Arvind Jain, the ex-Google engineer who now runs the $7.2 billion AI company Glean, says a decade of watching Sundar Pichai inside Google taught him a single lesson. The trait Pichai shares with Google co-founders Larry Page and Sergey Brin, Jain told Fortune, is the willingness to chase ideas that look foolish on paper. “You have to think crazy,” he said.
The interview, published June 28, 2026, distills what Jain calls the second lesson he took from the years he spent inside Google. He watched the trait compound as Pichai turned a dismissed browser project into the world’s most-used web browser. He went on to apply it twice over, at Rubrik first and then at Glean, the AI startup now valued at $7.2 billion that helps employees search across their company’s data. Glean was founded by Jain with three other co-founders, all of whom had prior Google, Microsoft, Meta, or Uber experience, per the company’s press materials.
The “Bad Idea” Inside Google That Became a Browser Empire
Inside Google, the moment that crystallized the lesson for Jain was Pichai’s early push behind Google Chrome. Browsers were Microsoft’s territory; Netscape had already tried and failed. Jain himself thought the project looked like a poor use of Google’s time.
“I felt like that’s such a bad idea,” Jain told Fortune. Microsoft’s then-CEO Steve Ballmer publicly dismissed Chrome as “a rounding error” in a September 2009 interview, when Microsoft itself said its browsers were at “right now about 74 percent” of the market. Pichai kept building. By 2012, Chrome had passed its rivals to become the world’s most-used browser, far bigger than Microsoft’s Internet Explorer. That arc put Pichai in line for Google’s CEO seat in August 2015, per Fortune.
- September 2008: Google launches Chrome, with Pichai among the internal champions; Microsoft controls the browser market.
- September 2009: Microsoft CEO Steve Ballmer calls Chrome “a rounding error to date” and puts Microsoft’s browser share at about 74 percent.
- By 2012: Chrome has passed its rivals to become the world’s most-used web browser, far bigger than Microsoft’s Internet Explorer.
- August 2015: Pichai becomes CEO of Google, with Chrome a centerpiece of his reputation inside the company.
The Chrome episode is what Fortune reports as the moment that “crystallized” the lesson for Jain. The September 2009 transcript of Ballmer’s full comments survives in the original 2009 transcript of Ballmer’s full exchange, and Pichai’s instinct for “crazy” bets is still on display in his recent public embrace of AI-coded weekend projects.
The Trait That Pichai, Page, and Brin Share
The trait Jain extracted from Pichai’s behavior at Google is not raw intensity or hard work alone. It is “the ability to think big and have confidence,” Jain said, an attribute he watched accumulate inside Google over time. Page and Brin showed the same trait, he added; they ran Google with “no sort of constraints in their minds on what’s possible.” Fortune’s profile frames it as the difference between two equally credentialed engineers, one who rises and many who do not. The lesson, in Jain’s telling, is not work ethic alone but the willingness to define success on terms the room rejects.
“The same attributes kept coming up,” Jain told Fortune: hard work, intensity, and the ability to think big. His one-sentence distillation was direct: “You have to think crazy.” Then unpacking it: “You have to say: we’re going to do this thing which everybody thinks is stupid, maybe unrealistic. That’s when magic happens.” The same principle brought Page and Brin back to Google’s most ambitious projects, including work that shaped the company long after they stepped back from day-to-day operations. Jain, who once felt like “an imposter” surrounded by MIT and Stanford PhDs, says he was trying to learn what makes one succeed.
Two Unicorns Built on the Same Lesson
Jain spent more than eight years inside Google before putting the lesson to work for himself. The first application was Rubrik, the cloud data management company Fortune says IPO’d on the New York Stock Exchange in 2024. The second application is Glean, the AI startup Fortune describes as a tool that helps employees “search and understand information across their entire company.”
Rubrik’s IPO took place in 2024. Fortune’s June 28, 2026 profile puts the opening valuation at “around $5.6 billion.” Rubrik sells cloud data management software to enterprises. The next chapter put the same lesson into a different product category: enterprise AI.
Glean’s valuation, per Fortune, now sits at the same $7.2 billion mark the company hit at its June 2025 Series F announcement.
The Series F raised $150 million, led by Wellington Management. New investors joining in the round included Khosla Ventures, Bicycle Capital, Geodesic Capital, and Archerman Capital. Existing backers in the round included Altimeter, Capital One Ventures, Citi, Coatue, DST Global, General Catalyst, ICONIQ, IVP, Kleiner Perkins, Latitude Capital, Lightspeed Venture Partners, Sapphire Ventures, and Sequoia Capital, per the announcement. Glean said in the release that the capital would support product development, partner expansion, and a new San Francisco office. Jain, in the same release, said Glean raised the capital “while we didn’t need to raise capital,” framing the round as flexibility.
| Attribute | Rubrik | Glean |
|---|---|---|
| What it does | Cloud data management | Enterprise AI search and knowledge |
| Public status (Fortune) | IPO’d on NYSE in 2024 | Private; Series F closed June 2025 |
| Jain’s role (Fortune) | Co-founder | Founder and CEO |
What “Crazy” Looks Like at a $7.2 Billion AI Startup
Glean’s June 2025 press release shows how the lesson plays inside a working AI company. Glean had “rapidly surpassed $100 million in annual recurring revenue (ARR) in its last fiscal year,” per the release. Glean Agents, the platform launched in early 2025, was already powering “more than 100 million agent actions annually.”
- $150 million: Series F raised in June 2025, led by Wellington Management
- $100 million+: Annual recurring revenue (ARR) reached in less than three years of launch
- 100 million+: Agent actions run annually on Glean Agents as of the round
Glean was named to the 2025 CNBC Disruptor 50 list, per the release. It also landed on Fast Company’s 2025 Top 10 Most Innovative Companies list, the only enterprise AI company on it. The release frames the build as turning “AI’s potential into measurable business outcomes.”
Jain’s full reflection on the lesson sits in the original interview where he unpacks what he learned at Google. He made a related case in a separate June 22 Fortune piece, arguing America remains “the land of opportunity” for outsiders building AI startups. Both conversations sit on the same foundation: a Google lesson in the 2000s still being applied at Glean today.
The Latest Lesson Comes From Gen Z Hires
The lesson that began with Pichai now loops back inside Glean, pointed at a different audience. Jain told Fortune he takes the most notes today from his youngest hires. “They’re the ones who have not seen the things that I’ve seen,” he said. “They have new points of view.”
The same logic that applied to Pichai inside Google now applies in reverse, with fresh hires questioning the assumptions of a CEO who once felt like “an imposter” surrounded by Stanford and MIT PhDs. The same loop shows up in Jain’s own framing of his Google years: people arrive with strong credentials, and some “grow and shine” while others do not. Glean’s broader context is harder than Google’s two decades ago: Alphabet’s AI-era search dominance is under pressure from ChatGPT and rivals. Jain’s bet, made through both the company he runs and the people he hires, is that the next big idea will arrive from someone the room is inclined to dismiss.
Frequently Asked Questions
What lesson did Arvind Jain say he learned from Sundar Pichai?
Jain told Fortune the trait Pichai shares with Google co-founders Larry Page and Sergey Brin is the willingness to pursue ideas that look foolish on paper. His summary phrase: “You have to think crazy.” He tied the same lesson to Page and Brin: “They had no sort of constraints in their minds on what’s possible,” he added.
When did Sundar Pichai become Google CEO?
Pichai became CEO of Google in August 2015, per Fortune’s June 28, 2026 profile of Jain. He had joined Google as an individual contributor a little more than a decade earlier.
What is Glean currently valued at?
Glean’s most recent cited valuation is $7.2 billion, per Fortune’s June 28, 2026 profile of Jain. Glean first hit the same mark with its June 10, 2025 Series F, led by Wellington Management.
What did Steve Ballmer say about Google Chrome in 2009?
Microsoft CEO Steve Ballmer called Chrome “a rounding error to date” in a September 2009 interview, when his own company put Microsoft’s browser share at about 74 percent of the market. By 2012, Chrome had passed Microsoft’s Internet Explorer to become the world’s most-used browser.
When did Rubrik IPO and at what valuation?
Rubrik, the cloud data management company Jain co-founded, IPO’d on the New York Stock Exchange in 2024 at a valuation Fortune’s June 2026 profile puts at “around $5.6 billion.”
