Stunted Adolescence: The One Call You Need to Make Before Signing

If you are a founder staring at a term sheet with a dizzying valuation, I am urging you to do one specific piece of diligence before you sign.

Find a founder from the “Class of 2021” who was in your exact shoes.

Find someone who raised a massive round at a 50x–100x multiple. Buy them a coffee and ask them:

• “Did the high price help you win or did it freeze you when the market turned?”
• “What does your cap table look like today?”

Why? Because I’m seeing a dangerous pattern re-emerge. We call it “Stunted Adolescence.”

In 2021, we confused tech-enabled services with software. We gave companies “adult salaries” (massive valuations) before they had “adult skills” (margin discipline). In 2026, we are doing the exact same thing with AI Tools vs. Platforms.

As Jason Lemkin noted on X: You can technically fix a valuation that’s too high. But there is no fix for raising more money than your exit value.

The Verdict: Don’t let the market rob you of your adolescence. Those awkward, scrappy years are where the real muscle gets built.

Do the homework before you sign!