Don’t use AI when emailing Paul Graham

Dear founders: your emails read different. Is it AI?

Paul Graham is a titan of the startup space. He cofounded Y Combinator, Silicon Valley’s hottest startup accelerator. He also coined “founder mode,” the management philosophy that’s swept tech in recent years.

He’s noticed a trend that worries him: people using AI to write their pitches.

“A lot of the emails I get from founders are now written in a hard-hitting journalistic style,” Graham wrote on X. “I know they’re written by AI, because no founder ever wrote this way before.”

Once he realizes the email is AI-generated, Graham wrote he gives up: “It feels like being lied to, and who would stand for that?”

Graham is not an AI pessimist. One commenter pulled a post from April in which he wrote that AI gave hardworking founders the “growth they deserve.” The commenter called it “cognitive dissonance.”

Graham responded: “You’re supposed to use it, but in the right way. Like any technology.”

The startup investor has long been on the lookout for signs of AI-generated writing. In 2024, he wrote that he looked for the word “delve” as a sign of ChatGPT’s influence.

Graham’s post sparked a debate — and got support from those building the large language models. Google DeepMind researcher Nataniel Ruiz wrote: “It’s so true that it’s hard not to ignore something written purely by AI.”

In response to Graham’s post, Boom Supersonic CEO Blake Scholl added that AI writing is “usually a bad idea.” He recommended that people do their own writing before asking AI for feedback.

Serial entrepreneur Zain Manji wrote that, when he writes, he will “turn on my AI slop radar and check myself.”

Former Microsoft Windows boss Steven Sinofsky commented that it reminded him of when he first used a “letter quality” printer as a freshman in college. His professors had mixed reactions.

“Many thought the ‘format’ distracted from the content and was some sort of ruse on my part,” Sinofsky wrote. “Others thought the formatting caused them to look more carefully at the work as a result. Still others told me to use a typewriter like a normal student.”

Then, the Macintosh computer premiered and “everything changed,” Sinofsky wrote. He wondered what that Macintosh moment would be for AI writing.

Graham is one of many leaders turning up their noses at AI-generated writing across industries. While Graham looks down upon AI pitches, HR managers contend with AI cover letters and résumés. Sometimes it works out; other times, it can get your application tossed in the trash.

Being overly polished could hurt a founder’s chances. In April, Instacart cofounder Max Mullen said that he looked for founders with dirty white sneakers. These founders aren’t focused on their appearance — a sign that they’ll work around the clock.

One commenter asked Graham why the AI-written email wouldn’t be a good sign. It could be seen as a signal that they’re “AI native” — the same reason techies are flaunting their high token bills.

Graham wasn’t impressed. “Any teenager can do that,” he wrote.