Investors asking Founders to have longer vesting and cliffs is seen as hostile

Investors asking founders to have longer vesting and cliffs (like 5-year vesting with 2-year cliff) is often seen as hostile by founders.

Here’s why this misconception happens:

Founders don’t realize how the VC path works: in early-stage startups, there’s always another round where new investors will scrutinize the company. The vesting is designed to safeguard the company and its cap table.

Think about it: Would you feel comfortable if a founder could leave the company in a year or two and take 20% of the company with them?

What does a new investor think about that 20%? Most likely that this company has 20% of its cap table not contributing to its success.