Trey Thoelcke
Wed, April 22, 2026 astatine 8:05 AM CDT 4 min read
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The acquisition of the PayPal Mafia is that serving arsenic a launchpad for superb radical does not warrant lasting outperformance.
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The expert who called NVIDIA successful 2010 conscionable named his apical 10 AI stocks. Get them present FREE.
PayPal Holdings (NASDAQ: PYPL) trades adjacent $51 a stock today, down astir 81% from 5 years ago. Meanwhile, alumni who near built Tesla, LinkedIn, YouTube, Palantir, and Affirm. That is the paradox astatine the halfway of 1 of fintech's astir striking stories.
The word "PayPal Mafia" was coined by Fortune successful 2007, which describes the web of founders and aboriginal employees who departed aft eBay's 2002 acquisition and reshaped Silicon Valley. The database includes Elon Musk (Tesla, SpaceX), Peter Thiel (Palantir, Founders Fund), Reid Hoffman (LinkedIn), Chad Hurley, Steve Chen, and Jawed Karim (YouTube), Jeremy Stoppelman (Yelp), David Sacks, Roelof Botha, Max Levchin (Affirm), and Keith Rabois. YouTube was sold to Google for $1.65 cardinal successful 2006. Microsoft acquired LinkedIn for $26.2 cardinal successful 2016. These alumni built companies that collectively generated trillions successful shareholder value. Yet, the institution that launched them has not kept pace.
PayPal's five-year instrumentality of −80.8% contrasts sharply with the S&P 500, which returned 69.2% implicit the aforesaid period. Anyone who bought adjacent the 2021 highest astir $310 endured 1 of the worst drawdowns successful large-cap fintech history. Long-term holders who bought a decennary agone are inactive up 26.2%, a reminder that duration matters successful assessing this company.
READ: The expert who called NVIDIA successful 2010 just named his apical 10 AI stocks
The banal gained 6.1% implicit the past week and 15.6% implicit the past month, but remains down 12.9% year-to-date.
Underlying financials archer a much analyzable communicative than the banal chart. Full-year 2025 gross reached $33.172 billion, with nett income of $5.233 billion, up 26.2% twelvemonth implicit year. Quarterly net maturation accelerated to 39.4% twelvemonth implicit year. The institution holds $10.4 cardinal successful currency and repurchased astir 86 cardinal shares for $6.0 cardinal implicit the trailing 12 months.
Q4 2025 exposed existent cracks. Interim CEO Jamie Miller acknowledged: "Our execution has not been wherever it needs to be, peculiarly successful branded checkout." Non-GAAP EPS of $1.23 missed the $1.29 estimate, and the banal fell 15% connected net day. The institution is present connected its 3rd CEO successful abbreviated succession, with Enrique Lores named incoming president and CEO.

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