Kennedy Saves the World

Episode: Happy Hour: Will Cain, Private Jets, & Winning The Lotto
Date: September 5, 2025
Host: Kennedy
Guest: Will Cain

Episode Overview

In this lively "Happy Hour" episode, Kennedy welcomes Will Cain for a fun, candid conversation that meanders through cocktails, surfing, travel, the lottery, and the allure—and perils—of comfort and luxury. Framed through their mutual value of freedom and humor, the episode delves into how personal happiness, ambition, and the pursuit of “the good life” are shaped by choices, hardship, and self-awareness.

Key Discussion Points and Insights

1. Craft Cocktails and the “Wonderful Will” (00:10–01:27)

• The episode opens with Kennedy mixing a custom drink dubbed the “Wonderful Will”: a mix of Mr. Wonderful’s tequila, Grapefruit LaCroix, citrus juices, orange liqueur, and Splenda.

• Both hosts share playful banter about cocktail choices, sugar substitutes, and their preferred drink experiences.

  Notable quote:

  • “Splenda is the jam in cocktails. I like it because you can sweeten them up.” — Kennedy [01:06]

2. Surfing: A Source of Joy and Humility (01:32–05:36)

• Will shares his recent surfing experiences, including booking a day at a Waco, Texas wave pool through a charity auction for the Adaptive Training Foundation—which supports adaptive athletes and veterans.

• The hosts discuss what surfing means for their self-image, the learning curve, and the joy found in being unapologetically “not good.”

• They swap stories of surf spots (Hawaii, Costa Rica, Fiji, El Salvador, Mexico) and the different challenges and vibes, especially between natural and man-made waves.

  Memorable exchanges:

  • “From the moment you catch your first wave, you are a surfer.” — Kennedy [03:19]
  • “Surfing is the thing in my life that I say I am unashamedly not good. And yet I love it.” — Will Cain [03:35]
  • On surfing humility:
    “No one ever looks at me and goes, wow, how long have you been sponsored? They’re like, oh, is today your first day?” — Kennedy [03:50]

3. Surf Destinations and Local Color (05:36–07:39)

• Will describes surfing in El Salvador, noting the perceived sketchiness and water pollution relative to Mexico and Hawaii.

• He recounts paddling out amid lots of trash and the discomfort of warm, dirty water.

  Notable dialogue:

  • “It’s as though people dump their trash... you would paddle out and you’re like, I got to clear a few, you know, Coke bottles or Sprite bottles.” — Will Cain [07:11]
  • “That does feel like you’re wading into a pudd—not the good kind.” — Kennedy [07:25]

4. What Would You Do With $1.4 Billion? (07:39–11:16)

• The conversation pivots to the hypothetical of winning the Powerball and the etiquette around disclosure.

• Both muse on whether they’d continue working, with Will emphasizing the risks of retiring and losing purpose. They note the ease of "ghosting" people in the digital age should one come into fortune.

  Notable quotes:

  • “There’s never been a better time to ghost people... you can block their number, you can change your number, you can block their email, you can unfollow them on social media.” — Kennedy [08:45]
  • “Would I quit my job? I don’t know the answer to that. But I do think I would continue to work.” — Will Cain [10:40]

5. Private Jets & The Allure of Luxury (11:16–13:08)

• Will recalls recently hitching a ride on a friend’s private jet, noting such luxury is best enjoyed when not footing the bill.

• The hosts laugh about “friends with jets” and how a jet would make surf-travel dreams a reality, but both are aware of their own limits regarding materialism and extravagance.

  Noteworthy moment:

  • “I’m not a glutton. I do like things. Not material things. I do like experiences.” — Will Cain [11:55]

6. The Need for Hardship and Seasons (13:08–14:03)

• Will and Kennedy reflect on the importance of hardship, seasons, and contrast in life. Both admit that endless comfort can dull appreciation for good things.

• The value of pushing oneself, especially after observing family and friends who struggled with retirement.

  Memorable exchange:

  • “If every day’s a sunny day, they stop being sunny days.” — Will Cain [12:39]
  • “I wouldn’t want to retire and just become a glutton and live a life of luxury. Because I actually think that life of luxury would stop being luxurious.” — Will Cain [12:58]
  • “But I would love a life of comfort.” — Kennedy [13:08]

7. From Cowboy Boots to Cole Haans: Comfort vs. Tradition (14:03–14:17)

• Will admits giving in to modern comfort with footwear despite his loyalty to cowboy boots, highlighting how age shifts the pursuit of comfort.

8. Playful Political Riffs: Dictators, Transplants, and Vanity (14:17–16:41)

• The episode takes a comedic detour as Kennedy and Will satirize Putin and Xi Jinping's rumored organ transplants and quest for eternal youth, riffing on global aristocracy and universal vanity.

• They connect the dots between human sameness, regardless of culture, status, or geography.

  Standout banter:

  • “I think that’s what Xi Jinping and Putin were talking about when they're talking about transplants, because they're like, let's keep pushing the boundaries. Let's get a new liver. Oh, my God. Wouldn't we look amazing if we each had a new liver?” — Kennedy [14:14]
  • “Even inside of a maniacal dictator killing people in Ukraine. In the end, he really just wants to be young.” — Will Cain [15:39]
  • “I love that. Like, there’s really, like, people are jerks everywhere... But people also have kids and they’re exhausted and they want to work hard and push the boundaries. And I think these two just go to show that inside each and every one of us is a middle aged woman who just wants to be hot.” — Kennedy [15:19]

Notable Quotes & Timestamps

• [01:06] Kennedy: “Splenda is the jam in cocktails. I like it because you can sweeten them up.”
• [03:19] Kennedy: “From the moment you catch your first wave, you are a surfer.”
• [03:35] Will Cain: “Surfing is the thing in my life that I say I am unashamedly not good. And yet I love it.”
• [07:11] Will Cain: “It’s as though people dump their trash... you would paddle out and you’re like, I got to clear a few, you know, Coke bottles or Sprite bottles.”
• [08:45] Kennedy: “There’s never been a better time to ghost people...”
• [10:40] Will Cain: “Would I quit my job? I don’t know the answer to that. But I do think I would continue to work.”
• [12:39] Will Cain: “If every day’s a sunny day, they stop being sunny days.”
• [12:58] Will Cain: “I wouldn’t want to retire and just become a glutton and live a life of luxury. Because I actually think that life of luxury would stop being luxurious.”
• [13:08] Kennedy: “But I would love a life of comfort.”
• [14:17] Kennedy: “I think that’s what Xi Jinping and Putin were talking about when they’re talking about transplants…”
• [15:19] Kennedy: “...inside each and every one of us is a middle aged woman who just wants to be hot.”
• [15:39] Will Cain: “Even inside of a maniacal dictator killing people in Ukraine. In the end, he really just wants to be young.”

Tone and Atmosphere

This episode is light-hearted, self-aware, and humorously irreverent—balancing light barroom banter with genuine reflections on privilege, persistence, and the human condition. Both Kennedy and Will display wit, candor, and self-deprecation, making for a conversation that’s accessible and relatable despite the larger-than-life topics of jets, lotteries, and global affairs.

Timestamps for Key Segments

• 00:10–01:27: Cocktail crafting & “Wonderful Will” recipe
• 01:32–05:36: Surfing, humility, and adaptive athletes
• 05:36–07:39: Surf destinations & environmental observations
• 07:39–11:16: Lottery wins, work ethic, and ghosting etiquette
• 11:16–13:08: Private jets, luxury, and purposeful work
• 13:08–14:03: The necessity of seasons and hardship
• 14:03–14:17: Comfort versus tradition and age
• 14:17–16:41: Political satire, vanity, and the universality of human desire

Conclusion

This episode offers a spirited, insightful exploration of aspiration, comfort, and freedom, combining humor, personal storytelling, and cultural critique. Whether you’re interested in surf culture, winning the lottery, or simply looking for laughs about dictators with youth obsessions, Kennedy and Will Cain provide an entertaining escape infused with wit and honesty.