Sad to see a useful product self destruct this way through what I would basically label as incompetence. The UI was always a bit of a mess but at least they had the community which made it tolerable. Like many old websites, it seemed to get by without any apparent major attempts to address any of that. Then they alienated meetup organizers by charging for starting new meetups and now they are sealing the deal by pissing off the users as well. Since plenty of alternatives seem to be available, including some open source ones, I don't think this will end well for them.

In short, this is corporate stupidity. The premise of properly running a site like this is that scaling it is relatively cheap and you can charge for add on services. Meetup.com never really bothered to do add on services. Now that they have a bloated organization with (apparently) clueless executives struggling to come up with a monetization strategy to justify years of hiring useless people doing useless things (as opposed to fixing their UX while not alienating their users and coming up with a plan for making some money).

For example, ticketing was never a thing on meetup.com. This was an obvious missing feature five years ago. Making that opt in for organizers and taking a cut would have made it an awesome tool for anyone organizing paid trainings or workshops. That money is mostly going to others like Eventbrite; which lacks any form of community but gets healthy revenue from people organizing paid events nevertheless. Back in the day lots of meetup.com events would actually tell you to go to eventbrite to get a ticket. That's how obvious the need was for this feature. Eventbrite got big on meetup.com being asleep at the wheel.

Another source of untapped revenue is facilitating commercial sponsoring deals. Many meetups are sponsored financially (and with venues, beer, and other support) by companies. Those companies might like to advertise that they are doing that with some branding. That's something you can charge for. Not a thing on meetup.com either.

If you have sponsoring and paid tickets, a next obvious thing to charge for is promoting the events to sell more tickets. Doesn't seem to be a thing on meetup.com either.

Most conferences are just big meetups. Not a thing on meetup.com either. Most paid events flock to other platforms because meetup.com doesn't do anything useful for them. Meetup.com has been leaving money on the table for as long as they exist and instead of fixing that, they are now self destructing.

Whomever ends up buying meetup.com from WeWork would do well to just get rid of the current management (because they add negative value) and rip out all forms of payments and pricing already in place and go back to basics. Then restore and nurture the user base back being healthy and start doing all of the above to make some money. I'd also recommend scaling down the team to a small core of developers, community management and a smart marketing team. Which is probably what it was in the early days. Focus the team on community growth and real monetization opportunities that serve instead of tax that community. That would be a new thing for them because they have never done that.