Podcast Summary: Holmberg's Morning Sickness – "Fully Supporting 40yo Aussie Woman Who Married 91yo Billionaire Who Died 2mos Later: Why Wouldn't You Shoot For That?"

Date: August 27, 2025
Hosts: John Holmberg, Brady Bogen, Brett Vesely, Female Co-host
Episode Theme:
A comedic, brutally honest roundtable exploring the viral news of 40-year-old Simone Rylander, who married a 91-year-old billionaire real estate tycoon in Australia (who died just 60 days later). The HMS crew debates love versus pragmatism, inheritance ethics, and why more people—especially women—don't go after old, wealthy partners.

Episode Overview

The hosts use Simone Rylander's story to launch a riotous takedown of romantic ideals, inheritance anxieties, and societal judgments about marrying for money (especially at the, um, far end of the age spectrum). They offer both tongue-in-cheek encouragement and sharp satire, discussing sexism, the economics of marriage, and double standards regarding gender, age, and gold-digging.

Key Discussion Points & Insights

1. Why Women Should Take Advantage like Simone Rylander Did

• John Holmberg launches the segment by mocking the ideal of marrying for “love” when there are better economic options:

  • "If I was a woman… I'd look over at Brady, realize I did this wrong." (02:21)
  • The hosts suggest that targeting rich, elderly men is a much better deal than slogging through ordinary relationships.

• Comparing Marrying Billionaires to Groupies:

  • Holmberg describes the parallel between groupies at rock concerts and groupies at high-end retirement homes:
    • "Go to old folks homes, the good ones… just hang around like groupies. [It’s] the same thing as that whoring way you did with celebrity. Now do it right." (03:49)

• Anna Nicole Smith as a ‘Role Model’:

  • Anna Nicole Smith is praised for her approach:
    • “Brilliant woman, and as dumb as she was, still knew… This is the route to go.” (04:36)

2. Swapping Gender Roles: What If Women Were The Billionaires?

• Holmberg flips the scenario:

  • Wonders why more men don’t “chase” elderly women with money.
    • "If there were as many women billionaires… we're going. We're gonna go to the old folks, give some old lady a bash for 60 days." (05:13)
    • "Brady's mom's out there, she's got money. What are we doing? Go up there and woo the old lady." (05:24)

• Elder Care Crossover:

  • Holmberg ties in elder loneliness and care, suggesting these relationships can be “beautiful”—if they’re genuine:
    • "If he's genuinely like there to be somebody's Companion for as long as they last, damn it all, that's beautiful." (08:27)

• Notable Analogy:

  • Caring for old pets = marrying old billionaires:
    • "If a dog was eight or nine… I consider it a beautiful thing when someone steps in and says, I'm gonna take this dog's last couple years… Why don’t we do that for our grandparents?" (08:56)

3. Inheritance: Why Kids (and Society) Get Mad

• Griping about “greedy” heirs:
  • Holmberg criticizes children upset about their parents’ estates going to new, younger spouses:
    • "If you're sitting there worried about your parents inheritance more than their happiness, who's the bad guy? Which? Who's the real bad person? The whore or you?" (15:41)
    • He flatly says he'd rather see his dad happy, even in “some weird puddle of his own poo,” than hoarding money for the next generation (14:09–15:17).

4. Comedy Tangents: Sex, Sacrifice, and Opportunities Lost

• Megan’s missed billionaire:

  • John shares a story of his wife being invited by an 85-year-old billionaire, Maurizio, to visit his Houston ranch:
    • "She even said, ‘My house here,’ and I'm like… do it, man… I'll help you out." (18:52)
    • “Dude died maybe a year later. I've done some dumb stuff… A year. That's all it would have taken. A year of sacrifice in your life to make me happier. Selfish.” (19:20–19:35)

• Mock-Reality TV Pitches:

  • The group muses about a show called “60 Day Whore,” comparing it to "The Bachelor" but more honest:
    • "You can be 60 days. I've seen you as a whore. You've done that before… That's different than the Bachelor?" (25:47–25:57)
    • "If you did that in real life where you told them, 'I'm dating 22 ladies… but whoever I choose is getting $2 million,' suddenly the love thing disappears." (27:06)

5. Gender, Economics, and Brutal Honesty

• Holmberg’s theory on men's ambition:

  • “The only reason we go to work every day is to make sure that the person that's across from us stays. Otherwise you just not go… You get success so you can get a higher level of ass, period. That's it. That's the truth.” (10:17–10:40)

• Questioning the Fairness of Judging Gold Diggers:

  • Holmberg pokes at sexism in shaming “gold diggers”—and why, by his logic, they should be celebrated for their shrewdness.

6. Final Thoughts and Riffs

• "If a billionaire old lady wanted me, I wouldn't even ask where I'd gone. I'd call you when she's dead." (23:27)
• “I like when old people die with nothing because that means they spent it all. That's a good thing. Go out doing that. That'll be my goal.” (31:55)
• "Her name’s Dixie. She’s a whore. Ken, I found a whore. She’s willing to grind up against it. That’s great. Good for you, John." (32:49)

Notable Quotes & Memorable Moments

• On love vs. money:

  • “No, you get a dime a dozen of these things over here. This guy is the dollar store of dick. Get over to that Mummy mountain ladies and quit wasting your time on people like us.” – John Holmberg (03:06)

• On male billionaires choosing partners:

  • “Do you think Chad Kroger’s swinging a lot of ass with that face? No, he looks like some of the stuff I’ve seen at those primate exhibits.” – John Holmberg (11:45)

• On Anna Nicole Smith’s approach:

  • “Brilliant woman… still knew… This is the route to go.” – John Holmberg (04:38)

• On romantic TV reality shows:

  • “How’s that different than ‘The Bachelor’? How’s that different than 30 chicks lining up for one dude in the promise of fame and money? They see that as romance.” – John Holmberg (25:57)

• On why women don’t date old billionaires more:

  • “And you dummies are looking at Brady going, ‘I’m doing this for love’. Stupid. Stupid. This is beautiful.” – John Holmberg (24:56)

• On children and inheritances:

  • “If you’re sitting there worried about your parents inheritance more than their happiness, who’s the bad guy? The whore or you?” – John Holmberg (15:41)

Important Segment Timestamps

• 02:07 – Holmberg introduces the Simone Rylander story and lays out his thesis.
• 03:49 – Comparison to groupies, and field report on rock star vs. billionaire targets.
• 04:36–05:15 – Anna Nicole Smith and the “correct route” for women seeking fortune.
• 08:56 – “Old dog” analogy for elder companionship and end-of-life happiness.
• 11:45 – Chad Kroger roast and comedian’s perspective on looks vs. money.
• 14:09–15:17 – The ethics of inheritance and priorities for aging parents.
• 18:52–19:35 – Holmberg’s Maurizio story and comedically failed “sacrifice.”
• 23:27 – “Hospice as porn”: acceleration jokes and calling after “the old lady dies.”
• 25:47–26:58 – “60 Day Whore” and brutal reality comparisons to The Bachelor.
• 27:06 – Love versus money once again, the real-world Bachelor scenario.
• 31:55–32:49 – Holmberg on old people spending all their money and the right of the elderly to enjoy it.

Tone & Style Overview

High-energy, irreverent, blunt, and often explicit, the episode is defined by group teasing, aggressive logic, comic hypotheticals, and a willingness to roast societal norms. The crew oscillate between sharp wisdom, outrageous jokes, and personal anecdotes, making serious points amid humor.

For Listeners Who Missed The Episode

This episode’s core message is: “Why chase ‘love’ when you could be financially set marrying someone at the end of their life—and society’s judgment is hypocritical, if not flat-out sexist?” The crew dives into every angle—from gender and money to familial resentment and the farce of romantic reality TV—arguing, ultimately, that the path taken by Simone Rylander is not only valid, but perhaps the smartest game in town. All delivered in unfiltered, comic fashion.

Note: Ads and sponsor segments excluded, per request.