Personal Investment Strategies, Effective Public Policies and Should We Tax AI?

Summary

Pivot – "Personal Investment Strategies, Effective Public Policies and Should We Tax AI?"

Podcast: Pivot
Host: Kara Swisher & Scott Galloway (New York Magazine)
Date: December 19, 2025

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Episode Overview

This end-of-year listener mailbag episode features Kara Swisher and Scott Galloway fielding bold, thought-provoking questions from their audience. The central themes: the implications of taxing AI, transformative public policies, and candid discussions about personal wealth, parenting after loss, and how the hosts actually live and invest. As ever, the discussion is rich with their trademark banter, irreverent honesty, and incisive insight.

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Key Discussion Points & Insights

1. Should We Tax AI and Companies Using AI?

[01:56–05:18]

• Listener Question: As AI threatens jobs, should governments tax AI or the companies utilizing it to offset impacts on displaced workers—or is that just taxing the rich by another name?

• Kara Swisher references Bill Gates’ previous calls to tax robots as workers. She admits, “I hadn't really thought about it about AI,” inviting Scott’s policy-focused take.

• Scott Galloway argues against industry-specific taxation:

  “The moment you start taxing specific industries, you weaponize special interest groups to come to their defense. …Is Microsoft an AI company?”

  “I want to go back to Reagan era taxation. …I would like to see an elimination of the capital gains tax deduction and raise those rates to current income and restore a progressive tax structure…. I think taxes need to go up.”

  — Scott Galloway [02:55–03:55]

• He advocates for an across-the-board approach: boosting capital gains rates, instituting a federal Alternative Minimum Tax (AMT) for ultra-high earners, and focusing on closing loopholes rather than targeting AI or other sectors.

  “We focus too much on tax rates, not on the tax code. …There's no reason why someone working for money should be taxed at a higher rate than someone… making money from investments.” — Scott Galloway [04:40]

• Kara adds: “Gosh, Lynn, what a great question. …There's going to have to be some mitigation,” underscoring the need to rethink workplace taxation and support for displaced workers.

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2. One Public Policy to Solve the Most Problems

[05:47–07:33]

• Question from Liam (High School Senior): If you could implement one policy to address America’s biggest structural problems, what would it be?

• Kara’s choice:

  “$25 minimum wage. …If people get paid more, they'll spend more. It creates a better economy…. It creates people that can do a living wage.” — Kara Swisher [06:12–06:22]

  • Runner-up: Rapid expansion of affordable housing.

• Scott’s answer:

  “If I could overturn Citizens United, I would. …A lot of our problems stem from the weaponization of Washington by corporate interest and corporate money.” — Scott Galloway [06:46–07:08]

  • Runners-up: Mandatory national service, universal child care, and gradually lowering Medicare age for near-universal coverage.

• Both hosts agree that meaningful, structural reforms—not “band-aid solutions”—are critical and deeply overdue.

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3. Personal Money Philosophies and Investment Strategies

[11:24–18:53]

• Listener Eric: Asks about Kara and Scott’s spending/saving/investing habits.

Kara’s Approach:

• “I don't think about money a lot. That's my problem. I'm not interested in it. And I make a lot of money. …I save a lot. I have a lot of savings, and I diversify. I'm sort of your basic bitch of investing. I have bonds… quite a bit of real estate… a basket of stocks… very diversified. I have a lot of cash right now.… I have way too much cash compared to what I need. But I like to have it.” — Kara Swisher [11:39–13:12]
• Major spending: Children (education, savings), some travel, modest lifestyle. “I'm more frugal than Scott.”

Scott’s Approach:

• “One of my addictions is money.… I continue to be too focused on it to the detriment of my mental health. …I spend between three and four hundred thousand dollars a month. I own homes all over the world. I have a plane.…” — Scott Galloway [14:03–15:02]
• Ethos: “We don't own money, we rent it.” Anything saved above his “number” goes to philanthropy. “My net worth has not increased in eight years. …there's no reason anybody needs to be a billionaire.”
• Investment lens: “I bought homes in all of those places except for Dubai… pretend Jeff Bezos is going to buy this home because the world is going to produce thousands of billionaires over the next 20 years.”
• Notable honesty:

  “Money is something I think a lot about because I didn't have a lot of it growing up. It's still a very big issue in my life.” — Scott Galloway [18:06]

Notable Exchange:

• “You live well, not opulently is the way I would describe it.” — Scott to Kara [18:50]

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4. Parenting After Loss: Advice and Reflections

[18:53–24:32]

• Lisa asks: As a widow, how do you keep a lost parent’s memory alive for kids? What did your own parents do right or wrong (Kara, after losing her father; Scott, raised by a single mother)?

Kara:

• “She [my mother] lost contact with my dad’s parents… She threw away a lot of pictures… I think she should have spent a lot more time talking about him… Make sure your kids know their relatives on your dad’s side and his friends.” — Kara Swisher [20:56–21:59]
• Kara names her son after her father and keeps his photos and letters visible.

Scott:

• Shares an emotional memory of his mother teaching him to drive and surprising him with a car, giving him confidence and affirmation.

  “If you tell your kids every day they have value, they start to believe you.” — Scott Galloway [22:59–23:03]

• Practical advice:

  “If you reverse engineer a young man’s problems to a single point of failure, it’s when he loses a male role model. ...especially important that you get men involved in your son’s life.” — Scott Galloway [23:13–24:10]

• “While boys are physically stronger, they’re emotionally and neurologically much weaker than girls.”

• Kara adds: “Let [kids] talk about [the lost parent] every day.… That’s critically important.”

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5. If You Had All the Money in the World, What Would You Do—and Why Aren’t You Doing It?

[28:55–31:28]

• Paul asks: If you had unlimited money, what would you spend your time on now—and why not now?

• Scott:

  “I'm doing it. Money plays. I'm doing exactly what I want to be doing every day.” — Scott Galloway [29:17–29:51]

  • Would double down on restoring American values and getting Democrats elected.

• Kara:

  “I’d take a bunch of money and solidify a progressive—not like hateful to conservatives—but… values that are about fairness and equity.”
  “I’d do the Mackenzie Scott [the billionaire philanthropist]—just suddenly show up with money and not be heard from again. …I would also create universal daycare.” — Kara Swisher [30:06–31:25]

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6. Behind-the-Scenes of the Pivot Live Tour

[31:39–34:40]

• Listener Brian: What happens backstage—any drama, wild parties?

• Kara:

  “No, we actually talk to each other....It's really quite civil. And then afterwards, we just go. We leave...Not tiring, but we just move on.” — Kara Swisher [32:19–33:03]

• Scott:

  “It was basically get up, get to the airport,…I would try and grab a workout… FaceTime my kids, and then start prepping for the show. …I drank less that seven days than I have in a long time. There was just no room for partying or alcohol.” — Scott Galloway [33:03–33:45]

• Both recount favorite moments (DC, LA) and the emotional, bonding nature of touring together.

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7. Tattoo Suggestions—A Pivot Tradition

[37:05–39:39]

• Kara reads out fan-submitted tattoo ideas themed around Scott—including:

  • “A roll of toilet paper with an S”
  • “Penis with his name embedded (‘SC’ on one cheek, ‘TT’ on another, ‘O’ as the asshole)”
  • “A barcode that, when scanned, says ‘the problem with Scott is…’”

• Scott suggests:

  “Just in case of emergency call Scott.”
  “A fortune cookie. And the fortune reads you will tolerate someone named Scott today.”
  “A tombstone that says rest in peace. Scott’s sanity taken by Kara.”

• This sign-off segment lets their famously spiky rapport shine.

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Notable Quotes & Memorable Moments

• On Progressive Taxation:
  “There's no reason why someone working for money should be taxed at a higher rate than someone… making money from investments.”
  — Scott Galloway [04:40]

• On Parenting After Loss:
  “If you tell your kids every day they have value, they start to believe you.”
  — Scott Galloway [23:03]

• On Living Well:
  “You live well, not opulently is the way I would describe it.”
  — Scott Galloway to Kara Swisher [18:50]

• On Spending Wealth:
  “We don’t own money, we rent it. …Hoarding money is a virus.”
  — Scott Galloway [14:03–16:04]

• On Having Enough:
  “I don't also—let me point out, my mom was a spendthrift, and it upset me… I was like, I'm always gonna have enough money.”
  — Kara Swisher [18:53]

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Timestamps for Major Segments

• [01:56] — Taxing AI and the future of work
• [05:47] — The one public policy fix (minimum wage, Citizens United)
• [11:24] — Discussing personal finance, saving, investing
• [18:53] — Advice for parenting after loss
• [28:55] — The “all the money in the world” question
• [31:39] — Behind-the-scenes of the Pivot tour
• [37:05] — Listener tattoo suggestions—lighthearted sign-off

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Tone & Dynamic

Swisher and Galloway’s exchanges are witty, frank, and brimming with the “bicker and banter” that makes Pivot distinct. They move from serious analysis to self-deprecating humor and deeply personal reflection—retaining sharp insight without ever losing their conversational edge.

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This listener-driven episode exemplifies the best of Pivot: sharp analysis, bold opinions, and genuine candor—whether talking about billionaires, healthcare, or the tattoos they’d (maybe) get for each other.

Transcript

[Kara Swisher]

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[Scott Galloway]

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[Kara Swisher]

Hi, everyone. This is Pivot from New York Magazine and the Vox Media Podcast network. I'm Kara Swisher.

[Scott Galloway]

And I'm Scott Galloway.

[Kara Swisher]

And, Scott, this is our end of the year listener mail episode. We're probably both elsewhere doing fun things, but 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?

[Scott Galloway]

Yeah. Yeah. Ready.

[Kara Swisher]

Okay. Okay, Scott, let's kick off with a question about taxing AI. Let's listen. Hi, this is Lynn. I've been wondering, as artificial intelligence continues to replace human jobs, do you think we'll ever see attacks on AI itself or on the companies that use it as a way to offset its impact on displaced workers and with that, in a sense, become a new way of taxing the rich? Of course, this would affect 401ks on a larger scale. Thank you. Bye. Gosh, Lynn, what a great question. Actually, I'm going to start. Many years ago, Bill Gates sort of set off a kerfuffle when he talked about taxing robots if they become workers the same way, because you aren't going to 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. Scott, I think you're more qualified to answer this.

[Scott Galloway]

I don't know if that's true. 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, I mean, at what point what qualifies as an AI company and not an AI company? Is Microsoft an AI company? What I'm a big fan of and I think that the collar is alluding to. I want to 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 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 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. 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. But I think you apply it to every company because a lot of. For example, the AI boom is going to make a lot of people in the construction industry very, very rich.

[Kara Swisher]

It is. That's one group of people that are benefiting.

[Scott Galloway]

Yeah.

[Kara Swisher]

Would you tax them? Right. Would you tax.

[Scott Galloway]

Oh, my attitude. There's so many loopholes right now. The only way we get there Is with an AMT. There should be an AMT. Anything above $10 million and anything above 3 million, you pay a federal AMT of 40%. Because what happens is guys like me weaponize the tax code and do 1202 and buy assets and we end up paying high teens in tax rates. So the stated we focus too much on tax rates, not on the tax code. And enough already. There is no reason why someone working for money should be taxed at a higher rate than someone who is making money from investments.

[Kara Swisher]

Although I don't see any wrong taxing robots if they're workers. I don't know.

[Scott Galloway]

That's an interesting one.

[Kara Swisher]

Yeah, yeah. When he said it and I thought, oh, Bill Gates. And 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 going to pay for that or get them different jobs. So there's going to be a lot of rethinking of all the way the workplace is taxed, how it's conducted, what people get paid, and obviously the damage that some of this AI is going to do. There's going to have to be some mitigation. Okay, Scott, next question. This one is a tough one. Let's listen. Hey, Scott and Kara.

[Scott Galloway]

I'm Liam, a high school senior from New York and I want to ask the following.

[Kara Swisher]

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.

[Scott Galloway]

At once, what would it be?

[Kara Swisher]

Thanks for taking the time to answer. Wow, that's a great question. I hate that. Just one thing. If I had to pick $25 minimum.

[Scott Galloway]

Wage, I like that.

[Kara Swisher]

Let me explain very quickly because I think it lists all votes. 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 people that can do a living wage. They spend money, they want to do things, they lean into the future. It would be great. The second One would be 8 million houses, more housing. But go ahead.

[Scott Galloway]

Once a program one is structural or legislative, I do think a lot of this reverse engineers to in terms of inability to get things done to Citizens United. If I could overturn Citizens United, I would. I think a lot of our problems stem from the weaponization of Washington by corporate interest and corporate money.

[Kara Swisher]

Oh, wow.

[Scott Galloway]

And then.

[Kara Swisher]

Wow, Bernie Sanders. I like that answer.

[Scott Galloway]

Well, I mean it's just true. There's more. There's more full time lobbyists living in D.C. working for Amazon than there are sitting U.S. senators, but you know, a close second. Mandatory national service, universal child care, lower Medicare eligibility by two years, a year for 10 years until three quarters of America has essentially socialized medicine. You know, I could go on and on.

[Kara Swisher]

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.

[Scott Galloway]

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[Kara Swisher]

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

[Scott Galloway]

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.

[Kara Swisher]

Can you share a little bit about.

[Scott Galloway]

Your investment, spending and saving philosophy in.

[Kara Swisher]

The context of your shared success? Thank you so much and hopefully see you soon. Gosh, thanks, Eric. A little personal. I don't think about money a lot. That's my problem. I'm not interested in it. And I make a lot of money. I do. Especially for a journalist. I'm like daddy war books a journalist 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, basic bitch of investing. I have bonds. I've got quite a bit of real estate that I hold on to for savings, as Scott calls it. I don't spend a lot of money. I really don't. It has nothing to do with me being frugal. I just don't. I don't like buying a lot of stuff. I'm wearing the same. All my clothes I've had for 20 years. I don't buy a lot of clothes. I don't buy drugs. I don't go out a lot.

[Scott Galloway]

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

[Kara Swisher]

Well, no one here buys drugs. Maybe you. I don't buy, like, I don't drink. I don't party. I'm trying to think, like, what costs money. I have a Chevy bolt, like an Ikea, so I don't really care about cars.

[Scott Galloway]

You're the primary breadwinner in a family of 4 billion people. Yeah, I mean, that in itself is, mommy's gotta make real money.

[Kara Swisher]

Mommy's gotta make real money. And so that's spent on the kids. I definitely get them through college. But I did those savings plans for college 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. And I did that 20 years ago for my older kids. Anyway, I have a basket of stocks. I've got real estate. I'm very diversified. I have a lot of cash right now. I really do. And I thought for a second of going into Bitcoin when Scott said it. And then I thought, I don't have the tolerance for it. It's because I need cash around. 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. 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 I'm sorry to say that people who love to save energy, but I think they're wonderful. And I will upgrade all the time. Like upgrade hotels and things like that. So 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 do. But I'm still More frugal than Scott. Scott is really. I really admire Scott's vacation spending. I don't know. Scott, what do you think?

[Scott Galloway]

Well, you know, I think a lot about this. One of my addictions is money. 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 I got through my senior year of college. On top ramen and bananas. That's not an exaggeration. I was in student debt even at the age of 27. I was not traumatized, but I had a difficult time paying for my mother's health care. 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. My approach to spending money, spending money is that we don't own money, we rent it. And I also. You collide that with my atheism. You know, 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 three and four hundred thousand dollars a month. I own homes all over the world. I have a plane. And I spend most of my money on homes and experiences, not gifts for Kara, just please. 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 and it keeps my. My net worth has not increased in eight years. And because I think hoarding wealth is a virus, there's no reason anybody needs to be a billionaire. But there's no. I can't stand it when wealthy people can't. Aren't good at spending money. I have an amazing time. I do things for my friends and family to get us all together in the same place. I never let money get in the way of a good time. I'm spending money like a 50s gangster just diagnosed with ass cancer, I think.

[Kara Swisher]

Is a nicer way of putting it. Scott is very generous. Let's just say to employees, Scott's a very generous person.

[Scott Galloway]

But we don't own money. We rent it. And I'll give my kids some money, but there's no reason why my kids need to inherit Tens of millions of dollars. So I'm going to spend it all on people I love and experiences and take advantage of capitalist society. And I'm also going to give a shit ton of money away to make sure that the things that made me rich are still available for younger people. So I love making money, I love spending it. I stopped making it eight years ago. And anything above a certain level I give away. In terms of my investments, I'm pretty well diversified. My quote unquote investment strategy is the following. I think income inequality, unfortunately is only going to get worse. And what I find is that people worth over $100 million are the most homogenous, boring people in the world. And that is, they all want to party in St. Bart's they all want to buy Hermes, they all want to send their kids to elite colleges and they want to live in one of five areas. They want to live in Dubai, London, Palm Beach, New York or Aspen. And I bought homes in all of those places except for Dubai. Big homes. And the way I refurbish them. And what I tell my contractor and my decorator is pretend. Jeff Bezos is going to buy this home because the world is going to produce thousands of billionaires over the next 20 years. And by the. I think it's a terrible thing about our society. I will vote for people to try and reverse that. But the free gift with purchase is that these homes, I want to make it impossible for my boys to avoid me and the conversation when they're say, at UC San Diego or something, we can go to Tijuana with our friends and eat lobster or we can go to Aspen, but we have to have dinner with my dad. I'm hoping that they'll say, yeah, let's go hang out with dad.

[Kara Swisher]

Oh, that's a bribe.

[Scott Galloway]

I spend a shit ton of money. I love it, I give it away. It's not, it's not virtue, it's not ethics. It makes me feel strong, it makes me feel masculine, it makes me feel American. But I'm planning to not increase my net worth. There is no reason anybody needs to be a billionaire. It's not going to make any happier. What's going to make you happier is doing amazing things with people you love and doing nice things for other people. And I spend to that and I very much enjoy it. And money is something. Money is something I think a lot about because I didn't have a lot of it growing up. It's still a very big issue in my life.

[Kara Swisher]

Yeah, it's interesting because I Grew up with a lot of money and so I guess I don't care. I've always had money.

[Scott Galloway]

You think about money less than almost.

[Kara Swisher]

Anybody I know, I know you get mad at me because I don't, I don't. I have enough. I like. I don't also let me point out, my mom was a spendthrift and it upset me and made me most. My brothers and I are very hard workers and we don't spend a lot of money. All of us are very like. My brother built a beautiful house in Pennsylvania where he lives. And it's beautiful and he didn't. It's gorgeous and he loves it and so that's what he spends money on. And I love that because I feel like it was money well spent because he enjoys it and it's quite beautiful. It's a beautiful setting. So we always spend money on homes, but not extremely, not like ridiculously. Same thing with Jeff has a beautiful home. I have a beautiful home.

[Scott Galloway]

You live well, not opulently is the way I would describe it.

[Kara Swisher]

Well, no, not at all. No. People are always surprised. I would have the luxury of not having to worry about money early in my life. But there was a lot of my mom being such a Spencer. She was always out of cash and she always had to scrounge for it from. And trick people, get her dad to write her a check. And I found that grotesque. I did. I was like, I'm always gonna have enough money. And I had money from a very early age. Cause my dad died. It was an insurance thing and I got a hold of it when I was 18 and I have not. I didn't want my mom near it. Cause she was. She would. She spent a lot of our money that we got from my dad. And so I've had control of my money for years. So I. I just don't care about it enough. I just don't. I wish I did. Like I want my boys to work hard, my older boys to work hard. And I think they do. Both of them are really hard workers. And again, just like Scott, they're gonna get the houses is what they're gonna get. Which I love the house. So it's something like that. All right, Scott, let's get to a question about parenting. Let's listen. 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. Tara, as someone who lost their father and also as someone who's raised children without a male partner and Scott as someone who's largely raised by a single mother, I'm looking for advice. Tara, 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 you would have done if, for example, she had had more financial resources? Thank you both. Man, these are good questions. They're highly emotional. I don't think my mom did a very good job. I hate to trash my mom this episode, but it's true. You know, she lost contact with my dad's parents and I re established it when I was in college myself. We were a kid. You were a little bit at cross purposes of loyalty and I thought that was not good. She threw away a lot of pictures which I recovered, some of which I spent a lot of time finding stuff about my dad. And I right now have a big box of letters of his that I just read one that was wonderful. I think she should have spent a lot more time talking about him. And I don't think she remembers herself, but I don't think she was kind to his parents. So that was one thing is if your grandparents are good people, make sure your kids know them and know they're relatives on your dad's side and they're 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. I think I've. There was a gay couple who my dad was lovely to and I didn't know that. It was a wonderful thing to find out. A young African American woman he tutored wrote me for now she was a doctor and said she wanted to thank him. An ex girlfriend of his wrote me saying it should have been me that married him, 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 name my. And I also name my son after my dad. So that's what I would say.

[Scott Galloway]

That's nice. Yeah, I mean, I'm just thinking about it stirs emotions. So when I was 15 and in California, you were what you drove and 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 when I was 15 and a half and honk the horn and we go into a garage of this giant apartment complex and she would teach me how to drive stick on her 19, like 77 opal green, you know, lime green Opal manta. 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.

[Kara Swisher]

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

[Scott Galloway]

Yeah, I'm good. The, the best thing, literally I think of any parent or any mother.

[Kara Swisher]

If.

[Scott Galloway]

You tell your kids every day they have value, they start to believe you.

[Kara Swisher]

Yeah, 100%. Scott, I bought you an Acura.

[Scott Galloway]

There you go.

[Kara Swisher]

For Christmas. That's what I needed to get you out of this. That is a beautiful story. I didn't know that. Why didn't I know that?

[Scott Galloway]

Just after the question where I'm bragging about my wealth. As you get older, the good news, you get more thoughtful. When I reverse engineer. All my blessings to two core things. It's big government assisted launch, Pell grants, University of California, darpa, the Internet. And also just hands down, I think I've always had a base of confidence that my mother gave me. The more 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.

[Kara Swisher]

100%.

[Scott Galloway]

Kara, you do a great job with this with your brothers.

[Kara Swisher]

I do. I didn't mention that I have my brothers. Both my brothers and friends have been critical part of my boy's upbringing, my older boy's upbringing. And it'll be the same for Saul because he needs a lot of man around him.

[Scott Galloway]

So anyways, get men involved in your son's life. What's weird is it's not as important for the girl. Girls have similar outcomes of college attendance and self harm in single parent homes. It ends up that while boys are physically stronger, they're emotionally and neurologically much weaker than girls. So the involvement of a male role model in your son's life is actually now is actually very important.

[Kara Swisher]

Yeah. Although I gotta say, I miss having my dad. I'm sure to say every day. One of the last things I would say is There's a great book called the Loss that is forever. I forget the author. I would recommend reading it. It's forever lost, so don't, like, pretend it's not. Don't underscore what the loss is. And I think about my dad every day. Every single day. And you should let them do that. And you should think and talk about him every day to them. I mean, I think that's critically important. All right, Scott, are you okay? Can we move on?

[Scott Galloway]

Yeah, I'm good.

[Kara Swisher]

All right. It gets worse from here, I think.

[Scott Galloway]

Yeah.

[Kara Swisher]

When Scott dies, he'll be like, you know, you remember, like at the end of the Orson Welles movie Rosebud.

[Scott Galloway]

Rosebud.

[Kara Swisher]

Acura.

[Scott Galloway]

Acura. Opal. I'm green Opal Mantle.

[Kara Swisher]

We had an Opal. I love an Opal.

[Scott Galloway]

Oh, God. We're just literally the lamest car in the world. Yeah. No, there's a reason I lost my virginity at 19.

[Kara Swisher]

We also had a Pacer with Navajo print. It was so embarrassing.

[Scott Galloway]

Pacer's kind of cool in a weird way, though.

[Kara Swisher]

I know, but not then. Okay, Scott, one more quick break. We'll be back and we'll answer another listener question. Support for this show comes from AT&T. Wireless companies love to make bold claims, like how they have the best coverage or how you'll never lose a call on their networks. And yet we've all had the experience of being stuck with spotty service or missing out because we couldn't connect. Well, one provider actually, actually has the goods to back it all up. AT&T. Based on third party metrics, AT&T has the rest beat. While the other guys are busy making claims they can't keep, AT&T is making connections on America's fastest and most reliable wireless network. So no matter if you're out at a concert, a huge sporting event, or out enjoying nature, you can post when you want to post, call when you want to call, and rest easy knowing no matter where you go, AT&T has got you covered. When you. When you compare, there's no comparison. AT&T based on RootMetrics. United States Root Score Report 1H 2025 tested with best commercially available smartphones on three national mobile networks across all available network types. Your experiences may vary. Root metrics rankings are not an endorsement of AT&T. Support for this show comes from Rubrik. A lot of companies are deploying AI agents now. They're automating tasks, handling work 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 governor 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.com rubrik.com.

[Scott Galloway]

Every startup, no matter how brilliant the tech or how committed the founders, will eventually face an unthinkable obstacle. Whether they choose to pivot or to double down is often the difference between success and failure. Like, did you know that autonomous drone delivery company Zipline originally produced a robotic toy? Or that Bolt went from an Estonian transportation company to one of the largest rideshare and food delivery platforms in the world? That's what Crucible Moments is all about. Hosted by Sequoia Capital's Roloff Botha, Crucible Moments deep dives into the make or break moments that set the course for some of the most important tech companies of our time, with interviews from some of the key players that made these companies a success. This season, you'll hear stories from the founders of Bolt, Zipline, Supercell, and many more. Subscribe to Crucible Moments today. You can [e-mail] or wherever you get your podcasts.

[Kara Swisher]

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 gotta think for a second.

[Scott Galloway]

I'm doing it. Money plays. And I realize how privileged I am, and I realize this is a function of my being born a white male heterosexual. I do exactly what money plays. Money as a construct puts no constraints on my life. I am doing exactly What I want to be doing every day. Every day 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.

[Kara Swisher]

All the money in the world.

[Scott Galloway]

Well, what I would be focused on right now, if I had say, hundreds of millions to waste, I'm going to 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 28.

[Kara Swisher]

That's what I do. Yeah, I would take a bunch of money and solidify a progressive. Not like hateful to conservatives, but like American values that are about fairness and equity and things like that. So I'd spend money on that I would spend money on. I do the mackenzie Scott. That's what I would be. That's what I just suddenly show up with money and not be heard from or seen from again. That's how I would do what she's doing, exactly what she's. And suddenly give Howard a whole bunch. She's done two gifts to Howard and she's. All of a sudden she's over at planned pare and then she's here. She's so diverse in her giving that I love it. And that's how I would behave. I would also create universal daycare. I mean, that's what I would do for people. Better childcare for all kinds of parents. I would somehow figure out a way to fund like right now New Mexico has it. Cause they have all this oil and gas or shale money. They can do it every state. We should have. Nationally, we should have universal daycare University. That's what I would do. I would spend less on health stuff. But I can see why. And again, money is. I don't spend a lot of money. So I wouldn't buy anything. I wouldn't. I'm trying. Would I buy anything? Maybe like my own Taylor Swift concert. Perhaps that's what I would do. Anything crazy you would buy.

[Scott Galloway]

I might buy a Gulfstream G800.

[Kara Swisher]

I'd invite Scott just to hurt him. Hurt his ears. You'd be so nice to Taylor Swift anyway. Something like that. Okay, Scott, let's hear another question. This one comes from Brian. Let's listen.

[Scott Galloway]

Hey, Karen, Scott, this is Brian living.

[Kara Swisher]

In Orange County, California. I just recently saw you guys in.

[Scott Galloway]

LA when you were on tour and.

[Kara Swisher]

Had an absolute blast. My question is, what happens behind the scene when you guys are on tour before the show? Are you guys partying?

[Scott Galloway]

Is Scott ripping Jack and Cokes while.

[Kara Swisher]

Kara's taking a nap on the couch.

[Scott Galloway]

Or what's going on? And afterwards, is Kara reading the New Yorker magazine while Scott disassociates? Would love to hear a little bit.

[Kara Swisher]

More about the inside drama of Pivot behind the scenes. Thanks.

[Scott Galloway]

I'll let you take this.

[Kara Swisher]

Oh, well, I'm ripping Jack and Cokes and Scott's taking a nap. No, we actually talk to each other. I mean, we talk about the show. We all have visitors. I have a lot of family members came during the thing, and so we chit chatted with them. Often the guests we have, we chit chat with them. We had a nice party in LA before the show with a whole gang of people. There were tons of people backstage, and it's not very, like, wild by any stretch. It's really quite civil. And then afterwards, we just go, we leave. And we typically went on to the next place we went. It's not tiring doing the shows, but we just move on. We read our. Our mail, we talk to our family. Stuff like that. Check in. I think it's so dull, comparatively. Backstage, correct, Scott?

[Scott Galloway]

Yeah, I was thinking it was seven cities and seven nights. So it was basically get up, get to the airport, get to where we're going, check into the hotel. I would try and grab a workout just to center myself, FaceTime my kids, and then start prepping because they're five hours out, and then start prepping for the show. And then I found the shows very rewarding, but emotionally very draining. As you said, we had a lot of friends and a lot of people, and people show up and they're excited and they come backstage and it's nice to see them, but it's also. I find it very exhausting. But I think I drank less that seven days than I have in a long time. There was just no room for partying or alcohol. I didn't go out or drink once. I just didn't. Is that true? I think that's true.

[Kara Swisher]

Yeah. We just. And usually we took off after the shows to go straight to the next show.

[Scott Galloway]

We'd be taking our luggage to the theater, and then we'd bomb straight to the airport.

[Kara Swisher]

Yeah. And then we'd have the morning free to do stuff or tape. We had other podcasts during that time. Scott had. Prof. G. I had on. And so I was taping those.

[Scott Galloway]

Yeah, I went. That was a whirlwind.

[Kara Swisher]

Yeah, it was fun. It was really fun. We had a great time, and we had A nice bonding experience ourselves. And Scott cried several times, which is par for the course. We had some fun at his experience.

[Scott Galloway]

Well, it was a week.

[Kara Swisher]

I mean, well, I know, but we had some great fun at. We had really a lot, a lot of fun. It really was. It was very. It was very.

[Scott Galloway]

I think D.C. was the most fun actually backstage.

[Kara Swisher]

Oh, yeah, that was fun. That was a good one. Yeah, Louisiana. And my mother insulting everyone.

[Scott Galloway]

That was great. Your mom and Don Lemon and Wonder Woman. Actually, LA was pretty good at Helms was hilarious.

[Kara Swisher]

Chelsea Handler was backstage, so.

[Scott Galloway]

Oh, she was great.

[Kara Swisher]

Yeah, we had a good time. We had a good time. And then Scott and I went to Bill Maher. He was on it. And I accompanied him because I can't ever leave his room.

[Scott Galloway]

That's right, you did. Come with me. I thought it was so great. You literally, like bombed into my dressing room, took off your shoes and started drinking like you're the expectant mother or wife. Like, you could not get more obnoxious. You're like, I'm here, I'm here. I'm with Scott. Where's his dressing room?

[Kara Swisher]

That's right. I would have been happy for you to do the same thing.

[Scott Galloway]

I was a nervous ride.

[Kara Swisher]

I know. You were great.

[Scott Galloway]

Like chatting. All the producers.

[Kara Swisher]

I was chatting. I like to chat people up. It's fun. Chat up Bill afterwards. We had a good time. Come on. We had a good time. Anyway, we appreciate your question. We had a great time. We'll probably be doing another in 2026. Okay, Scott, one more quick break. We'll be back with more from our listeners. When it comes to managing your company's spend, finance leaders face a brutal truth. You often have to choose to move fast and lose control or carefully control money and slow everything down. But not anymore. Brex breaks that trade off off. Brex is the intelligent finance platform that helps you spend smarter and move faster. With Brex, you get high limit corporate cards with built in expense management, plus a team of AI agents that handle manual finance tasks for you. Brex's AI agents do all the stuff you don't want to do, like collect receipts and memos, enforce your policy, and monitor transactions for abuse and fraud, all according to to your rules. So you're free to focus on the business. Over 30,000 companies run on Brex from anthropic to zoom. Join [e-mail]. if you're tired of database limitations and architectures that break when you scale, then it's time to think outside rows and columns. MongoDB is the database built for developers by developers. It's asset compliant, enterprise ready and fluent in AI. That's why so many of the Fortune 500 trust MongoDB with their most critical workloads. Ready to think outside rows and columns. Start building [e-mail] build.

[Scott Galloway]

Millions of players. One world. No lag. How's it done?

[Kara Swisher]

AWS is how epic games turn to.

[Scott Galloway]

AWS to scale to more than 100 million Fortnite players worldwide. So they can stay locked in with battle tested reliability.

[Kara Swisher]

AWS is how leading businesses power next level innovation. Okay Scott. We're back 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. It SC on one cheek and TT on the other. Get the O as the asshole. Get it? Get it. Okay. Groucho. Nose and glasses with Scott's nose and glasses. I don't like any of these. I do like the sctt. I'd say I need more Scott. Do you have any suggestions?

[Scott Galloway]

I would get some. I would just in case of emergency call Scott.

[Kara Swisher]

Oh my God. Break glass.

[Scott Galloway]

Or maybe a tiny raccoon holding a beer.

[Kara Swisher]

Oh you know what? I think that's good is what I should get. Just the words. That's good.

[Scott Galloway]

A barcode that if you scan it it said the problem with Scott is.

[Kara Swisher]

See you're better.

[Scott Galloway]

Let me see.

[Kara Swisher]

How about a cat and a dog sort of fighting but hugging at the same time.

[Scott Galloway]

Tattoo of a receipt. Total 000 item putting up with Kara. A broken halo with the caption Scott tried. A fortune cookie. And the fortune reads you will tolerate someone named Scott today.

[Kara Swisher]

How about one that just says at least he's not Scott Jennings.

[Scott Galloway]

That's right. That's right. No. I think there's a lot we could do here. I could go on.

[Kara Swisher]

There's a lot we could do. I may get a Scott tattoo. I may just do it as a surprise. I think I might. Maybe I'll make fake ones made and then trick Scott in some fashion.

[Scott Galloway]

A tombstone that says rest in peace. Scott's sanity taken by Kara.

[Kara Swisher]

These are your tattoos. We have tattoos that we made when we did that conference. The one we didn't make money at. This one we did.

[Scott Galloway]

Oh yeah.

[Kara Swisher]

In the middle of COVID we have tattoos. I'm gonna find those. There are Scott and Kara tattoo. They were good actually. Huh? All right, everybody, you gotta try harder. Come on, come on. Send more. Okay, Scott, that's the show. It's time to say goodbye. Thank you listeners. And again, I truly and so does Scott appreciate you. And we were very touched by all your questions on the tour. And we're touched by these questions too. And we truly appreciate it because we love our fans. So Scott, read us out.

[Scott Galloway]

Today's show was produced by Laura Nemenzoe, Marcus Taylor Griffin and Christine Driscoll. Ernie Hutt engineered this episode. Michael Manola Moreno edited the video. Thanks also to Drew Bros, Ms. Savira and Dan Shalon. Nishat Kurwass, Fox Media's executive producer podcast make sure to follow Pivot on your favorite podcast platform. Thanks for listening to Pivot from New York Magazine and Vox Media. You can subscribe to the magazine nymag.com pod we'll be back next week for another breakdown of all things tech and business. Right now is the AI gold rush. And that means everybody who builds an app, a platform, a piece of software, a gizmo that somebody, anything, everybody is trying to put AI everywhere. And for two weeks in a series on the Vergecast, we are talking through.

[Kara Swisher]

What that looks like.

[Scott Galloway]

We're talking to developers about what they're building and how they're building it and whether AI actually does make sense everywhere or is just going to ruin everything in the process. That's the AI miniseries on the Vergecast.

[Kara Swisher]

Wherever you get podcasts, this series is presented by MongoDB.

[Scott Galloway]

Does it ever feel like you're a marketing professional just speaking into the void? But with LinkedIn ads, you can know you're reaching the right decision makers. A network of 130 million of them. In fact, you can even target buyers by job title, industry, company seniority, skills. Did I say job title? See how you can avoid the void and reach the right buyers with LinkedIn ads. Spend $250 on your first campaign and get a free $250 credit for the next one. Get [e-mail] Campaign terms and conditions apply.

[Kara Swisher]

Support for the show comes from Charles Schwab at Schwab. How you invest is your choice, not theirs. That's why when it comes to managing your wealth, Schwab gives you more choices. You can invest and trade on your own. Plus get advice and more comprehensive wealth solutions to help meet your unique needs. With award winning service, low costs and transparent advice you can manage your wealth your way at Schwab. Visit schwab.com to learn more.