Where is the PayPal Mafia Today?

Laxmi Hamal
6 min readMay 10, 2024

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Pictures Credit: Google

Intro:

Have you ever wondered about the fascinating world of tech entrepreneurship and innovation? Be it Chrome skyscrapers piercing the clouds, bustling market places filled with holographic advertisements, Seamlessly integrating robots in everyday life, People learning new skills via immersive virtual reality simulations to scientists collaborating with advanced AI systems for ground breaking research.

The PayPal Mafia, Legendary group of individuals who not only revolutionized online payments but went on to become the most influential figures of the tech industry. Their journey went on to shape the future of technology from disrupting the financial landscape.

Who is the PayPal Mafia?
The term “Paypal Mafia” refers to the group of former Paypal employees and founders, who have established and lead some of the established tech companies in the world. Most members of the PayPal Mafia attended Stanford University or University of Illinois Urbana-Champaign.

To begin with, PayPal was a money-transfer service offered by a company called Confinity in 1999. It was bought by X.com and was later renamed as PayPal and purchased by eBay in 2002.

The original PayPal employees were struggling to adjust with the traditional corporate culture of eBay. Therefore, within four years 12 of the first 50 employees left and all remained connected as social and business acquaintances. Most of them worked together to form the new venture in the subsequent years.

This group of PayPal alumni became rife that the term PayPal Mafia was forged. The term “Paypal Mafia” has gained wider exposure after Fortune magazine used the phrase in a 2007 article.

Companies founded by former PayPal employees:

Peter Thiel:
Paypal founder and former CEO who was referred to as the “don” of the PayPal Mafia. Thiel served as CEO of Paypal until 2002, when ebay acquired it for $1.5billion and his 3.7% stake was worth $55 million according to SEC filing.

Thiel Co-founded Founders Fund, a venture capital firm which helped launch companies like SpaceX and Airbnb. He also Co-founded the big data analysis company Palantir in 2003. Thiel is now a billionaire worth over $8 billion.

In recent years, Thiel has drawn a lot of criticism by supporting Donald Trump and secretly funding Hulk Hogan’s lawsuit against Gawker Media which resulted in shutting down of Gawker Media.

As per the reports by Insider Business, Thiel has served as an FBI informant.

Max Levchin:
Max Levchin was the former founder and CTO at Paypal. He was called the “consigliere” of the PayPal mafia. (consigliere refers to an advisor to the boss). He made his contributions towards the anti-fraud efforts.

Levchin and Davik Gausebeck, who was technical architect at PayPal created the Gausebeck-Levchin test. The test is an early version of a CAPTCHA for commercial applications.

After Paypal’s acquisition, Levchin founded Slide, a media sharing service company that was later bought by Google. In 2011, He also founded HVF (Hard, Valuable and Fun) with the intent to explore and fund projects or companies in leveraging data such as data from analog sensors.

In 2012, Levchin founded Affirm. It is a fintech company that provides buy now and pay later services for in-shop and online shopping. Affirm went public in 2021, raising $1.2Billion in its IPO.

He was an early investor in Yelp.com a company which publishes crowd sourced reviews about businesses. He left the leadership position from Yelp in 2015. Levchin now serves as the CEO of Affirm.

Elon Musk:
Elon Musk founded X.com a payments company in 1999 which was merged with Thiel’s Confinity in 2000. Back then he was serving as the CEO of Paypal until he was ousted by the board in 2000 and replaced with Thiel. As the largest shareholder, he bagged himself with $165 million from a PayPal sale to eBay.

Musk Co-founded of Zip2, an online city guide software company with his brother Kimbal. The startup was acquired by Compaq for $307 million in 1999. That same year he founded X.com which merged with Confinity to form Paypal.

In 2002, He founded SpaceX, a spaceflight services company with the money he made from the sale of PayPal. In 2004, He became an early investor in electric vehicle company Tesla Motors.

In 2015, he co-founded OpenAI, a non profit artificial intelligence research company. He left the organization’s board in 2018 due to the conflict of interest with his work at Tesla. The following year he founded Neuralink, a neurotechnology company developing brain computer interfaces. And the Boring Company, a tunnel construction company.

In 2022, he acquired Twitter for $44 Billion. He merged Twitter with the newly created X. Corp and rebranded as X the following year. In March 2023, Elon founded xAI, an Artificial intelligent company.

Musk’s net worth as of April 2024 is estimated to be $178 billion.

David O. Sacks:
David was Chief Operating Officer at PayPal. After Paypal’s acquisition, he produced and financed Thank You for Smoking which was nominated for Golden Globes.

In 2006, he founded Geni.com, a genealogy website. In 2012, Geni was acquired by Myheritage.

In 2008, Sack and his co-founder Adam Pisoni spun off an internal communications tool into a standalone company called Yammer. In July 2012, Microsoft acquired Yammer for $1.2 billion as part of its cloud strategy.

In 2017, Sacks co-founded Craft Ventures and raised initial funding of $350 million. In 2021, Craft raised $1.1 billion which brought total assets under management to $2B. His angel investments include Facebook, Uber, Spacex, Palantir Technologies and Airbnb.

In 2023, Sacks developed and produced a biopic called Daliland about artist Salvador Dali.

Roelof Botha:
Roelof Botha was a former paypal Chief Finance officer. Post the PayPal’s acquisition Botha was given the opportunity to be CFO but he left to become a partner at Venture Capital firm Sequoia Capital. In 2017, he took the responsibility for sequoia’s US operations from Jim Goetz.

Botha is now considered as one of the top tech investors in the world. As of 2022, his active investments include Ethos, Evernote, GenEdit, Landis,Pendulum, Skiff, Temporal technologies and the Org.

Ken Howery:
Ken Howery, the former PayPal CFO, stayed on as eBay’s director of corporate development until 2003. After the acquisition, he became a partner at Founders Fund along with Peter Thiel.

He is a founding advisor to Kiva, an organization that facilitates loans to low-income entrepreneurs.

He has recently served as an US ambassador to Sweden. And is considered the good friend of Elon.

Jeremy Stoppelman & Russel Simmons:
Jeremy Stoppelman was the VP of technology in PayPal. Simmons was an Engineer. In 2004 both of them together founded Yelp, a platform where users leave recommendations about business in their area.

Stoppelman served as CEO, Simmions as CTO initially. Simmons left his role as CTO while Stoppelman continues to serve as Yelp’s CEO.

Steve Chen & Chad Hurley:
Steve Chen a former PayPal engineer & Chad Hurley founded-a former web designer founded Youtube, a Video sharing platform.

Steve Chen invested in actor Joseph Gordon-Levitt’s musical collaboration platform Hitrecord.

Hurley after stepping down as the CEO of Youtube in 2010, he backed up education startup Uptime and also invested in several sports teams.

Reid Hoffman:
Hoffman was the firefighter in Chief, noting there were many fires that needed putting out in the company’s early days. He was the former executive Vice President.

Later, he founded LinkedIn, a professional networking platform and was an early investor in Facebook, Aviary. He is considered one of Silicon Valley’s prolific angel investors.

Luke Nosek:
The former PayPal Co-founder and former Vice-president founded PayPal Mafia angel investor.

Dave McClure:
The former Marketing director of Paypal became a super angel investor for startup companies.

Premal Shah, former Product manager at Paypal became president of Kiva.org.

Conclusion:
Following PayPal’s acquisition by eBay in 2002, the key players left to pursue new Ventures. This group fueled by innovation and shared vision became the PayPal Mafia. All the Individuals went on to become the tech giants.

Their success attributes to the shared experiences, entrepreneurial spirit and resources from Paypal’s scale. Their influence on Silicon valley is fostering the culture of risk taking ability and innovation. Their story is a testament to the power of technology, collaboration and the enduring spirit of human ingenuity.

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Laxmi Hamal
Laxmi Hamal

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