My three biggest lessons from last weeks launch

_{Day 201/100}

Hey—It's Tim. 

Wave One of Penfriend.v3 dropped on Friday.
Here’s what I seem to forget every time we launch…

Start earlier…

We did a three-week “official” launch sitting on top of six months of slow seeding in this newsletter.

That combo worked - and I still felt late.

I wish I would have started a week or two sooner.
Because the final 7–10 days compress into weird chaos: pricing pages, copy swaps, legal commas, screenshots you thought you had, partners who say “can we post tomorrow instead?”.

When the countdown is real, people finally reply, real questions show up, and that’s when the story gets good.

I wanted two extra beats to let those moments surface without stealing time from the actual ship. Next time, I’ll give the clock more runway.

Your sleep pattern is the least of your problems

Every launch scrambles my circadian settings like an airport omelette.

First launch we did, I slid into PST while living in the UK.

This time, I was lights-out around 1–2am and bolt-awake at 6:30am. Both rhythms “worked,” neither was the real issue.

The drag is the stack of half-decisions that followed me into bed. I’ve worked out that I can operate tired IF the big calls are truly decided.

What kills me is lying there replaying pricing language, a nagging edge case, or whether that GIF actually loads on mobile.

Then I wake up and re-debate it all with launch adrenalin humming in my ears. By demo day, nothing’s technically broken—but I’ve spent all my focus on ghosts.

My body will survive a janky week or three; but my mind hates open loops.
I have to close them early or they follow me into every hour, rested or not.

Stripe is the worst thing. Every time.

We shipped a chunky pricing update with bonus credits.

Dev review, checks, deploy? Smooth.

Stripe? Like wrestling a polite octopus in a broom closet.

The “take money” part is frictionless; the “update literally anything” part turns into a scavenger hunt: products vs. prices vs. trials vs. proration, coupons that touch one plan but ghost another, a checkout link that worked yesterday deciding it’s allergic to taxes today.

I’ve genuinely spent less time pushing a release to production than renaming a price ID and confirming receipts look human. Every launch reminds me that code is deterministic; payment platforms are ass.

More launch lessons coming. Got questions? Hit reply - I’ll be as candid as you want.

For solo creators who want clean, publish-ready copy, you can check out the new Penfriend here.

See you tomorrow.

✌️ Tim "Stripe Any% Speedrunner" Hanson
CMO @Penfriend.ai

Same brain, different platforms: X, Threads, LinkedIn.

P.S. I’ve been keeping a log of all the sh*t that goes wrong during any launch we’ve done.
Should I drop it?

Penfriend.ai
Made by content marketers. Used by better ones.