With Bezos out as Amazon CEO, Zuckerberg is the last man standing

His stepping back is also the most visible symbol of a profound changing of the guard in the vaunted halls of Silicon Valley leadership, in which a generation of charismatic founders have left their companies in the hands of trusted deputies who are known as expert tactical operators but not necessarily visionaries. These deputies have also been saddled with an array of challenges in the form of regulatory scrutiny that arose from their visionary bosses’ style.

The transition in Silicon Valley has been underway for some time. It began in 2000, when Bill Gates stepped down as CEO of Microsoft and left his day-to-day role eight years later. Apple founder Steve Jobs passed away in 2011, leaving the company to be run by then-chief operating officer Tim Cook. Google founders Larry Page and Sergey Brin stepped back from their roles as CEO and president of Alphabet in 2019, handing the reins to Sundar Pichai, a trusted deputy of 15 years. Both Pichai and Cook have kept their companies’ profit engines steadily running but are seen as less creative than their former bosses.

Now, with Bezos off pursuing other “passions,” Facebook will be the only company in today’s elite circle of technology giants to be run by the man who founded it.

Facebook CEO Mark Zuckerberg is, in a sense, the last man standing. He is also the youngest founder and the one whose company is the most under siege.

“For Larry and Sergey, they looked to the next 10 years, and they knew what was happening next. You felt they were bored. For Bezos, he has been running this incredible grinding machine for 27 years, and he knows they are going to carry on doing that for another 10,” technology analyst Benedict Evans said in an interview. “But for Zuckerberg, there are so many problems and questions, you don’t know what is happening next. You’d probably want to hang around.”

The generation of founders that built Silicon Valley’s most valuable companies today all had their own visions and personalities. But the executives had similarities, too: They all shared relentless creativity and a knack for pushing the boundaries of what was possible in computing and services. They were also known for cutthroat competitiveness. They were frenemies, building competing app stores, devices, services and moonshot projects. Combined, those efforts made their businesses less distinctive over the years.

Bezos, who also owns The Washington Post, used Amazon’s position in e-commerce to build two adjacent businesses — cloud provider Amazon Web Services and Amazon’s third-party-seller marketplace — that have become wildly successful but were hardly sure bets at the time.

Google’s founders expanded their idea of free access to the world’s information, pioneered in 1998, into Google Maps, Gmail and YouTube, and transitioned into devices and cloud computing.

Zuckerberg turned his already massive core social network into a mega-social network after buying Instagram in 2012 and WhatsApp messenger in 2014. At the time, these moves were seen as attempts to secure Facebook’s viability as consumers transitioned to messaging and image-first apps.

Jobs revolutionized computing when he introduced the iPhone, a product that for the first time transformed a phone into a computer with an independent operating system and a novel keyboard-free interface.

Microsoft created the Windows operating system and a suite of Office products that are still the face of desktop computing today.

“Jobs, Brin and Bezos created their companies and had the moral authority to take risks that a reasonable person would reject,” said Yukari Kane, author of “Haunted Empire: Apple after Steve Jobs.” “It would be difficult for a deputy to get approval from the board, shareholders and even consumers” to take the same types of actions, she noted.

But the strategies of the founders, which turned their companies into massive businesses and led them to become some of the richest men in history, have also drawn scrutiny from governments around the world.

Regulators and politicians have questioned their growth and data collection, and their power over the most minute aspects of people’s lives. Google and Facebook are facing landmark antitrust cases in the United States, and Amazon is also battling antitrust charges in the European Union. The Supreme Court has allowed customers to sue Apple over anticompetitive practices in its app store. Even after its 2002 settlement with the Justice Department, Microsoft lived under terms of conduct it agreed to until 2011.

One key difference between Zuckerberg and the other founders is that he is a generation younger than his CEO peers. Bezos, who is 57, ran Amazon for 27 years before stepping down. Brin and Page, both 47, left their positions at Google after more than two decades.

Zuckerberg is 36 and Facebook is only 16 years old. His company was founded a decade after Amazon and six years after Google.

That means Zuckerberg may feel he has more work to do, Evans said.

When Bezos and Google founders Page and Brin chose new paths, they announced their departures at a high point, when their companies’ business prospects looked steady and strong in the years ahead. By the time they stepped down in 2019, Google’s founders had spent four years consolidating their empire into a parent company called Alphabet, which separated its moneymaking advertising and search divisions from its “other bets” — moonshot projects in health care, Nest cameras and self-driving cars. YouTube was becoming a significant ad revenue generator in its own right.

When Bezos said he was resigning as CEO, Amazon had just reported its first-ever quarter of more than $100 billion.

In his resignation letter, Bezos said that he believed “we are at our most inventive right now,” suggesting that the company had reached a peak moment of success.

In Brin and Page’s co-written resignation letter, they also noted that Alphabet was in a comfortable, settled place. “If the company was a person, it would be a young adult of 21 and it would be time to leave the roost,” they wrote.

When Gates finally stepped down from day-to-day operations in 2008, the company was in a midlife crisis — still making huge amounts of money off Windows but being overtaken in emerging areas of computing by younger rivals Apple, Google and Facebook. Gates was already the world’s richest man and was weary from the long antitrust saga.

The founders also left to their deputies future and ongoing antitrust headaches, as evidenced by Pichai being called to testify before Congress numerous times since the founders’ departure. Microsoft finally shed the last of its antitrust settlement agreement terms in 2011. Amazon’s Andy Jassy is also going to have to contend with new scrutiny over Amazon’s business practices and its treatment of workers that has led to the first major unionization drive in the company’s history.

Zuckerberg’s social network continues to be one of the world’s most profitable companies, but it is also the most beleaguered among the tech giants.

Facebook is plagued by low public approval, a massive antitrust case in the United States, regulatory scrutiny all over the world, and allegations that its platform is undermining democracy and is rife with disinformation.

And unlike Apple and Alphabet, Facebook has not groomed a second-in-command to take over the company. Chief Operating Officer Sheryl Sandberg, who is 51, has run the business side of the social network but is not seen as a technologist or an innovator. Chief Product Officer Chris Cox, a longtime deputy who is 38, is considered the most likely replacement were Zuckerberg to depart, but Cox only recently rejoined the company after resigning in 2019.

Jay Greene contributed to this report.