I would have several questions before negotiating seriously, and I could actually be in the market for such a beast.
At what multiple would you be comfortable considering selling? If revenue has dropped 85% from its peak, have you identified the cause of the drop? Has it been steady that past five years? Do you have a record of the time spent on it, or does it just feel minimal? How much of revenue is from ads vs subscriptions? Is it sticky mainly because a user can’t export things and import them to Google Calendar or something?
Is it custom software, heavily customized software, or are you basically selling the calendaring component of something like Citadel or Horde? What languages are in use? Does the buyer get just the site or full ownership of the codebase and the rights to derive new products and services from it? Does it come with the domain and trademarks?
Are you selling outright, or are you reserving some royalty for yourself?
What does the handover look like? Does the buyer just get an email with URLs and login credentials, or do you plan on familiarizing a buyer with the whole thing?
The site is localendar.com (you can reach me through the Contact Form there and I can share more financials). Short version: I started back in '99. There were no good calendaring engines back then so I had to build my own (with wicked performance btw ;_). The site is Java/SQL Server. It's sticky b/c it targeted webmasters who needed an easy-to-update calendar for their own site.
The original goal was to aggregate all these local events into a single searchable index and serve up local ads alongside. I never really got that part to take off, though I did get a very early patent for local search on the web. Since then, calendaring libs have come along which allowed many site-builder tools to offer a built-in solution.
The primary reasons for declines are 0) Not as many people build raw sites anymore; people migrate to things like Wordpress or Wix) 1) Google showing less profitable ads and 2) Webmasters w/ a popular site can remove ads via a subscription (which are drastically underpriced; some are still on a legacy $9.95/year). Everything is exportable (and importable) via iCal if desired. Buyer gets everything, w/ no residual royalties to me. I'd have to have an active role in the handover since it's all bespoke code. The buyer would need some level of Java+T-SQL since I don't want to teach coding from scratch.
I love my users and many rely heavily on the site - it's meant to be very simple to use and I tend to draw an older demographic that doesn't need a lot of fancy bells and whistles. 26+ years is a lot of time and I don't have the passion for it I used to. I had a recent health issue and my wife is concerned that she wouldn't know how to close this out gracefully if the worst ever happened.