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Kara Swisher and Scott Galloway Debate Their Money Strategies | Pivot

December 19, 2025 / 30:09

This episode of Pivot features listener questions on topics including taxing AI, economic policies, and personal finance. Hosts Cara Swisher and Scott Galloway discuss various listener inquiries, providing their perspectives on these pressing issues.

The episode begins with a question from Lynn about the potential for taxing AI and companies that utilize it to offset job displacement. Scott emphasizes the complexities of taxing specific industries and advocates for a more progressive tax structure.

High school senior Liam asks about implementing a single policy to address America's economic and social problems. Scott suggests a $25 minimum wage, while Cara proposes overturning Citizens United to reduce corporate influence in politics.

Eric from Brooklyn inquires about the hosts' spending and saving philosophies. Cara shares her frugal approach, while Scott reveals his tendency to spend significantly on experiences and homes, emphasizing the importance of generosity.

Lastly, Lisa seeks advice on parenting after losing her husband. Cara and Scott reflect on their own experiences with loss and the importance of maintaining connections to loved ones who have passed.

TL;DR

Cara and Scott answer listener questions on AI taxation, economic policies, personal finance, and parenting after loss.

Video

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I never let money get in the way of a
00:00:01
good time. I'm spending money like a 50s
00:00:03
gangster just diagnosed with ass cancer.
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>> Hi everyone, this is Pivot from New York
00:00:14
Magazine and the Vox Media Podcast
00:00:15
Network. I'm Cara Swisser
00:00:17
>> and I'm Scott Galloway
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>> and Scott. This is our end of the year
00:00:20
listener mail episode. We're probably
00:00:21
both elsewhere doing fun things, but are
00:00:24
you ready to hear some emails and
00:00:25
voicemails from our lovely listeners,
00:00:26
who by the way, we have a full new
00:00:28
appreciation for after meeting so many
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of them on our Pivot Live tour. I really
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enjoyed that. Are you ready?
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>> Yeah, ready.
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>> Okay, Scott, let's kick off with a
00:00:37
question about taxing AI. Let's listen.
00:00:40
>> Hi, this is Lynn. Um, I've been
00:00:42
wondering as artificial intelligence
00:00:45
continues to replace human jobs, do you
00:00:48
think we'll ever see attacks on AI
00:00:50
itself or on the companies that use it
00:00:53
as a way to offset its impact on
00:00:56
displaced workers? And would that in a
00:00:59
sense become a new way of taxing the
00:01:00
rich? Thank you. Bye.
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>> Gosh, Lynn, what a great question.
00:01:04
Actually, I'm going to start. You know,
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many years ago, Bill Gates sort of set
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off a kurfuffle when he talked about
00:01:09
taxing robots if they become workers um
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the same way because you aren't going to
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get those money that you get from human
00:01:16
workers and so they should be taxed in
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the same way. I hadn't really thought
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about it about AI. Uh Scott, I I'm I
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think I'm I think you're more qualified
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to answer this.
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>> I don't know if that's true. Uh my view
00:01:27
around taxation is that the moment you
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start taxing specific industries, you
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weaponize special interest groups to
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come to their defense and you also
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create some confusion around like is
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Oracle AI, you know, if if McKen I mean
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at what point what qualifies as an AI
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company and not an AI company? Is
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Microsoft an AI company? What what I'm a
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big fan of and I think that the the the
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caller is alluding to I want to go back
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to Reagan era taxation and that is
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there's no difference between I think
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the capital gains tax deduction is
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nothing but a transfer of wealth from
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young to old because somehow we've
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decided that sweat is less noble than
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money and that is the money I make on
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money gets taxed at a lower rate than
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the money that young people make on
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sweat. So I would like to see an elim
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elimination of the capital gains tax
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deduction and raise those rates to
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current income and restore a progressive
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tax structure. In my view, you do it
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across all income and all firms because
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I think the moment you start getting
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into this notion of let's put a super
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tax on this type of firm. I think that's
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I think you regulate them. I think you
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have an EPA, you have an AI act, you
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have privacy, you have laws, but in
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terms of taxation, I just think you say,
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look, above a certain level of
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profitability, when you sell a stock,
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you pay this much in tax. I think taxes
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need to go up. I think we need to do
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away. We need to raise long-term capital
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gains from 21 to 37%. It makes no sense
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that I'm paying lower taxes than people
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actually working for a living. But I
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think you apply it to every company
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because a lot of a lot of for example
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the AI boom is going to make a lot of
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people in the construction industry very
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very rich.
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>> It is that's one people group of people
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that are benefiting. Yeah.
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>> Tax them. Would you tax them? Right.
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Would you tax
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>> my out of there's so many loopholes
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right now. The only way we get there is
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with an AMT. There should be an AMT.
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Anything above $10 million and anything
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above three million you pay a federal
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AMT
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>> of 40%.
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>> Yep. Because what happens is guys like
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me weaponize the tax code and do 122 and
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buy assets and we end up paying high
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teens in tax rates. Yeah.
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>> So the stated the stated we focus too
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much on tax rates not on the tax code
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and enough already. There is no reason
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why someone working for money should be
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taxed at a higher rate than someone who
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is making money from investments.
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>> Although I don't see any wrong with
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taxing robots if they're workers. I
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don't know. I don't
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>> It's an interesting one.
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>> Yeah. I just I when he said it and I
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thought, "Oh, Bill Gates." And I
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thought, "Oh, actually he's really
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smart. I forgot. Anyway, it's an
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interesting question. We have to deal
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with all these things and what happens
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with displaced workers and how we're
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going to pay for that or get them
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different jobs. So, there's going to be
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a lot of rethinking of all the way the
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workplace is taxed, how it's conducted,
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what people get paid. Um, and obviously
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the damage that some of this AI is going
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to do. There's going to have to be some
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mitigation. Uh, okay, Scott, next
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question. This one is a tough one. Let's
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listen.
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>> Hey, Scott and Cara. I'm Liam, a high
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school senior from New York, and I want
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to ask the following. America certainly
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has its fair share of economic and
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social problems, but a lot of the time
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these problems stem from the same root
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causes. Too often though, our
00:04:31
politicians create costly band-aid
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solutions rather than trying to address
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the underlying issues. So my question to
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you guys is, if you could implement one
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single policy to try and solve the most
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problems at once, what would it be?
00:04:44
Thanks for taking the time to answer.
00:04:47
>> Wow, that's a great question. I hate
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that with just one thing. If I had to
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pick
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$25 minimum wage.
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>> I like that.
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>> Let me explain very quickly because I
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think it it lists all votes. If people
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get paid more, they'll spend more. It
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creates a better economy. I know there's
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initial costs for businesses that have
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these things, but it creates an people
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that can do a living wage. They spend
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money. They want to do things. They lean
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into the future. I just it it would be
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great. The second one would be 8 million
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houses, more housing. But go ahead. once
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a program, one is structural or
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legislative. Um, I do think a lot of
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this reverse engineers to in terms of
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inability to get things done to Citizens
00:05:30
United. If I could overturn Citizens
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United, I would I think a lot of our
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problems stem from the weaponization of
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Washington by corporate interest and
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corporate money.
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>> Oh, wow.
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>> Um, and then
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>> Wow, Bernie Sanders, I like that answer.
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>> Well, I mean, it's just true. There's
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more there's more full-time lobbyists
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living in DC working for Amazon than
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there are sitting US senators. So, what
00:05:54
do you know? Anyway, uh but you know, a
00:05:57
close second, mandatory national
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service, universal child care, lower
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Medicare eligibility by two years a year
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for 10 years until threequarters of
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America has essentially socialized
00:06:06
medicine. You know, I could go on and
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on.
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>> Yeah, I love it. I love that answer. I
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was not expecting it. Boy, that came out
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left field there, Scott. All right,
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Scott, let's take a quick break and
00:06:15
we'll be back with more listener
00:06:17
questions.
00:06:18
>> Support for the show comes from
00:06:19
Vanguard. To all the financial adviserss
00:06:21
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00:06:23
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00:07:15
All investing is subject to risk.
00:07:16
Vanguard Marketing Corporation
00:07:18
distributor.
00:07:22
>> Scott, we're back. The next listener
00:07:24
wants to know what we're doing with our
00:07:25
money. Let's listen.
00:07:26
>> Hi, Scott and Kira. It's Eric from
00:07:28
Brooklyn. Scott, you talk a lot about
00:07:30
how you spend, how you invest, and I
00:07:32
imagine how you save. Carrie, you don't
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and you come off as maybe a bit more
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frugal. Can you share a little bit about
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your investment in spending and saving
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philosophy in the context of your shared
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success? Um, thank you so much and uh
00:07:46
hope we'll see you soon.
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>> Gosh, thanks Eric. A little personal.
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Um, uh, I am not I don't think about
00:07:52
money a lot. That's my problem. I'm not
00:07:54
interested in it and I make a lot of
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money. I do. Um, for especially for a
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journalist, I'm like I'm like Daddy
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Warbucks, a journalist in that regard.
00:08:01
But I would say I save a lot. I have a
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lot of savings and I diversify. I'm sort
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of your basic person, uh, basic [ __ ] of
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investing. I have bonds. I've got quite
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a bit of real estate that I hold on to.
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This force savings as Scott calls it.
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Um, I, um, I don't spend a lot of money.
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I really don't. It's, it has nothing to
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do with me being frugal. I just don't
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I'm don't like buying a lot of stuff.
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I'm wearing the same All my clothes I've
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had for 20. I don't buy a lot of
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clothes. I don't buy drugs. I don't buy
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I don't go out a lot. Um I'm really
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boring.
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>> Don't buy drugs. Where did that come
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from?
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>> Well, no one here buys drugs. Maybe you
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I don't buy like I don't drink. I don't
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party. I I'm trying to think like what
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costs money. I have a Chevy Bolt like
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and a Kia. So, I don't really care about
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cars.
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>> You're the primary bread winner in a
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family of four people.
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>> Yeah.
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>> I mean, that in itself is
00:08:54
>> Y
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>> Mommy's got to make real money.
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>> Mommy's got to make real money. And so,
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that's spent on the kids. I definitely
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get them through college and but I did
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those savings plans for college for for
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my boys and I'm doing them for my little
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kids. That worked out really well
00:09:06
actually. I didn't have to think about
00:09:07
it. Um and I did that 20 years ago for
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my older kids. Um I think I um what I do
00:09:13
spend on I have way too much cash
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compared to what I need. But I like to
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have it. I'm one of those sort of
00:09:18
people. I do spend money on a couple of
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things. Um I always will upgrade. I mean
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I always get first class. I fly well.
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you know, I don't have a private plane,
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but I I would love to have one, but um
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I'm sorry to say that people who love
00:09:32
the same energy are going to think
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they're wonderful. Um and I I will
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upgrade all the time, like upgrade
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hotels and things like that. So, I I've
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gotten I got old very early and then I'm
00:09:45
like I didn't want to be in bad food. I
00:09:47
didn't want to stay in bad places. I
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suppose if I spend on anything a lot,
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it's vacations. I really I I do, but I'm
00:09:54
still more frugal than Scott. Scott is
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really I really admire Scott's vacation
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spending. Um I don't know Scott, what do
00:10:01
you think?
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>> Well, you know, I think a lot about
00:10:03
this. One of my addictions is money and
00:10:06
that is I continue to be too focused on
00:10:08
it to the detriment of my mental health
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and it takes time away from my family. I
00:10:14
grew up with a scarcity of money until,
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you know, I got through my senior
00:10:18
college on Top Ramen and bananas. That's
00:10:20
not an exaggeration.
00:10:22
I was in student debt. Um, you know,
00:10:25
even at the age of 27, I was traum not
00:10:27
traumatized, but I had a difficult time
00:10:29
paying for my mother's um, uh, healthc
00:10:31
care. So, I've been very focused on
00:10:33
money and got very lucky. And that's not
00:10:36
a humble brag. I think I'm a monster. I
00:10:38
think I'm talented and hardworking, but
00:10:39
I did get lucky. And now I am, by most
00:10:42
people's standards, wealthy. Uh, my
00:10:45
approach to spending money is that we
00:10:46
don't own money, we rent it. And I also,
00:10:49
you collide that with my atheism. You
00:10:52
know, I believe that this is all coming
00:10:54
to an end pretty quickly for me. So, I
00:10:56
spend a great deal of money. I spend
00:10:58
between $3 and $400,000 a month. Uh, I
00:11:01
own homes all over the world. I uh have
00:11:04
a plane and I spend most of my money on
00:11:08
homes and experiences
00:11:10
and
00:11:11
>> not gifts for Cara, just
00:11:13
>> but along those lines. The way I try and
00:11:15
keep in check is I think hoarding money
00:11:17
is a virus. When I hit my number eight
00:11:18
years ago, I decided anything above that
00:11:20
number I would give away. And what I do
00:11:22
each year is I look at my total spending
00:11:25
and I match it and I give that amount of
00:11:26
money away and it keeps my my net worth
00:11:29
has not increased in eight years.
00:11:31
>> Yeah.
00:11:31
>> And uh because I think hoarding wealth
00:11:33
is a virus. There is no reason anybody
00:11:35
needs to be a billionaire.
00:11:37
>> But there's no I can't stand it when
00:11:39
wealthy people can't aren't good at
00:11:41
spending money. I have an amazing time.
00:11:43
>> Yeah.
00:11:44
>> I do things for my friends and family to
00:11:47
get us all together in the same place. I
00:11:50
never let money get in the way of a good
00:11:51
time. I'm spending money like a 50s
00:11:53
gangster just diagnosed with ass cancer.
00:11:56
>> And
00:11:57
>> I think is a nicer way of putting that.
00:11:58
Scott is very generous, let's just say,
00:12:00
to employees. Scott's very generous.
00:12:02
>> We don't own money. We rent it. And I'll
00:12:04
give my kids some money, but there's no
00:12:05
reason why my kids need to inherit tens
00:12:07
of millions of dollars. So,
00:12:08
>> I'm going to spend it all on people I
00:12:10
love and experiences and take advantage
00:12:12
of capitalist society. And I'm also
00:12:13
going to give a [ __ ] ton of money away
00:12:14
to make sure that the things that made
00:12:15
me rich are still available for younger
00:12:17
people. So, I love making money. I love
00:12:20
spending it. I stopped making it 8 years
00:12:22
ago and I anything above a certain
00:12:24
level, I give away. In terms of my
00:12:26
investments, I'm pretty well
00:12:27
diversified. My quote unquote investment
00:12:30
strategy is the following. I think
00:12:32
income inequality, unfortunately, is
00:12:34
only going to get worse. And what I find
00:12:36
is that people worth over hund00 million
00:12:38
are the most homogeneous, boring people
00:12:39
in the world. And that is they all want
00:12:40
to party in St. Barts. They all want to
00:12:42
buy Hermes. They all want to send their
00:12:43
kids to elite colleges. And they want to
00:12:45
live in one of five areas. They want to
00:12:47
live in Dubai, London, Palm Beach, New
00:12:49
York, or Aspen. And I bought homes in
00:12:51
all of those places except for Dubai.
00:12:53
Big homes. And the way I I refurbish
00:12:56
them. And what I tell my contractor and
00:12:58
my decorator is pretend Jeff Bezos is
00:13:00
going to buy this home cuz the world is
00:13:03
going to produce thousands of
00:13:05
billionaires over the next 20 years. And
00:13:07
by the way, I think it's a terrible
00:13:08
thing about our society. I will vote for
00:13:10
people to try and reverse that. But the
00:13:12
free gift with purchase is at these
00:13:14
homes. I want to make it impossible for
00:13:15
my boys to avoid me. And the
00:13:18
conversation when they're say at UC San
00:13:19
Diego or something, we can go to Tijana
00:13:21
with our friends and eat lobsters or we
00:13:22
can go to Aspen, but we have to have
00:13:24
dinner with my dad. I'm hoping that
00:13:26
they'll say, "Yeah, let's go hang out
00:13:28
with dad." I spend a [ __ ] ton of money.
00:13:30
I love it. I give it away. It's not It's
00:13:32
not virtue. It's not ethics. It makes me
00:13:34
feel strong. It makes me feel masculine.
00:13:35
It makes me feel American. But I'm
00:13:38
planning to not increase my net worth.
00:13:41
There is no reason anybody needs to be a
00:13:43
billionaire. It's not going to make you
00:13:44
any happier. What's going to make you
00:13:45
happier
00:13:46
>> is doing amazing things with people you
00:13:48
love and doing nice things for other
00:13:51
people. And I spend to that and I very
00:13:53
much enjoy it and money is something
00:13:56
>> money is something I think a lot about
00:13:57
because I didn't have a lot of it
00:13:58
growing up.
00:13:59
>> Yeah.
00:14:00
>> Um it's still a very big issue in my
00:14:02
life.
00:14:02
>> Yeah. It's interesting because I grew up
00:14:03
with a lot of money and so I guess I
00:14:05
don't care. I I've always had money. You
00:14:07
think about money less than almost
00:14:09
anybody I know.
00:14:10
>> I know you you get mad at me because I
00:14:12
don't I don't I have enough. I had a
00:14:14
also let me point out my mom was a spend
00:14:16
thrift and it upset me and made me both
00:14:18
my brothers and I are very hard workers
00:14:20
and we don't spend a lot of money. All
00:14:22
of us are very we like my brother built
00:14:24
a beautiful house in Pennsylvania where
00:14:26
he lives and it's beautiful and he
00:14:27
didn't it's it's gorgeous and he loves
00:14:29
it and so that's what he spends money on
00:14:32
and I love that cuz I feel like it was
00:14:34
money well spent cuz he enjoys it and
00:14:36
it's quite beautiful. It's beautiful
00:14:37
setting. So we always spend money on
00:14:38
homes but not extremely like not like
00:14:41
ridiculously. Um same thing with Jeff's
00:14:44
has a beautiful home. I have beautiful
00:14:46
home and
00:14:47
>> you live well not opulently not at all.
00:14:49
No people are surprised. Um, I had the
00:14:51
luxury of not having to worry about
00:14:53
money early in my life, but I there was
00:14:55
a lot of my mom being such a spender.
00:14:57
She was always out of cash and she
00:14:58
always had to scrge for it from and
00:15:00
trick people getting her dad to write
00:15:02
her a check. And I found that grotesque.
00:15:03
I did. I was like, I'm always going to
00:15:05
have enough money. And I had money from
00:15:08
a very early age cuz my dad died. There
00:15:10
was an insurance thing. And I got a hold
00:15:12
of it when I was 18. And I have not I
00:15:14
didn't want my mom near it cuz she was
00:15:16
she would she spent a lot of our money
00:15:19
um that we got from my dad. And so I've
00:15:21
had control of my money for years. So I
00:15:23
I I just don't care about it enough. I
00:15:25
just don't I just I I wish I did. Like I
00:15:28
I I want my boys to work hard, my older
00:15:30
boys to work hard, and I think they do.
00:15:32
Both of them are really hard workers.
00:15:34
And again, just like Scott, they're not
00:15:35
going to get they're going to get the
00:15:37
houses is what they're going to get,
00:15:38
which is what which I love the house. So
00:15:40
it's something like that. All right,
00:15:42
Scott, let's get to a question about
00:15:43
parenting. Let's listen.
00:15:45
>> My name's Lisa. I'm the mother of a
00:15:48
17-year-old boy and a 13-year-old girl.
00:15:50
Two years ago, their father died
00:15:52
unexpectedly.
00:15:53
Cara, as someone who lost their father
00:15:55
and also as someone who's raised
00:15:57
children without a male partner. And
00:15:59
Scott, as someone who's largely raised
00:16:00
by a single mother, I'm looking for
00:16:02
advice. Cara, what do you wish your mom
00:16:04
did to keep your dad's memory alive?
00:16:06
What did she do right or wrong? Scott,
00:16:08
what did your mom do right to make you
00:16:10
feel like one parent was enough? What do
00:16:12
you wish you would have done if, for
00:16:13
example, she had had more financial
00:16:15
resources? Thank you both.
00:16:17
>> Man, these are good questions. They're
00:16:19
highly emotional. God Jesus,
00:16:22
>> I don't think my mom did a very good
00:16:23
job. I I hate to trash my mom this
00:16:25
episode, but it's true. You know, she
00:16:27
lost contact with my dad's uh parents,
00:16:29
and I reestablished it when I was in
00:16:31
college myself. uh when you're a kid,
00:16:33
you're a little bit at cross purposes of
00:16:36
loyalty and I I thought that was not
00:16:38
good. She threw away a lot of pictures
00:16:40
um which I recovered some of which I
00:16:42
spent a lot of time finding stuff about
00:16:44
my dad and I have right now have a big
00:16:46
box of letters of his that I just read
00:16:48
one that was wonderful. Uh um I I think
00:16:52
she should have spent a lot more time
00:16:54
talking about him and and I don't I
00:16:57
don't think she remembers herself, but I
00:16:59
don't think she was kind to his parents.
00:17:02
Um so that was one thing is if your
00:17:05
grandparents are good people, make sure
00:17:06
your kids know them and know their
00:17:08
relatives on your dad's side and they're
00:17:09
his friends. I wish I knew more about my
00:17:12
dad's friends. And I found out later
00:17:14
when I wrote a piece in the Washington
00:17:15
Post, I got inundated with friends of
00:17:17
his that my mother never told me about
00:17:20
that I then went and met and all these
00:17:22
stories. It was a as I think I've said
00:17:24
this for there was a gay couple who my
00:17:26
dad was lovely to and I didn't know
00:17:28
that. I I it was a wonderful thing to
00:17:29
find out. Uh a young uh African-American
00:17:32
woman he tutored wrote me for now she
00:17:35
was a doctor and said she wanted to
00:17:37
thank him. my an ex-girlfriend of his
00:17:39
wrote me saying it should have been me
00:17:42
uh that married him uh which was funny
00:17:44
like there's a picture of him behind me.
00:17:45
I have a lot of pictures of him around.
00:17:47
One thing I'm sad is my kids won't know
00:17:49
him. I name my and I also name my son
00:17:51
after my dad. So that's what I would
00:17:53
say.
00:17:54
>> It's nice.
00:17:56
Yeah.
00:17:58
I mean there's just thinking about it um
00:18:01
stirs emotion. So when I was 15 and in
00:18:04
California, you were what you drove and
00:18:07
or just having a car was everything. You
00:18:08
had no social life in high school in LA.
00:18:10
There was no public transportation
00:18:11
unless you had a car. We didn't have a
00:18:13
lot of money. My mom used to come home
00:18:15
uh when I was 15 and a half and honk the
00:18:17
horn and we go into a garage of this
00:18:18
giant apartment complex and she would
00:18:20
teach me how to drive stick on her 19
00:18:23
like 77 opal green, you know, lime green
00:18:28
opal manta. Mhm.
00:18:29
>> And then on my 16th birthday, when I
00:18:31
passed my driver's test, she came home
00:18:32
and she had bought this shitty Acura and
00:18:35
she put her arms on my shoulders and put
00:18:38
keys in my hand and said, "You're a
00:18:39
handsome young man and you have a car."
00:18:41
>> Oh, Scott, you're breaking my heart.
00:18:47
>> You okay?
00:18:50
>> Yeah, I'm good. The The best thing
00:18:53
literally I think of any parent or
00:18:54
mother
00:19:03
Um, if you tell your kids every day they
00:19:05
have value, they start to believe you.
00:19:07
>> Yep. 100%. Scott, I bought you an Acura
00:19:10
for your
00:19:10
>> There you go.
00:19:11
>> For Christmas.
00:19:12
>> That's what I needed.
00:19:13
>> Get you out of this. That is a beautiful
00:19:14
story. I
00:19:16
knew that.
00:19:17
>> The good news is you become more
00:19:18
thoughtful when I reverse engineer all
00:19:20
my blessings to two core things. It's
00:19:23
big government, assisted launch, Pell
00:19:24
Grants, University of California, uh
00:19:27
DARPA, the internet, uh and also just
00:19:30
hands down, I think I've always had a
00:19:32
base of confidence that that my mother
00:19:34
gave me.
00:19:34
>> Oh my gosh.
00:19:35
>> The more the more pragmatic piece of
00:19:37
advice is that
00:19:40
unfortunately, if you were to reverse
00:19:42
engineer a young man's problems to a
00:19:44
single point of failure, it's when he
00:19:46
loses a male role model. And you've had
00:19:49
your husband has passed. I think it's
00:19:51
especially important that you get men
00:19:53
involved in your son's life.
00:19:55
>> Uh Cara, you do a great job.
00:19:57
>> I do. I didn't mention that. I have my
00:19:59
brothers, both my brothers and friends,
00:20:01
they have been critically part critical
00:20:03
part of my boy's upbringing, my older
00:20:05
boy's upbringing, and it'll be the same
00:20:06
for Saul because he needs a lot of man
00:20:08
around him. I agree. Go ahead.
00:20:10
>> So, anyways, get Yeah. Get men involved
00:20:12
in your son's life. What's weird is
00:20:15
>> it's not as important for the girl.
00:20:17
girls have similar outcomes of college
00:20:18
attendance and self harm in single
00:20:20
parent homes. It ends up that while boys
00:20:22
are physically stronger,
00:20:24
>> they're emotionally and neurologically
00:20:25
much weaker than girls.
00:20:27
>> So the the involvement of a male role
00:20:30
model in your son's life is actually now
00:20:32
>> I say I miss having my dad. I have to
00:20:35
every day. One of the last things I
00:20:36
would say is um there's a great book
00:20:38
called The Loss That is Forever. I
00:20:40
forget the author. I would recommend
00:20:42
reading it. It's forever loss. So don't
00:20:45
like pretend it's not like don't under
00:20:47
don't underscore what the loss is. And I
00:20:51
I think about my dad every day, every
00:20:53
single day. And you should let them do
00:20:55
that. And you should think and talk
00:20:56
about him every day to them. I mean, I
00:20:59
think that's critically important.
00:21:01
>> All right, Scott, are you okay? Can we
00:21:03
move on?
00:21:03
>> I'm good.
00:21:04
>> All right. It gets worse from here, I
00:21:05
think.
00:21:06
>> Yeah.
00:21:07
When Scott dies, he'll be like, you
00:21:08
know, you remember like at the end of um
00:21:10
the Orson Wells movie, Rose Bud. It's
00:21:12
gonna be Acura.
00:21:15
>> Acura, Acura.
00:21:16
>> Opal.
00:21:16
>> Opal.
00:21:17
>> Lime green opal.
00:21:18
>> We have an Opal. I love an Opal, but the
00:21:21
Opal. We also literally the lamest with
00:21:24
Navajo print. It was so nice.
00:21:26
>> I know. There's a reason I lost my
00:21:27
virginity at 19.
00:21:28
>> P. Well, try having a pacer with Navajo
00:21:30
print. Okay.
00:21:31
>> Pacer's kind of cool in a weird way,
00:21:32
though.
00:21:32
>> I know, but not then. Okay, Scott. One
00:21:35
more quick break. We'll be back and
00:21:37
we'll answer another listener question.
00:21:40
>> Support for the show comes from Ziotics.
00:21:42
So, I drink a little bit less these
00:21:44
days. I'm trying to tone down my
00:21:46
consumption of alcohol as I think is a
00:21:48
good idea when you get to my age 50.
00:21:52
But when I do pour myself a cocktail, I
00:21:54
want to make sure my next day also feels
00:21:56
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00:22:34
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00:23:02
Okay, Scott. Moving on. This question
00:23:03
comes from Paul via email. I'll read it.
00:23:06
If you had all the money in the world,
00:23:08
these are such good questions. Let me
00:23:09
read this. If you had all the money in
00:23:11
the world, what would you be doing with
00:23:13
your precious time at this moment with
00:23:15
that money? And why aren't you doing
00:23:16
that? Oh my god, Paul. Wow, Paul, that's
00:23:20
a lot. Scott, you go first on this one,
00:23:22
and I'll I I got to think for a second.
00:23:24
>> I'm doing it. I realize how privileged I
00:23:27
am and I realize this is, you know, a
00:23:29
function of my being born a white male
00:23:32
heterosexual and, you know, um, I do
00:23:35
exactly what money had plays. Money as a
00:23:39
construct puts no constraints on my
00:23:41
life. I am doing exactly what I want to
00:23:43
be doing every day. Every day I'm I'm
00:23:45
blessed and I realize that there's
00:23:46
only.1% of the populace can do that. If
00:23:50
I had billions of dollars and I'd
00:23:52
started a private equity firm like
00:23:55
>> well what I would be focused on right
00:23:57
now if I had say hundreds of millions to
00:24:00
waste I'm going to spend millions but I
00:24:02
don't have tens or hundreds of millions.
00:24:04
I'm very very focused on restoring some
00:24:07
of the traditional American values and
00:24:08
getting Democrats elected in 26 and 28.
00:24:10
>> That's what I do.
00:24:12
>> Yeah. I would put a take a bunch of
00:24:13
money and solidify a progressive not it
00:24:17
not not like hateful to conservatives
00:24:19
but like American values that are about
00:24:22
fairness and equity and things like
00:24:24
that. So I'd spend money on that. I
00:24:26
would spend money on um I would I I' I'd
00:24:29
do the McKenzie B Scott. That's what I
00:24:31
would be. That's what I I just suddenly
00:24:33
show up with money and not be heard from
00:24:35
or seen from again. I would that's how I
00:24:38
would do what she's doing exactly what
00:24:40
she's doing and suddenly give Howard a
00:24:42
whole bunch. She's did two gifts to
00:24:43
Howard and she's all of a sudden she's
00:24:46
over at Planned Parenth she's so diverse
00:24:48
in her giving um that I I love it and
00:24:51
it's that's how I would behave. I would
00:24:54
um I would also create um uh uh
00:24:58
universal daycare. I mean that's what I
00:25:00
would do for people better child care uh
00:25:03
for all kinds of parents. Uh I I would
00:25:06
somehow figure out a way to fund like
00:25:08
right now New Mexico has it because they
00:25:10
have all this oil and gas or shale uh
00:25:13
money they can do it. Every state we
00:25:15
should have nationally we should have
00:25:17
universal care. That's what I would do.
00:25:19
I would spend less on health stuff but I
00:25:21
couldn't see why. Um again money is I
00:25:24
don't spend a lot of money so I wouldn't
00:25:26
buy anything. I wouldn't I'm trying
00:25:28
would I buy anything? Maybe like my own
00:25:30
Taylor Swift concert perhaps. That's
00:25:32
what I would do. Anything crazy would
00:25:34
buy. I I might buy invite Scott hurt him
00:25:37
hurt his ears.
00:25:39
>> You'd be so nice to Taylor Swift.
00:25:41
Anyway, something like that. Something
00:25:43
like that. Someone I enjoy like that.
00:25:45
All right, Scott. One more quick break.
00:25:47
We'll be back with more from our
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listeners.
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00:26:54
Okay, Scott, we're back and we're ending
00:26:56
on something very special. A few weeks
00:26:58
ago, I asked what tattoo I should get
00:27:00
for Scott. ideally on my ass. Let me
00:27:04
read some of the answers we got. A roll
00:27:06
of toilet paper with an S on one of the
00:27:08
sheets. The Professor Galloway memorial
00:27:10
tattoo should feature an angry but
00:27:12
dignified daisy duck with a lot of pink
00:27:14
shading. Interesting. A penis that
00:27:16
cleverly embeds his name on it. Essie on
00:27:19
one cheek and TT.
00:27:24
>> Get the O is the [ __ ] Get it. Get
00:27:27
it. Okay. Uh, Groucho nose and glasses
00:27:30
was Scott's nose and glasses. I don't
00:27:32
like any of these. I do like the SCT,
00:27:35
I'd say. Uh, I need more. Scott, do you
00:27:38
have any suggestions?
00:27:40
>> Uh, I would get some I would just in
00:27:42
case of emergency, call Scott.
00:27:45
>> Oh my god. Break glass
00:27:47
>> or maybe a tiny raccoon holding a beer.
00:27:50
>> Oh, I think that's good is what I should
00:27:53
get. Just the word.
00:27:54
>> Um, a barcode. a barcode that if you
00:27:58
scan it, it said the problem with Scott
00:28:00
is
00:28:02
>> um
00:28:04
you better.
00:28:06
>> Yeah.
00:28:06
>> Let me see. Uh I don't know.
00:28:09
>> I would How about a cat and a dog sort
00:28:11
of fighting but hugging at the same
00:28:13
time?
00:28:14
>> Something like that.
00:28:15
>> You know, tattoo of a receipt. Total
00:28:17
0000 item putting up with
00:28:19
>> Cara.
00:28:23
Broken halo with the caption Scott
00:28:25
tried.
00:28:28
>> Acura
00:28:29
>> uh a fortune cook a fortune cookie and
00:28:31
the fortune reads you will tolerate
00:28:33
someone named Scott today.
00:28:36
>> How about one that just says at least
00:28:37
he's not Scott Jennings.
00:28:39
>> That's right. That's right. No, I think
00:28:42
there's a lot we could do. I could go
00:28:44
on. I'm fine.
00:28:45
>> I may get a Scott tattoo. I may just do
00:28:47
it as a surprise. I think I might maybe
00:28:50
I'll get make fake ones made and then
00:28:52
trick Scott in some fashion. We have we
00:28:55
have tattoos of us
00:28:56
>> tombstone that says rest in peace
00:28:58
Scott's sanity taken by Cara.
00:29:01
>> These are your tattoos. We have tattoos
00:29:04
that we made when we did that
00:29:05
conference. The one we didn't make money
00:29:07
at. This one we did.
00:29:08
>> Oh yeah. In the middle of co
00:29:10
>> Yeah, we we have tattoos. I'm going to
00:29:12
find those. There are Scott and Cara
00:29:14
tattoos. They were good, actually. Huh.
00:29:16
All right, everybody. You got to try
00:29:18
harder. Come on. Come on. Send more.
00:29:21
>> Okay, Scott, that's the show.
00:29:24
>> It's time to say goodbye. Thank you
00:29:26
listeners. And again, I truly and so
00:29:28
does Scott appreciate uh you and we were
00:29:30
very touched uh by all your questions on
00:29:32
the tour and we're touched by these
00:29:34
questions too and we truly appreciate it
00:29:36
because we love our fans. So Scott, read
00:29:38
us out.
00:29:38
>> Today's show was produced by Lauren and
00:29:40
Zoe Marcus, Taylor Griffin and Christine
00:29:42
Driscoll. Bernie engineered this
00:29:43
episode. Manila Moreno edited the video.
00:29:46
Thanks also to Dubros, Ma and Dan
00:29:47
Shalon, Nash Kas, Vox Media's executive
00:29:49
producer podcast. Make sure to follow
00:29:52
Pivot on your favorite podcast platform.
00:29:54
Thanks for listening to Pivot from New
00:29:55
York Magazine and Vox Media. You can
00:29:57
subscribe to the magazine nymag.com/pod.
00:29:59
We'll be back next week for another
00:30:00
breakdown of all things tech and
00:30:02
business.

Badges

This episode stands out for the following:

  • 80
    Most heartbreaking
  • 70
    Most emotional
  • 70
    Most quotable
  • 70
    Best performance

Episode Highlights

  • Taxing AI and Wealth Distribution
    A listener questions the taxation of AI and its impact on displaced workers. Scott discusses the implications of taxing robots and wealth distribution.
    “I think the moment you start getting into this notion of let's put a super tax on this type of firm...”
    @ 01m 29s
    December 19, 2025
  • Minimum Wage Policy Proposal
    A high school senior asks for a single policy to solve multiple issues. Scott suggests a $25 minimum wage as a solution.
    “If people get paid more, they'll spend more. It creates a better economy.”
    @ 04m 50s
    December 19, 2025
  • Scott's Spending Philosophy
    Scott shares his approach to spending money, emphasizing experiences over wealth accumulation.
    “I spend a ton of money. I love it. I give it away.”
    @ 13m 30s
    December 19, 2025
  • A Mother's Love
    On his 16th birthday, Scott's mother gifted him a car with heartfelt words.
    “You're a handsome young man and you have a car.”
    @ 18m 38s
    December 19, 2025
  • The Value of Kids
    The importance of affirming children's worth every day is emphasized.
    “If you tell your kids every day they have value, they start to believe you.”
    @ 19m 05s
    December 19, 2025
  • Male Role Models Matter
    Discussing the critical role of male figures in boys' lives.
    “The involvement of a male role model in your son’s life is actually crucial.”
    @ 20m 30s
    December 19, 2025
  • Remembering Dad
    Scott shares how he thinks about his father daily and the importance of remembering loved ones.
    “I think about my dad every day, every single day.”
    @ 20m 53s
    December 19, 2025

Episode Quotes

Key Moments

  • Listener Questions00:12
  • AI Taxation Debate00:35
  • Minimum Wage Discussion04:50
  • Parenting Advice15:42
  • Mother-Son Bond18:38
  • Parenting Wisdom19:05
  • Role Models20:30
  • Daily Remembrance20:53

Words per Minute Over Time

Vibes Breakdown

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