Podcast Summary: "We're Here to Help" – Episode 210: A Ship-Load of Options (with Cat Reitman)

Podcast: We're Here to Help
Hosts: Jake Johnson & Gareth Reynolds
Guest: Cat Reitman
Date: September 24, 2025

Main Theme

This episode dives into workplace gender dynamics, generational shifts in authority and respect, and playful problem-solving with listener callers. With special guest Cat Reitman, the show balances heartfelt stories about industry mentors, subtly navigating sexism, and engaging audience calls, all delivered with the hosts’ trademark blend of irreverence and empathy.

Key Discussion Points & Insights

1. Remembering Ivan Reitman & Generational Leadership (00:24–14:13)

• Jake, Gareth, and Cat reminisce about Ivan Reitman, Cat’s late father, his leadership as a comedy director, and how he influenced their creative upbringings.
• Generational contrast: The trio discusses how authority and praise were differently navigated by older generations (“They don't say the compliment to you. They give you the note and the criticism.” – Cat, 08:36).
• Imposter Syndrome & Changing Workplaces: Cat and Jake reflect on being raised in an era of tough love, yet now leading in a world where kindness and affirmation are both expected and sometimes confusing ("We're not working in the business I entered. I'm working in this new business and everybody's so much, like, nicer." – Jake, 09:25).

2. Caller #1: Emily, the Charter Boat Captain – Dealing with Sexist Interference (17:25–44:49)

Situation (17:25–24:22)

• Emily (Long Island, NY): A 36-year-old small charter boat captain who dresses femininely and constantly faces unsolicited help and condescension from (usually male) peers and bystanders, questioning her expertise.
• Dual career: Also a middle school librarian.

Problem Statement (24:04–24:51)

• Emily wants a retort or strategy for handling unsolicited, condescending "assistance" from men at the dock—seeking a response that asserts her authority without “emasculating” or creating unnecessary conflict.

Advice & Ideas (24:51–43:40)

• Jake: Suggests humorous, visual responses, like a laminated sign: “No need to be impressed – I’m an amazing captain.” (25:47)
• Gareth: Proposes pretending to panic for comedic effect or handing out "Boat Captain Helper" pins, gently turning the encounter on its head (27:10 & 41:48).
  • Quote: “All we're looking to do is speed up Emily's moment, humiliate the guy a little bit... have one of the friends go, look at you. You had a big boy captain button." – Jake, 34:17
• Cat: Points out the emotional labor of “teaching lessons” and ultimately encourages Emily to internally "make a 'I don’t care' choice." “The best advice you’re going to get is that you’re going to have to make an internal switch where you don’t give a f---.” (28:31)
• Resolving Gendered Perceptions: Cat notes the unfair burden on women to dress or act a certain way to be taken seriously, but affirms Emily’s right to stay authentic (28:31).
• Final Solution: Emily settles on handing out “Boat Captain Helper” pins—a playful, non-aggressive way to acknowledge and disarm the behavior (42:19).

Notable Quotes

• “If I'm saying, hey, do you need help...and the lady just walks by and hands me a pin that says 'Boat Captain Helper,' I'll be embarrassed, but I won't feel like she's saying, 'let me teach you a lesson, men.'” – Jake (42:20)
• “All of our advice is going to be exhausting...you're going to have to make a decision not to care.” – Cat (28:31)
• “You don't learn unless you push through the mistakes.” – Cat, on authentic self-leadership (13:27)

Timestamps for Major Segments:

• [17:25] – Emily’s introduction
• [18:08] – Emily describes her charter business and dilemma
• [24:51] – Deliberating specific responses
• [41:48] – Gareth’s “Boat Captain Helper” pin idea
• [42:19] – Emily picks her favorite solution

3. Caller #2: Amy – The Tasteful Nude Painting of Jake & Gareth's Mom (46:18–54:18)

Context (46:18–47:50)

• Amy, a painter from Edinburgh, followed up on a (joking) request from Jake during an ad read for a “tasteful nude” artwork depicting Jake and Gareth’s mother, Pam.

Revealing the Artwork (50:07–53:43)

• Panel reactions veer between mortified (Gareth: “This is the worst thing I’ve ever seen.” – 51:07) and impressed (Cat calls out the “normal woman’s breasts” and realistic details – 51:01).
• Jokes abound about the painting’s symbolism and intentions, with Cat playing along with psychoanalysis (“She’s hungry for male connection” – 53:12).

Notable Quotes

• “The breasts feel like they’re so hot. They feel like a woman who's seen life.” – Jake (51:01)
• “As the artist… what’s Jake thinking about there?” – Jake (53:24)
• “What you did was a war crime.” – Gareth (54:18)

Timestamps:

• [46:18] – Amy's call opens
• [50:07] – Reveal of the painting
• [51:01] – Cat's artwork analysis
• [54:18] – Close of segment

4. Caller #3: Taylor & Brian – The Pickle and Chip Classic Showdown (54:49–76:23)

Backstory (54:49–56:16)

• Taylor, a pickleball coach in Sedona, AZ, set to play his cocky brother-in-law, Brian, after family banter and a previous podcast call.
• The high-stakes bet: loser must serve dinner in an elephant trunk Speedo, in front of family and friends.

Building Hype (56:41–70:11)

• Family involvement: custom t-shirts, crowd, and even the podcast’s infamous traveling vest (“like Sisterhood of the Traveling Pants”—60:39).
• Both men talk big game. Brian relies on “athlete instincts,” Taylor on formal coaching and training. Banter is playful and competitive throughout.
• Cat, Jake, and Gareth pick sides (Team Taylor for Cat & Gareth, Jake takes odds on Brian).
• Rules: Best 2-of-3 games to 11, win by 2, standard pickleball rules.
• Personal stakes, nerves, and crowd effect discussed.

Notable Quotes

• “I have aunts that are coming to the match already made...they've got t-shirts with, I hope me. I think they're rooting for me.” – Taylor (57:24)
• “Taylor’s the guy I want to take home to the family...But then there's Brian. He's a bad boy.” – Gareth (66:03)
• "Brian's not going to be nice about it...if he makes a couple of comments and the crowd starts laughing, the world could get really dizzy." – Jake (75:12)
• "Taylor, you are given. Golden boy, my man. You're the people's champ and you still have my vote." – Cat (74:16)
• "One of them’s going to have their butt cheeks out and everyone’s going to be dying, laughing.” – Jake (72:31)

Timestamps:

• [54:49] – Taylor’s follow-up call
• [56:16] – Explanation of the Pickle and Chip Classic wager
• [61:39] – Brian joins, pre-match banter
• [74:11] – Closing remarks and final predictions

Notable Quotes & Memorable Moments

• "We're not working in the business I entered. I'm working in this new business and everybody's so much, like, nicer." – Jake (09:25)
• “You don't learn unless you push through the mistakes.” – Cat (13:27)
• “If I’m walking my dog...and they say, ‘You sure you know how to take care of that dog?’...I’m handing them the plastic bag, right?” – Jake (30:17)
• “What you did was a war crime.” – Gareth, about Amy’s painting (54:18)
• “Taylor’s the guy I want to take home to the family, but then there’s Brian...he’s a bad boy.” – Gareth (66:06)
• "One of them's going to be wearing that thing and literally walk around with their butt cheeks out. Everybody else is going to be half cocked, dying, laughing." – Jake (72:31)

Conclusion

Episode 210 seamlessly juggles thoughtful explorations of generational respect, comic approaches to everyday sexism, and high-energy listener stories. Cat Reitman's insights on authority, imposter syndrome, and being a female leader ground the episode, while the playful advice for Emily and the humorous escalation of the Pickle and Chip Classic provides laughs and a sense of community. The show shines when sensitive subjects are met with both practical and delightfully silly solutions.

Quick Reference: Timestamps

• [00:24–14:13] – Generational lessons, Ivan Reitman memories, leadership
• [17:25–44:49] – Emily’s boat captain call and resolution
• [46:18–54:18] – Amy’s “tasteful nude” artwork call
• [54:49–76:23] – Taylor & Brian, The Pickle and Chip Classic
• [Major topic shifts indicated above]

For new listeners: Expect a mix of warmth, unfiltered humor, and actionable advice—all delivered “on your side,” but rarely in a straight line.