Olivia Watson

We're getting close to launching, and I keep feeling like there are a hundred things we could be doing right now, but probably only five that actually matter.

For those who have launched before:

• What were the most important things you did in the final few days?

• Which social platforms actually brought people to your launch?

• Did X, LinkedIn, Reddit, newsletters, communities, or personal outreach work best?

• Was there any small tactic that made a surprisingly big difference?

• What's something founders should never do before or during launch day?

A few months back I set up custom instructions for Claude stop opening with agreement, tag its confidence on claims, push back when I'm wrong instead of validating me. Then I mostly forgot about it. Kept getting the normal helpful-assistant experience.

Last weekend, mid-project, it started actually doing what I'd asked. Pulled up my own past chats and launch checklist to see what I'd actually committed to. Called out that I'd blown past my own launch deadline without noticing. Refused to let me reprioritize a payment-provider decision over just talking to five actual users.
Told me a "quick bug fix" I described was actually five missing subsystems.

Was it mean? Maybe, some of it. But all of it was annoying in the specific way that's actually useful the way a good cofounder or an honest advisor is annoying.

Felt strange, Do I need this? Should I tone down the instructions?
I don't know if everyone can replicate this exactly.
Curious who else has tried shaping how their AI pushes back, not just what it outputs.

Everyone perceives entrepreneurship completely differently, and the weight of certain challenges varies from case to case. You always see things differently depending on the stage of life and business you're in, because your position is different each time.

• When I was a teenager my biggest problem was "What will people think of me when I will start doing this?"

• In my early twenties my biggest problem was "What if I can't figure out accounting, taxes, legal stuff?"

• Now I have a different problem how do I scale something?