>both of them scoffed at the idea of paying for email.

The problem is? google provides better email service, for free[1], than most pay providers. I am /exactly/ the sort who would run a for-pay email service; I wrote my first sendmail .mc before I was old enough to drink, (and that was back when sendmail was still a thing) and I've been maintaining mailservers longer than that. Also, I have a reasonable reputation for transparency.

But I don't think I could compete with Google. I mean, sure, I could get you a much more private service, but for what people expect to pay, I just couldn't do as good of a job of actually maintaining the mailservers as google does. Hell, even if I could charge 1998 rates, like $5/box/month (which I can't) I don't think I could do a better job of that than google.

If you really want the full privacy benefits of having private email (e.g. being able to know something is /really deleted/ when you delete it,) you have to run your own mail server. Doing this well is a fair spot of work, probably more than $5/day worth of work (I mean, if you are compensated well enough that a latte is worth $5 more than a drip coffee with milk made at home. It is a non-zero amount of work, and you do have some sort of 'emergency' work every couple of years; something that is broken that is causing mail to bounce. Personally, I rate 'emergency' work as more expensive than the kind I can do on my own schedule.)

[1]I mean, in exchange for whatever monetary value they can extract from running their automated advertising tools against your data.

You might have been able to get my business if it wasn't too late - I've gone with fastmail.

The gmail web interface has become really annoying of late. I don't think it's an impossible task to do better than them by any means.

>The gmail web interface has become really annoying of late. I don't think it's an impossible task to do better than them by any means.

Google exposes the mail through IMAP, no? why don't you use your own mail client with the google backend?

I've written support software for and modified open-source pop3 and IMAP software, and I've gotten partway through writing my own SMTP server, but I never even /considered/ writing a client interface for mail. If I'm providing mail service, I will provide you mail service, and give you smtp and IMAP (encrypted, of course) interfaces to that mail service. Heck, I might support an open-source imap to web interface, too, but the way I see it? running the mailserver and running the mail client are two very different things. If you primarily choose your mail provider based on the provided web interface, you are probably not going to be a good customer for me, because I consider the mail client to be outside of my domain as a SysAdmin. Also, I come from an era where web-gateways to IMAP were considered some kind of cruel joke.

I'm not saying that interfaces are unimportant, but it's a very different product than just managing mail servers. I'm good at managing mail servers. I have a difficult time coming up with someone who would be less qualified to write a custom web interface. (I mean, unless the current open-source imap-to-web interfaces are good enough; I can manage open-source software just fine; I'm just not a UI kind of person.)

Personally, I wouldn't expect the sorts of companies that are best at running mail servers to also be the best at writing mail clients. That, and I wouldn't want to give up control of my client to other people, because a lot of what makes up a user interface is personal preference. That, and there's no real advantage to having the same people run the server and the client; IMAP is well-standardized.

It's not paying for email, it's paying for a particular kind of privacy: you're basically paying to prevent software from reading your email to better match ads. To me that is not worth much. I don't care if software reads my email, and I don't care if my email interface contains a few text ads.

As far as I can tell, paying for your email does not get you any real increase in privacy. Rackspace staff can read your email just as easily as Google staff can read Gmail (it's strictly against company policy in both places, but still technically possible). If the FBI issues a subpoena for your email, both Rackspace and Google will be legally compelled to give it up.

It is more than just privacy.

When we don't pay for email, we are at the mercy of free email providers. They can terminate our account for any reason, without no appeal whatsoever. It has happened before.

Email is fundamental, it is the one foundation on top of which we do things on the internet. Forgot password, bookings, registration on a new site - every single one of them is via email. And most of us happily trust Google (or Microsoft etc) with our email, without paying a penny. I'm not saying these companies aren't great, or willfully do something bad with our data (they won't - if anything, gmail is really nice, except for UI) - It is just that they have no incentive to help us when we get in trouble (account getting hacked, for example). After all, they are a business, not charity.

Email is just one example. It surprises me that people wouldn't pay for important things (even when they are cheap) but would happily pay for overpriced coffees, popcorns in theaters (huge rip off) etc. Same with those who buy only "branded" items, even though many times the non-branded items are nearly as good and are cheaper.

I agree that paying for email does not increase privacy. I have a domain and pay for hosting and email on it, and the staff there can just as easily read it as Google staff could read gmail.

However, there is a difference from an organizational pressure perspective: with gmail, I'm not really Google's customer. With hosting, I am the host provider's customer. As a result, the nature of the business relationship is more clearly defined and they have less incentive to play fast-and-loose with the "rules". (Excluding legal mandates, unethical employees, etc. which are an equal exposure either way)

The reason I pay for email is that the free services all do a poor job with their Web UIs in my opinion. Putting things like links to their other services, toolbars for their social networks, etc. in my email application is unwanted.

I feel that I was a bit late to the game at 24 to buy my own domain and host my email. For one, I can stick to atleast the address for my life unless, you know, the ICANN is overthrown or something. Having something professional costs way less than any of the impulse purchases that people around me make yet they scoff at the idea of paying $10 for domain and w/e else for email. You can also set it up for free if you spend a few hours on google.

It did take me time, but I have realized that emails and email addresses are NOT going away anytime soon, might as well have something permanent.

Actually people are making a wise financial decision when they do this -- email service is something that you cannot stop or easily change overnight; coffee is something you can. If and when they are in a serious financial crunch (and even the moderately rich worry about this happening), they can stop spending the $5 on the latte, but if they used a paid email service they cannot stop spending the money on the email service because it is usually very critical to a lot of their future. With free and relatively good email services like YMail, GMail and Outlook, it doesn't make sound financial sense to spend money on a paid service that is critical to your daily life that you cannot cut it off when you are in a financially bad situation. Also the same people would go for free coffee if someone did offer free coffee daily at the same quality level as their favorite latte shop.

That's somewhat backwards.

If you've told everyone your email address is myname@somefreeprovider.com, it's almost impossible for you to move for whatever reason. The switching costs are actually very high. If it's myname@mydomain.com, you can move your email provider at will, and you're unlikely to ever be forced to pay more than $10 per year, which is pocket money for most folk.

Actually, I don't know of a good solution to running your own email addresses on a custom domain that doesn't involve paying a little money.

So yes, if you don't mind having someone elses company name in your main identity on the web, that's fine (along with all the portability tie in problems and privacy). On the other hand if you want me@myname.com then you'll probably be shelling a little money out.

And fastmail provides other services too, that people might be more used to paying for, e.g. static webhosting with webdav support for upload, custom dns control. Contacts accessible through ldap, distribution lists, sms, detailed control over login including OTPs etc.

I've switched recently and do not regret it. It gives me a lot of the flexibility I had years back when I ran my own mail server, and none of the massive pain.

It's not an issue of feeling entitled to service. If there were no free email providers, or if the paid services were noticeably better on any of the axes I care about, then I would be happy to switch to a paid provider. But gmail exists, as do scores of other excellent providers with stellar reputations, and I don't see a point in paying a premium for equivalent service just for the sake of being a paying customer.