What’s your view on diversity in tech? Has it gotten better?
KARA SWISHER: I think it has not, no. It’s gotten worse. I mean, I used to at least know two women CEOs or positions of authority. I think there’s Lisa Su. I’m trying to think. Who else? There used to be at least three.
ALISON BEARD: The Wokcickis?
KARA SWISHER: No, she’s CEO of YouTube, which is really under Alphabet, so no. It’s not a separate company. I mean, I like Susan very much. I think she’s very smart. I guess Gwynne Shotwell at SpaceX, but Elon really runs the show, right? And he controls everything. She’s very smart too. No, no. And people of color, no, no. There’s the woman who runs Zoosk, but she’s now bought by Amazon, so she’s not running the show, really. So, yeah, no. No, no.
ALISON BEARD: Even at the lower ranks, you haven’t seen improvement?
KARA SWISHER: Sort of. Sort of. White men still run the whole show, really, with an occasional other kind of man there, but not really. It’s certainly not people of color. It’s certainly not women. There’s some people in strong positions of authority. There’s some very strong AI researchers at Google, for sure. Cheryl Sandberg sort of carried the weight for all these women, but then she got tarnished in all the controversies around that. But she was the COO, she wasn’t the CEO. She was the COO.
ALISON BEARD: Okay. Let’s talk about the future. What are the big tech companies that you talk to focused on now, and does that differ from what you think they should be focused on?
KARA SWISHER: Well, I think it’s a opportunity for tech to really reinvent itself right now. I spent the last day of my Code Conference talking about climate change tech. I brought in John Doerr, who I’ve covered for decades on other things. He was one of the first investors in Amazon and Google in the early days. Very legendary venture capitalist. He’s spending all his time on climate change tech. Same thing with Bill Gates. It’s really interesting. Same thing, Elon is quite involved too. Elon Musk. I’m really interested in climate change tech, so I think we’ll just push a little reset button and focus on the existential crisis we all face. I’ve written several columns saying I think this is the most important area for young entrepreneurs to go into. You could make a lot of money. By the way, if you don’t, we’re kind of finished.
ALISON BEARD: So, it’s not fixing the internet. It’s let’s solve the big challenge.
KARA SWISHER: I think we have to fix the internet. We have to make it safer, we’ve got to regulate it more. We’ve got to have privacy, more protective privacy as we move into the Metaverse, if we ever do. That’s a big if, by Meta, but we’ll see. I think you have to put things in place before they happen. You can think of all the disasters. I just interviewed Bob Iger from Disney, the former Disney CEO, and he was like, “Can you imagine all the bad things that could happen in a Metaverse versus a regular internet, a 3D, live version of the internet?”
You got to be thinking about where abuses could happen. You’ve got to be thinking about people’s health and addiction, and young people, especially, depression and things like that and that impact, just the way we think about cigarettes. Think about use of social media and other things, continue to do that. But at the same time, really, it’s sort of like thinking about electricity. It’s sort of runs the show. If we didn’t have electricity, none of this would work. So, the climate, if we don’t have the planet, it really hardly matters if you’re on a dating service if the oceans cover the land, right? The analog tends to win in the end, I would say.
ALISON BEARD: And one of the biggest criticisms of tech is that it did focus on things like dating and food delivery and cars at any time, instead of what we knew was a very big problem.
KARA SWISHER: Well, that’s where the money was made. But these things, it’s like anything else. These things boil slowly, and you’re like the frog in the water thing. I think it’s a very long term and very difficult problem, and so why not deal with food delivery services? Right? I mean, I don’t find that weird. I find it just normal if you make money in the here and now.
I just think we have to really bring our greatest minds together. I’ve been convinced by a lot of technologists, and it’s not only a technology solution, by the way, it’s going to be a political solution, a policy solution, a mindset solution of what our world is going to look like.
I mean, it was interesting, I got in an argument with, I forget, some right winger, they tend to try to bait me, which never works, because it just doesn’t. I’m like, “I’m a professional Twitter, Please don’t.” They were talking about the Democrats don’t believe in the future, and I said, “I have four children,” and I said, “How many do you have?” And he said, “None.” I said, “I believe in the future much more than you do.” I said, “I’m sorry. I’m sorry you don’t have children. But if I have children, it means I believe in the future.”
ALISON BEARD: Yeah. What is some of the coolest stuff that you’re seeing in the climate tech arena? What are people working on?
KARA SWISHER: Lots of things. By the way, that guy acknowledged that and he said, “I’m really sorry. I just was doing the typical reductive team thing.” Right? And then he thought about it, he’s like, “Of course you do.” It was great. That’s what I try to do a lot. I don’t try to immediately pick fights, but I will push back and say, “Think harder. Think a little harder, people, about everything.” Everyone’s not a team person, like I’m on team blue or team white. It makes you not very smart if you have to suck up all one side’s ideas and then ignore and denigrate other people’s opinions.
ALISON BEARD: Yeah, and it’s important to engage, right?
KARA SWISHER: Yeah, yeah.
ALISON BEARD: You can’t just mute the comments or whatever, because-
KARA SWISHER: I mean, when you’re talking to these crazy QAnon people, they’re just nuts. I’m sorry. Then you don’t even have to be polite. There’s no two sides to it. But some people, “Okay, why do you think this?” I think it’s better, even if you don’t come to an agreement, to at least acknowledge that not everybody is a lunatic. Whenever you have to a pick side, nobody wins, essentially. Even if you’re right, it’s not going to end well.
But I’m sorry, you asked about climate change. There’s all kinds of solutions technologically. One is carbon mitigation. That’s gotten a lot of funding. That’s taking it and putting it in algae or out in space or whatever. There’s all kinds of different things happening. Another is how to create energy to replace fossil fuels. I think that’s the top one. In fact, we’ve got to get rid of carbon emissions immediately to zero, not to 50%, but zero. The changes are already well established by most climate change scientists. My favorite part is if there’s 20,000 scientists saying one thing, we have to listen to the four who don’t agree. Stop it. Stop it. Stop it, media. Stop it. Don’t even listen to these politicians who do this.
Creation of new fuels, whether it’s hydrogen fuels. We had a really interesting entrepreneur from – an Israeli who was putting things on piers with waves. There’s some really interesting stuff in the way we do food. You’re thinking about all these empty buildings, commercial buildings. Well, why not fill them with vertical farming and bring food right… they’re too expensive now, these amazing strawberries, best thing I’ve ever eaten. You’re like, “What?” Because they taste good, as opposed to the shitty strawberries we all have to eat. What else did we have? We had a guy who’s taking all the furnaces out of, I forget, one city, and putting electric heat pumps in.
Obviously, the transportation stuff captures people’s imaginations, but building materials is another area. Huge contributor to emissions. Existing buildings are a huge problem, like replacing the things that cause carbon emissions. There’s all kinds of really… new materials, and obviously you have to get to people’s use. Recycling as a good business, try to figure out how to make recycling an actual business, food. Clothing is another area, new kinds of clothing materials. That’s a big contributor, clothing, just in that fast fashion. I contributr to that in that I never changed my clothes since I was in high school.
ALISON BEARD: Or your sunglasses.
KARA SWISHER: Or my sunglasses. I don’t change a lot. I look the same, me and Steve Jobs.
ALISON BEARD: Yeah. I’d love to now talk about you. You’ve made a lot of big career moves in your time. As you said, you studied government and policy, and you had worked at the Washington Post, so you could have been covering those issues, but you decided to cover tech, and then you jumped from the Post to the Wall Street Journal and to conferences and digital journalism with all things digital. Tell me about the big lessons that you learned launching that with Walt Mossberg.
KARA SWISHER: I learned it for myself, is that I didn’t really want to fall in line as an employee. I never was very good at that. So, I decided to be an entrepreneur and do things on my own. A lot of it had to do with taking control of my fate. I didn’t want to take orders, really, and I didn’t believe in some of the orders I was taking. I didn’t think they understood the changes that were happening and that you needed to have a number of revenues. Now everyone’s like, “Oh, yes, number of revenue streams,” but I had four of them many years ago. I was like, “If that’s not going to work, then this isn’t going to work. If this falls away, then you need this.” So, I spent a lot of time thinking about that. I was a business person as much as I was a reporter.
The things I learned about is take control over everything that you can. I think it’s critical. Right now, this new thing, I left the New York Times, people were like, “What? Who leaves the New York Times?” I’m like, “I do, because I want to own my stuff. I want total control over it.” They’re very good journalists at the New York Times, I just would rather do it myself. That’s all. No harm, no foul to them, but I have my ideas and the way I want to do it. I don’t want to ask permission.
ALISON BEARD: And in all of these ventures, you’ve been the face and the leader. What kind of boss are you?
KARA SWISHER: Well, I have a new thing where I call it staff zero, where I don’t want to have anybody as my staff. You’re not supposed to use that term anymore. Someone told me that.
ALISON BEARD: Team members. Team members. That’s what you’re supposed to say.
KARA SWISHER: But in any case, whatever you want to call anybody. I’m okay. I don’t like management that much. I don’t think I’m bad at it. I just don’t like to spend my days doing it. I think other people are better at it. I have an amazing producer named Nayeema Raza, who runs the team, and I tend to weigh in on the big things. I think people are surprised that I’m a lot nicer than they think I’m going to be.
One thing I did, I told everyone to take two weeks off when they take a vacation. I kind of forcibly did, because you can’t have a good vacation on one week. By the time you get back, you’re all relaxed and then you get back to work, and I don’t think it’s very good for your mental health. So, I would insist that people take two weeks vacation when they took a vacation. They’d resist it, and I’m like, “It’s good for me. You come back like nothing when you have one week off. You’re not a very good worker,” and so I use that argument, whatever. I just think it’s better.
ALISON BEARD: What do you look for in the people that you gather around to be part of your team?
KARA SWISHER: People who are outspoken. I like being challenged. I like disagreement. I like editorial tension. I like people that aren’t hurt about editorial tension. They don’t get anxious when you disagree. I’m talking about civilly disagree. I don’t mean… I don’t like that. But I do like people who really can push back, and also when they push back and it doesn’t go their way, they move on, right? I like people who are forthright, I like people who feel like they want to make something beautiful. I don’t like people who are quietly frustrated. I think if you’re frustrated, you should go. What are you doing living in a job that you don’t like? I don’t get that. I’ve never done that. I leave the minute I feel frustrated. So, I like people who are aware of the thing. I like people to leave.
Actually, one of the things I remember was Mike Isaac, I think, or one of my employees, and they’re like, “I didn’t want to tell you I was…” he was going to the New York Times. New York Times took a lot of my reporters from Recode, but he’s like, “I thought you’d be upset.” I’m like, “Why would I be upset that you’re doing better? I feel great for you. I would like people to move on to greater things and realize greater potential that they have.” So, I like people who are ambitious and eventually will leave me. I like that. I like that in people. I like people who enjoy their work. There’s far too many people really just don’t like what they’re doing.
Many people don’t have choices, but the people who do have choices and stay in jobs they hate, I don’t even understand. If I’m not having a great time, and I’m not talking about, because I’m not a partier, I don’t drink, I don’t smoke, I don’t take drugs, but it’s like if you’re not enjoying everything you do all day, why are you doing it? I can’t even begin to understand. So, I like people who are aware of their happiness in their work.
ALISON BEARD: Yeah. It’s a little bit ironic that you brought up taking time off, two weeks.
KARA SWISHER: I don’t take any.
ALISON BEARD: Yeah, so you don’t take any time off. You talk about it a lot.
KARA SWISHER: I do, for other people, yes. Do as I say, not as I do.
ALISON BEARD: So, where does that drive come from?
KARA SWISHER: Well, it’s not a drive so much. I have four children. Okay? I made that choice as to have that many kids. My older sons are 20 and 17, so they’re very nearly out of the house. I have another son who’s nine months old. But my older son, who I just adore, he’s amazing, he’s at NYU, he goes, “You were almost out, mom. You could have gone to Hawaii whenever you felt like it,” and I was like, “I know.” I was almost… but I chose it. I chose to have more kids. Everyone’s like, “You can do everything.” You can’t do everything. I’ve picked family and work. I cannot have endless vacations as the third.
ALISON BEARD: Yeah. So, you’re actually anticipating my next question, because you have had a major career, but then it is very clear from your Twitter feed and when you talk that you do adore being a mom. Talk about how you balance that, though. I ask this question of men too.
KARA SWISHER: Yeah. Yeah, that’s okay. Here’s how I balance it. I do what I want. I have my hours when I want to. That’s why I work for myself. I don’t work for other people. If I had to be in the office every day from a certain time period, I think I would suffer. So, I created a career where I could work until three o’clock and then meet them at school and have dinner. I used to take my sons to dinner. My ex-wife worked at Google. She had to stay there till eight o’clock at night. So, I got to have dinner with them and then I went back to work. Right?
Flexibility, the way I’ve designed my work, I can do it at different times, which is great. I think I was way ahead of… someone was talking about I was the original remote worker. I never went in the office. I hate the office. I hate the office. We did all of All Things D out of my cottage in the back of my house, and we did once a week get togethers, lunches that I thought were important for team building. But we did everything virtually. Then when Slack came, we used that.
ALISON BEARD: You know, as I was researching for this interview and then also thinking about the evolution of the tech industry, I realized that you are a lot like many of these leaders that you’ve covered. You’re smart, entrepreneurial, hardworking, pretty obsessed with your work, your focus, but willing to pivot. You’re always thinking about the future. So, do you feel a kinship with the Musks and the Bezoses of the world?
KARA SWISHER: Yes, I do. I do like the idea of their entrepreneurship, of thinking up an idea and making it happen. I marvel. I was at our last Code this year, I was looking around and I was like, “Look how many people I made jobs for.” I wasn’t patting myself on the back, but just one idea that Walt and I had provided jobs for 20 years to people. Really good jobs, really fun. Look at all the great content we made just from our idea. That to me is a big deal. You look around and you create jobs and ideas and things that people use. That feels great. That feels really great. I have to say it’s a really nice… an ability to be an entrepreneur and make things that then have impact on wide range of people, whether it’s your customers or your employees is really kind of cool.
ALISON BEARD: And why do you think you have that ability to quit while you’re ahead and jump to something new, even though you don’t know that it’s going to be as much of a success?
KARA SWISHER: Well, one thing is I’ve had a lot of success. Whenever I do that, it tends to work out, because I think really hard about my ideas. If it doesn’t work, I don’t care, then I’ll do something else. I always feel like… one time someone was saying that to me, like, “If you don’t do this, you’re going to be washed up at 28.” I remember, it was really something. I was like, “I could be a frigging waitress, I’ll be just fine.” You know what I mean? “I’ll be fine no matter what I do.” They were like, “You’re going to ruin your career.” I’m like, “Really? You think right now is the end of my career?” I say that to young kids, including my sons, my older sons. My son right now is all upset about college, and I’m like, “Don’t worry.” Tall, tall white man with wealth. Somehow you will overcome the odds.
I’m always like, “You can do what you want. You are lucky to be in a country that you can do what you want. Everything is up to you and you can make some choices.” I don’t say not to do anything, but at least think hard. So, I can leave because I’ll do something else. I’ll make something else. It always works out because if you stay at the fair too long, you just become stale and you’re just phoning it in. I find that depressing. I think it’s because my dad died when he was 34. I really think it informs everything I do. He’d just gotten out of the Navy, he was a poor guy, relatively poor family, lower middle class family, but couldn’t afford college and medical school, and so he went into the Navy and he paid for everything.
He gets out, he has this great new job, his first big, high paying job at the time, running an anesthesia department at a major hospital in New York. He has three kids, new house. He just was able to buy a new house, and he died. Think about that. Now, that was tragic because he was really looking forward to his next chapter, but I think about that all the time. I talked about that at the last Code. Steve Jobs made all the things he made when he was dying, all the things we remember him for when he was dying, every second he was dying.
So, I think about, he gave a great speech at Stanford that I read every month or so, which I referenced in my last Code, which is if he had too many days in a row where he said he wasn’t happy, he stopped and he changed. I think that’s a really good piece of advice for a lot of people who have the ability to do it. Not everybody does, as I said.
ALISON BEARD: Terrific. Well, Kara, it has been wonderful talking to you. Thanks so much for coming on the show.
KARA SWISHER: Great. Well, thank you for doing such a thoughtful and nice interview. I appreciate it.
ALISON BEARD: That was Kara Swisher, journalist, entrepreneur, and host of On with Kara Swisher, a Vox and New York Magazine podcast.
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This episode was produced by Mary Dooe, we get technical help from Rob Eckhardt. Hannah Bates is our audio production assistant, and Ian Fox is our audio product manager. Thanks for listening to the HBR IdeaCast. We’ll be back with a new episode on Tuesday. I’m Alison Beard.