The Memo

We are entering a 24-month window that will redefine venture capital, and most investors are still grading AI-native companies on outdated SaaS frameworks. Firms built for the last wave will be miscalibrated for this one. Here is the shift I'm watching, and the one thing about these companies I still can't price.

You build the deck. Twelve slides, maybe fourteen. You agonize over the order. Problem, then solution, then market size that you both know is made up. You export it to PDF so the formatting holds. You write the cold email. You rewrite the cold email. You find the partner's address through a friend of a friend, or you guess the format and hope it lands. You hit send. Then you wait.

Most founders are still drawing the org chart from the last decade, a pyramid that scales headcount with ambition. AInative founders are already building differently: two roles, not ten layers, orchestrators and agents. Drawn this way from the first week, a startup can test, pivot, and reach conviction before hiring anyone to scale.

Most founders who call themselves AI native are running a normal company with a ChatGPT subscription and a Cursor seat. The real ones build differently from the first week. Here are the three tests I run, and the questions I still cannot answer.