I run a small invite-only Matrix server for a handful of people, with federation turned off and the admin side reachable only over my Tailscale network. Your friends won’t need Tailscale at all. The usual pattern is a cheap VPS running a reverse proxy that faces the internet and passes traffic back to the box at home, so your NAS never gets opened up. Turning federation off also sidesteps most of the public-room and metadata worries people raised here, since it’s just your group. I also host Cinny next to it so there’s a web version nobody has to install, and I use it with SchildiChat Next on my phone to move files and notes between my PC and phone. For non-tech friends I’d point everyone at FluffyChat or the Cinny link and walk them through saving their recovery key on day one, because that’s where people get stuck.

Your end goal, friend, is noble, and I don’t mean to discourage you or gatekeep. And yet I must strongly advise you to slow your horses before you squander what I’d call your “social capital”, i.e. the willingness of the people close to you to follow your recommendations and try out new things. If they find their user experience greatly lagging behind what they’re used to, not only will they return to the services they were using prior to your suggestion: they will also be less likely to listen to you in the future and meet alternatives with skepticism, if not hostility. (“I’ve tried it and all this other stuff doesn’t work…”)

Thus, you need to make sure that they have an excellent first experience with whatever you throw their way. As a tinkerer, tech enthusiast, privacy advocate, or whatever you want to call yourself, you’re likely willing to accept a great amount of jankiness, pain, and lack of feature parity because you feel you get something more valuable in return. But that is not how most people use computers. Most people do not care about privacy, digital independence or any of the things you may cherish; they want things to “just work”.

And, to put it brutally bluntly (sorry!),

Like I think I’d need tailscale and docker (still dont get what docker really is)

this part alone tells me your solution is unlikely to “just work” for them. These are some basic skills to have if you want to try and compete with a billion-Dollar company and the convenience it provides to your friends.

So, my advice is this: don’t aim for “perfect”, aim for “better”. And basically anything is better than using FB Messenger, Whatsapp, Discord or whatever they may be using. Either go for one of the large public Matrix nodes (Matrix.org is unlikely to go down any time soon…) or move your comms to Signal messenger. Both may not be fully under your control (Signal is centralised, and Matrix nodes might be closed or defederated), but they’re e2ee and so professionally managed that your friends might actually enjoy them, use them on a day-to-day basis, and even pull other people over. That way, you’re also building social capital, so that once you’ve obtained the skill to run your own and get it to the level of polish it needs to have, they’ll be willing to follow you there too.

(If this posting sounds like I’ve learnt this the hard way, that’s because I have. Things are fine now, though: almost my entire social graph is reachable via Signal, and I’m preparing to self-host my own comms.)

You don’t need docker or tailscale or any of that crap. Your priority is controlling the service, not having the hardware physically at home: rent a vps and follow the social guidelines in https://runyourown.social/ . You don’t need fancy tech, only concrete social guidance.

I host Matrix and it is unfortunately not suitable to “normies”. There are just too many technical issues. I would recommend Fluxer instead.

But I can also confirm that the hardest part will be convincing your freinds to leave their beloved corporate platforms.

I moved away from matrix myself, too many tech issues, “normies” cannot use it (good fucking luck), all the apps are dookie, the public rooms have a CSAM issue, it was created within AMDOCS before being spun into The Matrix Foundation and I don’t trust AMDOCS, it pisses metadata and you basically have to federate with .org because it’s the “default.”

I’ve moved to Delta Chat, which runs off of Chatmail servers (and you can indeed host your own), the apps are good, It’s so easy your mother could use it (mine does), calls (video/audio) are working, location sharing on android, webXDC apps can be neat, they’re working on metadata (almost 0 iirc) and forward secrecy, it’s pretty good.

Bro, I heard you loud and clear. We don’t need no messenger. We’re in agreement - wind’s already blowing… When are the hookers arriving? 😆

Joke aside 😉 On containers]

you could host fluxer! They don’t have federation yet but they will soon, and I think there’s an easy multiple accounts switcher that helps. Fluxer has a nice user experience, closer to discord.

That said I use matrix with the sable or Fluffychat clients and it’s pretty alright, i’ve heard continuwuity is a decent server implementation. Sable has more features/functionality and fluffychat is more mature/stable

Matrix is indeed not so hard to setup , I have a couple running: one for a company with 50/60 users ( 3/4 years uptime and federated ) with synapse and some bridges and one for friends ( testing tuwunel) . The only important thing to remember is to save your recovery key for when you install another client. ( and in the latest times any decent agent can install and configure it for you )

Matrix isn’t trivial to host, at least with the official software, and I probably wouldn’t suggest to get into the topic with a “productive” service that’s a bit on the higher level to selfhost.

There’s some providers offering Matrix as a service, but they don’t seem cheap on my quick research.

There’s plenty it collectives offering Matrix for free and honestly them going down is not much more likely than you messing something up. If you don’t trust the smaller ones, you can still simply join matrix.org, which will probably last as long as Matrix is around.

I think with your anti slop, anti corporate friends I’d go for some leftist hobby nerd collective, check out this list: https://riseup.net/en/security/resources/radical-servers

I’ve set it up with docker as a service on a PC in my home and a rented virtual private server which the domain points to, which again routes the traffic to said pc using the static IP from Tailscale.

The rented server runs caddy which makes the routing more or less look like domain.tld { reverse_proxy <<pc_tailscale_ip>> }

Edit: The Matrix Server is the one thing I have not set up with docker, does not really matter for the setup