Ride with Benito Skinner and Mary Beth Barone

Episode: The Last Word + Making the Decision To Not Start a Business
Date: January 28, 2026
Podcast Network: Dear Media

Overview

In this lively, candid episode, comedic besties Benito Skinner and Mary Beth Barone return with razor-sharp wit and self-aware banter, fielding fan questions and unpacking the personal and cultural decision to not start a business. With topics ranging from fashion obsessions to the complexities of being funny, mindset advice for Gen Z, and the power of having the last word, the pair deliver their signature blend of playful irreverence and genuine insight. The episode’s core revolves around resisting unnecessary entrepreneurship, contemporary pressures to “make something,” and standing firm in their creative lanes.

Key Discussion Points & Insights

1. Fan Q&A & Car Chat Vibes

00:51 – 13:10

• Benito and Mary Beth adopt a “car chat” theme, positioning themselves as chauffeurs to their listeners, fielding eclectic fan-submitted questions.
• Dream fashion purchases:
  • Mary Beth wants a G-Wagon, while Benito lists a Louis Vuitton Murakami bag, Jean Paul Gaultier’s Robin Williams shirt, and vintage Prada pieces.
  • “For me, yeah. Chanel flats, size 14.” – Benito (02:37)
  • “My dream fashion purchase for Christmas...the Louis Vuitton Murakami multicolored white speedy bag from The RealReal.” – Mary Beth (02:06)
• On being “born funny” or trauma-induced humor:
  • Benito discusses overcompensating for feeling “unlovable” at school, testing jokes on siblings, and birth order influences.
    • “I did feel the need to overcompensate for feeling maybe unloved and unlovable at school. I needed protection; needed to be quick on my feet.” – Benito (04:11)
  • Mary Beth relates judging siblings’ choices and the nature vs nurture debate.
• Miscellaneous questions:
  • “Best burner on a stove?” (Mary Beth: front left; Benito: back right in Puerto Rico for high-output cooking) (07:35)
  • Favorite studio, time of day, childhood collections (Harry Potter Legos, Beanie Babies, McDonald’s toys).

2. The 25-Year-Old Mindset in 2026

06:50 – 09:05

• Mary Beth recommends being “fearless” and “shameless,” referencing her own younger self’s unfiltered texting:
  • “How about we just are fearless this year?” – Mary Beth (07:16)
• Benito highlights the importance of hope, juxtaposing the “hope” Obama campaign poster with 2026’s more cynical outlook.
  • “The 25-year-old mindset...keep hope. Hope is dying, but...I want hope back.” – Benito (08:12)
• Both encourage voting, particularly mobilizing for the midterms:
  • “We need to elect a lot more Democrats so we can impeach Trump.” – Mary Beth (08:41)

3. Humor, Grief, and the Passage of Time

13:34 – 14:10

• Benito and Mary Beth unpack platitudes about youth and grief:
  • “Youth is not wasted on the young. Youth is perfect and time does not help with grief.” – Mary Beth (14:10)
  • “You start to forget and then you feel guilty and terrible about the forgetting.” – Benito (13:43)
• They reflect on how grief intensifies as memories fade and the myths society tells itself to soften hard truths.

4. "Making the Decision to Not Start a Business"

21:10 – 29:03

• Benito and Mary Beth humorously champion opting not to found startups or launch new products.
  • “There are so many pants on earth. I don’t need to contribute more pants.” – Benito (21:46)
  • “I think maybe there are too many businesses that exist...not local artisans, but tech bro-y startups.” – Benito (23:00)
• Critiques of tech/startup culture:
  • They question the need for yet another startup, especially those with little real utility or led by straight white men, poking fun at HR tech ad overload:
    • “They’re advertising HR platforms on the subway...that should be in a newsletter for virgins.” – Mary Beth (23:21)
• On product launches and collaborations:
  • Benito and Mary Beth draw a clear line between creative collaborations and unnecessary brand launches.
  • “Leave it to the professionals. It’s like makeup brands—I’m like, leave it to the makeup artists.” – Benito (25:05)
  • They cite Miley Cyrus as an example of someone who declined to start a brand due to lack of passion (25:29).

Notable Tangents:

• Support for underrepresented businesses:
  • “More women and more LGBTQ-owned properties.” – Mary Beth (28:56)
• Real needs vs. manufactured needs:
  • “If there’s someone really passionate about [trans-specific underwear]...let it rip. The need is there.” – Mary Beth (27:51-28:05)

5. "Having the Last Word"

34:17 – 38:48

• Mary Beth rides for “having the last word”—in group chats, on stage, and in life:
  • “If I bring it up on here...that’s me saying, ‘well, that’s the period at the end of that interaction.’” – Mary Beth (34:50)
• She traces this habit to sleepover traditions with her Aunt Vicky and connects it to stand-up comedy, where a comic’s set is the “last word.”
• Benito admires how she’s grown less apologetic and recognizes the power of claiming space, especially as a woman or queer person in professional environments:
  • “I’ve watched you, actually...you move in business lately and it’s like, ‘we’re gonna do it this way.’” – Benito (36:34)

6. Other Notable Quotes & Moments

• On refusing to start a brand without passion:
  “I just find it hard to believe that everyone who’s launched a makeup brand is super passionate about filling a space in the market.” – Mary Beth (25:30)

• On straight guys and property:
  “Straight guys just have stuff like that, where they’re like, ‘I have this apartment in Toronto I gotta rent out.’” – Benito (29:59)

• Comedy as catharsis and scriptwriting:
  “Overcompensating season two does have a lot of my last words on plenty of things...that’s the statement.” – Benito (40:07)

Memorable / Highlighted Segments & Timestamps

| Timestamp | Segment/Highlight | | -------------- | --------------------------------------------------------------------- | | 02:06–03:29 | Fashion grails and dream purchases | | 04:00–05:22 | The roots of being “funny,” birth order, and sibling dynamics | | 06:50–09:05 | Fearlessness, hope, and political engagement in your mid-20s | | 13:34–14:10 | Myths of youth & grief—“time does not help with grief” | | 21:10–27:10 | Riff on not starting a business, startup oversaturation | | 27:45–28:05 | Real vs. artificial need in business (apparel for trans people, etc.) | | 34:17–38:48 | The philosophy and ethnography of “having the last word” |

Closing Thoughts & Community Shout-Outs

44:40-end

• Heartfelt appreciation for the “Baronis” community and fan content creators (TikTok out-of-context moments, fan cams, etc.).
  • “Thank you so much to all the people helping enhance this community. We love you so goddamn much.” – Mary Beth (45:07)
• Teasers for upcoming content (Overcompensating Season 2, Mary Beth’s stand-up special).
• Pledge to authenticity, collaboration, and continuing the show’s “ride” for, as Benito says, “making the decision to not start a business…every single day.”

Episode Tone & Character

Playful, breezy, and irreverent, but with sharp moments of real self-reflection. Mary Beth and Benito lovingly roast each other and their culture, blending pop-culture savvy with existential millennial/Gen Z insight. Banter oscillates between ridiculous (stove burner preferences, “the wagon”-style butts) and raw candor (grief, ambition, boundaries).

Summary

This episode stands as a manifesto for embracing restraint in a world obsessed with launching the next big thing. Benito and Mary Beth dissect why not every funny, creative, or ambitious person needs a side hustle, startup, or branded product. Choosing not to start a business—which requires both humility and resolve—is celebrated as a valid (even radical) stance. Added layers include empowerment around claiming your voice, embracing the last word, and championing authentic creativity and representation over unnecessary market clutter. The result? A funny, thoughtful ride through friendship, culture, and personal agency.