• Garry Tan said he once passed up a role on Palantir's founding team to stay at Microsoft.
• It was a "$2-4 billion mistake," he said. He learned not to chase "what was hot."
• Tan eventually joined Palantir as its 10th employee. He now leads startup accelerator Y Combinator.

Garry Tan was employee No. 10 at Palantir. He regrets that it wasn't single digits.

On "The A16z Show," the Y Combinator CEO said that he was offered a place on the company's founding team — but he turned it down to stay at Microsoft.

Tan was in Stanford University's Phi Kappa Psi fraternity. His frat brothers included Joe Lonsdale and Stephen Cohen, two Palantir cofounders. Both were interning at Peter Thiel's hedge fund, Tan said.

He described one of Thiel's strategies: "When you start a thing, you write down on a piece of paper all the smartest people who you need to go and hire."

Tan was on both of their lists, he said. So, Tan said that Lonsdale and Cohen flew him down from Seattle to have dinner with Thiel.

Thiel said, "I'm so sure this is the right thing for you," Tan recounted. He also offered Tan a $70,000 check, Tan said, which would have matched his Microsoft salary at the time.

"I said, 'Thank you very much, Mr. Thiel, but I might get promoted to level 60 this year,'" Tan said. "Which I did."

He called it a "$2-4 billion mistake."

Palantir has since become a $420 billion company. It popularized an entire job category — the forward-deployed engineer — that is now replicated by many Big Tech companies. Palantir's stock opened at $10 per share during its 2020 direct listing; on Thursday, it was trading at over $175 per share.

Tan chalked his mistake up to chasing what looks hot. He compared it to an early career move in which he worked on Windows Mobile rather than sticking with web development. Then, the Facebook boom happened.

"Joe and Stephen were among the smartest people I'd ever met," Tan said. "If not them, who was I going to be a cofounder with?"

The universe was speaking to him, Tan said, but he didn't listen. "All I cared about was what was cool, what was hot, what would a really good investor say," he said.

Tan eventually made it to Palantir, of course. He learned: "Everything that's awesome in my life is kind of a cult." That cult should start with "some sort of truth or belief that flies in the face of an orthodoxy," he said.

It's "very punk, actually," he said.

Do you work at Palantir? Contact the reporter from a non-work email and device at hchandonnet@businessinsider.com, or on Signal at henrychand.30.

• Cooley is joining a sudden rush of law firms creating their own AI technology, with help from Legora.
• Cooley Go Lab is an online portal built to help startups with routine contract review and drafting.
• The portal will be available exclusively to founders in Y Combinator's summer cohort to start.

Law firms know more clients are asking chatbots for advice before ever calling a lawyer. So legal giant Cooley is building technology that it hopes founders will use instead.

Cooley plans to give select startups access to Cooley Go Lab, an online portal where founders can upload files and ask questions about their documents, Matt Bartus, global cochair of Cooley's emerging companies and venture capital practice, told Business Insider.

To build it, Cooley teamed up with Legora, a fast-growing legal technology startup that sells to law firms and corporate legal departments. Last year, Legora entered a new line of business with what it calls "portals" — white-labeled workspaces where law firms and their clients can work together on legal matters.

Cooley Go Lab is aimed at catching a common startup problem early, Bartus said. Founders often handle routine contracts themselves to avoid outside counsel's hourly rates. That can leave startups with a trail of messy agreements that their first in-house lawyer has to unwind later.

Legora founder Max Junestrand knows the problem well. When he started the company at age 23, he said he used an early version of ChatGPT to rewrite contracts. Junestrand, a software engineer, not a lawyer, said he let some early contracts include an unlimited liability clause — a provision that can leave a company exposed to damages far beyond the value of the deal.

"When our general counsel started, she freaked out," he said.

Cooley is now trying to give the next crop of founders a way to use artificial intelligence to move faster, but with a law firm's guardrails around it.

Cooley Go Lab will have a limited rollout to start. It will be available first to startups in Y Combinator's summer cohort.

Much has changed for startups since Legora's turn in the famed startup accelerator. Teams can write code and release technology faster with coding agents. They are signing customers and growing revenue earlier, and the hottest companies seem to be raising funding nonstop. But moving faster also means legal work that once came later in a startup's life is being pulled closer to the beginning.

At Y Combinator, partner Gustaf Alströmer is seeing that shift play out in real time. In the last batch, a record 14 startups reached $1 million in annual recurring revenue — the amount of revenue a company expects to collect over a year. Alströmer said giving founders access to tools like Cooley Go Lab could help them keep that pace without creating contract-slop.

The portal includes features that review documents like nondisclosure and contractor agreements and flag issues for founders to consider. The tool also draws on Cooley Go, the firm's central hub of standard startup forms, templates, and guidance.

If you can't beat 'em, join 'em

Law firms like Cooley are facing a new reality. The better the frontier models get at legal work, the more founders and in-house lawyers may decide they can handle situations themselves rather than send them to outside counsel. Anthropic is trying to make that easier with new tools built for contract review and drafting.

Law firms are now figuring out how to stay relevant as more legal work becomes software-enabled. Some are building their own tech. Kirkland & Ellis has tapped Palantir to help it build tools to manage parts of the firm's private funds practice, while Freshfields is working with Anthropic on software that could eventually be sold to other law firms. Harvey, a leader in legal technology, says it's getting into training custom models for law firms.

Taken together, the moves point to a new attitude spreading across Big Law: If clients are going to use artificial intelligence anyway, law firms want to shape how they use it.

Bartus doesn't seem especially concerned about losing business to in-house legal departments. Cooley has been on a hot streak. Profits rose 6.7% to $922 million last fiscal year. The firm also scored a fair use win for Meta in a copyright case involving its model Llama last year, and it advised Jony Ive's hardware startup Io in a $6.5 billion sale to OpenAI.

Bartus is confident that companies will continue to depend on law firms for the important work. Cooley Go Lab, he said, is meant to help founders handle routine legal work more cleanly, not replace lawyers.

Cooley says the tool is not protected by attorney-client privilege, so founders will need to be careful about what they upload because those materials could be turned over in litigation.

"If you want actual legal advice," he said, "you need to talk to a lawyer."

• Young tech startup founders are having a moment in the AI era.
• From teenagers to 20-somethings, these founders are raising millions.
• Take a look at the pitch decks some of these founders shared with Business Insider.

Tech is no stranger to young founders.

Steve Jobs was 21 when he cofounded Apple in 1976. Mark Zuckerberg was 19 when Facebook launched. Whitney Wolfe Herd was 25 when she unveiled Bumble.

Many of today's startup founders are still young and scrappy. And in the age of AI, they're even more empowered to barrel ahead.

Some are following the footsteps of tech titans before them and dropping out of college. Others are opting out of the undergraduate experience altogether, with a few ditching high school to pursue careers in tech.

Arlan Rakhmetzhanov, founder of AI coding startup Nozomio, told Business Insider that he dropped out of high school in Kazakhstan after getting accepted into the competitive startup accelerator program, Y Combinator (YC). At the age of 18, he raised $6.2 million for Nozomio.

Rakhmetzhanov isn't the only teenager finding success in AI. There's also Toby Brown, a UK teen who raised $1 million for his AI project. There's also Zach Yadegari, the teenage cofounder of Cal AI, a nutrition app.

College-aged founders are also building companies and raising capital, such as the Yale students behind Series AI, a new social networking startup.

The median age for YC participants is now 24 years old, compared to 30 in 2022, YC's Pete Koomen told The New York Times in August.

Business Insider has interviewed the founders of 12 startups who are 25 years old or younger and have raised millions in funding since 2024 about the pitch decks they used to impress investors.

Read 12 pitch decks founders who are 25 years old or younger used to raise millions:

Note: Founders were 25 or younger when Business Insider published the following articles.

Series A

• Posh, an events platform, raised a $22 million Series A when its founders were 23. Read the 12-page pitch deck it used.
• Clyx, a startup trying to connect people via in-person events, raised a $14 million Series A when its founder was 25. Read 22 pages of its deck.

Seed

• Ditto, an AI dating startup founded by UC Berkeley dropouts, raised $9.2 million when the founders were 23 and 24. Read its 12-page pitch deck.
• Lyra, an AI video call startup, raised a $6 million seed out of YC when its founder was 23. Read the 8-slide pitch deck it used.
• Nexad, an AI adtech startup, raised a $6 million seed after wrapping up A16z's Speedrun accelerator. Nexad's CEO was 25. Read the 10-page pitch deck.
• Orange Slice, a YC-backed sales tech platform, raised $5.3 million when its founders were 23. Read the 7-page pitch deck.
• Golpo, a generative AI video startup, raised a $4.1 million seed out of YC when its founders — who are also brothers — were 19 and 20. Read its 7-page pitch deck.
• Bluejay, an AI agent startup, raised a $4 million seed coming out of YC when its founders were 23. Read its 9-page pitch deck.
• Novoflow, an agentic AI startup building tools for medical clinics, raised $3.1 million when its founders were 18 and 19. Read its pitch deck.
• CodeFour, an AI police tech startup, was founded by two 19-year-old MIT dropouts and raised $2.7 million coming out of YC. Read the pitch deck.
• Cerca, a dating app that connects people with mutual friends, raised a $1.6 million seed when its CEO was 23. Read the 10-slide deck.

Pre-seed

• Series, an AI social networking startup, raised a $3.1 million pre-seed when its founders were 21.

This story has been updated with additional examples.