The Prof G Pod with Scott Galloway - Raising Modern Men: A Mother’s Perspective (A Lost Boys Special)

Episode Date: August 22, 2025

We’re wrapping up the Lost Boys series in the Prof G feed with this final episode. Anthony Scaramucci and Scott Galloway sit down with a very special guest to explore a mother’s perspective on raising modern men –  from the challenges young men face today to how parents can help them thrive in a changing world. Subscribe to Lost Boys. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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I'm Henry Blodgett, and I'm launching a new podcast called Solutions, where every week I'll talk to an innovative, enterprising expert to cut through the doom and focus on how to build a better world. Follow Solutions with Henry Blodgett wherever you get your podcasts. The first episode will be out Monday, August 18th. Hey, everyone, Scott Galloway here. On this episode of The Lost Boys, Anthony Scaremucci and I take a look at the challenges young men face from a mother's perspective.

We're joined by a special guest to talk about what young men really need to thrive and how parents, especially moms, help guide them towards a better future. Let's bust right into it. Welcome to our. podcast, Lost Boys, where my friend Scott Galloway and I dig into the challenges young men are facing today. We're both very concerned that young men are failing to thrive, professionally, socially, and financially. And so we've been exploring this problem with some very smart people and trying to find suggestions of what we can all do about it. So, yeah, we've decided,

and we're going to try and look at this through the lens of, uh, women and mothers who obviously have invested interests in ensuring their sons and brothers or potential spouses have the resources and the support to succeed. And this is, we believe, a big part of the reason that we elected a convicted felon, that there's still a lot of women in America who will vote for a candidate who they perceive as best for their husband and their son. So today we're going to talk to a woman who's had a successful career in business before she started raising to boys, someone who's benefited from kind of the tearing up of old scripts, as Richard Reeves describes it, and who is now helping figure out how to write a new script for men as she raises

her own boys. And just to make things more relevant and odd at the same time, she's doing it while married to our friend Anthony Scaramucci. That's right. Today we're talking to Diedra Scaramucci, Anthony's wife. in addition to learning about the challenges of young men are facing from a mother's perspective, we can also learn about just how incredibly strange our gut feeling is about Anthony. She can validate or nullify that. Welcome. Welcome, Deidra. Thank you. Thanks for having me. It's good to have you here. So we've talked a lot about how women today have more opportunities in the past. Richard Reeves tells us that the old script for women has been ripped up. You had a successful business career.

When you were growing up, did you believe, you know, how, from your perspective, how have things evolved with respect to the expectation and kind of the traditional roles of women in today's America? Right. Well, I was growing up in a very traditional household. My dad was a blue-collar worker and my mom was a secretary. So basically, they told me, you know, you can do whatever you want to do, but this is kind of what you need to do. These are limited positions in the world for women, and they kind of steered me into the traditional ones. So I actually started off, like, as a secretary, a very traditional role, and I worked my way up. But in the beginning, no, I actually really didn't think there was much opportunity for me.

But I think that's basically because of where I was starting from. And my household was very old school. So I was kind of following their lead. And I assumed I would kind of go into the same role my mother had. which was, like I said, a secretarial role. So things have very much changed, and I proved myself over the years, so I moved up in the world and on Wall Street, but I was very nervous in the beginning.

It wasn't a comfortable situation for me. Yeah, by the way, my mother lived and died a secretary. Which is a very respectable role. I mean, it helped everybody, but it just wasn't like a challenging role or something that, you know, stretched you out of your comfort zone. It was a very kind of comfortable role for me, you know? Growing up in the 70s, you know, my mother was a single mother raised me on her own.

And if you're a woman without a college education, my mom was pulled out of school at the age of 13, you could do one of three things. You could be a secretary. You could be a real estate agent or you could be a travel agent. That was the universe of employment opportunities for women who weren't, you know, weren't blessed with the opportunity to get some sort of educational certification. That was it. You could be a real estate agent or basically a secretary. You couldn't even be a teacher, right? Because teachers require a certain level of certification.

You had to be self-taught in whatever role you were assuming, right? Yeah, but you also just couldn't, quite frankly, you might be handy. You couldn't be a plumber. No one was going to take a female plumber seriously. I mean, I don't think people really give us enough credit, and then we'll move to the topic here around how far we've come or just, or quite frankly, how fucked up we were with respect to or the expectation around what women could do or not do. Anyways, let's pivot to talking a little bit about raising boys.

What do you see out there, as you raise, we'll say raising two men, what do you see as the biggest challenges as it relates to? I mean, obviously, there's a lot of challenges raising boys just just in and among itself. But in terms of what society expects from them, some of the pressures that are placed on them, what are your thoughts or what surprised your overt observations do you have about raising men in today's America? Well, as we all know, I think parenting is an experiment. So I've not yet cracked the code on all of it. But in terms of our household, like I said, our kids are very young. But I think we are also carrying over the kind of traditional home that we both grew up in here a bit. And I think that's the foundation for our parenting. So there's still

a feminine energy. There's still a masculine energy. Because I believe the masculine energy right now is kind of something that people are poo-pooing for whatever reason. So I'm still trying to keep that like a constant thing in my boy's life. Like it's okay to be a man. Like you can you can have that masculine energy but you also have to be a gentleman. So I'm trying to teach them to embrace their masculinity but also be kind, have manners. I think also people don't make their kids do things that make them uncomfortable anymore. Like today, our son had to do the Pledge of Allegiance. He's in fifth grade. He's 11. He was freaking out on the way to school. And I was like, Nick, I know you want to run away right now and sit in the parking lot with me, but I'm going to make you go in

there and do it. And then after the two minutes of you saying that that pledge, you'll feel so much better. You'll have faced the uncomfortable feeling and the nature. I told him I was doing this podcast, which I'm, you know, I'm rusty at and Anthony excels at. And I said, I have to go do that. I'm afraid to do that with dad, but I'm going to do it. And I think that people don't push their kids to do these things anymore. They let them out of everything. And I feel like it affects their personality.

It affects their lives. Because as we all know, when you're never uncomfortable, you never grow. And I feel like you have to push, especially boys, which probably sounds terrible, you have to make them do things they don't want to do so they can become comfortable. and men and be confident. And I feel like there's a lot of that lacking. I feel like that's why, like, women my age love to watch Yellowstone or 1923 because we're all missing the John Dutton's or the Spencer Dutton's.

There's like this lack of this masculine energy where people are looking for that, you know? And on my end, I try to exude femininity to my kids so that they see what it is to be a mom, is to be a woman and I can be strong and I can be fierce, but I also can be soft, you know, so I'm trying to teach them the balance. And I think Anthony is a great role model. He's still, he's obviously born in the 60s, raised in the 70s, and he is very masculine. But he'll also change a diaper. He'll also burp a baby. Like that's a, that's also a shift. Like my dad was the best dad, but he never did any of that stuff. Like my brothers, Anthony, you know, they've embraced like the softer side, which is okay, too. And it plays off nicely of the masculine energy,

how he goes out to work, and he brings home the bacon, and I stay home, but he'll also help me with the kids. I feel like it's a balance, you know, to find a fine balance. So I feel like we need more of that, you know? Yep. Let's talk a little bit about school. So Richard Reeves, some of his work, has shown that he believes that K-12, the educational system is kind of inherently biased against boys. 60 to 80% depending on the school district of the teachers are women, that there's just not a lot of male role models for boys, K through 12. And if you think about the behaviors that we endorse in school, sit down, be organized, sit still, be a pleaser, raise your hand. You're basically describing the activities that, quite frankly, girls have an

easier time with than boys. Yeah. What is your observation as a mother with boys in school around the school system, how the school system interfaces with boys? Well, that's interesting because my school, the school that our kids go to, they actually had a male principal and they've each had at least two male teachers and they're only in fifth grade. So we happen to be lucky with that. But I think, yeah, when it's mostly women, it's more like you're being mothered again at home. You know, it's probably less modeling for how they should be behave or how they should strive to be. and more just like you said, sit down, don't talk, you know, be polite and all those things that your parents are already trying to teach you. So there's probably less example to follow. So that probably is an issue. But I don't know. I think that's just how it's always been and what people are used to. And I think a lot of the stuff that needs to be taught should really start at home. School is just an extension of it. But really your kid's personality is shaped

at home, you know, friends and school are all outside influences, but they shouldn't be the main influence. You know, I'm not, I'm not hoping my kids go to school and, and take on exactly what their teacher models or examples or says to them. I'm hoping that they, they go by us. It would be nice to have it reinforced at, at school, but if not, it's our job to do it, you know? What's the Scaramucci approach to screens with your kids? How old are your sons, Deidre? It's a rough time to raise a child. So seven, he'll be eight, and our other son just turned 11. And I think, like I always tell Anthony, we got totally punked at the time we have to raise these kids because in 2014, when I had Nick, screens were not this prevalent, right?

Now, I'm like, is this real life? Like, every day, I wish I could go back and parent with my parents. I have to fight with them about screens. I have to fight with them about social media. And these are young, young kids, right? So our youngest one has an iPad. So he'll play games or he'll watch YouTube. A lot of it is sports related.

But then sometimes I'm like, what is that? Like it goes down the rabbit hole of totally inappropriate. And there are topics that are completely age inappropriate. And I have to then explain to them or reel it back in. And they've been exposed to a lot of things that people their age never would have known about seeing her. of unless their parents were talking about it 20 years ago. And that's a big challenge. I think, you know, I've had to have the conversation, Anthony, too, about gender anonymity or, but even in the school we have that because there's, you know, all gender bathrooms. There's, and this is

elementary school. But we've had really tough conversations about sexuality and all types of things is that at seven years old, I never knew about. 11, maybe a friend here or there that was from, like, you know, a different kind of household would have mentioned and you'd be curious about, but it is at an all-time high. I think kids are growing up. Just to press, pause, Deirdre, as it relates specifically to screens, do you got, and let me come out of the closet as someone who's written books on technology is considered thought leader in technology, we have not figured this out.

My kid is addicted or at various times been addicted to devices. I have situations where my son will pretend to be in the bathroom so we can go in there with his phone and watch TikTok for an hour. And I have to bang on the door and tell him to start masturbating and get out of the bathroom to do what he's supposed to be doing. How old is your son? Well, mine are 14 and 17. And by the way, I actually think that you might,

your kids might end up with a healthier environment. because I do think legislation is coming down the pike. But what do you guys have rules in terms of screen time? Do you have certain periods where they're not allowed to have their phone? Have you kind of done what most of us have done and given up? Like, what are the rules? What are the guardrails in the Scaramucci household around screens? Well, I am a complete and total pushover in many ways.

So the screens, I would say, are a problem, a big problem, just like you. I, um, they're young enough now where I could still control it. Like, they, they don't have screens at school. There's no phones going to school. There's no iPads going to school. But, um, the minute they come home from school, they're running to the screen. Running, running, running. And I really, I look at them and I know that it's doing brain damage because they go from one video to the next. They just swipe up, swipe up. Their attention span is getting completely wrecked by these videos. Um, and by the way, it's total nonsense what they're watching. It's nothing helpful. so yes i try to cut it off during the week you know then there's homework to do there's sports fortunately my kids our kids love sports so that's a great way to get them off the screens they're gone for most of the afternoon into the evening um with either practice or games so that's really really good um and that's the only thing that keeps them unless they're sleeping or playing sports or at school they're on a screen that's the guy's honest truth yeah um so We did this crazy thing where we literally installed a full court basketball.

I know that this is ridiculous and not many people can do this probably out of touch, but we put a basketball hoop in the front entrance of our house so that, because our kids love basketball, they literally have cut down their screen time, I would say, by half, because they're constantly just playing basketball in the front of the house, whether their friends are over or the two of them together or the minute Anthony comes home, they ask him to play. So I kind of, like, did something ridiculous and put that there to try to coax them off the devices. I don't know. I think we just have to find other things for them to be doing. We'll be right back after a quick break.

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Yeah. Oh, hell yeah. Of course. It'd be cool to see something different and be pioneers. Even with the risk involved? I mean, we risk our lives when we walk out here on the streets. No, I would miss my family. They were all here.

I would not want to leave them behind. If I got paid for it, yeah. How much did you want to get paid for it? $10,000. That's it? Yeah? You got to ask her more. Okay, $1 million.

That's more like it. No, because the risk of death is too high. What are the risks? Have you seen the Martian? With Matt Damon? Yeah. Thank you. Living on Mars.

On today, Explained from Vox. Anthony, I want to bring you in just for a second because just in the spirit of candor, this is your second round. You've locked and loaded again, right? Yeah, I do, I duped him into having a whole other set of kids. Another brood. So my question for you, Anthony, is how are, what is your, how is your approach to raising kids changed? Is someone is a little bit older, probably a little bit more financially secure, hopefully a little bit wiser.

How are you, how are you editing, altering, changing your approach to parenting in round two? So, I mean, it's a seminal question, Scott. I had my first kids, my first son was born when I was 28. And just to set the scene, I had maybe still $100,000 a school debt. I was working at Goldman Sachs as a junior associate there. And the money was okay, but I was living in an apartment in Tarrytown, New York, above a nail salon because I frankly didn't have any money. And so I was living outside of the city, taking the train into the city. and so the level of financial anxiety I had raising my first set of kids on a scale of once, that was probably a 15. And so I was a workaholic. I was obsessed with work in an effort

to pay bills. And, you know, I did my best and I did, you know, but I would say I was probably being brutally honest, I would say more focused and obsessed on work than I was. okay, stay calm, here's the get. Also, I was an overreactor. You know, one of the things my dad, and I don't mean to say anything untoward towards my dad, because I have enormous amount of respect for him. He's now passed, but he was very overreactive as a parent. So he would beat the daylights out of us, God, if we did, if I left the light on, I don't know if you had this in your family, but, you know, my dad was like, we have no money, so make sure every light is shut in the house, unless you're actually in that room.

You know, there was corporal punishment for that stuff. So I never hit anybody, but I used to get bombastic and overreactive and overly emotional. And I think my daughter said, okay, here he goes. He's going Zulu again. That was their, I don't know, probably, that's probably not even allowed to say that. It's like a derogatory. But, I mean, like I was like in a war mode. And I think I'm a calmer parent now.

I think I'm wiser. I think I'm a better listener. I'm not perfect, sure. I'm distracted as well. I'm tired. Sometimes I come home from work, exhausted. But I think what I want to ask both of you is 1964's big year for Scott and I.

That's when we were born. And so we both got raised in the 70s and the 80s. You got raised, frankly, Deirdre in the 80s and the 90s. Right. What's different today? Like for me, the seminal difference is that we're apologists now to our kids. Okay, you know, like in the 18-

In the 1800s, the kids got set down into the field, shut up and don't speak until we tell you to speak. And if you dropped dead in the field, no problem, we're going to make another one. And in the 80s, I was a latchkey kid. I don't know if you were Scott, but, I mean, my parents didn't even know where the hell I was half the time, you know.

I was run out of paper route at age 11. My mother had no idea. I was taking the train to MEC games by myself. My mother had no idea. And now we're like, the kids are in control. There are our bosses. We're subordinate to them in every step of the way. That's my difference.

What are your differences? Guy, you want to answer? Sure. So it sounds like we had similar upbringing and some of it's good, some of it's bad. And that is, I was raised, like I said, by a singer-immigrant mother, lived and died as secretary, a lot of my life. We didn't have a lot of money, but it's not a lot of money. but it's not a sob story. It was fine.

I had what I call a remarkably unremarkable childhood, and that is from the age of eight, my mom couldn't find babysitters. It was expensive for, one was a religious freak and used to make me stand in the corner

with my arms raised like Jesus Christ if I said the word God. The next, I remember the next lady I had, when the ice cream truck would come, she'd give her kids 35 cents and me 10 cents, and my mom went crazy when she heard that. And so I said to my mom, I'll take the two bucks a week,

I'll take care of myself. And my mom used to leave the house before I got up and get home, you know, an hour before I went sleep. The television raised me. I was raised by I Dream a Jeannie and the Partridge family. And I would say that whenever, you know, my wife or anyone accuses me of being a sex or something, you got to keep in mind. I grew up on Yes, Master, and Jeannie go to your bottle.

I have come really far. I was raised on television. I used to come home at 3 and watch TV until 8 p.m. until my mom got home. I would make her a cup of tea. I'd already eaten dinner or not eaten dinner. So I had, but what I had like you, Anthony, was I'm not exaggerating. Saturday morning, I leave the house at 9 a.m. with an Abba Zababbar, a Schwinn bike, and 35 cents, and I would come home 13 hours later.

My mom had no idea where I was. I was negotiating with older kids who would beat you up. If you didn't have a big brother or something, they would run after you. we would go to 7-Eleven and my friends would shoplift. I mean, we were just like total hooligans. And, but some of that, quite frankly, was good. You negotiated your peer group. You figured out social capital.

You, you know, my mom was worried I was going to get into too much trouble. I'm worried my kids aren't going to get into enough trouble. If my kid is 10 minutes late home from school, we call MI6. And I don't think a lot of that is good. You learn a lot when you kind of have that type of freedom. Was some of it not productive? I went to public schools that quite frankly were just warehousing me. They weren't very good.

But, you know, like you, Anthony, you grew up. I think what we share is I very early connected the dots between a better life and money and wanting to take care of my mom and then ultimately wanting to have kids. with success. And that really created embers or fire of desire to try and make money. I wasn't, and I've said this very openly, I didn't want to be a better person, I didn't want to save the whales, I didn't want to find my passion. I wanted to make money. Because the biggest stress in my, in my mom's life, hands down, wasn't that my dad wasn't around, you know, it wasn't

that we didn't have enough time together. It wasn't any of that, or there was an emotional support. The biggest stress in our life was we just didn't have enough fucking money. It was just like a ghost following us around. Like, my mom being stressed because we couldn't find the first month deposit to find a new apartment, you know, it just is something the vacuum cleaner would break. And so we'd had a rake and we would rake our shag carpet because we couldn't afford to fix the vacuum cleaner. So those things were very seminal. But the difference today is the over-parenting, I'm worried we use so many sanitary wives on my kid's life that they're not going to develop their own immunities. So much is done for them. There's a problem at school. I constantly have to say to

my wife, you know, oh, he's not, he hasn't signed up for the ACT is going to miss it. I have to say, let him, let him figure out this shit has consequences that we're just not there to, you know, to save him every time. Unfortunately, they're pretty good kids, but it is entirely different. Deidre, had things gotten different by the 80s or 90s when you were raised? No, I was raised like you guys it's interesting like the gap between it there's 15 years between us but I was in the same kind of generation the way we were raised I went home after school my grandmother was there but then after she passed away I was a latchkey kid I did my own homework I made my own snacks you know my kids come home and they literally at the bus stop they hand me their book bags and I'm like but what I

can't figure out is where is the breakdown like when did we decide that we're so worried about our kids liking us that we don't want to enforce anything. And I'm so guilty of this. I just don't really know what happened. Was like our parents were too hard on us or was it too uncomfortable or did we make it in life? So now we think that they can just enjoy life because we know have temporary. Like what is the actual basis for this shift in behavior? I can't figure it out. And it seems like nobody our age can figure it out because we're all doing it. But it's such a stark contrast. from what happened in our lives. But I think, like you said,

we're so much more, you know, put together. I don't know. I think we're just literally have zero expectations and we do everything for them. And we are crippling them, but I can't stop. And I don't know, I need therapy.

I don't know how to gear up to, especially it seems like your wife has the same issues as I do. Like, natural consequences should be good enough, you know, like, oh, you don't have your Chromebook, You don't have your laptop. You have a test today.

You were supposed to do it on the test. I'm not bringing it. That would be somebody from, you know, our parents' generation. I'm running to the school. You know, every night I'm charging this stupid laptop for him. Like, you know, it's just, I don't know how it started, and I'm not sure how it'll end. So I want to hear both of you, your best example of how different things were

and something that strikes me. I, my mom didn't even sign my report cards. I signed them for her. So she had no idea of even what grades I was doing. I decided in the sixth grade to stay home from school, and she didn't know. And I just stopped going to school. And two weeks later, this red Mustang parked outside of our condo, and I recognized it, and it was the principal. And he came and knocked on my door, and he said, Scott, you need to come back to school.

He never called my mom. My mom never knew. I took two weeks off of sixth grade, and my mom never had any idea. Your turn. Anthony. I was at the landmark diner, the station diner at 2 o'clock in the morning eating pancakes with my cousins. And then I would slip in through the sliding glass door in the back of the house. I was probably 11, probably 12.

And no one knew. I used to do that. I don't know. I was in the fifth grade. I was doing that. Nobody knew. I probably shouldn't tell people this. But, I mean, there was a place called the Salem Inn.

and it was a strip joint, believe it or not, we had our local strip joint in town. And my uncle was a motorcycle owner of a motorcycle shop. At the age of 14, we were up there watching topless dancers. Okay, so that's 1978 and a smoke-filled strip joint. It's now an auto parts store in Port Washington Boulevard. So, I mean, I... You win. You win. I'm not trying to win.

I mean, I haven't even, I haven't even scratched the surface, okay? But I'm just, I'm just saying that we were so unparented. But it all goes back to technology, right? See, this is, this is me. So you ask the question. I would love to hear Scott's answer. I was so unparented. And if I'm being brutally honest, as a child, I was scared a lot of the time.

And I was like, what the hell? You know, and I was driving around delivering news. newspapers and I was scared some of the time. So when I became a parent, I was like, okay, I don't want my kids to feel scared. I'm going to put this safety umbrella around them because that scary feeling created a lot of cortisol in my body and probably a quasi eating disorder and all kinds of other shit that happened to me. So I'm going to try to not do that to my kids, but then it has a, I swung the pendulum too far and it has like a more perverse effect. We've all done a Deirdre, what you said really resonated that we know the princess and the peace syndrome

we're creating for our kids where they get to college. And I see this at NYU, their freshman year. They get their heartbroken. They get their first D. And they literally freak out because we have cleared out all the obstacles for them. We've figured out the tutors. We've figured out, you know, the ADHD medication if your kid's struggling. We figured out the right school such that they can at least get a B average. Right. And then they face the real world that is full of real obstacles that we can't clear for them. And they haven't developed the scar tissue or the immunities or the calluses. And something I'm not proud of, you know, I'm the pushover.

But once about every three months, I lose my shit. Yeah, that's how it. And I've grabbed my son by the scruff of his shirt and lifted him out of bed. I have physically kicked one of them in the butt. I'm not proud of that, but, you know, just, like, kicked them. I'm, like, proud to know you. Well, they threatened to report you because our kids did. Yeah, calls child services.

Just make sure I never leave a mark. But my partner, my wife has said to me, dad is out of control. You're having an outsized reaction. And I'm like, you know what? Their life is going to be filled with out of control, outsized reactions. I don't want to traumatize them. I don't want to scar them, but they need to understand that occasionally someone is going to have an outsized reaction to their bullshit.

And I look back on it, and I'm not proud of it, but I wonder if some of that is needed. And I'm just not one of these guys that wants to sit down with his boys and ask them how he feels about stuff when they're just behaving really inappropriately. I'm not a yeller, but I do yell. And I'm curious, Deirdre, as someone who observes, I think Anthony is probably more, is a little bit like me. Like, what is the balance between a dad, quite frankly,

having that sort of dad energy sometimes that quite frankly can be a little bit, I don't, scary, intimidating, and also, but ensuring you don't traumatize your kids. Well, I just, that's the thing that I'm going back to. It's like, I don't think my parents were ever like, oh, I'm traumatized. I know for shit sure I was traumatized plenty of times and I think I'm a fine today.

I'm a functioning adult. I don't know why we're so worried about traumatizing them if they'll like us, but we are. So I can't figure that out. But so I have the my brother, I have two brothers. One of them has kids. He will lose, he's a principal by the way. He will lose his shit on my nephews who are a little older than our kids. um rightfully so and i get so nervous and so uncomfortable i don't know what it is you know my dad was

kind of like you guys he was so calm until he wasn't then it was like calm until the bomb went off and then we were all like running for the hills because he exploded and also we felt bad that we disappointed him but um when my brother does that i'm like wow because he will get physical he will not like hurt them, but he'll be like, you don't get to do that or like he will pull them aside and my sister-in-law and I are like, or Anthony will sometimes get really strict and yell and raise his voice. One time he kicked a box of Bisquick and it exploded everywhere. My kids always say now, oh my God, dad's about to kick the Bisquick. He's about to go Bisquick. He's about to go Bisquick. So we use that to like say like, but.

knew this was a bad idea pairing the two of you together. But go ahead. Keep going on it. The bottom line is it makes me so uncomfortable. I hate conflict. I hate yelling. I hate all that. So maybe my parents did traumatize me and I, and now my reaction is to shy away from it all. But I do think that they need that sometimes, like a wake-up call. And Anthony pushes me to do things that I would let my kids slide on all the time. Like last night, again, Nick, fifth grade, spring concert. He's coming to me with a thermometer. He's showing me that it says 99. I'm working. I'm on a call.

He's showing me 99 on the thermometer. Okay, cool. He's showing me he has a bloody nose. Cool. Like he tried every which way to Sunday to get out of that concert. And I let him out of the Christmas one. So I was like, you have to go. You cannot miss both of these concerts.

And I had Anthony's voice in my mind. Like, sometimes they have to do things they have to do, you know? So we made him go. And not only did he go, but he actually sang, because a few concerts ago, he just stood there with an absolute face and attitude, and we went ballistic on him after. So, like, these are the kinds of things that they need to do. Like, you need to sing in the chorus. You need to say the stupid pledge. And I feel like sometimes I would totally let them slide. And Anthony's like, no, they have to do it, Deirdre. They have to do it. Like, you're making them into weenies. You've got to have them do it. So if not for him, I think that's where the whole

masculine feminine energy comes in. I feel like I'd be raising probably less than stellar people because I need Anthony's balance to help me. And I think that's a challenge because a lot of people are a single parent household and like they have to be both. And that's really hard. So I appreciate appreciate that about him. And your wife probably will in the long run when your kids are doing the right thing and have some sort of like, you know, meat and substance to them and they can make their way in life to probably look back and say that she appreciated the balance. So you should probably I hope so. A question for both of you, something that was hugely important for me growing up is in terms of male mentorship and having male energy in my life was I played sports my whole life

and it gave me something to do. It gave me a certain amount. I wasn't a great athlete, but I was an athlete. He gave me confidence, kept me out of trouble, introduced me to some coaches. At one point, I peaked athletically at like 14, but the coach used to come pick me up at my house and take me to the grounds and practice with me because he saw potential in me and it gave me a sense of worth, competition, playing with the team. What role does sports play in your children's lives? Huge. Huge.

Like I said, that's the only thing that gets us out of the house and off the screens, and they love it. And it's not a force thing, because I see a lot of that going on in our neighborhood or in our lives. They voluntarily want to go, and it motivates them. And I think it gives them purpose, exercise. which they need after all those hours on a screen, you need to, like, physically move your body and clear your head from all of that nonsense. So it's a daily thing.

Like, if you see our schedule, it's probably over-scheduled with sports. But I'll take it. Because if they want to go to five basketball games and playing three football games, I'm going, because that means we're outside, we're moving, and we're not on a screen. So it plays a huge role.

And I hope it always is. does. I always wonder what we would be doing if they didn't like sports. Um, so it plays a big role. I know that Anthony's older kids had different interests, um, more musical and more creative and artsy, but it, it was, they were still involved in things. Also, screens really weren't a thing then, so. No, there were, there were no screens. I mean, there, there was for my older kids, uh, fat, fat, fat screen computers. Right. And there were some video games that they played. but they weren't as sophisticated as like the Fortnite 4K videos, so they weren't as heavily addicted, you know.

And I would just say that sports has been massive. I would tell people, get your kids in sports. I mean, you know, I don't love, and Deerger can tell you this, I don't love the oversaturation where there's some kids at our town, Scott. They're 7 a.m. playing sports on a.m. and they're playing sports at 11 p.m. on a Sunday, and they go to school Monday exhausted. I'm not for that. I want the kids to play sports,

but not to be overdone to the point where they're, I mean, we do a lot of extremists, I think, particularly in our town with sports. Got your kids play, so your kids like sports? Oh, yeah. They have, I would say they have just the right amount of athletic ability, and that is they're good enough to play on their sports teams, but not a good enough to have any delusions of grandeur.

And, you know, they play well enough to play on the team, but they're never going to, you know, at one point, I recruit UCLA and the kids who are just amazing athletes, I almost think it's a bit of a curse because I have a lot of friends who spent the majority of their 20s training for the Olympics and got a bronze medal in Seoul and then we're calling me at 29 looking for a job. Anyway, I want to ask the two of you parenting questions I get and I can never answer. I haven't figured out the answer to. The first is... You know, Anthony, you know, I know you. I know you. I know you well, but I know you enough to make an assumption here on that is we're both economically successful. We both recognize that being born in the 60s, a white heterosexual male gave us kind of unearned wind at our back, not talented, but we were able to really capitalize on that talent to an extent that other people, the same levels of talent, didn't get the same opportunity as us. So let me just put that out for there. No question. But now having some of that economic success, it is really difficult. The reason I'm here with you right now, and I get to lead the life I lead, was, and I always say this, if I had what my kids have, I wouldn't have what I have. If I had the resources my kids have, the only thing I know I would have is a Range Rover and a cocaine habit. I was not, I was not born with natural grit.

And I worry that my kids, I face this age-old question of how do I instill those same fires that were ignited in me because of a lack of economic security, you know, the old question of how do you instill grit in kids when the reality is, you know, I say to my, I got upset at my wife, I said, my kids are in business class and I had this terrible moment where my, you know, this was like five years ago, my nine-year-old son is playing with his seat going back flat and up and this very elderly woman goes rolling by on our way to coach. And I'm like, okay, we got to put the kids in coach. And she said, all right, you're flying with them in coach because they won't let them fly alone in coach. And I work so fucking hard.

I'm not flying in coach. And so it's impossible not to let your kids enjoy some of the fruits of your hard work in economic security, at the same time recognizing that's probably not good for them. So long-winded way of saying, what do you do to try and instill that same sense of grit that we had? And I think we've really benefited from. I'm going to take a stab at that on, and then I'd like to hear you say something. But I'm going to say something about you, Scott. Again, we're getting closer, we know each other some extent. but there's something that you do that I admire. And so I'm going to tell you what it is.

You expose your vulnerability. And I listen to your podcast. You're on my Google Alert. Your podcast comes in. I listen where there's pivot, the one you do with Ed, which I really love. And you expose your vulnerability. And this is a gift you're giving your children.

Because I hang out with very, very rich people that do not expose their vulnerability. And Deirdre hates the word rich, but I just said it. because what happens is they write this story about themselves about a 45 degree angle up into the right. Their lives have been perfect and they've made every decision right. And I look at their kids, Scott, and they're overshadowed by that. And they never reach their fruition. And so you may be giving them creature comforts, but you're also providing space for them to fail. You're providing them, wait a minute, my dad, he had this upbringing or he did this wrong or he

this right. And there's a humanity and an authenticity that you're exposing your kids to that I admire, and I've said this to Georgia, I've tried to do that. I've tried to say, okay, look, got fire from the White House. I failed at this venture. My portfolio did this, or I had a, you know, a setback here or there because I think that's one thing. And then the other thing I would say is that you're very passionate about what you do. And I think that's the gift that I can give to my kids. And I tell my older kids, life is short. Mel Brooks said, relax.

None of us are getting out of here alive, enjoy your life. But pick something you really want to do. And so you've, I think you've met one of my sons. You know, he's very passionate about his fund. And therefore, he ended up going to Stanford Business School. I couldn't get him in there. I don't know anybody there. But he worked his ass off.

My other son is into the film industry. I could have told them, no, you got to go to Wall Street like your old man. I said, go to the film industry. You just got his film into the Tribeca Film Festival. By the way, I'd love to have you come to the premiere if you're in New York. But my point is, and my daughter's singing. And so to me, if you tell your two sons, I want you to pick the thing that you really love and go crazy doing it, but also understand you have space to fail, they're going to be very passionate and very energized. What do you think of that, babe?

Am I saying anything you disagree with? No, but the interesting thing is the space to fail is what probably makes them less resilient because most of the things our kids are able to do is because of the road that you guys have paved for them to do it, right? So we didn't have a choice. It was like, yeah, we kind of found something we like to do, but we also had to do it because you had to like pay your rent and you had to, if anything, you know, provide some Different generation, though, Ben.

Right. So I'm just saying the irony is that they can find something they're very passionate about and pursue it and have the room to fail because it literally doesn't mean they'll be living on the street like it might have been for somebody else, you know, when we were growing up. But I think, yeah, being vulnerable, Scott, I actually really do appreciate that about you. I enjoy your personality. And I think the only way that our kids will succeed is if they do find something that differentiates themselves from their parents that they're very passionate about and interested in because I see, like, and with myself also, when I really like something, I really like it. And I'll do anything to do that. When I'm meh about something or I really don't care, I could be the biggest bum and not do anything. So I think they have to like what they get into, whatever that may be. I don't know. But I think that would be my suggestion for our kids. Because obviously we've already sold, you know, sold the bag on not providing everything for them. They already have all of the stuff that someone would strive to attain. So I don't think it's about any monetary gain. I think it's about fulfilling themselves and feeling good about what they do and making their own way in life. So, which I know is a challenge when you have a parent who's, whatever you want to call it, a trailblazer. Um, so I don't know. I haven't figured that far now. The second question

I get behind closed doors, um, and I, we haven't figured it out is, okay, when, is money when they're older? When, do you plan, I mean, most of my friends have the following, say the following when the kids are young. Okay, I'm going to pay for their college, but once they're through college, they're through college, they're on their own because one of the most rewarding things about money is making it, and they need to have that reward and that opportunity and also that pressure. And then this is what has happened with almost every one of my friends that has resources. Kids a good kid. Graduates from college, their dream is to be on Broadway. But they can't live in New York. There's no way. So you help them out. We help them out. We want them

to pursue their passion. Things have gotten so expensive. I don't want to deny them of their dream. And then it's three, five years in, and they're still not self-sustaining in New York, because they give them a little bit of money. And then they meet someone and fall in love. And you think, well, I want them to live near us, and they can't afford a house near us. No young person can live near us. And I selfishly want my kids and my grandkids near them, so I give them enough money for the house. And then they can't afford that lifestyle. And they're good people. These aren't bad people. They're jobs, making good money, trying hard, but can't live the life we lead. And I have friends who, in a creeping

slow, benign way, have kids in their 40s and 50s who they are still supporting substantially. So, one, what is your thoughts about financially supporting your children when they're adults? And then the big one, when you guys pass, will you give it all to your kids? Or will you give some of it, most of it away? What is your approach to your, as you think about your estate and your approach to financially supporting your adult children? Well, Anthony thinks he's going to live to 150, so he hasn't thought about any of that. That's not true.

I got the whole thing. I got everything. Scott, don't listen to this. I have a file when I'm dead file. You open it up. Everything is there. All you got to do is call the attorney. lots of money flowing you'll be just fine but god if i do if i do die early you know there's a lot of

life insurance something hmm hmm you know the suspects abound we know we know where to look i just just letting you know there's suspects out there okay answer the question on no i i plan on obviously i've got some year marked for universities that i went to and some charities that are important to us as people. But I do have a blue-collar family, Scott. And so Deirdre will tell you that throughout my life, I have paid for tuitions. I've purchased cars, given down payments on houses. I've, someone has an emergency medical situation. I have provided money to, you know, overcompensate for potentially lack of health care insurance and things like that. And so I, you know, when you're from a family like mine,

you want to take everybody with you, Scott. You know, you're trying to help everybody in the equation. As I often say to, you know, charity begins at the home. So if one of her siblings or one of my siblings needs something, and again, I differentiate between want, I want a Rolls-Royce, need, you know,

here's a beautiful Subaru. You follow what I'm saying? My point is, so I will definitely make sure that they get... Is there anything such as a... Beautiful Subaru. No, right. I mean, I'm right. I know you don't like Subaru, but I mean, she's upscale, Scott.

She's uptown girl. But the point I'm making is I'm going to leave a reservoir of money for people that if they need something, there's going to be some availability. I, you know, I see that as part of the mission. And I see that, and this is another thing I love about you, you don't need to work, but you're working. and it creates vitality in you. It also creates intellectual fulfillment. And I want to work. I want to hopefully stay vital and healthy

where I can work longer than my dad. You know, my dad could not have made a day past 65, Scott. On a crane, 41 years, very physical, very hard work at 65. By the way, at 55, they took them off the crane and the union gave him a dispatcher's job where he was weighing trucks because it was just too physically demanding you know but we're not

we're beneficiaries of a white collar experience you know as opposed to a blue collar one so I have a lot of empathy for people that are not situated but for the grace of God you know you and I have been you know blessed but I think hard work industry of course but we've also been blessed with some levels of intellect

and some levels of industry that have made it happen. So, yeah, I plan on helping the people around me first and then the charities. But in my mind, charity begins at the home. Dieter, what's your approach to? Well, my thing is this. I think because of how we grew up and who we really are fundamentally, Anthony and I kind of grew up

very similarly, in my mind, we're just still the same people. Andrews just happened to be successful and is able to help everybody. But I think I'm just along with him for the ride, really. So what I try to remember, what I don't really need much help remembering is we try to live below our means. So, and we live in a town where we can kind of, you know, people are pretty successful. It's an affluent town. So we kind of blend in. So we kind of keep it at the rate of our surroundings.

So our kids don't see much of a difference between them and their friends. friends like we live in a neighborhood where we have a lot of friends that all go to the same school and you know the houses are all pretty similar so it's not like you know we live on this giant wicked estate where people are going up you know this long driveway to see us we i think that we kind of see ourselves as the people we are and how we grew up and we kind of keep it at that level of course there are things that we do that are probably a little bit um suspect if our kids were wondering if we're different. But we really do try to keep it low-key. Like, I was laughing about Anthony this morning because I opened an Amazon package for the seventh day in a row. And it was

an Amazon Superman t-shirt that he happens to be wearing. And I'm like, okay, this guy is 61 years old. He's permanently 12, apparently, and he shops on Amazon. That's his favorite, you know, marketplace for his wardrobe. So I feel like there's just very normal things that we kind of year for Superman, Scott Galloway, okay? This is July 11th. It's the return of Superman. Okay. If you're around, you want to come to the movies with me, Galloway, I'll buy you a bucket of popcorn, okay? It's a big year for Superman. You can take the boy out of Long Island, but you can't take the Long Island out of the boy. That's the thing. That's what Anthony exudes. And so I think our kids appreciate that. We're just kind of living the way we grew up in a little bit nicer

of a home, but nothing too extravagantly. Well, I always say that to dear to those guys. I don't want to go to a big estate somewhere because there's a paradox to this. Okay. There's a paradox to wealth. You give the big estate 15 acres. Now your kids are lonely. You're going to fly privately everywhere. Okay, great. But now you're into, you're going to go on the yacht. Okay, great. But you're by yourself. I want the kids socially connected to other kids because I think there's a paradox to wealth. I think it creates loneliness. And then it creates, I mean, I'm eccentric enough. I don't want to be, you know, live in that lifestyle. Where are going to be even more crazy.

Yeah, I respect that, but I don't do that. I mean, I think it's, I really respect the fact that you've maintained some semblance of where you come from and are still in your old neighborhood and living what sounds like, you know, below your means. We do not do that. And I'm not proud of that, but the way I rationalize it is. I had a number and I thought, okay, I could work 12, 14 hours. I have such a desperate need for relevance and affirmation and economic security.

I could easily work 14 hours a day for the rest of my life. And I said, I'm going to set a number. And once I hit that number, I'm going to slow down. And I hit that number. And now every year I meet with my folks and they tell me how much above that number I have that year. And we're very analytical about it. and I take that money and I either spend it or I give it away. I think hoarding wealth is a virus.

I don't think anyone should have. I'm a socialist this way. If you look at Daniel Kahnem and the Israeli-American psychologist, he's done so much good work on the relationship between money and happiness, and there is a relationship, middle income or happier than lower income, upper happier the middle. But once you get above a certain level of wealth, there's no incremental happiness.

So I'm a material consumptive person. I love to spend money. I'm really good at it. I'm outstanding at spending money. I really enjoy things. I think there's amazing things you can do with your kids, with your wife. And so I spend a shit ton of money, and then whatever's left, I give away. And every year, I'm determined to maintaining the same number in terms of my wealth, because I think anything above a certain number is really infecting America in terms of income inequality. Spend money, it puts it back into the economy, give money away. There's a lot of amazing charities out there. And I don't even do it out of ethics. I do it because it makes me

feel masculine and relevant and like a baller. I love it because it makes me feel strong and like I'm important. I don't give money away anonymously. I'm not that nice. I want people to know. I want to show up. I want to shake their hand. I want them to be impressed and laugh at my jokes. Or I spend it. But I have not taken, I am, I am not living in my old neighborhood. We live a crazy lifestyle. And I think the downside of that is I'm setting the bar too high for my kids. So I have And I don't know. I don't know if it's the right way. Sometimes I worry, maybe I've screwed up. But we take a, my attitude is, you know, I'm going to squeeze so much juice out of this lemon. I'm just going to, I'm really going to consume. That sounds awful. I hear myself talking and it sounds terrible. But yeah, we're not, we're not back in Tarzana where I grew up. We're just not. I don't think there's anything wrong with that. I think that's the whole freedom of it. Yeah. And you're real about it. And I know. I know. I know you have to hop, but what resonating message before we go, Scott? What, you know, when you reflect on your way you were parented and you reflect on your parenting,

what's the resonating message? What's the observable? So what's the teachable moment? It's a generous question, and it's an obvious question. I don't know if that. The first thing that popped into my mind, Anthony, is that I'm trying to be, I think some of the, my shortcomings is a man, some of my sexism, some of my real failures with relationships, including failing my first wife, come from just a lack of character. I can't blame on anyone

else, but some of it is my dad did not treat my mother very well. And so as I think about trying to raise good men, a lot of that is real motivation to just be really good to their mother. And I try to go out of my way to, you know, just be very supportive of her, be very loving, be very affectionate, talk her up to them, give her her own stages where she can get applause because dad gets so many applause on different stages. And because I think if you want your sons to have healthy relationships, you know, one of the fastest blue line passed to making sure that they can achieve what I think is the most rewarding thing. And that I was to partner with someone and have kids, that the upward spiral is to develop a practice

of just being really kind and generous. And I'm doing a lot of virtue signaling now, but I do try and practice it just be really good to their mom. Because my dad wasn't good to my mom. And I think that that set a bad example for me that haunted me through my younger years as a man, and my approach to relationships with women, I just wasn't as generous or as kind as I should have been. And so I've learned later in life that if you want to raise good men, one of the real hacks,

even if you end up getting divorced, is just to be really good to their mom. I think it's very well said. I think I think we can end it there, this episode of Lost Boys with Deirdre Scaramucci. Right. Soon to replace me as the co-host of everything that I do. I don't think so.

Deirdis Garamushi. As I was once told, Anthony is the flower and I'm the gardener. Okay, that is such bullshit, Scott. Don't listen to this bullshit, okay? Fly on the wall here. I think we've got to be, it's kind of be a weird. They're definitely, I see, if Anthony's whole crypto thing doesn't work out or if things hit, I can tell you, a reality TV show is coming our way.

I can just feel it. No, thank you. That's so good we'd have to pass. I am unbelievably boring, believe it or not. Scott, thank you, man. Thanks for joining us for this episode of Lost Boys. If you'd like more information, please go to our website, www.lossboys.men.

Be sure to like, follow, and subscribe to Lost Boys, wherever you get your podcast. And please, share it with someone who cares about this or should care about this and let's spread the word. Boss Boys is a production of Salt Media and the Casablanca Strategy Group, Barbara Fadita and Keith Suma, our executive producers. Tanya Salati is our researcher, Holly Duncan Quinn, and Stanley Goldberg, our editors. Special thanks to Christina Cassese, Mary Jean Rebus, and Drew Burroughs.