I ve been thinking about how much company knowledge never makes it into the docs. Someone leaves and all the files are still there. Slack is still searchable. But the reasoning behind decisions and all those you had to be there details leave with them. How are you handling this at your company?
They paid more than anyone else. They also consumed more of my time than everyone else combined. Weekly calls, custom requests, escalations that weren't escalations.
I fired them. Politely, with a transition plan, and a real reason they could understand.
I have been thinking about how much time we spend explaining the same things to AI over & over again. Our projects, preferences, day to day work & past decisions, sometimes it feels like conversations are same & starting it from scratch. As I'm working on this problem, i'm interested how others here handle it.
Some questions like Do you keep your notes to AI, feed them every information? & just rely on built in AI Memory? Do you have any better way to keep your context organized?
This question has sat in the back of my head for months and I still don't have a clean answer.
For internal work the bar is forgiving. A draft brief with rough edges, a slightly off tone in a Slack summary, a CRM note that's 80% right. You fix it and move on.
Last quarter I raised the price of a small subscription tool I work on from $19 to $27 per month, about 40%. I braced for cancellations. Zero. Not one. But something else changed: the people who used to email asking for discounts just stopped emailing and the new signups pay full price without asking.
I think price is a filter not just revenue. A low price attracts people who doubt the value a higher price attracts people who've already decided. The bargainers weren't the best customers, they were the most expensive ones in support time.
So for those who've raised prices significantly: did your "annoying" customers disappear too,or did you just get lucky with a small sample? And the harder follow up: if you lost customers what was the actual churn rate and did the revenue still go up?
Last month a paying user asked for a feature that would directly contradict the main use case of a product I work on. Not a small addition a change that would make it worse for every other user. I said no politely. He didn't cancel but he also stopped giving feedback and I've been second guessing that decision since.
The part nobody talks about is that "sticking to your vision" sounds clean in theory but in practice it means watching a paying user go quiet and not knowing if you were right.
So for those who've been in this exact spot: when a paying user asks for something that goes against a product's core do you say no and risk losing them or add it and risk the product? And the harder question: what did you actually do the last time it happened not what you think you should have done?
Over the past year I worked closely with 10 founders. The 3 who moved fastest had one thing in common: when data contradicted their decision they changed course the next day. No ego no "I already committed to this." The 7 who struggled were often smarter better at arguing their original position more attached to the first plan.
This isn't a scientific study it's 10 people but the pattern was hard to ignore. The ability to change your mind quickly seems to matter more than the ability to defend your first idea.
So for those who've worked with or observed founders: have you seen this too or is consistency more important than speed of changing your mind? And the harder follow up: when was the last time you changed your mind within 24 hours of seeing data, and what did it cost you to do it?
I've been double-checking app permissions lately and it's surprising how many basic utilities demand access to personal contacts or background tracking.
When a product explains why it needs certain info and lets you opt out without breaking core features, it builds way more trust. Sharing sensitive data by default just to try a new tool creates unnecessary friction during onboarding.
How do you decide if a software product actually needs your personal details, and what data do you strictly refuse to share?
