> If your company has 10 teams of 10 people, your most important action is not saving $500 a month. You're (hopefully) earning a proportionally higher amount for your 100 people and you should continue to focus on that. If the software stack helps, don't fiddle with it to save a few bucks.
This type of thinking is prevalent on HN, but it's not always realistic. Most companies of a certain size have financial controls, and even if $500/month is not a lot of money in a relative sense, the number of $500/month line items for nice-to-have, this-helps-a-little products and services is reasonably limited.
Getting a budget for something that isn't in a "checklist cost" category can be a real headache, every vendor relationship has overhead, and instituting a new SaaS for 100 people (and getting them to actually use it) may have its own costs (staff time, etc.).
> Make iDoneThis better at managing the ever-growing complexities of syncing information when you have 100/1000/10k staff members and you have no damned idea what they're doing.
That's a fundamentally different product than what iDoneThis has today. To support development of that product, it will need substantially more than $1,000/month in recurring revenue, or it will need additional funding.
> Especially because quite a few hackers are thinking "you know, I could make that app and sell it for a few bucks less." Don't race them to the bottom, because Twitter is at the bottom at $0p/m.
If you build a business around a simple concept that requires limited functionality, you can refuse to engage in a race to the bottom, but it doesn't change the fact that you will almost certainly be undercut if others see a worthwhile opportunity.
In other words, iDoneThis can keep its $5/user/month price point, but if this is an appealing enough concept, it will have competition, and cheaper competition, before it ever obtains enough revenue to "re-invest the highish costs" as you have suggested.