Dear Founder: Your email is different. Is it AI?
Paul Graham is a giant in the startup world. He co-founded Y Combinator, Silicon Valley’s hottest startup accelerator. He also coined “Founder Mode,” a management philosophy that has taken the tech world by storm in recent years.
He noticed a worrying trend of people using AI to create pitches.
Graham wrote about X: “Many of the emails I receive from founders are now written in a strong journalistic style. I know they are written by AI because no founder has ever written like this before.”
Graham wrote that once she realized the emails were generated by AI, she gave up, saying, “I feel like I’m being scammed. Who could defend that?”
Many of the emails I receive from founders are now written in a harsh journalistic style. I know it was written by an AI because no founder has written it this way before. And once you realize something was written by an AI, you can’t help but ignore it.
— Paul Graham (@paulg) May 25, 2026
Graham is not an AI pessimist. One commenter cited an April post that said AI gave hard-working founders “the growth they deserve.” Commenters called it “cognitive dissonance.”
“It should be used in the right way, just like any other technology,” Graham replied.
Investors in the startup have long been paying attention to the 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 discussion and gained support from people building large-scale language models. “This is so true, it’s hard not to ignore something written purely by AI,” Google DeepMind researcher Nathaniel Ruiz wrote.
In response to Graham’s post, Boom Supersonic CEO Blake Scholl added that AI lighting is “usually a bad idea.” He recommended that people write their own sentences before asking AI for feedback.
When writing, serial entrepreneur Zane Manzi writes, “turn on the AI slop radar and check yourself.”
Steven Sinofsky, former president of Microsoft Windows, commented that he remembered the first time he used a “text quality” printer as a freshman in college. His professors had mixed reactions.
“Many thought the ‘format’ was a distraction from the content and some kind of ploy on my part,” Sinofsky wrote. “Some thought the format made them look more carefully at their work. Still others told them to use the typewriter like any other student.”
Then came the Macintosh computer, and “everything changed,” Sinofsky writes. He wondered what that Macintosh moment could mean for AI writing.
Graham is one of many leaders across industries who are keenly aware of AI-generated writing. While Graham downplays the AI sales pitch, human resources managers are struggling with AI cover letters and resumes. Sometimes it works. The application may also be trashed.
Too much sophistication can hurt a founder’s chances. In April, Instacart co-founder Max Mullen said he was looking for a founder wearing dirty white sneakers. These founders don’t focus on their appearance. This shows that they work around the clock.
One commenter asked Graham why an email written by an AI wasn’t a good sign. This could be seen as a signal that they are “AI natives.” This is the same reason why techies flaunt high token fees.
Graham was not impressed. “Any teenager can do that,” he wrote.