Apple CEO Tim Cook says he doesn’t expect to be running the company a decade from now

Tim Cook Apple Park speech
Apple CEO Tim Cook in January.

  • Apple CEO Tim Cook has been running the company for just shy of 10 years.
  • In another 10 years, though, Cook expects to have stepped down from his role.
  • In a new interview, Cook said he didn’t know what’s next after Apple.
  • Visit the Business section of Insider for more stories.

Tim Cook became the CEO of Apple just shy of 10 years ago, following the death of cofounder Steve Jobs.

And in another 10 years, Cook doesn’t expect to still be at the company, he said in a new interview with The New York Times.

“Ten more years? Probably not,” Cook said. “I can tell you that I feel great right now. And the date’s not in sight. But 10 more years is a long time, and probably not 10 more years.”

Cook has been with Apple for over 20 years. He joined in the late ’90s and helped it to rethink operations. When Jobs died in 2011, Cook took over executive duties and became the new face of the company.

Since then, Cook has unveiled new iPhones, Apple Watches, and other products.

tim cook jony ive iphones
Jony Ive, Apple’s chief design officer, and Cook inspect the iPhone XR during an event on September 12, 2018, in Cupertino, California.

He oversaw Apple’s incredible rise in value: Its market cap is just over $2 trillion. He’s also taken on the role of government liaison and appeared multiple times with President Donald Trump.

As for what he’ll do after Apple, Cook appeared to be just as in the dark as everyone else.

“I don’t have a clue,” he said in the Times interview, “because I love this company so much that it’s hard to imagine my life without it.”

Got a tip? Contact Insider senior correspondent Ben Gilbert via email (bgilbert@insider.com), or Twitter DM (@realbengilbert). We can keep sources anonymous. Use a nonwork device to reach out. PR pitches by email only, please.

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A history of the decades-long feud between Steve Jobs and Bill Gates, whose love-hate relationship spurred the success of Microsoft and Apple

Steve Jobs Bill Gates
Steve Jobs, left, and Bill Gates.

  • Microsoft’s Bill Gates and Apple’s Steve Jobs never quite saw eye-to-eye.
  • While the two founders had periods of civility, at other times, they were at each other’s throats.
  • Jobs insulted Gates’ taste, while Gates described Jobs as “weirdly flawed as a human being.”
  • Visit Business Insider’s homepage for more stories.

Bill Gates and Steve Jobs never quite got along.

Over the course of 30-plus years, the two went from cautious allies to bitter rivals to something almost approaching friends – sometimes, they were all three at the same time.

It seems unlikely that Apple would be where it is today without Microsoft, or Microsoft without Apple.

Here’s the history of the love-hate relationship between Steve Jobs and Bill Gates.

Bill Gates and Steve Jobs weren’t always enemies – Microsoft made software early on for the mega-popular Apple II PC, and Gates would routinely fly down to Cupertino to see what Apple was working on.

Steve Woz Apple II
The Apple II computer.

Source: “Steve Jobs” by Walter Isaacson

In the early ’80s, Jobs flew up to Washington to sell Gates on the possibility of making Microsoft software for the Apple Macintosh computer, with its revolutionary graphical user interface. Gates wasn’t particularly impressed with what he saw as a limited platform – or Jobs’ attitude.

Steve Jobs
Steve Jobs, chairman of the board of Apple Computer, leaning on the new Macintosh personal computer following a shareholder’s meeting in Cupertino, California.

Source: “Steve Jobs” by Walter Isaacson

“It was kind of a weird seduction visit where Steve was saying we don’t really need you and we’re doing this great thing, and it’s under the cover. He’s in his Steve Jobs sales mode, but kind of the sales mode that also says, ‘I don’t need you, but I might let you be involved,'” Gates later said.

bill gates
Bill Gates in New Delhi in 2008.

Source: Fortune

Still, Gates appeared alongside Jobs in a 1983 video – a “Dating Game” riff – screened for Apple employees ahead of the Macintosh’s launch. In that video, Gates compliments the Mac, saying that it “really captures people’s imagination.”

bill gates 1983 mac launch event

Source: Business Insider

Microsoft and Apple worked hand-in-hand for the first few years of the Macintosh. At one point, Gates quipped that he had more people working on the Mac than Jobs did.

Mac computers 1984

Source: Yahoo

Their relationship, already kind of rocky, fell apart when Microsoft announced the first version of Windows in 1985. A furious Jobs accused Gates and Microsoft of ripping off the Macintosh. But Gates didn’t care – he knew that graphical interfaces would be big, and didn’t think Apple had the exclusive rights to the idea.

Bill Gates Windows 98
Bill Gates.

Source: “Steve Jobs” by Walter Isaacson

Besides, Gates knew full well that Apple took the idea for the graphical interface from the Xerox PARC labs, a research institution they both admired.

xerox

Source: “Steve Jobs” by Walter Isaacson

When Jobs accused Gates of stealing the idea, he famously answered: “Well, Steve, I think there’s more than one way of looking at it. I think it’s more like we both had this rich neighbor named Xerox and I broke into his house to steal the TV set and found out that you had already stolen it.”

bill gates 1992
Bill Gates, right, chairman and founder of Microsoft Corp., watches a video presentation prior to giving the keynote address at the annual meeting of the Washington Software Association in Seattle, Wash., Jan. 28, 1992. Looking on is Paul Grey, president of Softchec, Inc. of Kirkland, Wash.

Source: “Steve Jobs” by Walter Isaacson

From there, the gloves were off between the two founders. “They just ripped us off completely, because Gates has no shame,” Jobs once said. To which Gates replied: “If he believes that, he really has entered into one of his own reality distortion fields.”

steve jobs

Source: “Steve Jobs” by Walter Isaacson

Jobs thought that Gates was a stick in the mud, far too focused on business. “He’d be a broader guy if he had dropped acid once or gone off to an ashram when he was younger.”

Bill Gates

Source: “Steve Jobs” by Walter Isaacson

Gates said Jobs was “fundamentally odd” and “weirdly flawed as a human being.”

Steve Jobs

Source: “Steve Jobs” by Walter Isaacson

But Gates respected Jobs’ knack for design: “He really never knew much about technology, but he had an amazing instinct for what works.”

Steve Jobs

Source: “Steve Jobs” by Walter Isaacson

In 1985, Steve Jobs resigned from Apple after a power shift to start his own computer company, NeXT. But even though Jobs was no longer working for Microsoft’s biggest competitor, it didn’t improve relations between the two.

steve jobs
In this April 4, 1991, file photo, Steve Jobs of NeXT Computer Inc. poses for the press with his NeXTstation color computer at the NeXT facility in Redwood City, Calif.

Source: “Steve Jobs” by Walter Isaacson

Jobs thought that if NeXT lost and Microsoft Windows won, “we are going to enter a computer Dark Ages for about 20 years,” he told Playboy in 1985.

steve jobs neXT 1990
Vittorio Cassoni, from Ing. C. Olivetti & Co., speaking with Steve Jobs at the annual PC Forum in Tucson, Arizona, in 1990.

Source: The Telegraph

Still, Windows was winning. By the late ’80s, it became clear that Microsoft was just about unstoppable on the PC.

bill gates windows

Fast-forward to 1996, when Jobs appeared in a PBS documentary called “Triumph of the Nerds” and ripped into Gates and Microsoft, saying that they made “third-rate products.”

steve jobs

Source: PBS

Jobs went on in that same documentary: “The only problem with Microsoft is they just have no taste. They have absolutely no taste. And I don’t mean that in a small way, I mean that in a big way, in the sense that they don’t think of original ideas, and they don’t bring much culture into their products.”

Bill Gates

Source: PBS

By the late ’90s, Apple was in serious danger of going under. When then-Apple CEO Gil Amelio moved to buy NeXT in 1996 and bring Jobs back to Apple, Gates tried to talk him out of it.

amelio jobs

Source: “Steve Jobs” by Walter Isaacson

Gates said this to Amelio: “I know his technology, it’s nothing but a warmed-over UNIX, and you’ll never be able to make it work on your machines. Don’t you understand that Steve doesn’t know anything about technology? He’s just a super salesman. I can’t believe you’re making such a stupid decision.”

Bill Gates
Bill Gates.

Source: “Steve Jobs” by Walter Isaacson

But by 1997, Jobs was Apple’s CEO. At his first Macworld keynote, he announced that he had accepted an investment from Microsoft to keep Apple afloat. Bill Gates appeared on a huge screen via satellite link. The audience booed.

Bill Gates

Source: “Steve Jobs” by Walter Isaacson

Gates clearly admired Jobs, even if they didn’t always see eye-to-eye. When Apple introduced iTunes, Gates sent an internal email to Microsoft that said, “Steve Jobs’ ability to focus in on a few things that count, get people who get user interface right, and market things as revolutionary are amazing things.”

steve jobs imac 1998

Source: “Steve Jobs” by Walter Isaacson

When Apple introduced the iPod in 2001, Gates sent another email: “I think we need some plan to prove that, even though Jobs has us a bit flat footed again, we can move quick and both match and do stuff better.”

steve jobs

Source: “Steve Jobs” by Walter Isaacson

But Jobs was still pretty down on Microsoft, especially after Steve Ballmer took over from Bill Gates as CEO in 2000. “They’ve clearly fallen from their dominance. They’ve become mostly irrelevant,” Jobs once said. “I don’t think anything will change at Microsoft as long as Ballmer is running it.”

Steve Ballmer Bill Gates

Source: “Steve Jobs” by Walter Isaacson

Conversely, Gates thought much of Apple’s post-iPhone success came from Jobs himself, and not from Apple’s “closed” philosophy. “The integrated approach works well when Steve is at the helm. But it doesn’t mean it will win many rounds in the future,” Gates said.

bill gates microsoft 2001
Bill Gates in New Delhi in 2008.

Source: “Steve Jobs” by Walter Isaacson

And Gates didn’t think too much of the iPad. “[I]t’s not like I sit there and feel the same way I did with iPhone where I say, ‘Oh my God, Microsoft didn’t aim high enough.'”

Steve Jobs using an iPad

Source: CBS MoneyWatch

But Jobs didn’t think much of the Windows ecosystem either: “Of course, his fragmented model worked, but it didn’t make really great products. It produced crappy products.”

Steve Jobs

Source: “Steve Jobs” by Walter Isaacson

Jobs didn’t even have any mercy when Gates decided to quit Microsoft in 2006 to focus more on his foundation. “Bill is basically unimaginative and has never invented anything, which is why I think he’s more comfortable now in philanthropy than technology,” Jobs said.

bill gates melinda gates
Bill and Melinda Gates.

Source: “Steve Jobs” by Walter Isaacson

Still, in a weird way, the two men clearly respected each other. Appearing on stage together at the 2007 AllThingsD conference, Gates said, “I’d give a lot to have Steve’s taste.”

Steve Jobs Bill Gates

Source: The Wall Street Journal

And Jobs once said, “I admire him for the company he built – it’s impressive – and I enjoyed working with him. He’s bright and actually has a good sense of humor.”

steve jobs

Source: “Steve Jobs” by Walter Isaacson

After Jobs died, Gates said, “I respect Steve, we got to work together. We spurred each other on, even as competitors. None of [what he said] bothers me at all.”

bill gates

Source: Yahoo

Ultimately, both men claim quite a legacy: Jobs built Apple into what is now the world’s most valuable company, while Gates is the third-richest person on Earth.

steve jobs

Source: CNBC, Bloomberg

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Amazon’s Jeff Bezos is the latest major tech founder to step down as CEO. Here’s what others are up to now.

jeff bezos
Jeff Bezos poses with a Pikachu doll and drill in 1999.

  • Amazon founder Jeff Bezos is stepping down as the company’s CEO.
  • Bezos was among the few founders of major tech companies still running their “startups.”
  • Here’s what the former founder-CEOs of Google, Microsoft, and other tech giants are up to now.

Jeff Bezos started Amazon in his garage in 1994 as a way to sell books online. In 26 years as its CEO, he transformed the company into a behemoth in ecommerce, web services, logistics, robotics, groceries, AI, media, and more. 

On Tuesday, Bezos said he will step down as CEO in the third quarter of 2021, passing the reins to Amazon Web Services CEO Andy Jassy and taking a backseat as executive chairman of Amazon’s board of directors.

Before the pandemic hit, Bezos had spent several years mostly focused on long-term projects. and said in his letter to employees Tuesday that he plans to shift that focus to “other passions” like his space startup Blue Origin, philanthropies (Day 1 Fund and Earth Fund), and The Washington Post, which he acquired in 2013.

Bezos’ plans track closely with those of other high-profile tech founders who ran, and eventually left, their own startups-turned-tech-giants to pursue pet projects and philanthropic endeavors.

He was also one of the few remaining founder-CEOs of a generation of tech companies born in the past 50 years that played major roles in bringing computers, the internet, ecommerce, and social networking to the masses. That shrinking crowd still includes Facebook CEO and cofounder Mark Zuckerberg, Twitter CEO and cofounder Jack Dorsey, and Netflix co-CEO and cofounder Reed Hastings.

But Apple, Google, Microsoft, and others have since bid farewell to the founders who had led their companies for years. Here’s what those tech icons are up to now.

Apple cofounder Steve Jobs died in 2011.

Steve Jobs
Apple cofounder Steve Jobs in 1979.

After Steve Jobs and Steve Wozniak founded Apple in 1976, the company had a long line of CEOs. Jobs was eventually ousted after a failed board takeover in 1985, before returning in 1996 with a successful board takeover, eventually transforming the struggling company into the $2.3 trillion giant it is today.

Jobs left Apple in early 2011 as his health deteriorated, turning over the reins to CEO Tim Cook. Jobs died of pancreatic cancer in October 2011.

Wozniak, who left Apple in 1985 but is still technically an employee and is paid $50 per week, has since started multiple companies. Most recently, he launched a cryptocurrency business that helps companies raise money for eco-friendly projects, according to CNBC.

Microsoft cofounder Bill Gates is working on global health initiatives through his philanthropy.

Bill Gates 1998
Microsoft cofounder Bill Gates in 1979.

Bill Gates and Paul Allen cofounded Microsoft in 1975, and by the time Gates stepped down as CEO in 2000, he had helped build the company into such a dominant player in the tech industry that it became the subject of one of the biggest antitrust cases ever.

Gates stayed on the company’s board until March 2020, when he said he would focus full-time on his philanthropic work for the Bill & Melinda Gates Foundation. Gates has pledged to give away a majority of his wealth within his lifetime — though he and 75% of signatories of the “Giving Pledge” have actually become wealthier since signing on.

Gates has for years focused on global health and warned about the dangers of pandemics, and the Gates Foundation has poured $1.75 billion into coronavirus-related causes.

 

Google cofounder Larry Page is working on secretive flying-car startups.

Larry Page (L), Co-Founder and President, Products, and Sergey Brin, Co-Founder and President, Technology, at Google's campus headquarters in Mountain View, Calif. Google, the popular Internet search engine company, filed with the Securities and Exchange Commission on April 29, 2004 to raise as much as $2.72 billion in its long-awaited stock market debut. They founded the company in 1998. (Photo by Kim Kulish/Corbis via Getty Images)
Google cofounder Larry Page in 2003.

Larry Page and Sergey Brin founded Google in 1998, and Page led the company until 2001, when Eric Schmidt was brought in as “adult supervision.” But Page stepped back in as CEO in 2011 and eventually became the CEO of its parent company Alphabet in 2015, working mostly on “moonshot” projects and recruiting talented people.

Page and Brin stepped down as Alphabet CEO and President in December 2019, with then-Google CEO Sundar Pichai taking over, though both remain on the board. Page has since focused mostly on his investments in flying-car startups Zee.Aero and Kitty Hawk.

eBay founder Pierre Omidyar has invested in media, social impact fintech startups, and a basic income experiment.

GettyImages 799286 F 343440 11: Chairman and founder Pierre Omidyar and CEO Meg Whitman of EBay.com, the online auction service. California, June 15, 1998. (photo by James D. Wilson / Liaison Agency) ***EXCLUSIVE***
eBay founder Pierre Omidyar in 1998.

Pierre Omidyar launched Auction Web, which ultimately became eBay, in 1995. The company eventually brought in Meg Whitman as CEO in 1998, and Omidyar stayed on the company’s board until September 2020.

After leaving day-to-day operations at eBay, Omidyar — a Hawai’i resident — started a local investigative journalism outlet, the Honolulu Civil Beat, and founded First Look Media, a digital journalism company that owns The Intercept. He also launched a $300 million fund to back social impact-focused fintech startups, and has given to a range of philanthropic causes, including basic income and pandemic response.

 

AOL co-founder and CEO Steve Case got into venture capital and philanthropy.

America Online Inc chairman Steve Case talks to reporters at a Tokyo hotel April 14. In Tokyo to announce the launch of AOL's online service in Japan, Case said he expects the Japanese market to become the largest market outside of the United States of AOL's online services. Case declined to comment on market rumours of merger talks with CompuServe Corp, an affiliate of H&R Block Inc. JAPAN ONLINE
AOL co-founder Steve Case in 1997.

America Online, known to most people as AOL, was founded from the ashes of its short-lived predecessor, Control Video Corporation, by Jim Kimsey, Marc Seriff, and Steve Case.

Case ran AOL from 1991 until 2001, when the company completed its — ultimately ill-fated — merger with Time Warner, becoming chairman of the combined company until resigning that position in 2003 amid criticism from investors.

After leaving AOL’s board outright in 2005, Case launched a venture capital firm, Revolution, that has focused on funding startups outside of Silicon Valley. He has also launched a philanthropic foundation and chairs the board of the Smithsonian Institute.

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Billionaire tech mogul Larry Ellison says he and Elon Musk are ‘close friends.’ Here are 8 other tech exec friendships that have thrived in the competitive world of Silicon Valley.

Mark Zuckerberg driving car
Dropbox CEO Drew Houston, left, and Mark Zuckerberg.

  • Silicon Valley might be competitive, but it also appears to be a breeding ground for friendships among its famous execs.
  • Elon Musk is close friends with Google cofounders Larry Page and Sergey Brin, as well as Twitter’s Jack Dorsey. 
  • Larry Ellison gave the eulogy at Steve Jobs’ funeral, and he has a love/hate relationship with Salesforce’s Marc Benioff. 
  • Visit Business Insider’s homepage for more stories.

Bill Gates and Warren Buffett. Elon Musk and Larry Ellison. Jeff Bezos and Barry Diller. 

What do all these high-profile pairings have in common? They’re all close friendships within the world of tech. 

Silicon Valley may be known for its competitive spirit, but it’s also fostered several years-long friendships among some of its most famous executives. Microsoft cofounder Bill Gates and investor Warren Buffett, for example, have been buddies for nearly 30 years. And Larry Ellison and Marc Benioff have been friends for decades, even though their respective enterprise software companies are technically rivals.

Tesla and SpaceX CEO Elon Musk has several close pals in tech, including friends he’s defended online or taken for Tesla test drives. 

Here’s a closer look at some of the friendships among tech CEOs. 

Elon Musk and Jack Dorsey

Elon Musk Jack Dorsey
Elon Musk, left, and Jack Dorsey.

While it’s not clear if Tesla and SpaceX CEO Elon Musk and Twitter and Square CEO Jack Dorsey actually hang out in real life, they do seem to have a solid virtual friendship. 

As far back as 2016, Dorsey said Musk was “a really good model” for how to use Twitter. More recently, Dorsey said in an interview that Musk is his favorite Twitter follow, to which Musk responded, “Thanks Jack, Twitter rocks!”

Then, in January, Dorsey and Musk spoke over video chat in front of Twitter employees, and Musk gave Dorsey advice on how to improve the platform. 

In March, as Dorsey faced a possible ouster at the hands of an activist hedge fund, Musk publicly tweeted his support of the CEO. 

“Just want to say that I support @jack as Twitter CEO,” Musk tweeted. “He has a good <3.” 

Jeff Bezos and Barry Diller

Jeff Bezos Barry Diller
Jeff Bezos, left, and Barry Diller.

Amazon CEO Jeff Bezos and IAC Chairman Barry Diller appear to have been friends for years. 

In January 2016, Diller correctly predicted that Bezos would become the richest person in the world.

And in the last few years, as Bezos has gone through changes in his personal life, he’s been spotted hanging out with Diller and his wife, designer Diane von Furstenberg, more often. Diller and von Furstenberg have reportedly attended multiple parties hosted by Bezos, and Bezos and his girlfriend, Lauren Sanchez, have sailed aboard von Furstenberg’s yacht. The two couples were also reportedly spotted exploring Venice together.

Larry Ellison and Steve Jobs

Larry Ellison Steve Jobs
Larry Ellison, left, and Steve Jobs.

Oracle founder Larry Ellison and late Apple CEO Steve Jobs were friends for 25 years before Jobs’ death in 2011. 

Ellison and Jobs used to be neighbors in Woodside, California, and the pair often went hiking together. It was during one of those hikes that Ellison helped Jobs plot how to regain control of Apple after he was ousted — Ellison even suggested buying Apple himself and installing Jobs as CEO.

It was Jobs who came up with the idea that Apple should acquire his company, Next, instead. When Ellison questioned how the pair would make money, Jobs said to him, “Larry, this is why it’s so important that I’m your friend. You don’t need any more money,” Ellison said in a commencement speech in 2016. 

Ellison said he spent time with Jobs in his final days, taking shorter walks around the block with him as he became weaker. Ellison gave a eulogy at Jobs’ funeral. 

Elon Musk, Larry Page, and Sergey Brin

Sergey Brin Elon Musk Larry Page
From left: Sergey Brin, Elon Musk, and Larry Page.

Elon Musk has been friends with the cofounders of Google for a long time.

In the early days of Musk’s tenure at the electric car maker, he took Brin and Page on a test drive. Unfortunately, a software bug prevented the car from going any faster than 10 miles per hour, Musk recounted at a company shareholder meeting in 2016. Despite “the world’s worst demo,” however, the duo ended up investing in Tesla anyway, Musk said. 

Over the years, Musk and Page especially have become close friends — Musk even sometimes sleeps at Page’s house when he’s in town, and Page once said he’d rather leave his money to Musk than give it away to charity.

Brin, Page, and Musk also reportedly used to hang out in a Google-owned apartment and brainstorm ideas. 

“It’s fun for the three of us [including Google cofounder Sergey Brin] to talk about kind of crazy things, and we find stuff that eventually turns out to be real,” Page told Ashlee Vance, who wrote a 2015 biography about Musk.

Larry Ellison and Marc Benioff

Larry Ellison Marc Benioff
Larry Ellison, left, and Marc Benioff.

Ellison and Salesforce CEO Marc Benioff met when Benioff began working at Oracle when he was 23. He was a star early on, earning a “rookie of the year” award that same year and becoming Oracle’s youngest VP by age 26. He spent 13 years at Oracle, during which he became a trusted lieutenant to Ellison. 

The pair became such close friends that rumors swirled about their relationship’s backstory — people wondered if they were related, or if Ellison had been Benioff’s childhood babysitter. Ellison and Benioff took trips together, sailed on Ellison’s yacht, and went on double dates

Benioff began working on Salesforce with Ellison’s blessing, and Ellison became an investor, putting in $2 million early on. 

The duo has publicly feuded over the years — including when Benioff fired Ellison from Salesforce’s board — but Benioff has also described Ellison as his mentor. 

“There is no one I’ve learned more from than Larry Ellison,” Benioff said in 2013.

Read more: Oracle employees say Safra Catz and Larry Ellison don’t talk about their Trump ties internally. After the US Capitol siege, some want action: There’s ‘blood on their hands’

Bill Gates and Warren Buffett

Warren Buffett Bill Gates
Warren Buffett, left, and Bill Gates.

Berkshire Hathaway CEO Warren Buffett and Microsoft cofounder Bill Gates met in 1991 when Buffett was invited over to Gates’ mother’s house. Neither man was very interested in meeting the other, but they ended up hitting it off. Soon after, Gates asked Buffett for a business book recommendation, and Buffett loaned him his copy of “Business Adventures” by John Brookes — Gates still has it today. 

Since then, the duo has done everything from play table tennis together to participate in Berkshire Hathaway’s annual newspaper toss competition. And Gates, his wife Melinda, and Buffett launched the Giving Pledge together in 2010, vowing to give away the majority of their wealth in their lifetimes or in their wills. 

While Buffett owns a major stake in Apple, he’s said that he’ll never invest in Microsoft due to his friendship with Gates. 

Larry Ellison and Elon Musk

Larry Ellison Elon Musk
Larry Ellison, left, and Elon Musk.

Ellison and Musk appear to be two of the friendliest CEOs in tech, if their relationships with Benioff and Jobs, and Page, Brin, and Dorsey are any indication. So it’s not much of a surprise that the two moguls are “very close” friends with each other, too. 

Back in 2018, when Ellison was named to Tesla’s board of directions, he highlighted his relationship with Musk. 

“I think Tesla has a lot of upside,” Ellison said at the time. “I am not sure how many people know, but I’m very close friends with Elon Musk, and I’m a big investor in Tesla.”

It makes sense that Ellison and Musk would get along well, as they’re two of the most colorful personalities in tech. Ellison owns an entire $300 million island in Hawaii, likes to race yachts, and doesn’t mind trash-talking his competitors. Musk spends his money on rare cars, has had multiple high-profile relationships, and is often outspoken on Twitter. 

Mark Zuckerberg and Drew Houston

Mark Zuckerberg Drew Houston

Dropbox CEO Drew Houston and Facebook CEO Mark Zuckerberg have apparently been friends for years, with the former often turning to the latter for advice

“[Zuckerberg’s] given me a lot of advice just on company scaling, how do you organize people, how do you set up these systems,” Houston told Bloomberg in 2015.

That same year, a Fast Company profile on Dropbox described Houston as a “close friend” of Zuckerberg’s. The pair has been photographed together everywhere from Houston’s birthday party at a ping-pong club to the prestigious Allen & Co. conference in Sun Valley, Idaho. 

This past February, Houston was appointed to Facebook’s board of directors

“Drew brings valuable perspective to our board as a leader of a technology company with services used by millions of people and businesses,” Zuckerberg said in a statement at the time. “He thinks deeply about where technology is going and how to build a culture that delivers services that always work well.”

Kevin Systrom and Jack Dorsey

Kevin Systrom Jack Dorsey

Instagram founder Kevin Systrom and Twitter CEO Jack Dorsey started out as close friends, but it’s hard to tell where they stand these days.  

According to the book “No Filter: The Inside Story of Instagram” by Sarah Frier, the pair met when they were early employees at Odeo, the audio and video site created by eventual Twitter cofounders Ev Williams and Noah Glass. Dorsey expected to dislike Systrom when he joined as a summer intern in the mid-2000s, but the pair ended up bonding over photography and expensive coffee. 

Systrom and Dorsey stayed in touch even after Systrom got a full-time job at Google — he was an early proponent of Twitter (then known as Twttr), and when Systrom was working on Burbn, the precursor to Instagram, he reached out to Dorsey for guidance. Dorsey ended up becoming an early investor, putting in $25,000. When Burbn pivoted to Instagram, Dorsey became one of the app’s biggest fans, cross-posting his Instagrams to Twitter and helping the app go viral soon after it launched. Dorsey eventually attempted to buy Instagram, but Systrom declined, saying he wanted to make Instagram too expensive to be acquired, according to Frier. 

But the Dorsey-Systrom relationship appeared to have soured in 2012, when Dorsey found out through the grapevine that Instagram had signed a deal to be acquired by Facebook, Twitter’s biggest rival. According to Frier, Dorsey was hurt that Systrom hadn’t called him to discuss the deal, or to negotiate one with Twitter instead.

Dorsey hasn’t posted to his Instagram account since April 9, 2012, when he snapped a photo of an unusually empty San Francisco city bus — according to Frier, it was taken the morning he found out Instagram had sold. 

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