The Best One Yet
The Best One Yet

⛷️ “Wipeout” — Vail’s ski recession. Anthropic’s IPO leak. Man City’s soccer sham. +Probiotic Undies

September 30, 2026

AI Summary

5 min read

The AI Domino, Ski Resort Wipeouts, and Soccer's Fake Money Machine

Anthropic lost $42 billion last year on just $4.6 billion in revenue, yet the AI company is targeting a $2 trillion IPO — which would make it the biggest public offering in history, bigger than SpaceX. But here's the thing: one third of their IPO paperwork isn't about their business. It's about the end of the world.

Anthropic's Leaked IPO: Dreams vs. Doom

Anthropic's IPO paperwork leaked to Reuters late Monday night — possibly intentional, possibly a rogue employee, possibly "rogue AI," as the hosts joked. The numbers are staggering. Anthropic wants a $2 trillion valuation, double what it was worth just four months ago. But the leaked S-1 filing reveals $42 billion in losses last year, though most of that is accounting charges. The operating loss was a still-massive $8 billion — twice as big as SpaceX's losses.

Revenue grew 12X in 2025, faster than any company of comparable size. But for every dollar of Claude subscription revenue, Anthropic spends $1.60 on compute and $2.75 in total costs. They're selling something for one third of what it costs to produce.

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What you'll learn

  • 1 Main Outline
  • 2 (00:01) **Show Open & Trend Alert: "Care Wear"** - Nick and Jack introduce the show and launch into a trend alert about skincare-infused underwear.
  • 3 (04:45) **Story 1: Anthropic's IPO Paperwork Leaked** - The AI company's S-1 was leaked to Reuters, revealing massive losses and a $2 trillion valuation target.
  • 4 (06:54) **Anthropic's Dream vs. Doom Contradiction** - The IPO paperwork reveals a company torn between ambition and existential warnings.
  • 5 (08:46) **The AI Domino Effect Risk** - A botched Anthropic IPO could trigger cascading losses across the entire AI industry.
  • 6 (10:11) **Story 2: Vail Resorts' Ski Recession** - Bad snow and falling Epic Pass sales have hit Vail hard, with profits nearly halved.
  • 7 (13:13) **Vail's Disney-Inspired Turnaround Plan** - Activist investor Bob Chapek (former Disney CEO) joins the board to help attract back tourist skiers.

+ Full timestamped outline available in the app

Show Notes

Vail Resorts reported a 12% drop in season pass sales… so they’re using a trick from baseball.

Anthropic’s IPO paperwork leaked… it sells something worth $3 for just $1.

Man City soccer is guilty of 115 fake deals worth £900M… They’re Performance Enhancing Deals.

Plus, why apply skin cream when you can wear skin cream underwear?

$UL $MTN $ANTH

Grab your Tickets to the IPO Tour: Our In-Person Offering

Boston 10/14: https://tickets.citywinery.com/event/tboy-the-ipo-tour-in-person-offering-8cdhup

Seattle 11/4 (21+): https://www.axs.com/events/1446394/the-best-one-yet-tickets


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