• Reid Hoffman discussed on "Diary of a CEO" the lack of work-life balance in startup culture.
• He said startups needed to be intense and competitive to achieve success.
• Sacrifices that come with startup work include dinner at the office and working on the weekends.

Reid Hoffman got real about the lack of work-life balance when you're trying to build a company.

The LinkedIn cofounder said during an episode of the "Diary of a CEO" podcast that startup employees shouldn't expect that if they want their business to take off.

"Work-life balance is not the startup game," Hoffman said.

Before it became a large platform for professionals, LinkedIn was a startup. Hoffman said early employees with families were allowed to spend time at home — with the expectation that they'd also be getting work done.

"The people who think it's toxic don't understand the toughness of the startup game, and they're just wrong," Hoffman said.

The nature of building budding companies is intense, he said, and that intensity is necessary at any startup if its workers want it to be a success. That often means working on Saturday mornings and sacrificing time for a personal life.

"We served dinner at the office at PayPal, and that was a deliberate thing," Hoffman, who was a part of the company during its early days, said.

He added that there were only two instances when startup employees could balance their lives and work more evenly: a supersmall startup that doesn't have much competition or a startup where employees have worked hard enough to outpace competitors by a long distance.

Recently, business leaders such as Airbnb CEO Brian Chesky have popularized the term "founder mode" to describe being a present and detail-oriented leader. Chesky previously said that founders go wrong by letting go of their product and delegating tasks instead of getting into the details of their company.

Startup culture may sound toxic, but it's a choice, Hoffman said. He compared it to training to become an elite athlete — swimming only two hours a day probably won't lead you to an Olympic team.

"Choose what your life's about," he said. "No one says you have to do that."

• Reid Hoffman said there's a "greater than 50% chance" he'll receive retaliation for backing Kamala Harris.
• The LinkedIn cofounder made the remarks on an episode of "The Diary of a CEO" podcast.
• Hoffman was one of the vice president's most prominent Silicon Valley business supporters.

Reid Hoffman, the billionaire LinkedIn co-founder and outspoken Democrat, said he thinks it's likely that he will face retaliation from President-elect Donald Trump for supporting Vice President Kamala Harris' presidential campaign.

"I think that there's a greater than 50% chance that there will be repercussions from a misdirection and corruption of the institutions of state to respond to my having tried to help Harris get elected," Hoffman said on an episode of "The Diary of a CEO" podcast that aired on Monday.

Hoffman said that he hopes any retaliation from Trump would be fairly tame, naming possibilities like IRS audits or phone calls from the incoming president trying to hurt his business prospects.

"It could get much worse, but I don't really want to speculate on it because I don't want to give anybody any ideas," he said.

Any repercussions would, he added, be "undemocratic and un-American."

Regardless, Hoffman said that he has no plans to leave the United States.

Nearly 90 top business executives — including Hoffman — signed a letter endorsing Harris' candidacy ahead of the general election, touting her plan to expand tax deductions for small businesses. The letter said that Harris' White House bid was "the best way to support the continued strength, security, and reliability of our democracy and economy."

Hoffman was also part of a cohort of business leaders who put together an initiative to get right-leaning swing voters onboard with Harris' candidacy by stressing her pro-business stances.

On the podcast, Hoffman said he'd spoken to fellow billionaires during the campaign who applauded his political actions but declined to partake themselves for fear of getting "penalized" if Trump won.

"Part of the reason why I think less people were public about it this cycle was because President Trump was threatening personal and political retaliation, and so you had to have a certain degree of courage to stand up — and courage in the public area," he said.

Since winning a second term, Trump has put several Silicon Valley business leaders in prominent roles, from Department of Government Efficiency co-head Elon Musk to newly minted AI and crypto czar David Sacks.

Despite his dislike for Trump and many of his policies, Hoffman said that some of the president-elect's deregulation efforts could broadly benefit entrepreneurs.

"I think they're going to reduce regulation across the board for all entrepreneurs, so I think that's helpful for entrepreneurship," he said.

Representatives for Hoffman and Trump did not immediately respond to Business Insider's request for comment.

• Reid Hoffman said he'd faced threats after Elon Musk fueled a baseless conspiracy theory about him.
• Musk has amplified claims that the LinkedIn cofounder was a client of Jeffrey Epstein.
• Hoffman said he regretted his past association with Epstein and had hired security after threats.

Reid Hoffman, a cofounder of LinkedIn, said he had received threats of violence — and had to hire security — since Elon Musk fueled a baseless conspiracy theory about him.

Musk, the Tesla CEO who worked with Hoffman at PayPal, replied earlier this month to an X post in which a user implied Hoffman had visited the sex offender Jeffrey Epstein's private island.

He replied with the "100" emoji to a post saying: "This guy is TERRIFIED about Trump releasing the Epstein Client list after all his visits to Epstein Island."

Musk also made the claim during an October interview with the former Fox News anchor Tucker Carlson, in which he said Hoffman was among the "billionaires behind Kamala" who were "terrified" by the prospect of Epstein's client list being made public.

Speaking with the British newspaper The Sunday Times, Hoffman said Musk had developed a "conviction with no evidence" that he had a close relationship with Epstein.

"Elon's defamation makes me angry and sad," he said. "Angry because it is an ugly assault. Sad because it comes from someone whose entrepreneurial achievements I continue to admire."

He added that he didn't want to "dignify" the threats he had received by sharing any details but said, "I've hired security staff as a result."

After Epstein's suicide in jail in 2019, Hoffman apologized for inviting him to a dinner party in 2015 with other tech tycoons — including Musk, Facebook CEO Mark Zuckerberg, and Palantir's cofounder Peter Thiel — while fundraising for MIT's renowned Media Lab.

Hoffman said he was told Epstein's involvement in raising donations had been vetted and approved by MIT. But he later wrote in an email to Axios that he regretted not conducting his own research into Epstein, who died while awaiting trial on sex-trafficking charges.

"My last interaction with Epstein was in 2015," Hoffman said in the email. "Still, by agreeing to participate in any fundraising activity where Epstein was present, I helped to repair his reputation and perpetuate injustice. For this, I am deeply regretful."

He told The Sunday Times that he "went to no Epstein parties" and that he "didn't even know who he was."

Hoffman is a major Democratic donor who used X to voice his support for Vice President Kamala Harris in the presidential election. "My message for American voters and Russian bots: don't vote for the guy too busy selling you a scamcoin," he wrote in a post on X on Election Day. Donald Trump, then the Republican presidential nominee, launched his own crypto coin, World Liberty Financial's wlfi, in October.

Musk has become a close ally of Trump, having been tasked with leading a new advisory committee, the Department of Government Efficiency, alongside the pharmaceutical entrepreneur Vivek Ramaswamy.

Musk did not immediately respond to a request for comment.

• A group of early 2000s PayPal employees and founders came to be known as the "PayPal Mafia."
• The members have all gone on to impact Silicon Valley by founding and developing major companies.
• The group includes Elon Musk, Peter Thiel, Reid Hoffman, and the founders of both YouTube and Yelp.

What do the founders of YouTube, Yelp, Tesla, and LinkedIn have in common?

Apart from creating some of the biggest companies in tech, they all share a common résumé line item: they've all worked at PayPal.

Many of PayPal's early employees went on to become major names in tech and the venture capital world, founding, funding, and otherwise developing successful companies. This elite group came to be known as the "PayPal Mafia," a nickname that gained popularity after Fortune used the term in a 2007 piece alongside a photo of some of the members dressed in gangster attire.

Members of the group include Elon Musk, Peter Thiel, Reid Hoffman, and over a dozen others. Here's a rundown of the most prominent members of this exclusive group and what they're up to over two decades later.

Peter Thiel: PayPal's founder and the so-called "don" of the PayPal Mafia

Peter Thiel cofounded the company that would become Paypal — called Confinity — in 1999 alongside Max Levchin and Luke Nosek. Confinity was launched as a developer of security software for hand-held devices like the PalmPilot, but it later pivoted toward digital money transfers. 

Thiel served as CEO of PayPal until October 2002, when eBay acquired the company for $1.5 billion. Thiel's 3.7% stake was worth a $55 million, according to SEC filings.

Thiel went on to cofound Founders Fund, a venture capital firm that has helped launch companies like SpaceX and Airbnb.

Thiel, now a billionaire with a net worth of $15.9 billion, according to Bloomberg, cofounded the big data analysis firm Palantir in 2003. He was the first major outside investor in Facebook and contributed early funding to Yelp and LinkedIn, along with a number of other ventures launched by his PayPal peers. Thiel's also a partner of Founders Fund, a venture capital fund based in San Francisco.

Thiel has also drawn criticism in recent years for his support of President Donald Trump and for secretly funding Hulk Hogan's lawsuit against Gawker Media, which resulted in the company shutting down Gawker and selling the company's assets.

After facilitating talks between Trump and now Sen. JD Vance, Thiel gave a record-breaking $15 million to Vance's campaign, the largest donation ever given to a single senate candidate. 

Thiel later told The Atlantic he was taking a break from politics. Business Insider later reported that he served as an FBI informant.

While his and Trump's relationship has reportedly soured, Trump's recent announcement of Vance as his vice president pick has put Thiel back to playing kingmaker.

Max Levchin: PayPal cofounder and Chief Technology Officer.

Max Levchin is sometimes called the "consigliere" of the PayPal Mafia — in "The Godfather," a consigliere is an advisor to the boss.

Levchin made significant contributions to PayPal's anti-fraud efforts. Together with PayPal technical architect David Gausebeck, he helped create the Gausebeck-Levchin test, an early version of a CAPTCHA for commercial applications.

Levchin now serves as the CEO of Affirm.

After PayPal was bought by eBay, Levchin founded a media-sharing service called Slide that was later bought by Google. He was also an early investor in Yelp — at one point he was the company's largest shareholder — and he served as chairman of Yelp from its founding in 2004 until July 2015.

He founded fintech company Affirm, which allows consumers to finance online purchases at the point of sale and pay for them over time. Affirm went public in 2021, raising $1.2 billion in its IPO. Levchin is also the chairman of Glow, a fertility-tracking app that helps users improve their odds of conceiving.

Ken Howery: PayPal cofounder and CFO from 1998 to 2002.

After eBay bought PayPal, Howery stayed on as eBay's director of corporate development until 2003. After PayPal's acquisition, he served as cofounder and partner of Founders Fund alongside Peter Thiel.

Howery recently served as US ambassador to Sweden.

He was appointed by former President Trump in January 2019 and confirmed in September of that year. He also donated $1 million earlier this year to America PAC, a pro-Trump super PAC created by fellow PayPal mafia member Elon Musk.

Howery is active in several nonprofits and serves as a founding advisor to Kiva, an organization that facilitates loans to low-income entrepreneurs. Kiva was founded in part by Premal Shah, PayPal's former product manager.

Howery is reportedly still good friends with Elon Musk. 

Elon Musk: founder of (the other) X.com, which merged with Thiel's Confinity to become PayPal

In 1999, Elon Musk founded a payments company called X.com, which merged with Thiel's Confinity in 2000. He briefly served as CEO of PayPal before he was ousted by the board in September 2000 and replaced with Thiel. But as the company's largest shareholder, he still walked away from the PayPal sale to eBay with a cool $165 million.

Musk is currently the world's richest person.

Perhaps the best-known of all the members of the PayPal mafia now, Musk's estimated net worth is $362 billion.

Since his PayPal days, Musk has moved on to oversee companies like Tesla, SpaceX, the Boring Company, and Neuralink. He also bought Twitter and renamed it X, after buying back the X.com domain name from PayPal. 

Musk, who has been a vocal supporter of Trump's 2024 presidential campaign and donated more than $200 million to Republican election efforts, will also co-lead the newly created Department of Government Efficiency alongside former Republican presidential candidate Vivek Ramaswamy, Trump announced after winning the election.

Luke Nosek: PayPal cofounder and vice president of marketing and strategy.

Nosek was also reportedly the person who clued in Peter Thiel to cryogenic preservation, which Thiel has since invested in heavily.

Nosek explored angel investing.

In 2005, Nosek joined Thiel and Howery as a partner at Founders Fund. In 2017, Nosek left Founders Fund to launch investment firm Gigafund, which helped raise money for SpaceX.

Nosek was also the first institutional investor in SpaceX and is a board member. He also joined the board of ResearchGate, a platform where scientists and researchers can ask questions, follow topics, and review one another's papers.

Roelof Botha: PayPal's director of corporate development, vice-president of finance, CFO

Botha went to school to be an actuary. He said he never planned to get into tech, but when he saw the opportunity in Silicon Valley, his intuition told him it was where he needed to be.

He started as PayPal's director of corporate development, went on to become vice-president of finance, and later served as CFO.

Botha is now a partner at venture capital firm Sequoia Capital

Botha is now considered one of the top tech investors in the world.

Sequoia Capital has funded tech giants like Apple, Google, YouTube, and Instagram. 

Botha as served on the board at more than a dozen companies, including Square, EventBrite, Weebly, Tumblr, Instagram, YouTube, as well as 23andMe, which he resigned alongside the rest of the board in September over CEO Anne Wojcicki's proposal to take the company private.

Reid Hoffman: board of directors at PayPal, COO

LinkedIn cofounder Reid Hoffman served on the board of directors when PayPal was founded.

He eventually joined the company full-time as PayPal's COO. In a New York Times interview, Peter Thiel referred to Hoffman as PayPal's "firefighter in chief," noting that there were many fires that needed putting out in the company's early days.

When PayPal was acquired by eBay, Hoffman was the company's executive vice president.

Hoffman cofounded LinkedIn and is one of Silicon Valley's most prolific angel investors.

Hoffman was an early investor in Facebook, Flickr, Care.com, and many more. In 2017 he joined the board of Microsoft.

Hoffman has coauthored several books on startups and professional development. He hosts the "Masters of Scale" podcast, on which he interviews founders about how they launched and scaled their companies, and is a partner at VC firm Greylock Partners. He was an early investor in OpenAI and used to serve on its board, and cofounded Inflection AI.

Hoffman has also recently criticized business leaders, including his fellow PayPal mafia members, for supporting Trump.

 

David Sacks: PayPal COO

Like Hoffman, Sacks also served as COO at PayPal. Previously a management consultant for McKinsey & Company, David Sacks joined PayPal in 1999.

After PayPal was bought by eBay, Sacks produced and financed the box office hit "Thank You For Smoking," which would go on to be nominated for two Golden Globes. In 2006 he founded Geni.com, an online tool for building family trees.

 

Sacks founded several companies, became an angel investor, and was named Trump's AI and crypto 'czar'

In 2016, Sacks was briefly interim CEO at Zenefits, an HR software firm that was plagued by scandal, including allowing unlicensed brokers to sell insurance to its customers. In 2017, Sacks cofounded the early-stage investment firm Craft Ventures. 

Sacks is a serial entrepreneur and investor, with angel investments in Airbnb, Postmates, Slack, and many more. 

He's also a member of Elon Musk's inner circle and, like the Tesla CEO, is an avid Trump supporter, hosting a fundraiser for the president-elect at his home. Sacks reportedly urged Trump personally to choose Vance as his running mate, whom he was introduced to by fellow Paypal mafia member Thiel.

Trump said in December that he is appointing Sacks as his White House AI and crypto czar.

 

 

 

Jawed Karim, Chad Hurley, and Steve Chen met at PayPal during its early days.

Karim and Chen were engineers, while Hurley was a web designer.

In 2005, the trio launched the video-sharing platform YouTube. Karim uploaded the platform's very first video, "Me at the zoo," an 18-second clip of Karim in front of the San Diego Zoo's elephant exhibit. It's been viewed over 292 million times.

Today, Karim, Hurley, and Chen remain active entrepreneurs and investors with a hand in projects from finance to music.

Karim launched venture fund YVentures in 2008, through which he invested in Palantir, Reddit, Eventbrite, and Airbnb.

Hurley stepped down as CEO of YouTube in 2010. Since then, he's backed education startup Uptime and invested in several sports teams.

Chen invested in actor Joseph Gordon-Levitt's musical collaboration platform HitRecord, which in February secured $6.4 million in Series A funding.

Andrew McCormack: assistant to Peter Thiel at PayPal

McCormack joined PayPal in 2001, working as an assistant to Peter Thiel as the company prepared for its IPO.

In 2003, McCormack started a restaurant group in San Francisco. In 2008, he joined Thiel Capital and worked there for 5 years.

McCormack went on to launch VC firm Valar Ventures

McCormack partnered up with Thiel again in 2010 to found Valar Ventures, a venture capital fund.

Valar Ventures has invested in technology startups well beyond Silicon Valley, including some in Europe and Canada. In August, Crunchbase reported the firm had closed on a $150 million funding round for a new venture capital fund, Valar Fund V.

McCormack continues to serve as a managing partner of the firm.

 

Keith Rabois: PayPal's executive vice president

Entrepreneur Keith Rabois served as PayPal's executive vice president from 2000 to 2002.

He would go on to join his PayPal colleague Reid Hoffman at LinkedIn as its vice president for business and corporate development from 2005 to 2007. He was an early investor in startups like Square, where he spent two-and-a-half years as COO. 

Rabois joined Thiel, Howery, and Nosek as a partner at Founders Fund.

Rabois is the CEO of OpenStore and has served on the board of directors for Yelp, Xoom, and Reddit.

He was a general partner at Founder's Fund, where he cofounded OpenStore, before returning to Khosla Ventures in early 2024.

Russel Simmons and Jeremy Stoppelman: worked on technology at PayPal.

Simmons was an engineer and Stoppelman was the vice president of technology after joining PayPal from X.com.

In 2004, the pair came up with the idea for a platform where users could leave recommendations about businesses in their area. They pitched the idea to Levchin, who provided an early investment of $1 million, and Yelp was born.

Simmons left his official role at Yelp in 2010, while Stoppelman continues to serve as Yelp's CEO.

Simmons served as CTO at Yelp from 2004 until he left the role in 2010. Stoppelman is still CEO of Yelp, and has publicly spoken out in support of political issues like women's reproductive rights.

Jack Selby: PayPal's vice president of corporate and international development.

After leaving PayPal, Selby partnered with Thiel to start Clarium Capital Management.

In 2017, Selby was revealed to be the generous tipper behind "Tips for Jesus."

Selby later helped manage Thiel Capital, the Thiel's family office, and started his own venture capital fund, AZ-VC, where he serves as managing partner. He still serves as managing director at Thiel Capital.

Starting in 2013, Selby began anonymously leaving tips for unsuspecting waitstaff, ranging into the thousands, and signing them "Tips for Jesus." His identity was confirmed by a New York City bartender who served him prior to receiving a $5,000 tip.

Dave McClure: PayPal's director of marketing

McClure served PayPal's director of marketing as for four years beginning in 2001.

According to McClure's LinkedIn, he began a program called the PayPal Developer Network, which consisted of about 300,000 developers that were using PayPal. 

McClure left PayPal in 2004.

He had a brief stint at Founders Fund before launching 500 Startups, an early stage venture fund. McClure stayed at 500 Startups until June 2017, when he was accused of "inappropriate behavior with women" in a New York Times report and stepped down from his role at the firm, writing an apology post titled "I'm a creep. I'm sorry."

He's since become an investor and owner in a professional sports league for ultimate frisbee and cofounded Practical Venture Capital, according to his LinkedIn.

 

Several more former PayPal employees went on to have careers both in and out of tech.

• Yishan Wong was an engineering manager who later served as CEO of Reddit from 2011 to 2014. He then founded the reforestation company Terraformation in 2020, where he now serves as CEO.
• Jason Portnoy worked in finance at PayPal, and went on to work at Clarium Capital and Palantir. He's now a partner at VC firm Oakhouse Partners. 
• Premal Shah was a product manager at PayPal beginning in 2000, then went on to work at technology nonprofit Kiva. He's now president at financial-services startup Branch. 
• David Gausebeck was a technical architect at PayPal. Now, he serves as chief scientist at 3D modeling company Matterport. He cofounded 3D modeling company Matterport, where he now serves as chief scientist.
• Joe Lonsdale started his career as a finance intern at PayPal before moving into venture capital — he's worked at VC firms Clarium Capital, Formation 8, and 8VC. Lonsdale also cofounded Palantir, and has reportedly contributed to a Trump PAC.
• Eric Jackson was director of marketing at PayPal and went on to write a book about the company called "The PayPal Wars." He's currently the CEO of CapLinked. 

• LinkedIn cofounder Reid Hoffman hopes a second Trump term can usher in an era of AI innovation.
• In a recent op-ed for The Financial Times, he shared several concerns he has for the administration.
• Hoffman warned that Elon Musk shouldn't use his relationship with Donald Trump to boost xAI.

LinkedIn cofounder Reid Hoffman said Elon Musk has a "serious conflict of interest" when it comes to guiding a second Trump administration on AI policies in the US.

In an op-ed published Friday with The Financial Times, Hoffman said the advisory role Musk has taken up with Donald Trump could pose a conflict of interest if the xAI founder is guiding the president-elect on laws around artificial intelligence.

"With direct ownership in the fledgling AI start-up xAI, Elon Musk, who is advising Trump in many domains, has a serious conflict of interest in terms of setting federal AI policies for all US companies," Hoffman wrote. "Using his position to favor xAI in any way, such as awarding it government contracts, encouraging federal agencies to unfairly target AI companies, or imposing new regulations that limit exports will come at the expense of US technological, economic and cultural security and competitiveness."

Musk did not respond to a request for comment. Hours after the FT published the op-ed, Musk responded to an X post unrelated to Hoffman's column, criticizing people who post on LinkedIn.

"I instantly lose respect for anyone who posts on LinkedIn," he said. "Unbearably cringe."

Hoffman, who is also the cofounder of Inflection AI, shared his hopes and concerns for Trump's second term in the FT op-ed.

Hoffman credited the Biden Administration for leaving behind a "strong Democrat-engineered economy" and said he was hopeful that Trump could build on it, ushering in more business investments and technological innovations around artificial intelligence.

But he also warned that a Trump White House could stifle innovation by being unwilling to work with US global allies to develop technology such as AI.

"While Trump campaigned on the promise of making America more unilateral and insular, I continue to believe a pluralistic, multilateral approach is what creates innovation and prosperity in an increasingly networked world," Hoffman said. "That extends to AI. In contrast, I expect the administration will adopt a mercantilist AI policy that will bar long-standing global allies from accessing US models, infrastructure, and technology."

A spokesperson for Trump's transition team did not respond to a request for comment.

Hoffman and Musk have a bitter rivalry that dates back to the PayPal days in 2000, when Musk's online banking company at the time, X.com, merged with Confinity, a security software company, to become PayPal.

The two CEOs have recently been more public about their rivalry, particularly over political disputes. Musk, who has gradually shifted to the Republican Party over the years, has been a vociferous supporter of Trump. Hoffman supported Vice President Kamala Harris' campaign.

After Trump's victory on November 5, Musk has already been spending a lot of time in Trump's orbit and has been tasked to lead a new Department of Government Efficiency focused on reducing the size of the federal government.

Hoffman did not respond to a request for comment.