Son of a Boy Dad #390 – "LeBoyDad"

Podcast: Son of a Boy Dad
Hosts: Barstool Sports (Harry – aka Lil Sasquatch, Frankie, and guests/collaborators)
Episode Title: LeBoyDad
Date: April 7, 2026
Summary by [ASSISTANT]

Episode Overview

In this laid-back and witty episode, the Son of a Boy Dad crew—primarily Harry (Lil Sasquatch), Frankie, and a rotating guest—riff on everything from personal life changes to LeBron James’s golf skills, birthdays, taxes, fishing plans, and even birds. The main theme is Lil Sasquatch feeling “rudderless” after dropping out of college, looking to the group for the kind of real-world education and life wisdom you only get outside a classroom. Across their tangential, joke-packed banter, they reveal both the absurdities and the camaraderie that define early adulthood and adapting to life outside conventional plans.

Key Discussion Points & Insights

1. Shoe Talk, Materialism, & Letting Things Go (01:19–07:56)

• The crew compares sneakers and shoe habits, with Harry showing off chunky Clarks knock-offs, and a nostalgic discussion about retiring and rediscovering old shoes.
• Frankie admits: “I've always just been like ... you wear them until they fall apart and then you get a new pair.” (03:54)
• Purging closets becomes a metaphor for life changes; the struggle to Marie Kondo, sentimental value of L.L.Bean flannels, and the pitfalls of selling used clothes online.

2. Jewish Manhattan “Wire” Explained (08:09–10:14)

• The group discovers the “eruv”, a fishing-wire boundary around Manhattan that allows observant Jews to carry or push strollers on the Sabbath.
• Harry explains: “If you stay within that wire, then ... you can do those things [like use strollers or canes].” (09:11)
• The others react with confusion and cracks about “safe zones” and school zone-style borders.

3. Birthdays, Life Transitions, & Money (12:13–14:22)

• Frankie just turned 25—mused as “the beginning of the end of the downfall.” (12:22)
• The trio jokes about getting cash from parents despite their Barstool/standup incomes and the costs/pressures of living and paying taxes in NYC.
• “Ever since we talked about that [reasons for staying], I was like, I gotta ... taxes are insane,” admits Frankie. (13:00)

4. LeBron James & YouTube Golf Crossovers (13:56–17:26)

• The team imagines golfing with LeBron James after he watched one of their viral golf tournament clips.
• They ponder: “What am I supposed to do, playing golf with LeBron James? I'm not going to be able to move.” (15:16)
• Sharing nightclub run-ins with NBA stars, especially LeBron post-game with the Cavs, and the lengths athletes go for privacy and team bonding.

5. Golf Anxiety, Star Power, & Internet Invitational (20:12–28:31)

• Riffing on the surreal idea of LeBron playing their golf tourney, they discuss nerves, competitive personalities, and the fear of embarrassing oneself in front of icons.
• “People don't want to look bad on camera ... guys who aren't that good at golf are like, I need another year,” says the guest. (27:31)
• The crew speculates on LeBron's golf skill (20-25 handicap) and whether his championship mindset could overcome on-course jitters.

6. Influencer Life, Financial Realities & Taxes (41:09–44:14)

• A humorous but real look at handling standup comedian/influencer taxes: “I gotta up that withholding, brother.” (41:38)
• Tax write-offs are debated—home office deductions, gym memberships, and the "annoyingly by-the-book" accountants vs. slippery ones.

7. Moving, Real Estate & Barstool Wealth Gaps (49:40–52:01)

• Frankie laments not having money to move to Miami for tax reasons, joking he’d be the "poorest person" in Miami for tax purposes.
• They compare lives of Barstool colleagues buying houses at a young age: “This is just someone I have nothing in common with. Buying a house at 24. Kidding me.” (51:44)
• Reflections on gigs at unusual venues and influencer-heavy crowds.

8. Upcoming “Fish Week” & Bird Watching (54:54–60:41)

• Plans for “Fish Week” in Florida: tarpon, grouper, snapper, and intense fishing camaraderie.
• “I hope we make Sydney proud,” says a host, referencing an earlier fishing trip with a guide named Sydney. (56:22)
• Bird talk pivots to ospreys, hawks, and the awe of nature’s flyers. “Ospreys are great birds. Their name is like a shitty restaurant or something ... but they should be respected!” (59:06)

9. The Absurd Finales & Gun Week Proposal (65:16–67:03)

• Idle musings: what if they bought guns in Florida and discarded them because they can’t fly home with them ("What is this question?"), spiraling into jokes about “Gun Week”—buying, selling, and flipping guns.
• “Gun week is really, really good.” (66:46)

10. From ICE Agents to The Bar Exam (67:13–70:26)

• After discussing the allure of becoming an ICE agent due to rumors of high pay, the group swaps wild secondhand tales of cop and ICE hiring challenges.
• “Apparently it's harder to become an ICE agent than it is to become a lawyer.” (70:25)
• They segue into jokes about failing the bar exam and the resilience of future Attorney Generals.

Notable Quotes & Memorable Moments

• On Tax Reality & Living in NYC:
  Frankie: “Everything's gone ... like I feel like I've been making more money and then I just ... it just stays the same or I lose Money.” (13:24)

• On LeBron’s Fame:
  Guest: “He's one of the least real, like, 10 humans on the earth.” (15:38)

• On Being Starstruck:
  Guest: “No matter what, the star power's there.” (15:43)

• On Embarrassment in Golf:
  Guest: “People don't want to look bad on camera ... they don’t want to present back greatness—ineptitude.” (27:31)

• Bird Thoughts:
  Harry: “Ospreys are great birds ... osprey should be a respected bird.” (59:06)

Timestamps for Key Segments

• 01:19–07:56 – Shoes, materialism, and purging closets
• 08:09–10:14 – Jewish eruv in Manhattan explained
• 12:13–14:22 – Birthday talk, cash gifts, NYC living
• 13:56–17:26 – LeBron James: golf, nightclub stories
• 20:12–28:31 – LeBron at the Internet Invitational, golfer nerves
• 41:09–44:14 – Tax strategies for comedians/influencers
• 49:40–52:01 – Moving for taxes, young Barstool millionaires
• 54:54–60:41 – “Fish Week” Florida trip, osprey and hawk appreciation
• 65:16–67:03 – Gun Week, the wayward gun disposal plan
• 67:13–70:26 – ICE agent rumors, bar exam jokes

Tone & Language

• Spontaneous, irreverent, and full of inside jokes; reality is filtered through sarcasm and rapid-fire tangents.
• Language is conversational, self-deprecating, and at times purposely absurd in keeping with Barstool’s comedic brand.
• Names and identity references (“LeBoyDad”, “Fish Week”, “Gun Week”) serve as running gags reinforcing the group’s in-jokes.

Conclusion

LeBoyDad is a quintessential slice of "Son of a Boy Dad": quick-witted, meandering, and loaded with the kind of everyday concerns and fantasies that define life as a Barstool twenty-something. The crew’s chemistry, their anxieties over money, tax, and fame, and their sardonic takes on everything from LeBron to birds and fishing plans make for an episode that’s both hilariously meandering and sneakily insightful. Whether you’re rudderless after college or just looking for a laugh, there’s something weirdly reassuring in their shared uncertainty and improvisational wisdom.

Upcoming:

• “Fish Week” in Florida – chasing tarpon, snapper, groupers
• Stand-up dates for Frankie and others
• Potential guest appearance from George Bush (joking reference)
• Watch out for “Gun Week” as a future bit!

For fans old and new, this episode is an ideal example of Son of a Boy Dad’s freewheeling humor and unfiltered look at young adulthood.