Stripe Could Buy PayPal for Less Than a Quarter of Its Own Valuation
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Show Notes
Stripe x PayPal, Workday's AI Pivot, and the J-Mail Story | Four Insights 003
Description:
Day 3 of the daily show. Workday funds the AI pivot but the market doesn't care. Stripe ($159B) circles PayPal ($43B) in what could be the biggest fintech M&A deal ever. And two engineers built what the DOJ said was impossible.
TIMESTAMPS: 0:00 — Intro: Day 3, the Legacy Infrastructure Thread 1:30 — Workday: AI Revenue Hits $400M, Market Still Punishing 5:30 — PayPal: $1.75T in Transactions, 82% Off Its Peak 9:00 — Stripe's Play: $159B Buying $43B 11:00 — Reducto & J-Mail: Parsing What the DOJ Couldn't 14:00 — Closing: What Would You Do With PayPal?
SOURCES & CREDITS:
Workday earnings: App Economy Insights / How They Make Money (Substack)
Bloomberg: Stripe Considers PayPal Acquisition (Feb 24, 2026)
Sheel Mohnot (@pitdesi) — Better Tomorrow Ventures
The Verge: AI PDF parsing / Reducto
Reducto (reducto.ai) — YC 2024
FIS earnings: ModernTax Daily Beat (Feb 24, 2026)
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