Tag: Inflection AI

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
Microsoft A.I. Chief Mustafa Suleyman Sounds Alarm on ‘Seemingly Conscious A.I.’

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Mustafa Suleyman joined Microsoft last year to head up its consumer A.I. efforts. Stephen Brashear/Getty Images

Will A.I. systems ever achieve human-like “consciousness?” Given the field’s rapid pace, the answer is likely yes, according to Microsoft AI CEO Mustafa Suleyman. In a new essay published yesterday (Aug. 19), he described the emergence of “seemingly conscious A.I.” (SCAI) as a development with serious societal risks. “Simply put, my central worry is that many people will start to believe in the illusion of A.I.s as conscious entities so strongly that they’ll soon advocate for A.I. rights, model welfare and even A.I. citizenship,” he wrote. “This development will be a dangerous turn in A.I. progress and deserves our immediate attention.”

Suleyman is particularly concerned about the prevalence of A.I.’s “psychosis risk,” an issue that’s picked up steam across Silicon Valley in recent months as users reportedly lose touch with reality after interacting with generative A.I. tools. “I don’t think this will be limited to those who are already at risk of mental health issues,” Suleyman said, noting that “some people reportedly believe their A.I. is God, or a fictional character, or fall in love with it to the point of absolute distraction.”

OpenAI CEO Sam Altman has expressed similar worries about users forming strong emotional bonds with A.I. After OpenAI temporarily cut off access to its GPT-4o model earlier this month to make way for GPT-5, users voiced widespread disappointment over the loss of the predecessor’s conversational and effusive personality.

“I can imagine a future where a lot of people really trust ChatGPT’s advice for their most important decisions,” said Altman in a recent post on X. “Although that could be great, it makes me uneasy.”

Not everyone sees it as a red flag. David Sacks, the Trump administration’s “A.I. and Crypto Czar,” likened concerns over A.I. psychosis to past moral panics around social media. “This is just a manifestation or outlet for pre-existing problems,” said Sacks earlier this week on the All-In Podcast.

Debates will only grow more complex as A.I.’s capabilities advance, according to Suleyman, who oversees Microsoft’s consumer A.I. products like Copilot. Suleyman co-founded DeepMind in 2010 and later launched Inflection AI, a startup largely absorbed by Microsoft last year.

Building an SCAI will likely become a reality in the coming years. To achieve the illusion of a human-like consciousness, A.I. systems will need language fluency, empathetic personalities, long and accurate memories, autonomy and goal-planning abilities—qualities already possible with large language models (LLMs) or soon to be.

While some users may treat SCAI as a phone extension or pet, others “will come to believe it is a fully emerged entity, a conscious being deserving of real moral consideration in society,” said Suleyman. He added that “there will come a time when those people will argue that it deserves protection under law as a pressing moral matter.”

Some in the A.I. field are already exploring “model welfare,” a concept aimed at extending moral consideration to A.I. systems. Anthropic launched a research program in April to investigate model welfare and interventions. Earlier this month, the startup its Claude Opus 4 and 4.1 models the ability to end harmful or abusive user interactions after observing “a pattern of apparent distress” in the systems during certain conversations.

Encouraging principles like model welfare “is both premature, and frankly dangerous,” according to Suleyman. “All of this will exacerbate delusions, create yet more dependence-related problems, prey on our psychological vulnerabilities, increase new dimensions of polarization, complicate existing struggles for rights, and create a huge new category error for society.”

To prevent SCAIs from becoming commonplace, A.I. developers should avoid promoting the idea of conscious A.I.s and instead design models that minimize signs of consciousness or human empathy triggers. “We should build A.I. for people; not to be a person,” said Suleyman.

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Alexandra Tremayne-Pengelly

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August 20, 2025
Nvidia’s Billion-Dollar A.I. Pitch: How the Chip Giant Ramps Up Startup Bets

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Jensen Huang prepares to throw out the ceremonial first pitch before the game between the San Francisco Giants and the Arizona Diamondbacks at Oracle Park on Sept. 03, 2024 in San Francisco. Lachlan Cunningham/Getty Images

There’s no question that Nvidia (NVDA) is one of the biggest winners of the A.I. boom so far. Funneled by an insatiable demand for its graphics processing units (GPUs), the chipmaker’s stock has skyrocketed by more than 450 percent since early 2023. As Nvidia’s market cap and revenue soar, so does the pace of its investing in A.I. startups. More than half of the company’s startup investments since 2005 took place in the past two years.

The value of the company’s startup investments reportedly totaled more than $1.5 billion at the beginning of 2024, a significant jump from the $300 million a year prior. The chipmaker has participated in more than ten $100 million-plus funding rounds for A.I. startups in 2024 alone, according to data from Crunchbase, and has backed more than 50 startups since 2023. That’s not to mention a flurry of activity from the company’s venture capital arm NVentures, which separately made 26 investments in 2023 and 2024.

Nvidia’s seemingly unflappable upward trajectory took a hit yesterday (Sept. 3) after reports surfaced that it had received a subpoena from the U.S. Department of Justice as part of an antitrust probe. The company’s stock dropped nearly 10 percent, shaving $279 billion off its market cap, which currently stands at $2.6 trillion.

But its falling stock price doesn’t mean the company is slowing down in its startup department. In addition to eyeing an investment in an upcoming funding round in ChatGPT-maker OpenAI, Nvidia yesterday unveiled its participation in a more than $100 million funding round for the Tokyo-based Sakana AI, a company that specializes in accessible A.I. models trained on small datasets.

“We invest in these companies because they’re incredible at what they do,” Nvidia founder and CEO Jensen Huang told Wired earlier this year. “These are some of the best minds in the world.”

From companies specializing in humanoid robots to autonomous vehicles, here’s a look at some of Nvidia’s most significant startup investments:

Perplexity AI

Huang hasn’t been shy about his love for Perplexity AI, the A.I.-powered search engine positioned as a competitor to the likes of Google. The Nvidia CEO uses the startup’s tool nearly every day for research, according to Huang’s interview with Wired.

He has also put his money where his mouth is, with Nvidia partaking in a $62.7 million funding round for Perplexity AI in April that valued the startup at $1 billion. Led by investor Daniel Gross, the round included participants like Amazon (AMZN)’s Jeff Bezos. It wasn’t the first time Nvidia has backed the company—the chipmaker also invested in Perplexity AI during another funding round in January that valued the startup at $73.6 million.

Hugging Face

Hugging Face, a startup providing open-source A.I. developer platforms, has long had close ties to Nvidia. The chipmaker participated in a $235 million funding round in Hugging Face in August 2023 that valued the company at $4.5 billion. Other corporate investors participating in the round included Google, Amazon, Intel, AMD and Salesforce.

Hugging Face has previously included Nvidia hardware among its shared resources. In May, it launched a new program that donated $10 million worth of free, shared Nvidia GPUs to be used by A.I. developers.

Adept AI

Unlike more well-known A.I. assistants from companies such as OpenAI and Anthropic, Adept AI’s primary product doesn’t center around text or image generation. Instead, the startup is focused on building an assistant that can complete tasks on a computer, such as generating a report or navigating the web, and is able to use software tools. Nvidia is on board, having participated in a $350 million funding round in March 2023.

Databricks

After receiving a giant valuation of $43 billion last fall, Databricks became one of the world’s most valuable A.I. companies. The data analytics software provider unsurprisingly uses Nvidia’s GPUs and has been backed by the chipmaker alongside other investors like Andreessen Horowitz and Capital One Ventures, all of whom participated in a $500 million funding round in September 2023. “Databricks is doing incredible work with Nvidia technology to accelerate data processing and generative A.I. models,” said Huang in a statement at the time.

Cohere

A formidable opponent to OpenAI and Anthropic, the Canadian startup Cohere specializes in A.I. models for enterprises. The company’s growth over the past five years has attracted backers such as Nvidia, Salesforce and Cisco, which funded Cohere during a round held in July. Nvidia also took part in a May 2023 funding round that brought in some $270 million for the startup.

Mistral AI

Mistral AI is a French startup focusing on developing open-source A.I. models. It was founded by former Google DeepMind and Meta employees in April 2023. Nvidia has participated in two of the startup’s fundraising rounds, a $518 million round in June and a $426 million round in December 2023. The collaboration between the two companies doesn’t end there—in July, Nvidia and Mistral AI jointly released a small and accessible language model for developers.

Figure

Huang has long reiterated his belief that A.I.-powered robots able to work among humans will constitute the next wave of technology. It is, therefore, no surprise that Nvidia is a backer of Figure, a startup developing humanoid robots for use in warehouses, transportation and retail. Nvidia reportedly funneled $50 million towards the company during a February funding round that raised a total of $675 million and included participants like Bezos and Microsoft.

Scale AI

To properly train A.I. tools like OpenAI’s ChatGPT, tech companies need vast amounts of data. This is where A.I. startups like Scale AI, which provides troves of accurately labeled data and is headed by billionaire Alexandr Wang, come in. Nvidia participated in a $1 billion funding round for the company in May alongside Big Tech players like Amazon and Meta.

Wayve

Autonomous driving is another area of interest for A.I. leaders across the tech world. Huang himself said that “every single car, someday, will have to have autonomous capability” in a recent interview with Yahoo Finance. One of the startups at the forefront of this wave is the U.K.-based Wayve. Nvidia participated in a $1 billion funding round in the startup in May.

Inflection AI

Out of the 92 startups Nvidia has backed throughout the decades, Huang’s company has only been a lead investor in 20 rounds. One of these occurred in June 2023, when Nvidia led a staggering $1.3 billion round for Inflection AI. The chipmaker co-led the round alongside Microsoft, Bill Gates and former Google CEO Eric Schmidt.

The A.I. startup, which was co-founded by LinkedIn (LNKD) co-founder Reid Hoffman and Google DeepMind co-founder Mustafa Suleyman and most recently valued at $4 billion, produces a chatbot known as Pi. Much of the round’s funding went towards bolstering Inflection A.I.’s computing cluster of 22,000 Nvidia H100 GPUs.

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Alexandra Tremayne-Pengelly

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September 4, 2024
Stability AI CEO resigns because you can’t beat centralized AI with more centralized AI | TechCrunch

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Stability AI founder and chief executive Emad Mostaque has stepped down from the top role and the unicorn startup‘s board, the buzzy firm said Friday night, making it the second hot AI startup to go through major changes this week.

Stability AI, which has been backed by investors including Lightspeed Venture Partners and Coatue Management, doesn’t have an immediate permanent replacement for the CEO role but has appointed its COO Shan Shan Wong and CTO Christian Laforte as interim co-CEOs, it said in a blog post.

Stability AI, which has lost more than half a dozen key talent in recent quarters, said Mostaque is stepping down to pursue decentralized AI. In a series of posts on X, Mostaque opined that one can’t beat “centralized AI” with more “centralized AI,” referring to the ownership structure of top AI startups such as OpenAI and Anthropic.

He additionally asserted that it was his decision to step down from the top role as he held the most number of controlling shares. “We should have more transparent & distributed governance in AI as it becomes more and more important. Its [sic] a hard problem, but I think we can fix it..,” he added. “The concentration of power in AI is bad for us all. I decided to step down to fix this at Stability & elsewhere.”

Mostaque’s departure from Stability AI, a startup known for its popular image generation tool Stable Diffusion, comes amid an ongoing struggle at the startup that was spending a reported estimate of $8 million a month as of October 2023, according to Bloomberg, which also noted that the startup had unsuccessfully attempted to raise new funding at a $4 billion valuation.

Mostaque, it appears, wasn’t prioritizing revenue growth about a year ago. In a post on X last year, he expressed his amusement at the generative AI companies’ “strange focus on revenue” even as “the technology is useful but far from vaguely mature as new breakthroughs happen almost daily.” He cited several examples, including MagicLeap, which spent billions before generating revenue.

“The payoffs on proper generative AI R&D are clearer and faster to market than just about anything we’ve seen. It’s going to create way more economic value than self driving cars for example, the total investment in that has been $100b with no revenue pay off,” he wrote.

His comments on Reddit last month offered insights into a shift in focus. “We are doing fine and ahead of forecasts this year already. Our aim is to be cash flow positive this year, think we could get there sooner rather than later,” he wrote.

“The market is huge and open models will be needed for edge and all regulated industries. This is why we are one of the only companies to open data, code, training run details and more. Custom models, consulting and more are huge markets and very reasonable business models around this as we enter enterprise adoption over the next year or so, last year was just testing.”

Stability AI’s announcement caps a remarkable week for the AI industry. Inflection AI, a startup that had raised about $1.5 billion, announced on Monday that two of its co-founders as well as several other staff had joined Microsoft, which led the startup’s most recent funding round.

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Manish Singh

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March 22, 2024