No two tech executives are quite as enigmatic and private as Google co-founders Larry Page and Sergey Brin. The two men, who started Google more than 20 years ago while computer science graduate students at Stanford University, have hardly been seen or heard from in the last half-decade or so, since restructuring the company to create Google parent Alphabet and leaving Sundar Pichai in charge of a newly streamlined Google.

Yet on Tuesday afternoon, Page and Brin dropped a bombshell announcement: they’re relinquishing control of Alphabet to current Google CEO Sundar Pichai as well, and effectively stepping away from management for good. The news, while it sounded like a big development, felt inevitable. Page and Brin haven’t been deeply involved in the day-to-day operations of the company for some time it seems, and the announcement was making it official. It’s the Sundar Pichai show now, from top to bottom. (Page and Brin will retain their controlling shares and seats on the board, and both plan to keep in regular communication with Pichai.)

Larry Page and Sergey Brin are stepping back for good

It’s a fitting end for two of the most mysterious tech leaders of a generation, who are both exiting their company as it hovers near $1 trillion in market cap. But it’s also a troubling time for Google. The search giant has faced increasing scrutiny from employees, media organizations, activists, regulators, and lawmakers since Page and Brin first stepped back in the summer of 2015. And many of those controversies are problems of Page and Brin’s creation, either because the duo didn’t foresee the ways in which Google could do harm or because they explicitly steered the company in a direction that flouted standard corporate ethics.

In that context, it’s important to look back at the big moments in both men’s careers and how the actions they took have had an outsized impact not just on the tech industry, but on the internet and society itself. What Page and Brin have built will likely last for decades to come, and knowing how Google got to where it is today will be an important piece in the puzzle of figuring out where it goes in the future.

AUGUST 1996: Larry Page and Sergey Brin meet at Stanford University, develop PageRank, and launch Google

Page and Brin met at Stanford University in 1995, as both were in the school’s computer science graduate program. The origin of Google is a story about the origin of an idea, and that idea was Page’s vision that a World Wide Web search engine could rank links based on how often they were being linked by other pages. With Brin’s help, the idea turned into PageRank, the foundational algorithm of Google Search. The search product went live on Stanford’s network in 1996.

1996: Brin’s resume contains hidden “objective” detailing his future lifestyle

Brin’s 1996 resume remains accessible on as part of Stanford’s online archives, and you can still go read it right now. Among the projects he was working on at the time, prior to forming Google, include a movie rating platform and a code conversion tool for turning academic papers into HTML files.

But if you inspected the source code on the webpage, you’d find Brin’s hidden “objective” laid out bare: “A large office, good pay, and very little work. Frequent expense-account trips to exotic lands would be a plus.” Lucky for Brin, he would very much get to enjoy that lifestyle in his later years at Google after he moved on from being co-president with Page to heading up the company’s experimental divisions.

1998: Page and Brin rail against ad-supported search engines in Stanford paper

Although Google is now one of the most powerful forces in online advertising on the planet, Page and Brin weren’t too keen on turning their prototype search engine into an ad-selling machine, at first. In a Stanford paper titled, “The Anatomy of a Large-Scale Hypertextual Web Search Engine,” the duo laid out the case for a search engine that would not be biased toward entities that paid top dollar for higher placement:

In general, it could be argued from the consumer point of view that the better the search engine is, the fewer advertisements will be needed for the consumer to find what they want. This of course erodes the advertising supported business model of the existing search engines. However, there will always be money from advertisers who want a customer to switch products, or have something that is genuinely new. But we believe the issue of advertising causes enough mixed incentives that it is crucial to have a competitive search engine that is transparent and in the academic realm.

1999: Page and Brin try to sell Google for $1 million, then $750,000

While Page and Brin had officially incorporated Google, and smartly changed its name from Backrub, in 1998, the two men shortly after thought they might sell the company, apparently not quite aware of the potential of the product.

In fact, Page and Brin tried to sell Google for $1 million to internet portal company Excite in 1999, as recalled by Khosla Ventures founder Vinod Khosla. The prominent venture capitalist was able to negotiate Page and Brin down to as low as $750,000, but Excite CEO George Bell still wouldn’t take the deal. Google is now worth nearly $913 billion.

2000: Google adopts “Don’t be evil” slogan as its primary corporate value

Accounts on the genesis “don’t be evil” differ. Gmail inventor Paul Buchheit wrote in his personal blog back in 2007 that he coined the phrase during a meeting on corporate values, as a way to “jab at a lot of the other companies, especially our competitors, who at the time, in our opinion, were kind of exploiting the users to some extent.”

But early engineer and future Yahoo CEO Marissa Mayer was once quoted as saying early engineer Amit Patel wrote it on a whiteboard in 1999. Buchheit also corroborates a portion of that account, saying after the corporate values meeting, in which he says both he and Patel lobbied for “don’t be evil,” that Patel went around the company scribbling the phrase on whiteboards to help spread it around the company.

Either way, Page and Brin agreed to make the slogan an official corporate value some time around the year 2000, convinced by Buchheit and Patel that the motto helped enshrine the company’s engineering-first approach and would stave off money-hungry tactics from the increasing number of business and sales employees Google was hiring to help sell more ads. The phrase would later become an official company motto when it was included and explained on the company’s prospectus, as part of its S-1 filing to go public. “We will live up to our “don’t be evil” principle by keeping user trust and not accepting payment for search results,” Page would write in the S-1.

August 2001: Page gives up CEO role to Eric Schmidt

After officially incorporating and launching Google to the public in 1998, Page and Brin were overseeing one of the fastest-growing companies in corporate history. For the graduate school dropouts, it was a bit much. Especially after Page’s high-profile attempt earlier that year to fire all of Google’s project managers, a move the company eventually reversed in an embarrassing public refutation of his leadership.

Eventually, Page and Brin, at the behest of investors, brought on Novell CEO Eric Schmidt to provide, as Brin famously painted it in a 2001 television interview, “parental supervision.” For Google stakeholders and the company’s more experienced executive leadership, it was a way to sideline the stubborn but socially awkward Page from doing too much damage to the company while it was still growing exponentially.

Ultimately, however, Page’s ability to let others step in and take the reins, a learning he would draw throughout his career, was a recognition that power and forward-facing leadership don’t always go hand in hand, and that he and Brin could both be effective at the company and retain their influence without overseeing every aspect of the business. Although at the time, Page was notoriously unhappy about having to relinquish control to non-engineers.

2002: Yahoo wants to buy Google for $3 billion, but Page and Brin don’t bite

If you someone from the year 2019 traveled back in time and told you about the eventual fate of Yahoo, it would have been hard to believe. In 2002, Yahoo was an internet giant of unprecedented size, and it wanted in on Google’s fast-growing search business. So much so that Yahoo was willing to pay up to $3 billion for it, a then-unconscionable amount of money for a startup with what Yahoo CEO Terry Semel considered lackluster revenue.

Props to Yahoo for seeing the value in Google — Yahoo leadership was right after all, about Google becoming a big thing — but Page and Brin weren’t in the mood to sell. Just three years after they were willing to take $750,000 for Google, it had grown into an entity they felt was worth more than 4,000 times that price.

Flash forward a decade and a half or so and Yahoo has been sold off to Verizon and folded into Oath, a media conglomerate ultimately rebranded as Verizon Media. Rumor has it people still use its email service.

August 2004: Google goes public at a valuation of $27 billion; Page and Brin create super-voting Class B shares

Just a few years after hiring Schmidt, Google was on a fast-moving rocket to the upper echelon of not just the tech industry, but the broader American business landscape. It filed for an initial public offering, which took place in August of 2004 and raised $1.7 billion, giving Google a valuation of $27 billion.

One particularly notable aspect of Google’s IPO was Page and Brin’s decision to create a so-called super-voting Class B stock that only they, Schmidt, and a handful of other executives were granted. That Class B stock came with 10 times the voting power of a Class A share, meaning Page and Brin would hoard just over 50 percent of it as a way to maintain control of the company in perpetuity, and that remains the case even today following their official departure.

At the time, Page described the move, which would later be copied by a number of high-profile Silicon Valley companies including Facebook, as a way to “maximize value in the long term.” That was a goal the co-founders believed shareholder concerns, which focus on near-term profit, might jeopardize. “We are creating a corporate structure that is designed for stability over long time horizons. By investing in Google, you are placing an unusual long term bet on the team, especially Sergey and me, and on our innovative approach,” Page wrote.

August 2005: Page buys Android for $50 million, without telling Schmidt

One of Page’s most prescient business calculations was the rise of mobile computing, and he moved quick to snap up a small startup by the name of Android in the summer of 2005 to the tune of $50 million. He did so without telling Schmidt, who was then still CEO, because Page believed so strongly that Android co-founder Andy Rubin could help the company make inroads in the mobile software market.

Of course, Android would go on to become the most popular mobile OS in the world. The project underwent a last-minute course correction after Rubin watched Apple CEO Steve Jobs unveil the iPhone in 2007, famously viewing the presentation on a laptop while riding a cab in Las Vegas. But with the 2008 announcement of the T-Mobile G1 / HTC Dream, the first Android phone was out in the wild and would form the foundation for the world’s first open source mobile operating system.

October 2006: Susan Wojcicki convinces Page and Brin to approve YouTube acquisition

Susan Wojcicki was the 16th employee at Google and the person whose garage the company was literally started out of. That meant she often had the confidence of Page and Brin, but it did take some convincing on her part to get Google leadership to approve the the landmark $1.65 billion acquisition of an online video site called YouTube.

Wojcicki, who oversaw Google’s own fledging video platform, quickly and early on identified YouTube as the clear winner in what would become a contested online video race. So she moved fast to buy it while Google still had an upper hand at the negotiation table. “I saw an opportunity to combine the two services,” Wojcicki recalled in venture capitalist John Doerr’s book Measure What Matters. ”I worked up some spreadsheets to justify the $1.65 billion purchase price... and convinced Larry and Sergey.” Sounds like listening to Wojcicki was a smart decision, discounting of course the never-ending YouTube controversies of late.

September 2008: Google launches Chrome browser, thanks to Sundar Pichai

After Page and Brin hired a number of developers from Mozilla Firefox, and at the suggestion of superstar product manager Sundar Pichai, Google embarked on its quest to build a better web browser. This was despite then-CEO Schmidt’s insistence that Google stay out of what he later categorized as the “bruising browser wars.” The eventual product was Chrome. The browser’s eventual domination of the market is one of Pichai’s most stunning business successes, and it helped push the product chief toward the CEO role years later.

At the time, however, Schmidt had to be convinced it was worth the time and effort, and it was Page’s job to do so. “It was so good that it essentially forced me to change my mind,” Schmidt said at a press conference in 2009 of the original Chrome demo, developed by the former Mozilla engineers. Page responded during that interview that he thinks they “just wore [him] down.”

January 2011: Page takes over as CEO again and Schmidt shifts to executive chairman

After 10 years at the helm, Schmidt ended his tenure at Google with the cheeky tweet, “Day-to-day adult supervision is no longer needed.” In what was then the biggest executive shakeup in Google’s history, Page took the reins back as CEO and Schmidt took on an advisory gig as executive chairman of the board.

All three men retained their super-voting class stock that gave them complete control of the company’s direction, but the move signaled a big shift for Google. “One of the primary goals I have is to get Google to be a big company that has the nimbleness and soul and passion and speed of a start-up,” Page told The New York Times of the shift.

It was the beginning of a new era for the company as Page and Brin would employ their newfound control of the company to launch its Google X skunkworks, and delve further into experimental hardware and long-term projects far outside the bounds of its core product offerings.

June 2012: Brin shows off Google Glass prototype with live skydiving demo

Brin, who at this point held the official title of “Co-Founder” and who was responsible mostly for exploring new products, will forever be remembered for being the person to debut Google Glass, the first mass-produced face computer. Developed as one of the first products out of Google X (now simply just X), the internal skunkworks lab known as “the moonshot factory,” Google Glass was an early attempt at a heads-up display that would go on to fail rather publicly over privacy concerns, design criticism, and an overall messy and chaotic launch.

But when Brin debuted the device onstage at Google I/O in 2012, it seemed like the future had come falling out of the sky — literally. Google had hired a team of skydivers to jump out of an airplane above San Francisco while live streaming the jump from a Glass prototype. It was far and away the most impressive tech demo since the unveiling of the iPhone, and it was very much Page and Brin telling the world that Google was about much more than boring web products. They were signaling to everyone in attendance and watching online that Google would deliver the future faster than any of its competitors.

2012: Page suffers from vocal chord paralysis

Page was largely silent for most of 2012, a product of vocal chord paralysis that the newly re-minted CEO revealed the following year in a Google+ post. The condition has affected Page at various points in his life, but it hit him particularly hard the year after he took the reins back at Google. It caused him to miss the company’s 2012 I/O conference as a result.

Although Page would go on to give a speech at the 2013 I/O conference just a few days after disclosing his condition, this admission would mark the moment Page began drastically cutting down on his speaking engagements. In subsequent years, Page began skipping earnings calls and would rarely speak to the press, as his voice became increasingly quiet and hoarse due to the condition’s impact on his breathing.

May 2013: Page discusses his vision for Google Island

One of Page’s most high-profile talks and one of his last public speaking engagements took place in May of 2013 at the company’s I/O conference, one year after Brin used the same stage to announce Google Glass. There, wearing a bright red shirt under a jet black jacket, Page detailed his vision for a so-called Google Island, where technological progress could march on unabated by silly concerns like regulatory requirements and ethics.

It was mostly just Page riffing on his desire for a different kind of tech industry that didn’t have to be so beholden to corporate interests, shareholders, and advertising. He wanted a slice of the world that could just develop new tech for the sake of it and to better humanity.

But it was a weird speech, and it definitely felt like the beginning, or at leas the first public sign, of Page’s evolution into the ultra-rich, detached founder who just can’t be bothered with the day-to-day struggles of normal human beings. (As my colleague Casey Newton just wrote, Page began taking on a kind of Doctor Manhattan status over the years, and this certainly felt like a turning point in that shift.) Of course, you can’t recall this moment without mentioning tech journalist Mat Honan’s iconic and imaginative speculation about life on Google Island he wrote for Wired, now an infamous piece of tech industry fan fiction.

September 2013: Google creates Calico to focus on life extension

Following the launch of Google X, the debut of Google Glass, and the unveiling of the company’s self-driving car project, the search giant turned its sights on the sciences. In particular, Page was interested in life extension. So the company, through its Google Ventures investment arm, created Calico, a company effectively aimed at curing death. It’s headed up by Bill Maris, the founding partner of Google Ventures, who recruited former Genentech CEO Art Levinson to be its chief executive.

It was yet another signal that Page’s Google was willing to put down huge sums of money toward problems far outside the realm of online search and mobile operating systems. Calico, however, has so far seemingly failed to yield any meaningful advancements in the life sciences, medicine, or biotechnology industries. It is unclear what, if anything, the company is focused on right now.

2014: Brin has extramarital affair with employee Amanda Rosenberg

You can trace the end of Brin’s time as the exuberant, Tony Stark-like futurist face of Google to a disastrous series of headlines in early 2014 detailing his extramarital affair with an employee on the Google Glass team. The most prominent of the stories was a Vanity Fair article detailing the intricacies of the affair from start to finish as it played out the previous summer.

Amanda Rosenberg, who became a marketing manager for the device as it was moving from the experimental Google X lab to a full-fledged product, began a relationship with Brin while Brin was married to fellow Google employee Susan Wojcicki’s sister Anne Wojcicki, who was the founder and CEO of genomics company 23andMe. Rosenberg herself was publicly dating Android vice president Hugo Barra, who later moved to China to take a job with Xiaomi.

The fallout was a rare but highly visible blot on Brin’s career, although his holdings in the company would have prevented any attempt to oust him. (He retained his role as overseer of Google X.) Brin and Wojcicki divorced, and Page reportedly stopped talking to his co-founder for some time over the situation. More recently, Rosenberg has begun publicly discussing the effects the affair had on her career and personal life, and she’s also penned a book about living with bipolar disorder.

In an oral history of Google’s early days, Brin was playfully accused of being “the Google playboy” due to getting sexually involved with employees, and early HR manager Heather Cairns called him “a sexual harassment claim waiting to happen.”

October 2014: Andy Rubin leaves Google, but Page chooses not to disclose sexual misconduct claim

Amid Brin’s relationship with Rosenberg, Google was also dealing with another instance of sexual misconduct, although this one much more serious. In late 2013, Android co-founder Andy Rubin, who at that point in the company’s history was overseeing Google’s ominous-sounding Replicant robotics division, left the company. As reported to the press, it was on good terms. “I want to wish Andy all the best with what’s next,” Page said in a statement at the time. “With Android he created something truly remarkable — with a billion-plus happy users.”

But behind the scenes, Rubin was pushed out after an employee accused of him of coercing her into performing oral sex in a hotel room. Google investigated the claim, deemed it credible, and decided Rubin had to go, but Page, Brin, and other members of the executive team allegedly decided not to reveal that information to the press.

Rubin was sent on his way with a $90 million exit package an addition $150 million stock grant. None of this would be made public until The New York Times published a story in October of 2018 detailing the allegations against Rubin and how it was handled at upper levels of Google leadership. Rubin went on to found smartphone company Essential, while Google decided to disband its robotics division and sell off its most valuable asset, robot maker Boston Dynamics, to SoftBank.

Google parent company Alphabet is now conducting an internal investigation into how its executives handled claims of sexual misconduct, after numerous other incidents similar to Rubin’s were brought to light, and following a massive employee protest in 2018 known as the Google Walkout which formed in response to the Rubin revelations.

August 2015: Google restructures as Alphabet

By the summer of 2015, Google was a remarkably different company than when Page had reassumed his CEO role four years prior. The company was involved in self-driving cars, wearable technology, the Nexus smartphone line, and numerous other product and experimental research efforts spanning artificial intelligence, cloud and quantum computing, and even fiber internet.

Given that complexity, it was time, in Page and Brin’s eyes, to shake things up. “Our company is operating well today, but we think we can make it cleaner and more accountable. So we are creating a new company,” Page wrote in a blog post.

The new company would be called Alphabet, and it would remove Page and Brin from any day-to-day operations at Google proper and elevate them to CEO and president, respectively, of what is effectively a holding company. The process made Google’s financials a bit easier to parse as the various experimental divisions got broken out from Google proper. More importantly it raised Sundar Pichai to the position of Google CEO.

In the broader scope of Page and Brin’s careers, this is the moment both men decided to let go of the steering wheel and the beginning of their more serious retreat from the public eye. Of course, both still retained their super-voting class shares, and Pichai reported directly to Page. In the process of the restructuring, Google ditched “Don’t be evil” as an official motto, replaced as “do the right thing” in the Alphabet code of conduct. (Page and Brin retained the phrase in the separate Google code of conduct.)

2016: Page begins investing in “flying cars”

Page more or less disappeared off the face of the Earth after relinquishing control of Google proper to Pichai and taking on his new role as Alphabet CEO. He still made regular appearances at the company’s all-hands meetings and could be found wandering various parts of the Googleplex campus alongside Brin. But he never again would speak on an investor call, to the press, or at a product event.

What he did end up getting involved in was flying cars. More accurately, they’re eVTOLs, short for electric vertical takeoff and landing vehicles. Page now has his hands in numerous startups, as an investor and advisor, dedicated to bringing aerial electric vehicles to market. It’s not quite clear why he’s so interested in this technology or why he has spent his years post-Alphabet restructuring putting his money toward this particular market — he has not given an interview about his interest. But it does have the air of an older, rich celebrity developing a fondness for luxury cars, with an appropriate tech twist.

January 2017: Brin makes rare public appearance to protest Trump’s immigration order

Just as Page pulled off a disappearing act in 2015, Brin too became a hermit of sorts. It’s hard to find any information on what he’s been up to in the years since becoming president of Alphabet and leaving his role at Google proper. He is reportedly working on a giant “sky yacht,” an aircraft that will ferry supplies for humanitarian missions, and joined a chorus of fellow tech leaders last year in voicing concern for the rapid development of AI. But that’s kind of it.

He did, however, show up in a personal capacity to a protest of President Donald Trump’s immigration-related executive order at San Francisco International Airport in January 2017; Brin is a Russian immigrant. That naturally made headlines, as did speeches Brin and Pichai gave to employees shortly after on the company’s commitment to supporting immigrants and opposing Trump’s executive order. Brin has not made any public appearances in support of political causes since.

September 2018: Breitbart leaks video of Page and Brin all-hands meeting after Trump’s election

While Page and Brin receded from public view starting around 2015, they were reportedly quite active in Google’s famous weekly TGIY all-hands sessions, in which executives would answer questions from employees and address big-picture topics at the company and in the news. One such session, occurring just after Donald Trump was elected president in 2016, was two years later leaked to conservative news outlet Breitbart.

“Most people here are pretty upset and pretty sad,” Brin is seen saying as the meeting kicks off. “I find this election deeply offensive, and I know many of you do too. It’s a stressful time, and it conflicts with many of our values. I think it’s a good time to reflect on that. ... So many people apparently don’t share the values that we have.”

This is perhaps the last time the public will ever see Google’s co-founders speaking in front of a crowd, and that feels more certain to be the case after Tuesday’s announcement. Earlier this month, Pichai announced to employees that Google will be scaling back its weekly all-hands meetings due to leaks, as pressure mounts internally and externally on Google leadership and how it has been handling the tumultuous few years since the Alphabet restructuring. But Page and Brin, although they are no longer involved in the company’s operations, do remain in control of the company given their super-voting class shares.