The Prof G Pod with Scott Galloway

Lost Boys Special: "Raising Modern Men: A Mother’s Perspective"

Release Date: August 22, 2025
Guests: Anthony Scaramucci, Deidre Scaramucci (Anthony’s wife and mother of two boys)
Main Theme: Exploring the modern challenges and expectations around raising boys today, focusing on a mother’s perspective in a rapidly shifting social and economic landscape.

Episode Overview

In this "Lost Boys" special, Scott Galloway, alongside co-host Anthony Scaramucci, welcomes Deidre Scaramucci to examine "Raising Modern Men" from a mother’s perspective. The conversation explores how gender roles, educational environments, and parenting philosophies have shifted over generations, with frank accounts of personal experiences and family dynamics. The trio discusses the loss of traditional scripts for both women and men, societal expectations for boys, the challenges of "overparenting," the impact of technology and screens, the role of sports, and navigating privilege and financial legacy.

Key Discussion Points & Insights

1. Gender Roles: From Traditional to Transformational

Timestamps: 03:48 – 06:05

• Deidre describes her upbringing in a blue-collar, old-school household where expectations for women were sharply limited:

  "My dad was a blue collar worker and my mom was a secretary... They kind of steered me into the traditional ones." (Deidre, 04:17)

• Both Scott and Anthony reflect on narrow work opportunities for their mothers and emphasize how much societal roles for women have evolved since the 1970s.

• The idea that scripts for women have been "torn up," as described by Richard Reeves, leads to an acknowledgment of new scripts being needed for today’s boys and men.

2. Raising Boys Now: Masculinity, Challenge, and Balance

Timestamps: 06:05 – 10:01

• Deidre shares her philosophy:

  "...people don't make their kids do things that make them uncomfortable anymore ...when you're never uncomfortable, you never grow. And I feel like you have to push, especially boys...to become comfortable and men and be confident." (Deidre, 07:49)

• She insists on embracing both masculine and feminine energies in the home, modeling gentleness and firmness.

• Notable cultural references (Yellowstone, 1923) illuminate a "longing" for masculine archetypes, tied to a perceived lack in contemporary society.

• Anthony’s contributions often balance the need for higher expectations with acknowledgment of changing generational norms.

3. School Systems: Female Dominance, Role Models & Home vs. School

Timestamps: 10:01 – 12:04

• Scott references Richard Reeves’ finding that the K-12 educational system is disproportionately staffed by women, potentially biasing it against boys’ development.

• Deidre notes her sons have had both female and male teachers, highlighting variability, but stresses:

  "I think a lot of the stuff that needs to be taught should really start at home. School is just an extension..." (Deidre, 11:18)

4. Screens & Digital Distraction: Parental Battles

Timestamps: 12:04 – 16:43

• Both Deidre and Scott confess to struggles with screen time for their children, openly acknowledging failures to fully control device use.

• Scott candidly shares:

  "I have situations where my son will pretend to be in the bathroom so he can go in there with his phone and watch TikTok for an hour..." (Scott, 14:13)

• Deidre discusses practical interventions:

  "We literally installed a full court basketball ...I would say [the kids] have cut down their screen time by half because they’re constantly just playing basketball in the front of the house." (Deidre, 15:54)

5. Parenting Generational Change: Then vs. Now

Timestamps: 19:12 – 28:37

• Anthony offers a vivid before-and-after comparison of parenting, influenced by economic pressure and his own upbringing:

  "The level of financial anxiety I had raising my first set of kids ... was probably a 15. And so I was a workaholic. I was obsessed with work in an effort to pay bills." (Anthony, 19:41)

• The guests recount stories of childhood independence, benign neglect, and even "hooligan" behavior, contrasting sharply with today’s parental hyper-vigilance.

• Scott frames the shift as possibly leading to "overparenting,” which may be coddling and under-preparing children for adversity:

  "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." (Scott, 25:39)

6. The Pendulum of Toughness vs. Comfort

Timestamps: 30:10 – 37:21

• A recurring motif is the pendulum swing from the harshness/anxiety of previous generations toward overcompensation and fragility.

• All three share how difficult it is to enforce natural consequences and accept their own "pushover" tendencies as parents.

• Deidre details her discomfort with conflict and discipline:

  "The bottom line is it makes me so uncomfortable. I hate conflict, I hate yelling...But I do think that they need that sometimes. Like a wake up call." (Deidre, 35:11)

7. Sports, Mentorship & Building Grit

Timestamps: 37:21 – 41:24

• Scott credits sports as a formative force in his own life—confidence, camaraderie, mentorship—that he wants to pass on.

• Deidre and Anthony agree sports are critical in their parenting toolkit for balancing screen use and teaching resilience.

  "If they want to go to five basketball games and play in three football games, I'm going because that means we're outside, we're moving, and we're not on a screen." (Deidre, 38:14)

• Anthony warns against overscheduling but affirms:

  "I would just say that sports has been massive. I would tell people, get your kids in sports." (Anthony, 39:14)

8. Privilege, Grit, and Passing on Wealth

Timestamps: 41:24 – 58:41

• Scott addresses the "paradox of success":

  "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." (Scott, 41:31)

• All grapple with how to instill grit and passion, worrying that their children won't experience the same urgent need to succeed.

• Anthony praises Scott for modeling vulnerability and authenticity:

  "You expose your vulnerability. And this is a gift you're giving your children..." (Anthony, 43:04)

• They discuss the dilemma of "helping" adult children with money, recognizing the slow creep from well-intended support to dependency.

• Scott and Anthony differ on wealth display—Deidre underscores their intent to "blend in" and model moderation; Scott is forthright about his consumption:

  "We do not do that...I am not living in my old neighborhood. We live a crazy lifestyle...I'm really good at spending money." (Scott, 55:51)

9. Defining the Core Parenting Message

Timestamps: 59:07 – End

• Scott closes with a reflection on cycles of behavior, intent on "being really good to their mother" as a leading example to raise good men:

  "If you want your sons to have healthy relationships ... [the] upward spiral is to develop a practice of just being really kind and generous. And... I do try and practice it. Just be really good to their mom." (Scott, 59:17)

Notable Quotes & Memorable Moments

• On Social Change:

  "I think that's basically because of where I was starting from ... My household was very old school." (Deidre, 04:17)

• On Digital Parenting Failure:

  "My kid is addicted or have at various times been addicted to devices." (Scott, 13:56)

• On Overparenting and Weakness:

  "I'm so guilty of this, I just don't really know what happened ... we are crippling them. But I can't stop." (Deidre, 26:51)

• On Wealth & Grit:

  "If I had what my kids have, the only thing I know I would have is a Range Rover and a cocaine habit." (Scott, 41:32)

• On Vulnerability:

  "You expose your vulnerability... And this is a gift you're giving your children." (Anthony, 43:04)

• On the Practicality of Giving:

  "I have a file, when I'm dead file, you open it up, everything is there." (Anthony, 49:47)

• On Family Example:

  "If you want to raise good men... just be really good to their mom." (Scott, 59:17)

Important Segments (with Timestamps)

• Traditional roles and gender expectations: 03:48 – 06:05
• Raising boys, discomfort, and masculine/feminine balance: 06:51 – 10:01
• School and (lack of) male role models: 10:01 – 12:04
• Challenges with kids and screens: 12:04 – 16:43
• Intergenerational comparison in parenting: 19:12 – 28:37
• Overparenting admissions and (comedic) discipline stories: 30:10 – 37:21
• The role of sports: 37:21 – 41:24
• Privilege, grit, and modeling values: 41:24 – 58:41
• Parting wisdom on modeling relationships and raising men: 59:07 – End

Tone & Style

Frank, direct, and at times comedic, the episode is rich with personal anecdote, self-deprecation, and introspection. There's vulnerability, accountability, and a willingness to admit parenting failures—often with humor or irreverence (e.g., "kick the Bisquick"). The speakers balance nostalgia for a freer, rougher upbringing with recognition of the need for adaptation in a changed world, all while grappling openly with the contradictions and challenges of modern parenting and privilege.

Summary prepared for listeners who want the key takeaways, insightful moments, and colorful discussion from this episode.