Do what you know how to do.

Perhaps the #1 mistake I see in seasoned executives in SaaS that start companies is Grass is Greener Syndrome.

I see in particular seasoned Oracle execs wanting to do freemium because it’s so much “easier” and “the sales cycles are so much shorter”. They don’t see the high churn and the total mismatch for their skill sets.

We all get to the first $1m in ARR differently. The fastest, best way to get there is to do what you know. Enterprise folks doing enterprise. SMB folks doing SMB. Etc.

You don’t have to. But if you don’t, you’ll setting aside domain expertise and possibly a superpower. That’s a few strikes against you that you don’t need to have.

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