First Mover Advantage:
Why was the PayPal Mafia so successful? Yes, all of these guys made out with millions after PayPal was bought by eBay for one and a half billion but that alone wouldn’t guarantee this massive run of new successful companies.
Quibi raised $1.75B from investors, when was the last time you watched something on Quibi?
What the PayPal Mafia had that founders today don’t is the dawn of the internet.
In 2002 when PayPal sold, nothing we think about as legacy tech had been built yet. Videos on the internet? Steve and Chad started Youtube. Professional networks online? Ried starts LinkedIn. Need to pick and find a restaurant? Russel starts Yelp.
I’m not saying it was easy to start these companies but we’re not talking about rocket science* here, these aren’t niche SaaS data interoperability companies. These are the “We just got the internet what should we make?” kinds of companies.
*With the exception of Elon's next ventures. SpaceX was literally rocket science.
Even better, tech was going through a bust cycle in 2002. Not only did the PayPal Mafia had the money to build and invest in tech startups, the field had just been cleared by the dot com bust. The opportunities were endless.
Network Power
Venture capital is all about networks. VCs have to find great companies and founders to invest in. Founders have to find VCs who will invest in them. Friends in common make it much easier for both parties to trust the other. In other words, your network greases the wheels. Which is fundamentally unfair but very human.
Peter Thiel was introduced to Mark Zuckerberg by Ried Hoffman. Jawed Karim, founder of Youtube, told Keith Rabois about the video-sharing startup he was working on, Keith told Rolef Botha at Sequoia, and Sequoia ultimately invested.
For the PayPal Mafia, the power of their network to find investors and find investments was unparalleled. Today it reminds me most of Y Combinator.
Members Only: It is worth noting that the PayPal Mafia is entirely men and almost entirely white. In part, that was undoubtedly because in the ‘90s there were even fewer women writing software than today — this was back in the era when Time Magazine was publishing stories with titles like The Golden Geeks about Netscape founder Marc Andreessen.
But given the Mafia’s prevalence, that lack of diversity likely had an impact on the makeup of Silicon Valley companies for years.
That's not to say that The PayPal Mafia wouldn’t invest in women-led companies given the opportunity, it’s just that they clearly didn’t know any women in tech. If they had there would have been a couple at PayPal and in the Mafia.
Given VC is all about your network, if the PayPal Mafia only had men in their network... You see where this is going.
Aside: Interestingly, companies like Chief are today trying to build their own networks of power brokers, but only within minority groups.
TLDR
The PayPal Mafia spawned a ridiculous amount of incredible tech companies including Youtube, LinkedIn, Affirm, Tesla, SpaceX, Palantir, and Yelp.
Their success came from fantastic timing — they exited PayPal in 2002 when the internet was dawning and after competitors had folded in the dot com bust — and a tight-knit network that served to help founders raise capital and help investors find new opportunities to invest in.