Start Your Own Mafia!

Shoresh Shafei
4 min readMay 15, 2021
Photo Credit: Fortune

I was a bit hesitant about using the title above until I found out that Reid Hoffman has already used it in his book. As you will see, by Mafia here I refer to a group of like-minded people that lift each other up in career and professional life.

I learned about PayPal Mafia in Reid Hoffman’s celebrated book, The Startup of You! and it has stuck with me over the years. The name was given to a group of entrepreneurs that created PayPal and stayed in touch after leaving it. Among the notable members of the Mafia, Reid cofounded LinkedIn, Peter Thiel founded Clarium Capital and Palantir, Elon Musk built the electric car company, Tesla, and Max Levchin started Affirm.

What made them being identified as Mafia was “their difficulty adjusting to traditional corporate culture”, according to Wikipedia. However, in this post I focus on the nature of the relationship between the Mafia members after their departure from PayPal and what I have learned from it. In Peter Thiel’s words

The first team that I built has become known in Silicon Valley as the “PayPal Mafia” because so many of my former colleagues have gone on to help each other start and invest in successful tech companies.

After PayPal was sold to eBay, members of the Mafia continued their relationship and supporting each other, stayed connected as “social and business acquaintances”, advised startups founded by other members and refereed talented employees, invested in each other’s ideas, “even shared office spaces” and some of them worked together to build new companies.

As Hoffman describes, the group had no membership fees or dues. It was not about organization and affiliations but more an informal collaborations between high quality individuals that had something in common like a shared experience. The members trusted each other and everybody wanted to collaborate and share which in turn led to innovative ideas bouncing back and forth between them. Hoffman also points out that the physical proximity gave the group the advantage to collaborate closely and that enabled a timely feedback and criticism of each other’s work.

PayPal Mafia formed organically! This makes total sense considering it started during the dot-com bubble days of Silicon Valley where thousands of entrepreneurs were working on new ideas that…