Month of Microsoft: Gmail v. Hotmail

My good friend Barbara Darrow of GigaOm just posted an awesome rant about Gmail and other Google apps. (“Hey, new-and-improved Google, please fix your apps.”) This was prompted by a Marissa Mayer appearance where she said Larry Page is really focused on products and users, and really wants to streamline everything at Google. (Have you noticed lately, with Page’s one-year anniversary as CEO approaching, the way the people around him are out beating the drums about what a great CEO he’s been, and all the big changes he’s making, and how it feels like a brand new place, and everyone is so excited, etc.? I’m waiting to see which publication gets the big Larry interview for the anniversary. I know it’s not us. We tried, but Larry’s PR person wouldn’t even meet me for coffee. Oh well.)

Anyway, here is Barb’s money quote:

So what explains the nightmare that is GMail? And, to put it gently, Microsoft Word doesn’t have that much to fear from Google Docs. (This is coming from someone who is not enamored of Office’s bloated feature set.)

I don’t hate Gmail as much as Barb does, but I can tell you this. A few weeks of using Hotmail has been a really good experience. It feels cleaner and less cluttered and just all around like a nicer experience. And, no creepy ads that somehow know what’s in your email and start trying to match it. Want to have fun? Start exchanging email with a friend and talk about hemorrhoids, or sex toys, or the new Patagonia Primo jacket, and then see what happens.

Yes, I realize it’s just a computer that’s “reading” my email. It still feels creepy. The problem is that even if it’s just a computer doing it, it makes you aware that your email isn’t really private, and that no doubt if some human inside Google wanted to read my email, they could. And yes, I know that this is always the case, with every mail system. And so, in a twisted way, maybe Google is doing us a favor by constantly reminding us that nothing we send over email is truly private. I think somehow I’d rather live with the illusion that the only people reading my email messages are the people to whom I’m sending them.

And frankly it kind of bugs me that someone is trying to “monetize” my email. And, it’s pointless, because whatever I’m writing about in an email, I’m never writing that email hoping that somehow a computer will spot something in my message and deliver me an ad. I’m not writing email as part of a shopping expedition.

That said, the one problem with using a or address is the stigma of having a or email address. It marks you as a dork. All the cool kids are on Gmail. It’s not as bad as having an AOL address, but almost.

The other problem is that since Hotmail and have been around so long, all the good names are taken. So, for example, I was unable to get danlyons, dlyons, dan.lyons or dan_lyons and instead had to create a name with a number at the end.

Here’s an idea: Someone (like Microsoft) could create a brand new email system where we could all start fresh and choose good names. And make it cool, somehow.

And Google could keep talking about focus and streamlining and user experience, and they can keep saying that they’re going to fix Gmail and fix their apps and make their products nicer looking and easier to use. But I don’t think they’ll ever get there. It’s not in their DNA. It’s just not.

And for all the talk about less clutter, a lot of what they’ve done recently (Search Plus Your World, smearing Google+ across everything) has made things more clusterfucky, not less. And what genius at Google came up with a product name that reduces to an acronym (SPYW) with the word “spy” in it?

The fact is, Google is starting to become Microsoft: the gang that couldn’t shoot straight, and always seems to be acting to its own advantage rather than to the advantage of its customers.

Which means Microsoft has the opportunity to go be someone else. I hope they take it.

27 Responses to “Month of Microsoft: Gmail v. Hotmail”

  1. Blarkon

    When Hotmail got categories (functionally the same as Google’s labels) and kept folders I switched back.

    I was able to transfer my 6 GB or so of gmail across without too much problem and then set up rules to file it into folders and apply labels/categories.

    I realize that Hotmail has a bigger userbase (and Yahoo a bigger one still) – but Hotmail has been a joke in most geeks eyes for a long time.

    Google gave MS a big kick up the backside and it looks like they took the hint and raised their game. However Google seems to be content to cruise and Hotmail looks like it caught up and passed them.

  2. Eric S. Mueller

    I ended up with an address from a brief stint with Verizon DSL. That never seemed as bad as hotmail or, eve though it’s the same service.

    I’ve toyed with the idea of switching from gmail lately. Hotmail has definitely improved. Gmail has gotten flaky lately.

  3. Drwin

    There is already a company that doesn’t screw over their customers like this. Their name is Apple.

  4. Steve Ballmer

    How about “Windows Mail.”

    See? How hard was that? I never got the “Live” part either.

  5. Mary Branscombe

    you can keep your gmail account and read your gmail messages on Hotmail; I know it might not fit the terms of your month, but it lets the cool kids feel cool with a gmail account without the pain & suffering…

  6. Brian Zibricky

    Dan, aren’t you a little old to worry about what the “cool kids” are doing? That attitude is exactly what I hate about the tech industry – very often tech is led by trends instead of what’s better. And what’s wrong with the LIVE extension? It’s short, ties in with other MS services, like Xbox Live for instance, and sounds cool. Hotmail on the other hand is antiquated, but the service is flat out better and deserves accolades regardless of any preconceptions brought on by the ignorant masses who think it’s so 5 minutes ago.

  7. Ken

    If you like Hotmail but don’t like, go to and set up your own @domain. It’s free (bring your own domain registration), and you can have whatever email address you want.

  8. faddah

    “the gang that couldn’t shoot straight”? wouldn’t that be most old media publishers, like say… newsweek? oooooh, snap! sorry, couldn’t resist. {snicker!}

  9. Jason

    That’s exactly what I have done and also what I was going to suggest, damn you for beating me off the mark…

  10. r00fus

    Like Google’s “do no evil” … there should be another purge at Microsoft “say no to live”.

    It’s a meaningless brand that just confused everyone.

  11. PythagorasGamer

    $500 to $800 every year for a new device…..Making sure the old devices are quickly obsolete….iTunes DRM….REALLY????? Are you an Apple employee or something?

  12. Vanessa Howell

    I’ve tried just about every mail system from Yahoo to Hotmail to Outlook Web App to Gmail. I must admit that on balance I prefer Gmail, but Hotmail has gotten a lot better over the last few years.

    Both Gmail and Hotmail let you setup mail through a custom domain, so if you want to choose your email address it’s possible (though not trivially simple).

    For years I eschewed Hotmail because it didn’t integrate at all well with Outlook Windows client. More recently I’ve found it to be less efficient to work through large amounts of email than Gmail. I also rely on Google Docs, Voice and other services quite a lot so it made sense to use both

    I wrote a bit about my experience leaving Outlook for Gmail here:

    For full disclosure, I currently work at Google (not on the Gmail team). I’m really happy to see how much all the mail systems have improved over the last few years (competition FTW).

  13. Tom

    Wouldn’t “Hotmail for your domain” solve this and a bunch of other problems?

    I’ve been using gmail via GAFYD for years and no one knows/cares… there’s no stigma, because all they see is my last name as the domain.

    In fact… this product already exists (I just learned) but who’s ever heard of ‘windows live admin center’?

  14. Alistair

    Hi Dan,

    It would be great if you could go into more depth in the comparison. The article you reference (and you yourself) only vaguely mention some kind of design issue, but I don’t see it.

    Personally I haven’t used hotmail in a long time, but I find gmail makes great use of scree space, is really quick (it uses spdy i believe) and has a good UI.

    Some more specifics would be great on what hotmail is doing better.


  15. TinmanTinman

    With this article your assimilation into the borg empire is complete. You are already starting to sound like rest of the tech media . Congratulations.You will fit right in with click whores and hit men.

    You are already using your ‘feelings’ to decide something is ‘creepy’ rather than just knowing the fact that some server somewhere is just reading text and displaying more text as ads.

  16. Sean

    Serious questions from a Gmail user:

    Does Hotmail:

    - have email threading?
    - let you easily create unlimited and fine grained mail filters, including the ability to forward mail to another email address?
    - have email tagging?
    - have a system to encourage you to not permanently delete old messages?
    - block 100% of spam from your inbox? (I haven’t received a single spam message in the 3 years I’ve been using Gmail)
    - allow quick switching between reply and forward modes, without having to restart your message?
    - have Undo, letting you undo most of your actions?

    If Hotmail has even half of these features, I’ll be impressed. It would have come a long way.

    I honestly couldn’t live with an email system that’s missing most of these features. And I really can’t give a crap about the Gmail ads.

  17. Ken


    Does Hotmail have:

    - email threading? Yes.
    - rules including forwarding? Yes.
    - fine grained rules? Matter of opinion
    - email tagging? Yes, they call them catergories.
    - encourage not deleting? Matter of opinion, but I don’t delete
    - block 100% of spam? My last real spam is dated 2010
    - switch between reply and forward? Who does that?
    - Undo? I’m surprised to say that it doesn’t seem to support undo.

    So that’s five out of seven, and I still question the utility of #6.

  18. Ryan


    Since gmail started supporting IMAP, I just use the interface to change settings.

  19. Sean

    Thanks @Ken. That’s an eye opener. I’ll have to try out hotmail sometime.

  20. Victor Casale

    Dear Friends,
    I’m from Brazil. As I work with technology, i have tested both GMAIL(GOOGLE APPS) and HOTMAIL(LIVE DOMAINS) with personalized domains. I think that they both have good things and some things that they should improve. Some of my clientes, prefer hotmail because it offers up to 500 users for free/per domain when google apps offers only 10. Some of my useres prefer Hotmail because of Agenda and Calendar/Todo List easy sync with them mobile phones, when google syncs only Agenda and Calendar but not Todo… I have 2 different domains, one working with google and another with Live and in my opinion, each user have its own needs. Some people do prefere not workign with free solutions so they prefer paying a provider for its mail, some people do prefere hosting them own mail server… I think that both solutions are very well.

  21. AngelicOne

    I wish I knew the answers to this.

    To me, it’s simple. I use Gmail for mail and GROWN UP things and my children use Hotmail as it let’s you have a cute little icon that looks like a six yr old (as does Yahoo, I seem to recall).

    I think the additions to Hotmail/Live/MSN (whom????!)PROGRAM-wise are SUPER and use my ‘got it when I didn’t know any better’ hotmail address to log in and take advantage of these services if needed, but, even if Hotmail had ALL of the above in gold plating…I’m STICKING WITH GMAIL…for NOW, at least.

    I even tried the PLUS. Yes, it sucks, so I closed it. UNLIKE FB, my ‘comments, photos and LIFE’ did not remain on display, along with my photos!!!

    Sean, TY for saving me the time and effort of listing that which makes Gmail SUPERB, USER-FRIENDLY and (being over 21 ergo,) not really CARING if I’m seen as a ‘nerd’ by the local (and NOT so local) ‘youf’…I’m staying put!

  22. AngelicOne

    oops…and proofreading when writing in a hurry ALWAYS a good idea… ‘comments, photos and LIFE’…..along with my FRIENDS’ photos! (sorry!)

  23. Brian

    I currently prefer hotmail. The ‘Schedule Clean up’ feature is really neat. Esp with newsletters or online deals that comes almost daily. Auto-delete after 3 or 10 days. Makes my inbox clean.

    Does gmail have a duration-based auto-archive/delete feature?

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