All Stories

Jul 22, 2026

The Nut House Coup: How PayPal Fired Its CEO — And Then Fired the Guy Who Replaced Him

I was at a coffee shop with an old business partner last month, someone I went through one of my...

11 min read

Dec 1, 2025

The PayPal Mafia Photo: The Story Behind Fortune's Most Famous Portrait

I was standing in line at the post office last week – the kind of line that does not move...

8 min read

Sep 22, 2025

How PayPal Survived Four Near-Death Experiences Before Going Public

The power went out at my house last week – just a blown transformer, nothing dramatic – and I sat...

7 min read

Oct 23, 2024

The PayPal Mafia: How One Startup Produced the Founders of YouTube, LinkedIn, and Tesla

I was scrolling through my phone at two in the morning last week when I saw someone on Twitter list...

9 min read

Sep 27, 2024

David Sacks: From PayPal COO to Hollywood to White House Crypto Czar

I was cooking dinner the other night and had a news stream on in the background when I heard David...

9 min read

Sep 20, 2024

Max Levchin: The Ukrainian Refugee Who Co-Founded PayPal with $700

I have been fascinated by immigrant founders for a while now. I wrote about Elon Musk leaving South Africa at...

9 min read

Sep 16, 2024

Roelof Botha: From PayPal CFO to the Most Powerful Investor in Silicon Valley

I have been tracing the paths of PayPal Mafia members for a while now, and I keep noticing that the...

10 min read

Aug 17, 2024

Three PayPal Engineers Started YouTube Because They Couldn't Find a Video Online

I was mapping the companies that emerged from the PayPal alumni network when I started digging into the YouTube origin...

8 min read

Aug 12, 2024

Reid Hoffman Built LinkedIn in His Living Room Six Months After Leaving PayPal

I was reading the newspaper on a quiet Sunday morning and saw yet another article about LinkedIn’s AI features, which...

8 min read

Aug 8, 2024

How PayPal Started as a Way to Beam Money Between Palm Pilots

I was at a parent-teacher meeting last month and another parent Venmo’d me for a class gift, and I thought...

9 min read

Jun 15, 2024

The Story of PayPal's First Customer — And the $10 That Changed Fintech

A guy at the gym asked me last week what I was reading on my phone between sets, and I...

7 min read

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