At what point did you stop relying on inbound and start doing outbound?

One thing I've noticed while reading founder stories is that many SaaS companies eventually hit a point where waiting for inbound traffic isn't enough.
Content, SEO, referrals, and word of mouth can work, but they often take time to compound.
What I'm curious about is when founders decided to actively pursue customers instead of waiting for customers to find them.
Was there a specific revenue milestone, growth plateau, or realization that pushed you toward outbound?
Looking back, do you think you started outbound too early, too late, or at exactly the right time?
I'd be interested to hear how other SaaS founders approached that transition.

Author: Vane1st