The Toast | “Category is Business”

Date: February 17, 2026
Hosts: Jackie & Claudia Oshry

Episode Overview

This episode is a vibrant blend of personal anecdotes, pop culture deep-dives, reality TV recaps, business banter, and advice. Jackie and Claudia, in their signature fast-talking, irreverent style, catch up on their President’s Day weekend, celebrity encounters, and reality TV obsessions before launching into a new possible business venture and introducing a lighthearted new recurring segment, “Businessman of the Week.” The hosts also dig into trending stories, including Nicole Kidman's suitor, Olympic Village antics, and the Frida Baby controversy, before wrapping up with their “Dear Toasters” advice segment tackling listener questions both trivial and outrageous.

Main Themes & Purpose

• Business—Entrepreneurial Energy: The episode explores the hosts’ newfound business inspiration, channeling the “category is business” theme both playfully and seriously.
• Pop Culture Hot Takes: From celeb sightings to reality TV, Jackie and Claudia offer snappy recaps and definitive opinions.
• Women in Community: With honest, millennial wit, the hosts detail their hobbies, family, and audience connection.
• Advice & Support: The "Dear Toasters" segment provides listeners with empathetic, often funny guidance on awkward life dilemmas.

Key Discussion Points & Insights

President’s Day Weekend & Celebrity Sighting

• Claudia’s Celebrity Beach Encounter:

  • Claudia recounts spotting Scott Borchetta (Big Machine executive known for the Taylor Swift masters dispute) at the beach in a “Big Machine” shirt, causing a wave of excitement and Swiftie banter.
  • [01:04] “You don’t expect to wake up and see Scott Borchetta, like, scorned music executive out in the streets at the beach.” —Claudia

• What Would You Do?

  • Claudia jokes about the internet asking if she sang Taylor Swift lyrics to him (“Did you go up to him and sing Father Figure?” [02:05]), but insists she acted like a normal person and took covert pics.

• Career & Politics of Association:

  • Discussion on whether it’s taboo or career-limiting to sign with Borchetta due to his past with Swift.
  • [03:17] “Being associated with Scott Borchetta, like, sorry, people need jobs, they need labels.” —Claudia
  • Both hosts muse that Swift, given her advocacy, should start her own label (“She’s always fighting for artists rights. So it’s like, start a good artist rights.” [03:48])

Reality TV Recaps: Obsession & Analysis

Shahs of Sunset Recap

• Deep Dive into ‘Shahs of Sunset’

  • Jackie is binge-watching the show, praising the casting and the cultural nuances.
  • [06:02] “The OG is like people who have been reality stars for many years. Like, Reza is a perfect reality [star].” —Jackie
  • She critiques certain cast behaviors (especially MJ’s dramatics), but lauds new additions and the authentic Persian representation.

• Real-Time Drama Connection:

  • Discussion on Mercedes and Tommy’s relationship breakdown paralleling their real-life divorce coverage.

Southern Charm’s Downward Spiral

• Jackie Tries to Catch Up; Shows Disappoint:

  • Jackie critiques the current season for overuse of FaceTime scenes, pet storylines, and recycled drama.
  • [08:56] “I don’t like boys yelling, so I’m not loving the central drama.” —Jackie

• Craig Hate Discourse:

  • Claudia, friends with Craig offline, voices frustration with how the show’s audience treats him:
  • [09:59] “There isn’t a more genuine, charitable individual than Craig. I can’t turn on the TV and see my friend being hated on.” —Claudia
  • Both lament the lack of engaging storylines—gossip about labiaplasty among cast members—calling out the absurdity and misplaced focus.

• Craig Conover Name Confusion:

  • Jackie shares a comical story of booking a guest—Dr. Craig Conover—on her husband’s podcast, only to find it’s not the reality TV star.

Hobbies, Brains, & Girl Talk

• Mahjong Obsession:
  • The hosts celebrate their increasing skill and mental engagement from playing Mahjong, even dreaming of a celebrity Mahjong tournament.
  • [15:04] “I’ve been playing for 10 years and I always play very sporadically… when you’re in a good groove, you get so good.” —Claudia
  • The segment is full of camaraderie, jokes about being “mahj hot,” and playful shade toward slow players.

Business Brainstorm & “Businessman of the Week”

• A (Secret) New Venture:

  • Jackie and Claudia tease a soon-to-be brick-and-mortar business idea, involving hospitality, food and beverage, and South Florida real estate.
  • [17:07] “We came up with a business idea over the weekend… industry shifting…” —Claudia
  • They debate which “Shark Tank” shark, if any, would be the ideal partner, but declare their business is beyond the Tank’s scope.

• Businessman of the Week – NEW SEGMENT!

  • Inspired by Nicole Kidman’s new billionaire suitor, the hosts launch a “Businessman of the Week” segment to spotlight intriguing business leaders.

  • Paul Salem:

    • Chairman of MGM Resorts, rumored to be pursuing Nicole Kidman romantically.
    • [29:30] “He will obviously be our inaugural businessman of the week…” —Claudia
    • Hosts lampoon the unusual PR cycle around the “courtship” and the randomness of such stories.

  • Ross Stevens:

    • CEO of Stone Ridge Asset Management, pledging $100M to support U.S. Olympians financially.
    • [30:25] “If you go to the Olympics and represent our country, this guy’s giving you 200 grand.” —Claudia

• Reflection:

  • The hosts muse on men in business, media rumors, and the fun to be had reading business news.

Trending Stories & Hot Takes

• Frida Baby Controversy:

  • The parenting brand’s humor-driven (and possibly over-the-line) marketing draws criticism.
  • [33:52] “You don’t get it. We’re funnier than you. And this is mature humor. Get over it.” —Jackie (satirizing Frida’s attitude)
  • Claudia points out that while some jokes missed the mark (e.g., “baby threesome”), the brand’s refusal to fully apologize is unusual but “authentic.”
  • Jackie emphasizes that parental product companies must be held to a higher standard but agrees not to “punish herself” with a boycott.

• Olympic Village Runs Out of Condoms:

  • Classic Olympic coverage—athletes deplete the supply in 3 days.
  • [48:07] “The village does foster like a sense of community. I believe there are probably gatherings.” —Claudia
  • Hosts riff about the realities of young, fit athletes cohabiting, and speculate on who brings their own condoms (“If you brought your own condom to the Olympics, like, you’re not winning gold.” [49:21])

• Brooks Nader’s Private Jet Mishap & B-Day Bash:

  • Model Brooks Nader gets food poisoning on a private jet on her way to her birthday. The hosts gossip about “bad sushi” being an excuse for something else (possibly a GLP-1 mishap) and gush over her fun, glamorous life.

Media & Music Industry Intrigue

• Joshua Bassett’s Memoir & Olivia/Sabrina Saga:

  • Discussion of Joshua Bassett’s new book and the infamous pop triangle (“he stopped dating Olivia Rodrigo and started dating Sabrina Carpenter and then created, like, two of the biggest pop stars on the planet.” [45:02])
  • Claudia details her conspiracy theory that Taylor Swift helped launch Sabrina’s career in response to a falling out with Olivia Rodrigo.

• Masked Singer Obsession:

  • The hosts are obsessed with figuring out the identity of “Pug Caso” on The Masked Singer, analyzing fan theories and clues, demonstrating their devotion to trash TV.

Dear Toasters: News, Drama, and Salacious Dilemmas

(Timestamps: from [58:02])

1. The Ex-Fiancé’s Sister’s Dollar

• Listener receives a random $1 Venmo from ex’s sister, with a cryptic message about her baby’s due date.
• “Is this weird?”
• Both agree: “Don’t engage, don’t look back. She sounds crazy.” [59:55]

2. The Tampon Slap

• Listener drunkenly slaps her boyfriend with her tampon during attempted period sex.
• “Do we bring it up or forget it ever happened?”
• “If he doesn’t bring it up, you move forward. He was down for drunk period sex—he can survive a tampon slap.” [62:08]

3. The Disappearing “Work Trip” Boyfriend

• Listener sees her casual boyfriend partying on a Miami bachelorette, wearing a “Bride’s Bestie” sash, while he claims he’s on a work trip.
• “Is he gay? Is this a red flag?”
• Jackie: “He’s the big gay.” [66:07]
• They agree the lying is worse than the bachelorette party, but acknowledge the classic “bride’s bestie” is almost always a gay man, and recommend asking him directly.

Meta-Advice

• Claudia clarifies they prefer not to answer detailed or explicit sex advice, given the sisterly format of their show:
  • “There’s so many benefits to doing a show with your sister… one of them is like, we really can’t talk about sex.” [63:49]

Notable Quotes & Memorable Moments

• [01:04] “You don’t expect to wake up and see Scott Borchetta… at the beach.” —Claudia
• [03:48] “She’s always like, fighting for artists rights. So it’s like, start a good artist rights [label].” —Claudia (on Taylor Swift)
• [06:02] “The OG is like people who have been reality stars for many years. Like, Reza is a perfect reality.” —Jackie
• [08:56] “I don’t like boys yelling, so I’m not loving the central drama.” —Jackie
• [15:04] “When you’re in a good groove [with Mahjong], you get so good.” —Claudia
• [17:07] “We came up with a business idea... industry shifting...” —Claudia
• [29:30] “He will obviously be our inaugural businessman of the week…” —Claudia
• [33:52] “You don’t get it. We’re funnier than you. And this is mature humor. Get over it.” —Jackie (mocking Frida Baby)
• [45:02] “He stopped dating Olivia Rodrigo and started dating Sabrina Carpenter and then created, like, two of the biggest pop stars on the planet.” —Claudia
• [49:21] “If you brought your own condom to the Olympics, like, you’re not winning gold.” —Claudia
• [66:08] “He’s the big gay.” —Jackie (on the lying “Bride’s Bestie” boyfriend)

Important Timestamps

• 00:48: Scott Borchetta sighting & Taylor Swift label talk
• 05:00: Shahs of Sunset analysis
• 08:56: Reality TV recaps: Southern Charm gripes
• 15:00: Mahjong and brainpower
• 17:07: Business idea teased
• 26:34: Nicole Kidman/Paul Salem romance headline
• 29:30: Launch of “Businessman of the Week” segment
• 33:43: Frida Baby controversy response
• 48:01: Olympic Village condom story
• 55:03: Brooks Nader’s B-Day; “bad sushi” speculation
• 58:02: Dear Toasters advice: ex’s sister, tampon mishap, suspicious boyfriend

Tone & Style

• Fast-paced, high-energy, riff-heavy.
• Irreverent honesty: Plenty of off-the-cuff jokes, inside sister references, and deliberate hyperbole.
• Empathy and camaraderie: Even while ribbing their listeners or each other, the hosts foster belonging and communal laughter.
• Pop-culture obsessed but with a sharp, wry edge.

Conclusion

This episode is a lively sampler platter of everything The Toast’s listeners adore: reality TV breakdowns, personal confessions, new business schemes, and no-holds-barred advice. Whether plotting their next venture or dissecting a scandal, Jackie and Claudia keep things moving and hilarious, all while staying deeply, deliciously themselves. This “category is business”—but The Toast always delivers much, much more.