I had a letter of intent for a large order right before the company froze budgets and the point of contact left, it was for $9k/year if I built an API for them to manage their domains inhouse. Currently they had a vendor they were paying $15k/mo and then on top of that $150 each time they wanted to add or edit a new link or domain. It was a win/win, our service remained viable, I could afford to make it better, and they have a 90% reduction in cost for that service.

Even if it had worked out, it still really wasn't worth it to increase revenues by $9k unless I was closing this sized deal at least monthly.

TBH, the price difference makes me think you underbid.

If the service is worth 150k a year, you could of sold it for 75k. Then it becomes possible to hire someone else to handle the day to day.

I think you made the right choice, having 10$ a month clients who expect hours of support per month isn't practical.

Interesting. I would think that $9k a month rather than year would've been better. $9k a month is really undercutting it. I've also seen that higher prices actually make customers more willing to buy, not less, especially big ones.

This was after many back-and-forths. So we put together a contract that would be the same price as if they were a customer using our UI, but they would pay all at once instead of each time they added a domain, and they would get an API to manage their domains.