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PayPal Holdings | February 2026
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The PayPal Mafia, founders such as Peter Thiel and Elon Musk who once dominated Silicon Valley, built a legacy of disruption. But that pioneering spirit has long since faded.
Today, PayPal is no longer a nimble innovator. Instead, it has become an institutional giant fighting a two-front war to remain relevant. On the consumer side, the once-dominant PayPal button is losing its frictionless advantage to Apple Pay and Google Pay, which are embedded directly into smartphone hardware. Meanwhile, its merchant-focused Braintree division is locked in a war of attrition with Adyen and Stripe as payments become increasingly commoditized.
Despite losing roughly 80% of its market value since 2021, PayPal remains a formidable cash-generating machine. In this deep-dive podcast and 40+ page report, we examine the industry, assess PayPal’s competitive advantages, and confront the central question: Is PayPal a genuine turnaround story, or a falling knife still in free fall?
Disclaimer:
Nothing in this podcast can be considered financial advice. This is for educational purposes only. We may hold positions in the businesses discussed. Do your own research.
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