I'll start with the punchline. This is what I use (I'll go into detail on each piece later):
- Postbox for email, calendar and address book. Great thick client email client for Windows or Mac.
- Fastmail.fm for great IMAP.
- Lightning add-in for Postbox to add calendaring to Postbox.
- Google Calendar provider add-in for Postbox as the back-end store for Lightning calendar.
- Zindus add-in for Postbox as contact sync between Postbox and Google contacts.
- Virtual Identity plug-in for Postbox to manage multiple aliases off the same email domain.
Here's some more info about each piece.
It's a derivative of the open source Mozilla Thunderbird and founded by one of the long time engineers on Thunderbird (a really smart guy that I originally hired out of MIT a long time ago at Netscape). You can read more about the PostBox folks here and also visit their main site.
Postbox has a lot of capabilities beyond Thunderbird, but the #1 killer thing for me is that everything is completely indexed. Just type a piece of text and anywhere it exists in Postbox up it comes. Searches can be without context or can be directed to find text in a particular field of email). Beyond that it has the best conversation view I've ever used which can help a lot when you've got a lot of email. Unlike Thunderbird, it isn't free, but it doesn't cost much either and I find it more than worth it, particularly when it's paired with the other tools in the set.
You can find a more comprehensive list of features here.
Fastmail.fm (great IMAP)
I've been a long time IMAP user. The benefits of server-based email are obvious to anyone who accesses their mail from multiple places. But, nowadays you need a lot more than just plain IMAP. I've had previous IMAP providers that were very poor compared to Fastmail.fm. When I started with Fastmail.fm, Google didn't have IMAP. Google is a more interesting option now that's it's free and has IMAP, but they still don't have everything you will see below. These are the kinds of features I use at Fastmail:
- A large amount of storage (fastmail gives you 6GB of space in their enhanced package that I use). The whole deal about server-based storage starts to break down if you run out of storage and have to start archiving your email somewhere. As soon as you do that, you can no longer get to your stuff from anywhere. You need lots of online space. Fastmail also has a nice feature that you can set certain folders to "age" away after an email gets to be a certain age. This works great for implementing a document retention policy or for just cleaning up your trash folder regularly or for folders where I have mailing lists sent to as they just automatically age away old emails in 90 days - never any manual cleanup required.
- Server-side filter rules. If all your mail filters aren't on the server, then they don't work everywhere. Fastmail has a rich server-side set of rules. You can either define rules in their web interface or you can even geek out and define your own logic in SIEVE which gives you limitless logic possibilities for rules. You can base a rule on any RFC 822 header field. Compared to Outlook, here's where it's nice that you have full access to everything that internet mail has and knows about.
- Great anti-spam. There's nothing more frustrated than being so inundated by SPAM that email is just frustrating to use. You crank up the protection and then you start losing important emails. I honestly don't know how fastmail does their anti-spam, but it is simply amazing and it really works. I went from hundreds of undesired spam emails a day to one or two a week and I've had no reports of a missed email from a false positive in the last year. I know that their server blocks lots of attacks before they get to your mailbox by blocking many techniques that spammers use. If you want to make it even better, you can train it with Bayesian techniques by just giving it a bunch of samples of good mail and bad mail. It also has white lists and black lists, but honestly I don't use that stuff. What they have just works. By comparison my gmail email account (which I don't even use of give out the address to anyone) gets multiple SPAM mails every single day.
- Web Access. Fastmail.fm has a pretty decent web access. I don't use it regularly and it's not meant to compete with gmail for web features, but if you need access to your mail from the web, it works.
- My own domain. Fastmail.fm has lots of different options for using your own domain.
- Multiple mailboxes. I use an anti-spam technique where I give a different mailbox address to every single web-site on the web that I use (facebook at the-friend-family.com, linkedin at the-friend-family.com, smugmug at the-friend-family.com, for example). Fastmail.fm lets me send these all to the same mailbox or designate some of them as separate mailboxes. This way, if I start getting a bunch of SPAM from somewhere, I can see who gave out my email address, I can change my email address on that site (if I want to stay a member with them) and I can then block all the email from that address forever. You'd be surprised to see who sells your email address. It's really pathetic. Those of you who know me know I love to play golf. As such, I use some of the online golf reservation systems. These guys are terrible. They either have horrible security and get broken into or they sell your email address all the time. Fortunately, I can just kill a SPAM email address in a minute or so and never get another bad email on an email address that got away to the spammers.
- Good, rock solid IMAP. Oh yeah, the big one is rock solid IMAP. Fast, reliable, secure (runs over SSL), hierarchical folders, etc... This may seem like a no-brainer, but I've seen some bad reliability on the service I used before this one. I have literally never seen an IMAP outage with fastmail.fm.
- Good, rock solid SMTP. Let's me do what I need to do (including sending from all my various email aliases). Authenticated SMTP, ability to send large files, works over SSL, etc...
- Allows good sized attachments (sending and receiving). Fastmail.fm allows attachments up to 50MB in size. I've lately been sending around a lot of legal documents (doing work for lawyers, not in trouble with the law) and it's really nice to be able to just attach and send and not wonder if you're bumping into the 2MB attachment file size limit that many systems have.
Lightning for Calendar
If you install the Lightning add-in for Postbox, you get a decent individual calendar inside of Postbox. If you further add the Google Calendar plug-in, you can keep your calendar on Google (as a server-based calendar), but access it through Postbox. Just configure multiple copies of Postbox on different computers to point at the same calendar and you now have the same calendar view everywhere. You can also use the web access to Google calendar at anytime to see/modify your calendar from a browser. In a nice twist with Google calendar, you can also specify one or more users that you can share your calendar with (like my wife or an assistant, for example). You can designate them separate access without giving them your Google login. And, now that your calendar is on Google, you can of course synchronize a range of phones with Google. Google supports ActiveSync for contacts, calendar and email so any phone that supports ActiveSync can sync with Google (that's a lot of phones - all Windows Mobile phones, iPhone, many Nokia phones and Pre for example). And, of course, all Android phones can sync with Google. This is by far the richest mobile support you get anywhere.
Zindus for Contact Sync
Zindus is a another plug-in for Postbox and it gives you contact sync with Google Contacts. While I don't use Google Contacts directly, what this lets me do is to sync multiple computers of Postbox with the same set of contacts. And, in a pinch, my contacts are available online if I need to look something up.
Zindus works great, but it is a bit in it's infancy. It will currently only sync one address book so if you use multiple address books, it is a bit compromised in that regard. It also doesn't handle distribution lists in Postbox yet. Apparently there is some design flux in the how the APIs access distribution lists and that has kept Zindus from getting this done. There also isn't a perfect match between the address book fields in Postbox and Google Contacts, but all the basics that I use are there. Here's the FAQ on syncing the two. I had to tweak a few things to make it work well, but after that it's been trouble free. To handle the few distribution lists that I use regularly, I put them into Google groups so they are now true mailing lists (and thus they work everywhere).
One of the ways I manage SPAM is by using lots of disposable email addresses. Since I have my own domain, I can configure email@example.com to go to the same mailbox. Then when I sign up for a new web-site (let's say it's widgets.com) and I have to supply a working email address in order to register, I just give it the email address of firstname.lastname@example.org. Now that web-site has a unique email address. If I suddenly start getting a bunch of new SPAM, I can see exactly what email address the SPAM came from and I can kill that email address if I want. So, what does all this have to do with the virtual identity plug-in that this section is supposed to be about?
Well, the virtual identity plug-in for Postbox makes it easy to reply to a disposable email address using the same "From" address that the email was addressed to. So, if I am using a disposable email address in an online forum and someone sends me an individual correspondence, it will come into that disposable email address. If I then want to reply to that individual, I don't want to reveal my real email address, I want to keep using the disposable email address. Microsoft Outlook plain can't do this. Thunderbird or Postbox can do it by themselves only if you set up an identity for each disposable email address. Since I use hundreds of these, that is kind of a pain. This is where Virtual Identity comes in. By default, every reply is sent From the same address that it came in to. So, if the email comes in from email@example.com and I reply to that email, it will be sent out as From: firstname.lastname@example.org. It's not quite as simple as that because the plug-in doesn't always know which address it should use, but when composing the reply, you can simply set which identity to use as the From address at any time. All-in-all, it makes using disposable email addresses just work.
OK, now you want all of this functionality to be mobile on your favorite smart-phone. Only two years ago, this was basically not possible. Now, you can do a pretty darn nice job. Email is on a first-grade IMAP server. Lots of smart-phones support IMAP. That gets you you email. And, because it's server-side storage, when you read an email or delete an email or file an email, it all happens on the server so all your other views of your email will reflect the change automatically.
Contacts and Calendar are on Google and they can be synced with just about any smartphone these days. Google supports Microsoft ActiveSync so any phone that supports ActiveSync can sync with Google (that includes all Windows Mobile phones and iPhone). All Android phones come with built-in support for syncing with Google. There are other phones and sync options listed on the site above. Getting my contacts synced to the phone is a big deal to me.
And, all this syncing is over-the-air so you never have to plug your phone into your PC to do any sort of USB sync. I don't currently have an Android phone, but I am thinking about the upcoming Droid phone from Motorola on Verizon as it's about iPhone size, has full slideout keyboard and has the latest release of Android on it and could do all this.