Don't Use AI When Emailing Paul Graham - Business Insider

Paul Graham just rejected founders because their emails sounded like AI wrote them.

That should tell you something important — and it's not "never use AI."


If you've paid for an AI tool that nobody on your team actually uses, you're not alone. Most business owners hit the same wall. The tools are confusing, the promises are vague, and somehow the results never match the pitch.


Here's the real lesson from the Paul Graham story:

AI fails when it replaces the human judgment call. It wins when it handles the repetitive work behind that call.

Founders got rejected not because they used AI — but because they used it in the wrong place. Relationship-building moments require your voice. Data sorting, draft prep, and follow-up scheduling don't.

That's the distinction most AI consultants never teach you. They sell you a tool. Nobody shows you where the boundary is.


One thing you can do this week: identify one task your team does more than three times a day that follows the same pattern every time. That's your first AI candidate. Not your sales pitch. Not your client emails. The repetitive back-office stuff nobody enjoys.

That's where your first real win lives.


What's one task you keep doing manually that you suspect AI could handle — but you haven't trusted it enough to try?


#AIForBusiness #SmallBusiness #BusinessStrategy #AIImplementation

Original Source

Y Combinator cofounder Paul Graham wrote that founders were emailing him in a "hard-hitting journalistic style" — which he considers a clear AI ...