Tag: Keith Rabois

Where the ‘PayPal Mafia’ Is Today: Founders, Fortunes and Feuds
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Peter Thiel, PayPal’s first CEO, turned his fintech fortune into a far-reaching empire of influence spanning venture capital, politics and power. Marco Bello/Getty Images

In 2007, Fortune magazine reimagined a classic mafia scene with a Silicon Valley twist: 13 male founders and early employees of PayPal, all long gone from the company, posed at a San Francisco café with slicked-back hair, poker chips and dozens of whiskey glasses. The crowd included some of the most recognizable names in today’s tech scene, like Elon Musk, Peter Thiel and Reid Hoffman. The magazine dubbed them the “PayPal mafia,” not for their time at the fintech company, but for their outsized impact on Silicon Valley through the companies they launched afterward.

PayPal went public in early 2002 and was acquired by eBay for $1.5 billion the same year. Most of its early employees left the company after the acquisition. They went on to found YouTube, SpaceX and LinkedIn, among other legendary names in Silicon Valley. However, like their cinematic namesake, the group hasn’t avoided controversy. These former colleagues have built billion-dollar businesses while also finding themselves in the crosshairs of public criticism.

For instance, Thiel has faced controversy over his political affiliations and, most notably, for funding Hulk Hogan’s 2012 lawsuit against Gawker Media with $10 million — a case that ultimately drove the online media company into bankruptcy. Musk has also faced criticism for his takeover of Twitter and his prior role in the Trump administration, where he led widespread federal employee firings.

Here’s what they are up to these days:

Peter Thiel: venture capitalist

Peter Thiel. Marco Bello/Getty Images

Peter Thiel, Max Levchin and Luke Nosek founded PayPal in 1998, originally as a software security company. After merging with Elon Musk’s X.com (unrelated to the social media platform he owns today), PayPal shifted its focus to digital payments.

Thiel served as CEO from 1998 until 2002, leaving after the company was sold to eBay. He then co-founded Palantir Technologies, a major U.S. government contractor providing data analytics services. The company now has a market capitalization of $439 billion.

Thiel is also known as a prolific angel investor. He co-founded Clarium Capital, Founders Fund, Valar Ventures and Mithril Capital. In 2004, Thiel became Facebook’s first outside investor after acquiring a 10.2 percent stake in the company for $500,000.

Thiel is among the many former PayPal employees who have entered political and high-profile public arenas. An active donor to the Republican Party, Thiel supported Donald Trump’s 2016 presidential campaign but withheld donations during the 2024 election. He is also credited with helping JD Vance reach the Vice Presidential ticket.

Elon Musk: entrepreneur, the world’s richest person

Elon Musk. Kevin Dietsch/Getty Images

Elon Musk briefly served as PayPal’s CEO before being ousted by the board in 2000. He went on to build one of the most influential portfolios in technology, spanning electric vehicles, space exploration, social media and A.I.

Musk founded SpaceX in 2002 and has led Tesla since 2008. He also founded Neuralink and The Boring Company, expanding his reach into brain-computer interfaces and infrastructure. In 2022, Musk gained global attention for acquiring Twitter for $44 billion, later rebranding it as X.

His ties to A.I. run deep: Musk co-founded OpenAI with Sam Altman in 2015 but left in 2018 over strategic disagreements. In 2023, he returned to the field by launching xAI, a research venture focused on building A.I. that is more understandable for humans.

Today, Musk is the richest person in the world, with an estimated net worth of $400 billion. He is also perhaps the only PayPal alumnus to ascend into direct political influence. During the Trump administration, he led the Department of Government Efficiency (DOGE)—a name shared with his cryptocurrency venture—before stepping down in May after clashing publicly with the President.

Max Levchin: computer scientist

Max Levchin. John Lamparski/Getty Images
- Position at PayPal: co-founder, chief technology officer from 1998 to 2002
- Companies later founded: Affirm
- Net worth: $1.8 billion
As PayPal’s chief technology officer, Max Levchin helped lead the company’s anti-fraud efforts by co-creating the Gausebeck-Levchin test—the foundation for the widely used CAPTCHA security tool. After leaving PayPal, he launched the media-sharing platform Slide in 2004, which was acquired by Google in 2010. Levchin briefly served as Google’s vice president of engineering until Slide was shut down the following year.

In 2012, he co-founded Affirm, a leading “buy now, pay later” (BNPL) company, where he continues to serve as CEO. Today, Affirm has a market capitalization of $27.5 billion, with 21.9 million consumers and more than 350,000 merchant partners on its platform.

Levchin has also held board positions at Yahoo and Yelp. In 2015, he became the first Silicon Valley executive appointed to the U.S. Consumer Financial Protection Bureau’s advisory board, emphasizing the importance of collaboration between companies and regulators.

Reid Hoffman: entrepreneur, investor

Reid Hoffman. Kimberly White/Getty Images for WIRED
- Position at PayPal: chief operating officer
- Companies later founded: LinkedIn, Greylock Partners
- Net worth: $2.5 billion
Before joining PayPal, Hoffman worked as a senior user experience architect at Apple, contributing to the company’s online social network eWorld. He later became director of product management at Fujitsu. After his online dating startup, SocialNet, folded, Hoffman joined PayPal in 2000 as chief operating officer.

In 2003, he co-founded the career networking site LinkedIn. Following Microsoft’s $26.2 billion acquisition of LinkedIn in 2017, Hoffman joined Microsoft’s board, a move that greatly increased his wealth.

Over the years, Hoffman has served on the boards of Airbnb and OpenAI, where he was also an early investor. Through the venture capital firm Greylock Partners, he has backed dozens of A.I. startups. In 2022, he co-founded Inflection AI with Mustafa Suleyman, who now serves as CEO. Earlier this year, he teamed up with cancer researcher Siddhartha Mukherjee to launch Manas AI, a startup focused on drug discovery.

David Sacks: investor, White House A.I. and Crypto Czar

David Sacks currently serves as the White House A.I. and Crypto Czar. JC Olivera/Variety via Getty Images
- Position at PayPal: chief operating officer from 1999 to 2002
- Companies later founded: Craft Ventures
- Net worth: $200 million
Since leaving PayPal, David Sacks has built a career spanning film, tech, investing and politics. In 2005, he produced and financed a political satire that earned two Golden Globe nominations. The following year, he founded Geni.com, a genealogy-focused social network that later spun off Yammer, one of the earliest enterprise social networking platforms. He went on to co-found Craft Ventures, the startup Glue, and the podcast platform Callin.

Today, Sacks serves as the White House’s Special Advisor for A.I. and Crypto, a role created by the Trump administration to guide policy on artificial intelligence and cryptocurrency.

Jeremy Stoppelman: engineer, Yelp CEO
- Position at PayPal: vice president of engineering
- Companies later founded: Yelp
- Net worth: $100 million
Jeremy Stoppelman joined Musk’s X.com in 1999 and became vice president of engineering after its transition to PayPal. In 2004, he co-founded Yelp, where he has served as CEO ever since. Under his leadership, the company turned down a 2010 acquisition offer from Google and went public two years later. Stoppelman’s net worth is estimated at more than $100 million.

Ken Howery: investor, U.S. ambassador
- Position at PayPal: chief financial officer from 1998 to 2002
- Companies later founded: Founders Fund
- Net worth: estimated $1.5 billion
Ken Howery served as PayPal’s chief financial officer from 1998 to 2002. After PayPal’s sale to eBay, he became eBay’s director of corporate development until 2003. He later joined Peter Thiel at Clarium Capital as vice president of private equity and went on to co-found Founders Fund as a partner. Beyond investing, he is a member of the Explorers Club, a nonprofit dedicated to scientific exploration, and an advisor to Kiva, the micro-lending nonprofit founded by former PayPal colleague Premal Shah.

Howery is also among the former PayPal executives who have moved into politics. He has donated at least $1 million to Donald Trump’s campaign through Elon Musk’s political action committee. During Trump’s first term, Howery was appointed U.S. ambassador to Sweden and today serves as the U.S. ambassador to Denmark.

Roeloth Botha: venture capitalist

Roelof Botha joined PayPal as director of corporate development shortly before graduating from Stanford University. He later became vice president of finance and went on to serve as chief financial officer until the company’s acquisition by eBay.

After leaving PayPal, Botha joined Sequoia Capital, where he oversaw investments in YouTube and Instagram. He currently sits on the boards of MongoDB, Evernote, Bird, Natera, Square, Unity and Xoom.

Russel Simmons: entrepreneur
- Position at PayPal: software architect from 1998 to 2003
- Companies later founded: Yelp, Learnirvana
Russel Simmons helped design PayPal’s payment system as a software architect. After leaving the company, he and fellow PayPal alum Jeremy Stoppelman set out to build a platform for restaurant reviews. With a $1 million investment from Max Levchin, they launched Yelp in July 2004. Simmons served as chief technology officer until his departure in 2010. At the time, Yelp said he would remain a “significant” shareholder, though the size of his stake—and whether he still holds it—remains unclear.

In 2014, Simmons co-founded Learnirvana, an online learning platform.

Andrew McCormack: entrepreneur
- Position at PayPal: assistant to Thiel from July 2001 to November 2002
- Companies later founded: Valar Ventures
Andrew McCormack began his career as an assistant to Peter Thiel at PayPal and followed him into subsequent ventures. From November 2002 to April 2003, he oversaw operations at Thiel’s hedge fund, Clarium Capital.

In 2010, McCormack co-founded Valar Ventures with Thiel and James Fitzgerald, focusing on fintech investments. He remains a general partner at the firm.

Luke Nosek: investor
- Position at PayPal: co-founder and vice president of marketing and strategy from 1998 to 2002
- Companies later founded: Founders Fund, Gigafund
In 2005, Luke Nosek joined Peter Thiel and Ken Howery to launch Founders Fund, a San Francisco–based venture capital firm that has backed companies such as Airbnb, Lyft and SpaceX. While his exact net worth is unclear, Nosek has made substantial investments through his venture firms. At Founders Fund, he led one of the firm’s earliest major deals with a $20 million investment in SpaceX, later serving on its board.

In 2017, Nosek left to co-found Gigafund, which went on to invest $1 billion in SpaceX, according to the company. He also sits on the board of ResearchGate.

Premal Shah: entrepreneur
- Position at Paypal: product manager
- Companies later founded: Kiva
Three years after leaving PayPal, Premal Shah co-founded Kiva, a nonprofit that provides loans to entrepreneurs in underserved communities worldwide. He also serves on the boards of other nonprofits, including the Center for Humane Technology, the Change.org Foundation, Watsi and VolunteerMatch.

Keith Rabois: investor
- Position at PayPal: executive vice president of business development
After leaving his executive role at PayPal, Keith Rabois became an active investor, backing companies including Slide, YouTube and Palantir. He also invested in LinkedIn, where he served as vice president of business and corporate development, and Square, where he was chief operating officer.

Rabois joined venture capital firm Khosla Ventures from 2013 to 2019 and was a partner at Founders Fund from 2019 to 2024.
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Irza Waraich

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October 5, 2025
Opendoor Board Chair Thinks the Company Should Cut Its Workforce by 85 Percent

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If you work for Opendoor, the online real estate platform, you might consider polishing up your resume. The chair of the company’s board recently let it slip that he thinks the firm could stand to lose almost all of its employees.

During a recent appearance on CNBC’s “Squawk on the Street,” Keith Rabois, a former member of the PayPal Mafia, told a reporter that he felt that the majority of the people at his company were expendable. “There’s 1,400 employees at Opendoor. I don’t know what most of them do. We don’t need more than 200 of them,” Rabois remarked. He added that “the advent of AI and other technologies” made the workforce reduction a “simple problem” to solve.

Rabois’ apparent disinterest in maintaining a majority of Opendoor’s workforce is somewhat humorous given how well the company’s been doing lately. Indeed, the company’s stock is up 500 percent this year. That said, the stock performance appears to largely be the result of a wave of retail investors becoming interested in the firm due to online advice spread by a hedge fund manager. As a result, the company has been dubbed a “meme stock,” which Rabois disputes.

It’s unclear whether Rabois’s ruthless comment was just an effort to inspire confidence in the profitability of the company. After all, if you fire almost everybody at a firm, there’s a much bigger chance you’ll turn a profit.

The stock soared this week, but other developments also helped buoy investor confidence—namely, the appointment of former Shopify executive Kaz Nejatian as its new CEO. CNBC notes that “investor” pressure had spurred the exit of former Opendoor CEO Carrie Wheeler. On Thursday, the company’s stock rose a whopping 78 percent, before dipping down 13 percent on Friday, the outlet notes.

Rabois had more to say about his efforts to transform the online real estate platform: “The culture was broken,” he said, of the firm’s previous management. “These people were working remotely. That doesn’t work. This company was founded on the principle of innovation and working together in person. We’re going to return to our roots.”

Rabois also took the opportunity to dunk on the company’s diversity, equity, and inclusion initiatives, noting that, under its previous leadership, the firm had gone “down this DEI path,” and that Rabois intended to “fix all that.” Gizmodo reached out to Opendoor for more information about its apparent plan to upend its workforce.

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Lucas Ropek

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September 13, 2025
Catching up with Keith Rabois on the state of VC, his newest bet, and who he’s backing for president | TechCrunch

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Chances are that however busy you are, Keith Rabois is busier. He’s an active investor as a general partner at Founders Fund, the early-stage outfit co-founded 18 years ago by Peter Thiel. He’s also the CEO of OpenStore, the company that he co-founded in 2021 to acquire and scale commerce brands on Shopify’s platform. And he has two young children to chase around.

He’s doing it all of it mostly from Miami, to which he moved roughly three years ago and from where Rabois talked with us recently about a lot of things. Among them was politics (he likes U.S. presidential candidates Nikki Haley and Governor Ron DeSantis, but compared Vivek Ramaswamy’s “foreign policy knowledge” to that of his two-year-old). We also talked about why his venture firm cut its newest fund in half, the deal in the Founders Fund portfolio that seems to have him most excited right now, and what he thinks of Marc Andreessen’s latest manifesto. Excerpts from our chat follow, edited for length and clarity. You can hear our longer conversation here.

How big a fund are you currently investing?

That’s a good question because we had announced a large amount that we wound up cutting in half. I don’t remember the official number.

I was wondering when we might see this kind of thing happen. A million years ago, of course, Accel and some other venture firms reduced the size of their venture fund when the market turned.

After we had the commitments, and we were proceeding, we realized that there wasn’t a great way to generate venture returns with that size fund in the world we live in.

How much time are you actually spending at Founders Fund right now, given that you’re not just the co-founder but also the CEO of OpenStore?

I’m a general partner at Founders Fund. That’s my primary activity in life, finding extraordinary entrepreneurs and giving them the advice, counsel and money so they can achieve their ambitions or increase the probabilities of success. Secondarily, I co-founded a company in Miami has roughly about 130 employees where I serve as CEO. Most of the people at Founders Fund have founded companies successfully. . . Obviously, it helps you generate returns because you have proprietary deal flow [but also] your advice and counsel is probably more astute and more insightful. The process of actually running a company or building a company allows you to both commiserate with founders but hopefully also be insightful because you’re suffering through the same challenges.

VCs co-found companies and sometimes run them as CEOs but not forever, typically. Is this a permanent state or will you hand this off to someone in six months?

There are key milestones or key inflection moments, and when we achieve those goals and it becomes more [about] operational excellence and [less about] innovation and problem solving, maybe we consider a different model. But problem solving and confronting challenges with innovative solutions is something I can do really well.

Marketplaces have long been interesting to you, of course. You also co-founded Opendoor. The first check from your newest fund went to Traba, which is a jobs marketplace that connects hourly workers with fulfillment centers. Is that right? Why is that interesting?

Traba connects hourly workers to mostly “light industrial” is the official vertical, which is typically a warehouse and there are ad hoc events — like a major concert, where you need a lot of workers. Light industrials have massive markets — about $50 billion a year — and very few people have built products to serve that industry. Light industrial depends on variable staffing — 40% of all e-commerce occurs during the holiday season, so it doesn’t make sense if you’re running a warehouse to have full-time employees for the entire year. And there are other unique features and value propositions that business customers require in this vertical, and Traba is doing very well at defining it. Then you expand from there.

You just led Traba’s Series B round, but it also raised a Series A last year led by your former employer, Khosla Ventures, and Founders Fund joined that round.

Our history with Traba goes back to approximately June of 2021, when we led the seed financing . . .this is the third time Founders Fund will be investing [and at a] significant increase in valuation, which is pretty rare these days.

What’s its post-money valuation?

I don’t know if we’ve disclosed that or not. I would say it’s increased meaningfully — call it like 40% or more from the prior financing.

Did you have a preexisting relationship with the founder, Mike Shebat?

When I moved to Miami, he reached out to me on LinkedIn. At the time, he was still working as a product manager at Uber, but I kind of knew in the back of my brain that he wanted to found a company, so when he did start Traba, we were excited to lead that financing.

Faire is another marketplace in which you’re involved. It connects indie brands and retailers. You’re on the board. Its valuation soared, too. It was assigned a $7 billion valuation in June of 2021, then suddenly a $12.4 billion valuation later that same year. I saw it raised a $416 million extension round last year, so what happens now?

It will be worth tens of billions of dollars. Literally, at YC Demo Day, when they presented, as they finished the presentation, I said, ‘That’s a $100 billion company right there.’ The founders are fantastic, the metrics are great, the market opportunities wonderful, even though most people missed it.

But is there a down round before it goes public? It’s a tough market right now.

I don’t think the company will need more capital.

You probably noticed we did not lead either of those two financings. So other people may have been spending years paying prices that may or may not have made sense, right? But I think at Founders Fund. We were pretty disciplined at [Khosla Ventures] back in my day. My six years there were extremely disciplined. So if the rest of the world wants to lose money as venture capitalists, sometimes it’s in a founder’s interest to take that money, especially if they can parlay that into real traction. But fortunately a company like Faire has really good financials and is performing really well. I doubt we would do another private financing

Are you doing a lot on the secondary market?

We do occasionally buy secondary shares, we’re open to it. I wouldn’t say never, but very rarely will we buy secondaries without a massive substantial primary position [first], but we don’t have any aversion to buying a secondary.

Are you an investor in OpenAI?

We are. Founders Fund invested in the more recent financing.

Of secondary shares — employee shares.

Yeah, they are. It’s an extremely complicated transaction, but yes.

Is this the round Thrive Capital just led, in a deal that valued the company at a reported $80 billion?

No, the prior round.

Last week, Marc Andreessen published his newest manifesto. What did you think of it?

I mean, it’s directionally interesting. Obviously I believe in the future technology. I’m not one of these techno skeptics or I wouldn’t have been doing venture investing, angel investing or entrepreneurial endeavors for 23 years of my life.

I don’t think it’s particularly unique in any in any real sense. But I think having a tangible, concrete document to rally people around, to remind people why we do what we do, to remind them that there’s lots of people who believe, is very hopeful actually. Because if you just read the New York Times every day, you’d be very depressed.

You’re outspoken on the political front. I don’t really care about this personally, but I did see that you were backing Ron DeSantis and now you’re hosting fundraisers for Nikki Haley.

I love the governor of Florida. We couldn’t be happier here. I think Governor DeSantis is by far the best governor in the country. I am supporting Nikki Haley for President. I think she’s phenomenal. I’ll be super excited when she’s the nominee; if she is, she’ll easily defeat Biden. Like, it’ll be like a landslide. So I’m excited about that. But it’s not a criticism of the governor. We do have restrictions. As you might know, I can’t actually give money to the governor of Florida. We have LPs that are state entities. So there’s very significant restrictions on VCs giving money to state elected officials, meaning even if I wanted to give money to him, I’m legally prohibited from it.

But you also think she’s got a better shot.

She is phenomenal.

What do you think of Vivek Ramaswamy? He’s an entrepreneur.

I think he’s a clown. He’s a savvy businessperson, but I don’t think he realizes that politics is real, and it’s very serious and not something you just pick up on a dime. His domestic policy ideas are actually pretty good and directionally correct. Some of his cultural critiques are dead on. But his foreign policy level of knowledge is literally like my baby. My two-year-old probably has better [sense] than he does. Two months ago at the Republican debate, he proposed defunding Israel, which would have been literally the most catastrophic decision by an American in 50, 60, 70 years. He’s trying to walk that stuff back, but he keeps making silly, uneducated mistakes. He makes Trump look incredibly disciplined and smart, which is, you know, an accomplishment in and of itself.

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Connie Loizos

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October 27, 2023