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Kara Swisher and Scott Galloway Debate Their Money Strategies | Pivot

Kara and Scott take questions from listeners about how they manage their money, how to fix the American tax system, and which public policy would help the greatest number of people. Plus…all the audience suggestions for Kara’s next tattoo. #pivot #karaswisher #scottgalloway #ai 00:00 Intro 00:36 Taxing AI? 4:15 What’s One Policy You Would Implement? 7:23 Investment Strategies 15:45 Advice for Single Parent 23:02 If You Had All the Money in the World… 26:55 Tattoo Talk Producers: Lara Naaman Zoë Marcus Taylor Griffin Christine Driscoll Video Producer: Manolo Moreno Vox Media's Executive Producer of Podcasts: Nishat Kurwa Subscribe to Pivot on Apple Podcasts: https://podcasts.apple.com/us/podcast/pivot/id1073226719 Subscribe to Pivot on Spotify: https://open.spotify.com/show/4MU3RFGELZxPT9XHVwTNPR Follow us on Instagram and Threads at: https://www.instagram.com/pivotpodcastofficial/ Follow us on TikTok: https://www.tiktok.com/@PIVOTPODCAST Send us your questions by calling us at 855-51-PIVOT, or email pivot@voxmedia.com

Scott GallowayhostKara SwisherhostLynnguestLiamguestLisaguest
Dec 19, 202530mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:000:36

    Intro

    1. SG

      I never let money get in the way of a good time. I am spending money like a '50s gangster just diagnosed with ass cancer.

    2. KS

      (laughs) (instrumental music) Hi, everyone. This is Pivot from New York Magazine and the Vox Media Podcast Network. I'm Kara Swisher.

    3. SG

      And I'm Scott Galloway.

    4. KS

      And Scott, this is our end-of-the-year listener mail episode. We're probably both elsewhere doing fun things, but, uh, are you ready to hear some emails and voicemails from our lovely listeners who, by the way, we have a full new appreciation for after meeting so many of them on our Pivot Live Tour? I really enjoyed that. Are you ready?

    5. SG

      Yeah, ready.

    6. KS

      Okay, Scott.

  2. 0:364:15

    Taxing AI?

    1. KS

      Let's kick off with a question about taxing AI. Let's listen. (screen whooshes)

    2. LY

      Hi, this is Lynn. Um, I've been wondering, as artificial intelligence continues to replace human jobs, do you think we'll ever see a tax on AI itself or on the companies that use it as a way to offset its impact on displaced workers? And would that, in a sense, become a new way of taxing the rich? Thank you. Bye. (screen whooshes)

    3. KS

      Gosh, Lynn, what a great question. Actually, I'm gonna start, you know, uh, many years ago, Bill Gates sort of set off a kerfuffle when he talked about taxing robots if they become workers, um, the same way, 'cause you aren't gonna get those money that you get from human workers, and so they should be taxed in the same way. I hadn't really thought about it about AI. Uh, Scott, I, I, I'm, I, I think I'm ... Yeah, I think you're more qualified to answer this.

    4. SG

      I don't know if that's true. Uh, m- my view around taxation is that the moment you start taxing specific industries, you weaponize special interest groups to come to their defense, and you also create some confusion around, like, is Oracle AI? You know, if, if McKinn- ... I mean, at what point ... What qualifies as an AI company and not an AI company? Is Microsoft an AI company? What, what I'm a big fan of, and I think that the, the, the caller is alluding to, I wanna go back to Reagan-era taxation, and that is, there's no difference between ... I think the capital gains tax deduction is nothing but a transfer of wealth from young to old because somehow we've decided that sweat is less noble than money. And that is, the money I make on money gets taxed at a lower rate than the money that young people make on sweat. So, I would like to see an elimi- elimination of the capital gains tax deduction and raise those rates to current income and restore a progressive tax structure. In my view, you do it across all income and all firms because I think the moment you start getting into this notion of let's put a super tax on this type of firm, I think that's, I think you regulate them, I think you have an EPA, you have an AI Act, you have privacy, you have laws. But in terms of taxation, I just think you say, look, above a certain level of profitability when you sell a stock, you pay this much in tax.

    5. KS

      Mm-hmm.

    6. SG

      I think taxes need to go up. I think we need to do away, we need to raise long-term capital gains from 21 to 37%. It makes no sense, and I'm paying lower taxes than people actually working for a living.

    7. KS

      Mm-hmm.

    8. SG

      But I think you apply it to every company 'cause a lotta, a lot of ... For example, the AI boom is gonna make a lot of people in the construction industry very, very rich.

    9. KS

      Yeah. Ha- it is. That's one people that, group of people that are benefiting. Yeah. Yeah, do you tax them?

    10. SG

      Your thoughts, Kara?

    11. KS

      Would you tax them, right? Would you tax-

    12. SG

      Oh, uh, my out of ... Uh, uh, there's so many loopholes right now. The only way we get there is with an AMT.

    13. KS

      Yeah.

    14. SG

      There should be an AMT.

    15. KS

      Yeah, 100%.

    16. SG

      Anything above $10 million and, uh, anything above 3 million, you pay a federal AMT of 40%.

    17. KS

      Yep.

    18. SG

      Because what happens is guys like me weaponize the tax code and do 1202 and buy assets-

    19. KS

      I don't even know what that is.

    20. SG

      ... and we end up paying high teens in tax rates.

    21. KS

      Yeah.

    22. SG

      So the stated, the stated ... Uh, we focus too much on tax rates, not on the tax code, and enough already.

    23. KS

      Yeah.

    24. SG

      There is no reason why someone working for money should be taxed at a higher rate than someone who is making money from investments.

    25. KS

      Although I don't see anything wrong with taxing robots if they're workers. I don't know. I don't know. It's-

    26. SG

      It's an interesting one.

    27. KS

      Yeah.

    28. SG

      Uh-

    29. KS

      Yeah, I just, I, when he said it and I thought, "Oh, Bill Gates." And then I thought, "Oh actually, he's really smart. I forgot." Anyway, it's an interesting question. We have to deal with all these things and what happens with displaced workers and how we're gonna pay for that or get them different jobs. So, there's gonna be a lot of rethinking of all the way the workplace is taxed to how it's conducted, what people get paid, um, and obviously the damage that some of this AI is gonna do. There's gonna have to be some mitigation.

  3. 4:157:23

    What’s One Policy You Would Implement?

    1. KS

      Uh, okay, Scott, next question. This one is a tough one. Let's listen. (screen whooshes)

    2. LI

      Hey, Scott and Kara. I'm Liam, a high school senior from New York, and I wanna ask the following. America certainly has its fair share of economic and social problems, but a lot of the time these problems stem from the same root causes. Too often though, our politicians create costly Band-Aid solutions rather than trying to address the underlying issues. So my question to you guys is, if you could implement one single policy to try and solve the most problems at once, what would it be? Thanks for taking the time to answer. (screen whooshes)

    3. KS

      Wow. That's a great question. I, I hate that we're ... Just one thing? If I had to pick, (sighs) $25 minimum wage.

    4. SG

      I like that. Um-

    5. KS

      And, uh, let me explain very quickly.

    6. SG

      Yeah.

    7. KS

      Because I think it, it lists all boats. If people get paid more, they'll spend more. It creates a better economy. I know there's initial costs for businesses that have these things, but it creates an, uh, uh, people that can do a living wage, they spend money. They wanna do things. They lean into the future. I just, it, it, it would be great. I, I, the second one would be, uh, uh, eight million houses, more housing, but go ahead.

    8. SG

      One's a program. One is structural or l- legislative. Um, I do think a lot of this reverse engineers to, in terms of inability to get things done, to Citizens United.

    9. KS

      Mm-hmm.

    10. SG

      If I could overturn-

    11. KS

      Oh.

    12. SG

      ... Citizens United-

    13. KS

      Yes.

    14. SG

      ... I would ... I think a lot of our problems stem from the weaponization of Washington by corporate interests and corporate money.

    15. KS

      Oh, wow.

    16. SG

      Um, and then-

    17. KS

      Wow, Bernie Sanders. I like that answer.

    18. SG

      Well, uh, I mean, it's just true. Uh, there's, there's more, there's more full-time lobbyists living in DC working for Amazon than there are sitting US senators. So what do you know? Uh, anyway, uh, but, uh, you know, a close second, mandatory national service, universal childcare, lower Medicare eligibility by two years a year for 10 years until three-quarters of America has essentially socialized medicine. And you know, I could go on and on.

    19. KS

      Yeah.I love it. I love that answer. I was not expecting it. Boy, that came out left field there, Scott. All right, Scott, let's take a quick break and we'll be back with more listener questions. (instrumental music)

    20. NA

      Support for the show comes from Vanguard. To all the financial advisors listening, let's talk about bonds for a minute. Capturing value in fixed income is not easy. Bond markets are massive, murky, and let's be real, lots of firms throw a couple flashy funds your way and call it a day. But not Vanguard. Vanguard bonds are institutional quality. Institutional quality isn't a tagline, it's a commitment to your clients. It means top grade products across the board. The lineup includes over 80 bond funds. They're actively managed by a 200% global squad of sector specialists, analysts and traders. Lots of firms love to highlight their star portfolio managers, like it's all about that one brilliant mind making the magic happen. Vanguard's philosophy is a little different. They believe the best active strategies shouldn't be locked away with one person, they should be shared across the team. That way, every client benefits from the collective brain power, not just one individual's take. So, if you're looking to give your clients consistent results year in and year out, go see the record for yourself at vanguard.com/audio. That's vanguard.com/audio. All investing is subject to risk. Vanguard Marketing Corporation, distributor. (instrumental music)

    21. KS

      Scott, we're back.

  4. 7:2315:45

    Investment Strategies

    1. KS

      The next listener wants to know what we're doing with our money. Let's listen.

    2. SG

      Hi, Scott and Kara. It's Eric from Brooklyn. Scott, you talk a lot about how you spend, how you invest, and I imagine how you save. Kara, you don't, and you come off as maybe a bit more frugal. Can you share a little bit about your investment, spending, and saving philosophy in the context of your shared success? Um, thank you so much and, uh, hope we'll see you soon.

    3. KS

      Gosh, thanks Eric. A little personal. Um, uh, I am not ... I don't think about money a lot and that's my problem. I'm not interested in it. And I make a lot of money, I do. Um, for, especially for a journalist, I, I'm like, I'm like Daddy Warbucks of journalists in that regard. But I would say I save a lot. I have a lot of savings and I diversify. I'm sort of your basic person, uh, basic bitch of investing. I have bonds, I've got l- quite a bit of real estate that I hold onto as f- for savings, as Scott calls it. Um, I, um, I don't spend a lot of money. I really don't. Uh, it's, it, it has nothing to do with me being frugal, I just don't ... I'm not, I don't like buying a lot of stuff. I'm wearing the same ... All my clothes I've had for 20 year ... I don't buy a lot of clothes, I don't buy drugs, I don't buy ... I don't go out a lot. Um, I'm really boring. (laughs)

    4. SG

      You don't buy drugs? Where did that come from? (laughs)

    5. KS

      I don't buy ... Well, n- no one here buys drugs. (laughs) Maybe you. I don't buy th- like I don't drink, I don't party. I, I'm trying to think-

    6. SG

      Right.

    7. KS

      ... like what costs money. I, I have a Chevy Volt, like, and a Kia, so I don't really care about cars.

    8. SG

      You're the, you're the primary breadwinner in a family of four-

    9. KS

      4 billion.

    10. SG

      ... 4 or 6 people.

    11. KS

      Yeah. I-

    12. SG

      I mean, that in itself is-

    13. KS

      Yeah. Yep.

    14. SG

      Mommy's gotta make real money.

    15. KS

      Mommy's gotta make real money. And so that's spent on the kids. I definitely get them through college and ... But I did those savings plans for college for, for my boys and I'm doing them for my little kids. That worked out really well actually, I didn't have to think about it. Um, and I did that 20 years ago for my older kids. Um, I think I, um ... What I do s- spend on, I have way too much cash compared to what I need, but I like to have it. I'm one of those sort of people. I do spend money on a couple of things. Um, I always will upgrade. I mean, I always get first class. I fly, well, you know, I don't have a private plane, but I, I would love to have one, but, um, I'm sorry to say that, people who love to save energy, but I think they're wonderful. Um, and I, I will upgrade all the time, like upgrade hotels, a- and things like that. So, I, I, I've gotten ... I got old very early and then I'm like, I didn't want to be in bad food, I didn't want to stay in bad places. I suppose if I spend on anything a lot, it's vacations. I really, I, I do. But I'm still more frugal than Scott. Scott is real- ... I really admire Scott's vacation spending. Um, I don't know. Scott, what do you think?

    16. SG

      Well, you know, I think a lot about this.

    17. KS

      Mm-hmm.

    18. SG

      One of my addictions is money.

    19. KS

      Yeah.

    20. SG

      And that is, I continue to be too focused on it to the detriment of my mental health, and it takes time away from my family. I grew up with a scarcity of money until, you know, I got through my senior year of college on Top Ramen and bananas. That's not an exaggeration. I was in student debt, um, you know, even at the age of 27. I was traum- not traumatized, but I had a difficult time paying for my mother's, um, uh, healthcare. So I've been very focused on money and got very lucky. And that's not a humble brag. I think I'm a monster. I think I'm talented and hardworking, but I did get lucky, and now I am, by most people's standards, wealthy. Uh, my approach to spending money is that we don't own money, we rent it. And I also ... You collide that with my atheism and I believe that this is all coming to an end pretty quickly for me. So I spend a great deal of money. I spend between 3 and $400,000 a month. Uh, I own homes all over the world. I, uh, have a plane, and I spend most of my money on homes and experiences. And-

    21. KS

      Not gifts for Kara, just so you know.

    22. SG

      (laughs)

    23. KS

      Just-

    24. SG

      But along those lines, the way I try and keep in check is I think hoarding money is a virus. When I hit my number eight years ago, I decided anything above that number I would give away. And what I do each year is I look at my total spending and I match it and I give that amount of money away.

    25. KS

      You are very generous.

    26. SG

      And it keeps my ... N- My net worth has not increased in eight years.

    27. KS

      Yeah.

    28. SG

      And, uh, because I think hoarding wealth is a virus. There's no reason anybody needs to be a billionaire. But there's n- I can't stand it when wealthy people can't, aren't good at spending money. I have an amazing time.

    29. KS

      Yeah.

    30. SG

      I do things for my friends and family to-

  5. 15:4523:02

    Advice for Single Parent

    1. KS

      (swoosh sound)

    2. LI

      My name's Lisa. I'm the mother of a 17-year-old boy and a 13-year-old girl. Two years ago, their father died unexpectedly. Kara, as someone who lost their father and also as someone who's raised children without a male partner, and Scott, as someone who was largely raised by a single mother, I'm looking for advice. Kara, what do you wish your mom did to keep your dad's memory alive? What did she do right or wrong? Scott, what did your mom do right to make you feel like one parent was enough? What do you wish she would have done if, for example, she had had more financial resources? Thank you both. (swoosh sound)

    3. KS

      Man, these are good questions. They're highly emotional (laughs) . God, Jesus.

    4. SG

      Yeah.

    5. KS

      I don't think my mom did a very good job. I, I hate to trash my mom this episode, but it's true. Uh, you know, she lost contact with my dad's, uh, parents, and I reestablished it when I was in college myself. Uh, you, when you're a kid, you're a little bit at cross-purposes of loyalty, and I, I thought that was not good. Uh, she threw away a lot of pictures, um, which I recovered, some of which I spent a lot of time finding, stuff about my dad. And I have, right now have a big box of letters of his that I just read one that was wonderful. Uh, um, I, I think she should have spent a lot more time talking about him, and, and I don't, I don't think she remembers h- herself. But I don't think she was kind to his parents. Um, so I, that was one thing, is if your grandparents were good people, make sure your kids know them and know their relatives on your dad's side and therefore his friends. I wish I knew more about my dad's friends. And I found out later when I wrote a piece in The Washington Post, I got inundated with friends of his that my mother never told me about, that I then went and met, and all these stories. There was a g- as, I think I've said this before, there was a gay couple who my dad was lovely to, and I didn't know that. I, I, it was a wonderful thing to find out. Uh, a young, uh, African American woman he tutored wrote me from... Now she was a doctor, and said that she wanted to thank him. Like, an ex-girlfriend (laughs) of his wrote me saying it should've been me, uh, that married him (laughs) , uh, which was funny. Like, there's a picture of him behind me. I have a lot of pictures of him around. One thing I'm sad is my kids won't know him. I named my s- and I also named my son after my dad, so that's what I would say.

    6. SG

      It's nice. Yeah. (sighs) I mean, there's a... Just thinking about it, um, stirs emotions. So when I was 15 and in California, you were what you drove and e- or just having a car was everything. You had no social life in high school in LA. There was no public transportation unless you had a car. We didn't have a lot of money. My mom used to come home, uh, when I was 15 and a half and honk the horn, and we'd go into a garage at this giant apartment complex and she would teach me how to drive stick on her 19, like, '77 Opel green-

    7. KS

      Oh, yeah.

    8. SG

      ... you know, lime green Opel Manta.

    9. KS

      Mm-hmm.

    10. SG

      And then on my 16th birthday when I passed my driver's test, she came home and she had bought this shitty Acura, and she put her arms on my shoulders and put keys in my hand and said, "You're a handsome young man and you have a car."

    11. KS

      Oh. Scott, you're breaking my heart.You okay?

    12. SG

      Yeah, I'm good. The, the best thing, literally, I think of any parent or any mother. Um, if you tell your kids every day they have value, they start to believe you.

    13. KS

      Yeah, 100%. Scott, I bought you an Acura for your-

    14. SG

      There you go.

    15. KS

      ... for Christmas. (laughs)

    16. SG

      That's what I needed.

    17. KS

      I gotta get you out of this. Uh, that is a beautiful story.

    18. SG

      No, but I-

    19. KS

      I didn't know that.

    20. SG

      When I, when I-

    21. KS

      Why didn't I know that?

    22. SG

      You know, you get... The good news is you become more thoughtful. When I reverse engineer all my blessings, the two core things, it's big government, assisted launch Pell Grants, University of California, uh, DARPA, the internet, uh, and also just hands down, I think I've always had a base of confidence that, that my mother gave me.

    23. KS

      Oh my God, I can't believe-

    24. SG

      The more-

    25. KS

      ... your mother did this.

    26. SG

      ... the more, uh, pragmatic piece of advice is that unfortunately if you were to reverse engineer a young man's problems to a single point of failure, it's when he loses a male role model. And you've had, your husband has passed. I think it's especially important that you get men involved in your son's life.

    27. KS

      100%.

    28. SG

      Uh, Kara, you do a great job, uh-

    29. KS

      I do. I didn't mention that.

    30. SG

      ... with, with your brothers.

  6. 23:0226:55

    If You Had All the Money in the World…

    1. KS

      Okay, Scott, moving on. This question comes from Paul via email. I'll read it. "If you had all the money in the world ..." These are such good questions. Let me read this. "If you had all the money in the world, what would you be doing with your precious time at this moment with that money, and why aren't you doing that?" Oh my God, Paul. Wow, Paul. That's a lot. Scott, you go first on this one. And I'll, I ha- I gotta think for a second.

    2. SG

      I'm doing it. I realize how privileged I am, and I realize this is, you know, a function of my being born a white male heterosexual. And I, uh, you know, um, I do exactly what I'm ... Money ha- plays, uh, money as a construct puts no constraints on my life. I am doing exactly what I wanna be doing every day. Every day. I'm, I'm blessed, and I realize that there's only 0.1% of the populace can do that. If I had billions of dollars, and I'd started a private equity firm like-

    3. KS

      All the money in the world.

    4. SG

      W- well, what I would be focused on right now if I had, say, hundreds of millions to waste, I'm gonna spend millions, but I don't have tens or hundreds of millions, I'm very, very focused on restoring some of the traditional American values and getting Democrats elected in '26 and in '28.

    5. KS

      Yeah, that's what I'd do. Yeah, I would do, put a, take a bunch of money and solidify a progressive, uh, a pr- not a, not, like, hateful to conservatives, but, like, in American values that are about fairness and equity and things like that. So I'd spend money on that. I would spend money on, um-I would, I'd, I'd f- I'd do the MacKenzie Ba- Scott. That's what I would be. That's what I ... I just suddenly show up with money and not be heard from or seen from again. I would ... That's how ... I would do what she's doing, exactly what she's doing, and suddenly give Howard a whole bunch. She's d- done two gifts to Howard and she's ... All of a sudden, she's over at Planned Parenthood and then she's here. She's so diverse in her giving, um, that I, I love it, and it's, uh, that's how I would behave. I would, um, I would also create, um, uh, uh, universal (laughs) daycare. I mean, that's what I would do for people. Better childcare, uh, for, uh, all kinds of parents. Uh, uh, I, I would somehow figure out a way to fund. Like right now, N- New Mexico has it 'cause they have all this oil and gas or shale, uh, money. They can do it. Every state, we should have, uh ... Nationally, we should have universal daycare.

    6. SG

      Yeah.

    7. KS

      Universal daycare. That's what I would do. I would spend less on health stuff, but I can see why ... Um, again, uh, money is ... I don't spend a lot of money so I wouldn't buy anything. I wouldn't ... Uh, I'm trying to ... Would I buy anything? Maybe like my own Taylor Swift concert perhaps. That's what I would do.

    8. SG

      Yeah, I might buy-

    9. KS

      Anything crazy you would buy?

    10. SG

      I might, I might buy a Gulfstream G800.

    11. KS

      I'd invite Scott just to hurt him, play with his ears. (laughs) You'd be so nice to Taylor Swift. Anyway, something like that, something like ... Someone I enjoy like that. All right, Scott, one more quick break. We'll be back f- uh, with more from our listeners. Support for this show comes from Rubrik. A lot of companies are deploying AI agents now. They're automating tasks, handling workflows, and making decisions. But here's the thing, sometimes they mess up. What a surprise. They might delete the wrong files, make changes you didn't authorize, or just go off script. And when that happens, you're stuck trying to figure out what went wrong and how to fix it, unless you're using Rubrik Agent Cloud. Rubrik Agent Cloud is a platform that allows you to monitor, govern, and rewind AI agent actions. One platform to help you unleash more agents faster without the risk. It's running in the background the whole time watching what's happening, making sure things stay on track so you get full visibility, set guardrails so agents don't go rogue, and if something breaks, you just roll it back. If your business relies on AI agents, you need the ability to monitor, govern, and rewind their actions. Right now, our listeners get exclusive early access to Rubrik Agent Cloud. Head to rubrik.com. That's R-U-B-R-I-K dot com. Rubrik.com. Okay, Scott, we're back

  7. 26:5530:08

    Tattoo Talk

    1. KS

      and we're ending on something very special. A few weeks ago, I asked what tattoo I should get for Scott, ideally on my ass. Let me read some of the answers we got. "A roll of toilet paper with an S on one of the sheets." "The Professor Galloway memorial tattoo should feature an angry but dignified Daisy Duck with a lot of pink shading." Interesting. "A penis that cleverly embeds his name on it."

    2. SG

      Hmm.

    3. KS

      "SC on one cheek and TT on ... (laughs) other." (laughs) Get the O is the asshole? Get it? Get it?

    4. SG

      Yeah.

    5. KS

      Okay.

    6. SG

      I get it.

    7. KS

      Uh, "Groucho nose and glasses with Scott's nose and glasses." I don't like any of these. I do like the SC TT I'd say. Uh, I need more. Scott, do you have any suggestions?

    8. SG

      Uh, I would get some ... I would just s- "In case of emergency, call Scott." Um, or-

    9. KS

      Oh, my god. Break glass? Okay.

    10. SG

      Or maybe a tiny raccoon holding a beer-

    11. KS

      Oh.

    12. SG

      ... because it says-

    13. KS

      You know what? I, uh ... I think, "That's good," is what I should get, just the words-

    14. SG

      Um-

    15. KS

      ... "That's good."

    16. SG

      ... a barcode, a barcode that if you scan it, it said, "The problem with Scott is ..." Um ... (laughs)

    17. KS

      (laughs) See, you're better.

    18. SG

      Uh-

    19. KS

      Yeah.

    20. SG

      Let me see. Uh, I don't know. Um-

    21. KS

      I would ... How about a cat and a dog sort of fighting but hugging at the same time? Something like that?

    22. SG

      You know-

    23. KS

      No?

    24. SG

      Tattoo of a receipt, "Total: zero, zero, zero."

    25. KS

      Right.

    26. SG

      "I am putting up with Kara."

    27. KS

      Ha ha ha ha ha.

    28. SG

      Um-

    29. KS

      Uh ...

    30. SG

      A broken halo with the caption, "Scott tried."

Episode duration: 30:08

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