Top 10 reasons to ditch gMail for Microsoft

[photopress:BringItOn.jpg,full,alignright]OK, you knew I had to respond to this. I brought my flame proof suit. I used to work on Exchange, Outlook and Outlook Web Access when I was a ‘softie. Galen’s last post was very Roeper, and I’m going go Ebert on him. I have 3 sets of 3 words and 10 reasons for my buddy Galen.

The 3 set of 3 words
Windows Live Mail
Outlook Web Access
Bring It On

The 10 reasons

  1. So your cheap and use Firefox. Well I agree Hotmail sucks, but Windows Live Mail is damn near OWA good, does very well against gMail thank you very much.
  2. Try using gMail w/o internet access. Where’s the offline functionality? I’m sorry folks but Verizon EVDO and those T-Mobile hot spots aren’t everywhere yet. Have you tried using an AJAX app w/ a slow cellular net connection? (talk about a fate worse than water torture). Wanna gMail on a plane? Sorry, no can do. Until ClearWire takes over the world, a desktop / offline e-mail is a requirement for me.
  3. If you use POP/SMTP w/ Outlook and store your mail client side, your limited only by your computer’s hard drive space. (didn’t Google’s CEO say 2GB ought to be enough for anyone) 🙂
  4. That said, web e-mail is also a requirement for me. Which is why I use Outlook Web Access 2003. OWA still kicks the living snot out of Gmail (on IE anyway). Remember kids, the OWA team practically invented AJAX (they called it Remote Scripting back in 90s). They were the team that convinced the IE team to include an XMLHTTP object with the browser! Without them, there would be no gMail. That said, the FireFox version of OWA 2003 sucks. In partial defense of MS, the last version of OWA shipped before Firefox 1.0 was released. I’ve heard OWA 2007 will have much better FireFox support. But if you use Firefox only (I use IE & Firefox), then I admit OWA 2003 won’t do it for you.
  5. Hosted Exchange servers aren’t that expensive. I currently use Intermedia and have the ability to add/remove mail boxes, change storage quota, etc. I’ve heard 1AND1 is even cheaper.
  6. Privacy. What if the US government decided to Subpoena Google and read your e-mail? Don’t think it doesn’t happen. Granted, Live Mail would also be a target of govt. snooping, but my Exchange server probably would not be.
  7. Calendaring. Can you type “2 weeks from Friday” into a gmail appointment form and have it resolve to “Fri 9/15/2006”? You can with Outlook! Get a real date parser!
  8. Contacts. Where the heck is the mapping integration w/ address info in gMail? OWA & Outlook have had this since the Web 1.0 days. I know cause I wrote that feature for OWA for Exchange 5.5 (way back in 1998)!
  9. Looking for Tasks & Notes? Sorry Google doesn’t have that either.
  10. API support – Google may offer an API in the future, but Microsoft offers that today

Galen can keep his gMail. But, you can pry Live Mail, OWA, Exchange and Outlook away from my cold dead hands! Offline scenarios still have value to people. Feature rich Windows/Mac/Linux apps (Outlook, Entourage, Evolution, etc) can still clobber web only apps (no matter how much AJAX & Flash you try to put into them). I’ll freely admit the Redmond evil empire’s shortcomings (see the above “Hotmail sucks” & “OWA’s 2003 firefox support is weak” remarks), but Google is going have to do much better than have better Firefox support than OWA 2003 to convince me it’s better than Microsoft’s e-mail technology. E-mail mindshare, well that is another debate…

Let the e-mail Jihad begin! Who & what do you use for your e-mail and why? Would you pay for e-mail service or is free ad supported e-mail the only way to go? How important is your domain name to you? Does your e-mail server use SMTP/POP, IMAP, or HTTP? How important is offline to you? What do you look for in a web e-mail client? What about them Blackberry’s, Q’s and cell phone sized devices that do e-mail? Is Galen the one on crack or am I? (or are we both right)?

29 thoughts on “Top 10 reasons to ditch gMail for Microsoft

  1. Like I said, mindshare is another battle… Google’s got it right now and MS doesn’t. MS screwed up big time by coming late to the Firefox support party. Also disbanding the IE team after Win XP while the ashes of Netscape were turning into Firefox was another big screw up. It’s unfortunate that it took Firefox / Google bitch slapping Microsoft a couple times before they woke up and got serious about the net again.

    Maybe MS has to build a better search engine than Google in order to be taken seriously again (they got a ways to go here), despite the fact that’s it’s live offerings are very competitve w/ the gTeam?

    The up side of all this is that Microsoft and Google are going to keep each other honest in their battle for world wide web domination.

    I’ve tried to use gMail and every time I do, I long for OWA.

  2. Five and half good reasons.
    1. As good? That’s not a reason. And you can’t use it for your company, right? Like they won’t let you host on
    2. Gmail has free pop3 access, so you can do all the offline work you want (I do mine in Thunderbird). Not a reason.
    3. See number 2 – you can download whatever you want when you hit the wall. The storage capacity is nearing 3GB right now – it grows with every passing minute. Not a reason.
    4. If you say it’s better, I believe you, regardless of the history of ajax. But no firefox support until some undisclosed future date? Sounds like it doesn’t work on a Mac. That’s a half a reason!
    5. Costs something versus nothing? That’s an unreason.
    6. This is a great reason – data mining is gross. That said, the government actually could just as easily monitor your server. Point awarded, nonetheless. (1.5!)
    7. If that’s what is important for you in a Calendar. Score! (2.5!)
    8. I’m not sure I understand. If an email has an address in it, gmail has a link to map it on the right hand side. Maybe contacts can’t have addresses that are easy to map? I’ll leave it as a point. (3.5!)
    9. True. (4.5!)
    10. True. What is here now is important. (5.5!)

    Here’s mine: Skype works nicely with Outlook and is nearly good enough to replace an office phone system. That’s a good deal.

    Robbie, I’m sure Windows! Live! Mail! is just as good as gmail. Yahoo mail beta is pretty spiffy too (but oh so slow). That’s not the point. The point is that with Google’s new offering it is extremely easy to do all of the basics of maintining your email and calendaring system even if you didn’t spend a few years at Microsoft.

    You’re comparing two products that individually add up to a much better product, but separately one costs money and requires paid techies and the other is free and all your employees appear to work at (and they don’t have calendars).

    If Microsoft released a system that had free hosted email and calendar, I would recommend that use it in favor of exchange servers and expensive software too.

    How much is Outlook and a hosted exchange server for an office of 20 (no cheating with a Microsoft discount here!)? I actually have no idea. Can you get Office without Outlook? Again, no idea. I would like to point out that I am NOT recommending google spreadsheets or documents for “real” use – that would be crazy.

  3. “Try using gMail w/o internet access Where’s the offline functionality?”
    Offline? Offline is so yesterday

  4. Well look at that, Microsoft has
    Office Live Beta
    , which has most of the same features. It looks a little more controlled (do you have to use their web hosting?) and it doesn’t offer a Calendar, but otherwise I would consider using this in place of Outlook and a managed server too. Unless they actually force you to use their web hosting – that would mean no WordPress blogs!

  5. Galen,

    1. You can use your own domain. See
    2. Fair enough, but POP3 is a simple download only protocol. I don’t think it can sync offline changes with the online version when you get connected again. I think IMAP might be able to do this, but I don’t know. Does GMail do IMAP or just SMTP/POP? Outlook/Exchange definately can via HTTP/DAV (or MAPI RPC if your old school and like pain)
    3. Agree. That was more a joke reason…
    4. OWA 2003 has 2 modes. IE only AJAX up the wazoo really slick mode and legacy browsers mode (which Firefox is definately not, but it gets treated the same as Netscape 4, because it didn’t exist yet when MS wrote it). I can understand w/ Firefox guys bash it. However it’s like bashing Sgt. Pepper sounds crappy because the Beatles didn’t have SACD and DVD audio back in 1967. Exchange 2007 is supposed to ship in early 2007. I really hope the Firefox OWA is worthy of the browser. On the Exchange blog they’ve claimed they done a lot of work to narrow the gap. I know when I worked there, we busted our butt so IE 3 & Netscape 3 era browsers would have as an equal experience as we could (so I think it’ll be much better, but will it be IE version good, the jury is still out). That’s ancient history though. The IE version will rock your world however.
    5. Live Mail is free. Exchange/OWA is not. However, if you do a hosted Exchange account, you do get a copy of Outlook/Entourage and OWA access w/ it.
    6. I agree. The govt could look at any server. However, if they go snooping at random their going to visit MSN, Yahoo, Google, and AOL before they visit my server.
    7. Outlook has other cool calendar stuff, but I just picked a feature that I knew nobody else had (I’ve heard some cool Outlook date parser war stories over the years). I suspect if I was pressed I could find others.
    8. It’s also a cheap shot. An engineer at Google could fix it in 5 minutes if they wanted too.
    9 & 10. We agree.

    My phone co. (Ecuity) is VOIP based and has universal messaging, so all voice mail gets e-mailed to me. I’m not a big Skype user, but I’ve been impressed when I used it. Haven’t really used MSN voice / chat recently, (MS Net Meeting was pretty good in it’s day of analog modems, but that’s a history lesson)

    BTW – I’ve played w/ live mail a bit more since I posted, and it’s calendaring doesn’t seem as slick as gCalendar though (it does have calendaring). It does have tasks, notes and reminders though. I still like live mail more gMail though. (OWA still kills both of them though).

    A hosted Exchange solution from 1 and 1 is $7/month per mailbox. (So a 20 person company works out to $140/month). Intermedia has a plan w/ 25 mailboxes for $295/month. It’s not free, but if you can afford to pay the salary of 20 employees and keep the lights on, you can afford hosted Exchange. Both plans include copies of Outlook or Entourage. I also have used Evolution via HTTP DAV once against my Intermedia account (and it mostly worked surprisingly enough).

    You may find Intermedia’s press release informative.

  6. I spotted the hosted domains thing after that post. I maintain that $140 a month is nowhere near the actual cost of hosted Exchange – you aren’t including the admin costs.

    Do both versions include OWA or is that an added cost? (I had never heard that acronym before, BTW). How about Calendars? Shared Calendars with multiple owners?

    I think we agree then, each has it’s merits. I would still try the google hosted solution over the Microsoft for email and Calendars if I had an offline company (i.e. not internet-focused) with 5 – 20 employees. And you wouldn’t touch it with a stick.

    And you love Google.

  7. Let’s not forget… when you work with google you aren’t partnered with a convicted monopoly abuser or worse yet supporting same with your dollars.

  8. DISCLAIMER: I assume 1and1 admin tools is similar to what Intermedia offers. 1and1 web site states they offer OWA & Outlook as part of their $7/month fee. Intermedia offers OWA, Outlook and Entourage for their monthly fee ($10-$15/month).

    I used Intermedia because that’s what my current day job employer did. In fact they were the ones who pointed it out to me! They are a small company with 30-ish people. (At MS they obviously hosted their own Exchange servers, but MS is anything but a small company).

    At Intermedia they have a simple web interface for quota, domain mapping, adding users, shared folder permissions, etc. What admin costs? Your admin is the HostPilot web app. If you can send web mail, you can admin your Intermedia Exchange settings.

    I don’t pay anything other than my monthly $30/month for 3 e-mail addresses (Intermedia has a 3 address minimum, which kinda sucks for me since I’m a 1 person company at the moment – but since were talking about a 5-20 person company, that’s not an issue). They offer free 24×7 tech support, so if you need a real mail admin, you can get a hold of one via web or e-mail.

    Yes, that monthly fee includes OWA and Outlook. Yes, you can have Shared Calenders, Shared Contacts, Shared Tasks, etc. via public folders which you can admin yourself via the web. Yes, you can set permission on those folders so only certain people can see them.

    Yeah gMail/gCalendar is pretty good, but OWA/Exchange still kicks the snot out of it and steels it’s lunch money.

    Google search is better than Microsoft’s, but their e-mail isn’t.

  9. Alex Garcia

    Though I agree that offline is yesterday. The problem is we still live in a world of back hoe denial of service attacks, ISP net outtages, and sometimes good Cisco routers go bad (I’ll assume Google never goes down). Wireless net access is getting better all the time, but it’s not quite at broadband everywhere and everytime yet. I can’t web surf on a plane yet. I agree that offline becomes less necessary with each passing day. But it’s still a nice feature to have in case you need it (because you never know when your going to lose net access).

    After all, electricity has been around for what a 100 years and we still have outages. I like to keep the candles and flash lights around, just in case I need them.

  10. As a small-business owner, I have 10 agents and 2 full-time staff, I use MS Exchange on our own server. The results have been great and agents are comfortable with the remote access. I even use a VPN on my home desktop and my laptop. Just last weekend I was in Colorado and working in Outlook via VPN and it felt as if I were back in Atlanta at my desk.

    However, with all of that said…free is very enticing. I would consider trying gMail just because it’s free. We do have problems from time to time and admin costs definitely add up fast. The hardest part about changing over is the CHANGE.

    – Great Post and Comments!

  11. Brad,

    BTW – If you ever decided to go free, would you ever consider Live Mail (or even Yahoo)?

    When I started Caffeinated, I was wondering if I should host my own Exchange server or let somebody else worry about being my admin. Email admin can become a huge time sink (which is why I figure the $10/ month / mailbox was money well spent). I get to avoid those headaches because I subcontracted my e-mail out to professionals. I’m sure I’m missing some flexibility, but I don’t miss it yet. If hosting your own Exchange server ever becomes to much of a hassle, I’d recommend Intermedia.


    What did you guys do before Gmail? Were you aware of hosted exchange as an option (even if you’d never actually consider using it)?

    I think the biggest problem with hosted Exchange is general awareness. There’s a billion companies out there that do hosted & SQL Server, but only handful that do hosted Exchange (so nobody knows that it’s an option). It’s sad, but even I didn’t even know about it until after I left Microsoft.

  12. What is the mailbox size limit on Exchange? The people at Microsoft are still struggling with 100 MB mailboxes. GMail has close to 3 GB!

    Considering Yahoo and MSN have been more forthcoming when it comes to handing over search results when the government comes calling, I would avoid them like the plague.

  13. With 1and1 and Intermedia, you get up to 1 GB. It’s not 3 GB, but it’s more than enough. Intermedia’s Exchange deployment isn’t what Microsoft’s is.

    I suspect the 100 MB limit on the MS campus is probably partially due to requirements from the legal dept. (Less e-mail = less legal risk). I agree the quota should be higher and if you are on “dogfood” it usually is (I think I had 200 MB before I left). I wonder what Scoble’s mail quota was?

    I believe Exchange 2003 Standard Server SP2 has a 75 GB store limit (it used to be 16 GB – all mailboxes on the server). And the I believe Exchange 2003 Enterprise Server has a 16 TB limit. Of course, if you need that much e-mail storage power you need $$$ (or create script a to sign up for 16,000 gmail accounts and time to get past the the 16,000 CAPTCHAs).

  14. Truthfully, it probably is a little personal and maybe I need an engineer from the gMail team to put me in place. But dang it, I’m tired of these gMail lovers who think a lot of hard drive space is a replacement for kick ass AJAX code.

    Google is very lucky MS uses OWA to sell Exchange CALs instead of web ads, otherwise gMail would be in same boat that MSN search is in.

  15. offline is so yesterday…right…NOT..offline is the only way to get your work done..the internets wild west unstable environment is just saveing a stamp…I’m in no hurry and you should rethink your lifestyle…SLAVE

  16. Gmail is a great system…

    Think of how many people have wasted how many hours on setting up outlook…
    Think of how many people have wasted how many hours on spam…


    Think of how many people have lost hours working with gmail and spam…

    I’m 24, and I have always hated outlook, perhaps I am an anomaly but I think the future generation will agree.

    It’s as easy as
    1. use an easy web based email program [ie gmail]
    2. pop your messages locally once a week [for professionals etc]

    I can see gmail getting beat out by another webmail system but all in all when the rubber hits the road you should not have to think about what processes your email… IT JUST NEEDS TO WORK.. outlook will suck your will to live, I have seen it personally.


  17. Well, I’m currently working on the next version of Exchange Server, so stay tuned… I think it’s safe to say that the competition is going to intensify.

  18. 1. OWA blows chunks on anything but IE. Who uses IE anymore?
    2. I use gmail offline all the time… it’s called Thunderbird. You are attacking a web client for not handling an offline situation, which it inherently can’t do. That’s like attacking OWA for being unavailable offline. Compare apples to apples.
    3. See #2.
    4. I don’t run windows, and wouldn’t use IE even if I did(except for testing websites for bugs caused by proprietary bs). Hence, OWA blows.
    5. Why would I do that when I can get Google Apps for my domain for free?
    6. If you’re worried about the government reading your e-mail you have bigger problems. For them to care, you are likely doing something illegal, in which case, search away.
    7. You can not only do this in gCal, you can also type “at ” and it automatically looks it up in google maps.
    8. Your contacts get full profiles, I don’t know where this comes from.
    9. No tasks or notes… no problem. That’s what docs and “Remember the Milk” is for. Both handle notes and todos better than the tasks and notes in exchange.

  19. I use Exchange for work and GMail for personal. I’d rather use Gmail, it is faster, doesn’t log me out every 2 minutes and I like the way the messages are formatted.

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