Imagine starting a company to change the world of finance right before an epic stock market crash.

Elon Musk famously said that PayPal wasn’t a hard company to create. It was a hard company to keep alive.

In 1999, three future titans of technology—Max Levchin, Peter Thiel, and Elon Musk—charge straight into the blaze to bring payments and finance into the internet age. This is the story of how a handful of brilliant founders and their team navigate from crisis to crisis, face constant near-failure, and create the first successful internet payments solution. From the wreckage of the dot com bubble, they emerged refined—the founders, investors, and builders who would go on to shape the next two decades of Silicon Valley—and a lot of the world we live in today.

Chapters

(01:20) Mr. Buffett on the Stock Market

(02:17) The stock market in 1999

(05:21) Intro to Max and Peter

(09:49) Intro to Elon

(15:45) Why they choose to do startups this late in the cycle

(20:51) Insight of eBay as a perfect market for p2p payments

(22:51) Competition between Confinity and X

(26:55) Confinity and X merge

(34:09) Novel business model & technology innovation

(37:29) The stock market crash dynamics

(43:25) How PayPal navigates post-9/11 slump with an IPO

(48:42) The PayPal Mafia

(50:40) Nature vs. nurture

(54:02) Takeaways on market timing

(55:24) The internet delivered on its promise

References

The Founders: The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley by Jimmy Soni (Link)

The PayPal Wars: Battles with Ebay, the Media, the Mafia, and the Rest of Planet Earth by Eric M. Jackson (Link)

PayPal S-1 Filing in 2002 (Link)

Mr. Buffett on the Stock Market, Nov. 22nd 1999 (Link)