TIP417: THE INCREDIBLE STORY OF THE PAYPAL MAFIA

W/ JIMMY SONI

27 January 2022

Trey Lockerbie sits down with author Jimmy Soni, to discuss his new book The Founders – the story of Paypal and the entrepreneurs who shaped Silicon Valley. The original team at Paypal has become known as the “Paypal mafia,” because nearly all of them went on to found other multi-billion dollar companies. For example, Elon Musk went on to found Tesla and SpaceX. Peter Thiel went on to found Palantir. Reid Hoffman went on to found LinkedIn and there’s more! Max Levchin with Affirm and others. David Sacks founded Yammer. How on earth did all of these founders get lightning to strike more than once? It all originated with Paypal. This is a story widely understood, but hardly explored in depth. 

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IN THIS EPISODE, YOU’LL LEARN:

  • Members of the Paypal mafia and their origin stories.
  • How Paypal came to be.
  • The many trials that Paypal endured.
  • The culture at Paypal and how it developed.
  • Jimmy’s main takeaways having personally interviewed each billionaire and years of additional research.
  • And a whole lot more!

TRANSCRIPT

Disclaimer: The transcript that follows has been generated using artificial intelligence. We strive to be as accurate as possible, but minor errors and slightly off timestamps may be present due to platform differences.

Trey Lockerbie (00:00:03):
Today’s episode is a fun one where I sit down with author, Jimmy Soni, to discuss his new book, The Founders: The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley. The original team at PayPal has become known as the PayPal Mafia, because nearly all of them went on to found other multi-billion-dollar companies. For example, Elon Musk went on to found Tesla and SpaceX. Peter Thiel went on to found Palintir. Reid Hoffman went on to found LinkedIn. Max Levchin with Affirm. And others, David Sacks founded Yammer. I mean, the list goes on. How on earth did all of these founders get lightning to strike more than once? It all originated with PayPal. This is a story widely understood, but hardly explored in depth.

Trey Lockerbie (00:00:46):
In this episode, we discuss members of the PayPal Mafia and their origin stories, how PayPal came to be, the many trials that PayPal endured, the culture at PayPal and how it developed, Jimmy’s main takeaways having personally interviewed each billionaire and years of additional research, and a whole lot more. This is the kind of story that would make a great movie. You’ll be able to see quickly and clearly that Jimmy has done an immense amount of research and provide some amazing insights. I hope you enjoy it. Here’s my conversation with Jimmy Soni.

Intro (00:01:21):
You are listening to The Investor’s Podcast, where we study the financial markets and read the books that influence self-made billionaires the most. We keep you informed and prepared for the unexpected.

Trey Lockerbie (00:01:41):
Hi, everybody. Like I said at the top of the show, I’m here with Jimmy Soni, the author of The Founders. Jimmy, welcome to the show.

Jimmy Soni (00:01:48):
Thank you so much for having me.

Trey Lockerbie (00:01:50):
I find the story of the PayPal Mafia just endlessly fascinating because at this point, it has all this almost myth and lure around it where it’s like The Avengers story. All these folks have gone off and just created more and more billion-dollar companies. And there have to have been something in the water that they were drinking in the PayPal office or something at some point. So I would love to, first of all, take a step back for those who aren’t familiar and just describe who the PayPal Mafia is. And then I want to lead into what made you want to write a book about them.

Jimmy Soni (00:02:27):
The Avengers is a good metaphor. I haven’t used that, but I think I might borrow it. I’ve always been using the 1990s Chicago Bulls. This is last dance with Silicon Valley where you have all these amazing people who come together at one time. So just to give your listeners some background, I suspect that most of the people who listen to you are familiar with the names of the alumni, certainly the better known alumni from PayPal. It includes people like Elon Musk and Peter Thiel and Max Levchin and Reid Hoffman, David Sacks, Keith Rabois, among many, many, many others. There are also folks, the CEO of ancestry.com is a PayPal alum. Some of the senior-most people at Facebook. Several high level people in government are ex-PayPal.

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