Today, Sammi uncovers one of the most iconic origin stories in tech: how a scrappy, chaotic startup from the late ’90s — PayPal — became the launchpad for a generation of founders who went on to build Tesla, LinkedIn, Yelp, Affirm, Palantir, SpaceX, and more.
Before they were billionaires or household names, Elon Musk, Peter Thiel, Reid Hoffman, Max Levchin, and the rest of the now-famous “PayPal Mafia” were just a band of stubborn twenty- and thirty-somethings coding through the night, fighting fraud in real time, burning millions a month, and trying to stay alive as the dot-com bubble exploded around them.
From a bitter rivalry between X.com and Confinity, to the explosive merger that created PayPal, to the legendary coup that ousted Musk while he was on his honeymoon, this episode charts the near-death moments, the brutal decisions, and the relentless ambition that forged Silicon Valley’s most influential alumni network. Sammi breaks down how their survival tactics became the blueprint for today’s startup culture — contrarian thinking, founder myth-making — and why the ripple effects of PayPal still shape tech more than two decades later.
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Here’s what Sammi covers today:
00:00 The PayPal Origin Story
01:03 The X.com and Cofinity Rivalry
02:07 The PayPal Merger and Growth
02:38 16 Hour Work Days and Sleeping Under Decks
03:50 The Infamous Honeymoon Coup and Aftermath
05:29 The PayPal Mafia Feature
08:23 The Legacy of the PayPal Mafia
11:33 How to Show Social Currency Some Love
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