Who are the famous ‘PayPal mafia’?

Jesse Benjamin Quagraine
6 min readDec 1, 2023

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Which names make up the famed group of former PayPal employees & founders who elevated Silicon Valley’s reputation for unicorn companies? Let’s find out.

PayPal is pretty much one of the biggest brands in the fintech space. Some consider them to be one of the pioneers of the billion (possibly trillion)-dollar fintech industry.

And few would disagree. The unicorn company generated nearly $18 billion in annual revenue in 2019, a whopping increase by $10 billion barely 5 years prior to that.

PayPal is super popular too. An estimated 87.5% of online buyers use it for their online transactions. And with a current user base of almost 300 million, this online tech giant is here to stay for a long time.

There are more mind-blowing facts (just search “PayPal facts” on Google), but what fascinated me was discovering the many genius tech names connected to the history of this company.

Many of PayPal’s founders and ex-employees have gone on to establish or play key roles in other tech companies. Some are even unicorns!

Check out a few of the famous tech names who once worked at PayPal and became unofficially known as ‘The PayPal Mafia’.

Peter Thiel

Peter is one of the most recognizable names in the tech industry. A Stanford graduate, you can call him the IronMan of the PayPal Mafia. And you can say that PayPal’s history began with him.

Spotting an opportunity to tap into digital money transfers in the growing online space, Thiel’s company Confinity, created PayPal. After becoming CEO, he steered PayPal’s fast growth, leading the young tech company to go public in 2002.

Barely 5 months later, eBay acquired PayPal, making it in one of the quickest acquisitions in tech history.

He was also the outside investor in Facebook in 2004. With an estimated net worth of around $8 billion, Peter’s one of the richest guys in the PayPal mafia.

Peter has since founded Palantir Technologies and is involved in many ventures including Founders Fund, a VC firm. He also launched the Thiel Foundation, which supports young entrepreneurs with $100,000 over two years to build their own companies.

Elon Musk

The only name in this group that needs no introduction. Musk founded X.com (sound familiar?), an online payment company that merged with Thiel’s Confinity to became PayPal.

Musk is the founder of SpaceX, Tesla, and Neuralink and the owner of X (formerly Twitter). He’s involved in several high-profile ventures and is known for his super-ambitious projects in space exploration, electric vehicles, and AI.

Max Levchin

Levchin was a co-founder of PayPal and the company’s CTO, where he was the main brain behind the company’s anti-fraud technologies.

After the acquisition, Levchin used the money he earned from the sale to found another company, Slide. Slide would also be successfully acquired by Google in 2010 $182 million.

In 20212, Levchin founded Affirm, a fintech company, and was involved in various ventures as an investor and advisor, including Yelp and Evernote.

Steve Chen, Chad Hurley, & Jawed Karim

These three guys were early employees at PayPal. They were instrumental in the company’s early functioning and success.

After leaving PayPal, Chen, Hurley, and Karim co-founded YouTube, which they later sold to Google. Since then, they’ve been involved in other business ventures.

Steve went on to found AVOS Systems, which later created MixBit. Hurley also co-founded AVOS Systems and has been involved in the growth of other companies, and Jawed Karim is a tech startup investor. He’s also known for his work on the educational platform, Khan Academy.

Reid Hoffman

Hoffman was an executive VP at PayPal, where he was responsible for all external relationships including payments infrastructure (Visa, MasterCard, ACH, Wells Fargo), business development (eBay, Intuit, etc.), government (regulatory, judicial), and legal stuff.

After exiting PayPal, Hoffman co-founded LinkedIn in 2003. He sold LinkedIn to Microsoft for $26.2 billion in 2016 and remains a board member. Reid is now an active investor and a partner at Greylock Partners, a VC firm.

Jeremy Stoppelman & Russel Simmons

Jeremy and Russel were both early software engineers at PayPal. Jeremy rose through the ranks to VP level.

After the sale of PayPal to eBay, Stoppelman and Simmons co-founded Yelp, a crowd-sourced review website, in 2004. Stoppelman is still the CEO of Yelp, which went public in 2012.

Simmons was the CTO at Yelp but later moved on to found Learnirvana, a teaching and learning platform. He’s also a startup investor and advisor.

David Sacks

David Sacks was PayPal’s chief operating officer towards the end of the company’s period before it was acquired. He was the one overseeing product, sales, marketing, and international operations. Sacks was instrumental to PayPal’s growth and helped grow the company‘s annual revenue to over $200 million before it was acquired.

David met Elon Musk at PayPal and the duo have been close friends ever since.

Sacks is a serial entrepreneur and founded Yammer in 2008. Yammer was basically what Slack is now. It was one of the fastest-growing software, leading to Microsoft acquiring it for $1.2 billion. Till today it is still the fastest billion-dollar SaaS exit (from founding to exit) in tech history.

Sack has been a prolific angel investor and venture capitalist, involved in various companies and tech projects. He also co-hosts the popular All-In podcast which has over 200k monthly listeners.

Keith Rabois

Rabois was an executive VP at PayPal in charge of Business Development, Public Affairs & Policy. He left after the eBay acquisition.

Rabois is a venture capitalist and was involved with LinkedIn (VP), Square (COO), and other startups. He joined Square when the startup had less than 900 customers and helped grow the its valuation from $40m to over $3.6 billion. In his time at Square, it was recognized as the 3rd most innovative company by Fast Company in 2013.

Since Square, Keith has been an avid investor in tech startups. He’s a General Partner at Founders Fund, a VC firm that has invested in companies like SpaceX and Stripe.

In 2021, Keith founded OpenStore, a platform that buys Shopify stores.

Luke Nosek

Interestingly it was Luke Nosek who introduced Levchin to Peter Thiel and the 3 of them got PayPal started off the ground. Luke was the first VP in charge of Business Development, Marketing, and Strategy.

Luke was the brain behind PayPal’s “Instant Transfer” product that made the company profitable, attracting 1 million customers in just 3 months.

Nosek is now a partner at Gigafund, a VC firm where he spends his time, investing, advising and nurturing ambitious entrepreneurs.

Honourable mentions:

  • Andrew McCormack: Former assistant to Peter Thiel at PayPal. Founder of Valar Ventures, a VC firm.
  • Ken Howery: Co-founder and first CFO at PayPal. Co-founder of Founders Fund, a VC firm.
  • Roelof Botha: VP of Finance. Now a partner at Sequoia Capital. Invested in Instagram, Square, and Evernote.

References

  • Linkedin profiles of featured names.

I am a Tech Journalist, Certified LinkedIn Marketing Insider and Digital Marketer. Follow me to read more content about tech, digital marketing, SaaS, and LinkedIn tips, tricks and strategies.

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Jesse Benjamin Quagraine

Digital Marketing | Content Writer | LinkedIn Growth Expert | Football Manager fan | Connect with me on LinkedIn | My words drive leads and 3x your revenue.