Valentine’s Day is approaching, and I have to say that I’ve always considered myself a bit of a romantic. This was a great year for my partner Kelly and I so I wanted to come up with something really great for Valentines this year.

I’m nursing a bad cold, so my Saturday morning was going to be spent catching up with my newsfeeds, finishing one of my many draft posts I’m itching to get out, and coming up with something special for Valentines for Kelly. If I had time I was going to to upgrade one of my machines to the new Office 2007 and Vista while I was reading news on Google Reader.

Instead I had my heart broken by Microsoft, fell in love with Stormhoek and Hugh MacLeod’s sense of humor and found the perfect Valentine gift for my girlfriend in the process.

Microsoft Breaks my Heart with a Silenced Paperclip Shot Not Heard Round the World

It happens quite often as I scan hundreds of news feeds that a few disparate posts all of a sudden come together and hit me in the head with an insight for a post. This time, it was my heart.

I flew by this article about Microsoft officially killing the much hated Clippy. (via Slashdot).

I had a passing thought about how stupid it was that Microsoft quietly killed Clippy by passing it off to UI coherency rather than acknowledging loudly it was most likely the most hated innovation in user interfaces. Almost every Microsoft employee I know hates the Clippy and has for years and everyone knows that users hate the Clippy. Microsoft was ignoring users and their own employees while defending the Clippy back when Office 2003 came out. While it’s great they have cleaned UI for Office 2007, the answers about Clippy’s death were arrogant by not saying to users “We heard you loud and clear and agree with you”.

For all the work Scoble and other great Microsoft bloggers have done, I was a little saddened that no one thought to just admit that Clippy was a condescending little shit pimping for a complicated user interface that made users feel stupid when they went to look for help.

I’m the first to admit that I love Office and am a serious power user. I use it every day and am incredibly productive with the suite. I have spreadsheet models that are too complicated for Google Spreadsheets (as of now) and I have more plug-ins running to pimp up my experience then most users. Despite some small experiments I’m doing with online office suites for collaboration with various projects, I’m generally a happy Office fan. I am looking forward to testing the new Office 2007 upgrade which I’ve been hearing great things about.

I passed it by without further thought, thinking that I have to get around to upgrading to Office 2007.

It would take a bit of time to realize what had just occurred.

Hugh Seduces me with Big Love

So it was an hour later while browsing my feeds from Gaping Void that my plans for the day where thrown for a loop.

I’ve mentioned before that I’m a fan of Hugh MacLeod.

The Hughtrain Manifesto plays a role in how I look at my angel investments, the projects I get involved with and is a central theme to my two current startups. It contains many insights into how to succeed in social media and how communities of change can be formed.

I knew from his blog that Hugh does some marketing work with a wine company Stormhoek - but since I stopped drinking last year (I’m getting healthy for my various startup projects - I’ve lost 85 lbs. since May 2006) and am not the type of wine collector to import wine into Canada, I never really explored Stormhoek further and was happy to enjoy his cartoons & blogging conversations.

So when I ran through my feeds and start to see the series of new video’s he is doing for Stormhoek leading up to Valentines my morning was lost in ensuing entertainment and this blog post that he inspired.

As you can see, Hugh has put himself out there in a hilariously naked conversation. He is inviting us to laugh with him, and share his journey. His heart isn’t just on his sleeve, it’s on his product and part of his story and I immediately wanted to show Kelly knowing that she is going to enjoy these.

Humor and love go hand in hand. When you can share your humor with someone it builds a strong bond if it’s done in an authentic way.

It was this comment from Hugh recent post that brought the pieces together,

3. New Marketing Paradox: Vulnerability Equals Strength. JP explains it better than I can.

Part of love is taking risk, being vulnerable and putting yourself out there for someone else and leaving your own sense of self importance aside.

The disparity between Microsoft’s Clippy approach and Hugh’s Global Microbrand approach to marketing caused my heart to sadden.

By experimenting with funny videos Hugh entertained me for awhile, and caused me to purchase a bunch of Stormhoek swag for Kelly and lithographs for my office. I can’t find anywhere where he is selling a good lithograph copy of my favorite Hughtrain image (which is my investment philosophy) but the Stormhoek ones are great for our the office wall at Project Ojibwe.

I ended up spending the morning checking out Stormhoek learning more about how they are building their microbrand. The entire time I was increasingly getting frustrated about Microsoft’s lack of humor, imagination and the wasted opportunity to engage and entertain me that they passed up.

Microsoft’s Marketing Muscle Mangles My Heart

Hugh’s microbrand marketing with simple authentic humor and love had me engaged and spending a couple hundred bucks on swag. Microsoft’s lack of humor or creativity in marketing Office 2007 or Vista ended up bothering me, and made me dislike them for not even trying to show they listened to users and have a sense of humor.

Amid Microsoft’s marketing muscle being flexed for Vista and it’s $500 million dollars quickly resulting in Vista everywhere marketing (Including a increasingly annoying number of interstial web ads that are annoying me across the web) we have Microsoft bungling so many opportunities to generate good will.

Roger Ehrenberg has a great review of Microsoft activities and made the following comment about Bill Gates appearance on the Daily Show and an interview he did with my friend Steven Levy.

Bill’s Public Persona Isn’t Helping Matters

Bill’s quick exit from the set of The Daily Show aside, he has not been doing Vista or Microsoft any favors with his recent performance. Contrast this with his alter-ego, Mr. Jobs, who even in the face of controversy surrounding the Apple options backdating scandal can get up on stage and wow his employees, his customers and the technology community at-large. Steve is a rock star. Bill looks as if he’s been living under a rock. Check out some of his answers in a February 1st interview with Steven Levy of Newsweek:

NEWSWEEK: If one of our readers confronted you in a CompUSA and said, “Bill, why upgrade to Vista?” what would be your elevator pitch?
Bill Gates: The most effective thing would be if I could sit down with them and just take them through the new look for a couple of minutes, show them the Sidebar, show them the way the search lets you go through lots of things, including lots of photos. Set up a parental control. And then I might edit a high-definition movie and make a little DVD that’s got photos. As I went through, they’d think, “Wow, is that something I could use, would that make a difference for me?”

********************
You also talk about improved security in Vista.
Yes, although security is a [complicated concept]. You’re [referring to] the fact that there have been some security updates already for Windows Vista. This is exactly the way it should work. When somebody comes to us [after discovering a vulnerability] we’ve got [a fix] before there is any exploit. So it’s totally according to plan, and that’s why we have the whole Windows Update thing. We made it way harder for guys to do exploits. The number [of violations] will be way less because we’ve done some dramatic things [to improve security] in the code base. Apple hasn’t done any of those things.

********************
Are you bugged by the Apple commercial where John Hodgman is the PC, and he has to undergo surgery to get Vista?
I’ve never seen it. I don’t think the over 90 percent of the [population] who use Windows PCs think of themselves as dullards, or the kind of klutzes that somebody is trying to say they are.

How about the implication that you need surgery to upgrade?
Well, certainly we’ve done a better job letting you upgrade on the hardware than our competitors have done. You can choose to buy a new machine, or you can choose to do an upgrade. And I don’t know why [Apple is] acting like it’s superior. I don’t even get it. What are they trying to say? Does honesty matter in these things, or if you’re really cool, that means you get to be a lying person whenever you feel like it? There’s not even the slightest shred of truth to it.

Does the entire tenor of that campaign bother you, that Mac is the cool guy and PC—
That’s for my customers to decide.

Are you kidding me? Bill sounds a little like Glenn Close in Fatal Attraction, and that he is getting ready to boil Steve Jobs’ bunny. First off, Bill, after having spend an amount exceeding the GDP of several sovereign nations - $500 million - to launch Vista, don’t you think you could have spent even a little of that on media training? THAT is your elevator pitch? Sorry, Bill, but you’re not getting the VC funding you desire. You’re not even getting out of the elevator. Your answer on security: poor. Your paranoia and irritation at Apple’s successful branding and image-making? Nauseating. You’re the richest guy in the world. You do lots of great things with your money. You’re a brilliant man. The Apple threat and a changing world is making you become unhinged. Do something about this. Fast. For your shareholders sake. Please.

I couldn’t agree more. I respect Bill a great deal for the work he is doing with his foundation and think he’s an incredibly intelligent person - but his lack of vulnerability (and some media training) is hurting Microsoft.

I immediately was struck with what a wasted opportunity the death of Clippy was for Microsoft. If I were a marketing manager at Microsoft I would have gotten $250k to sponsor a prize pool for user submitted animations, videos and mockumentaries about the death of the Clippy. Eulogies to this much hated user innovation would be hilarious.

Allow users to submit videos and split the prize money with a charity of their choice. Give the grand prize to the best video that shows the Office 2007 Ribbon User Interface taking the rightful place from Clippy and leave the rest in a prize pool for various categories like Apple vs. Clippy, Tux vs. Clippy, or How a Ninja would Kill Clippy or any other funny ideas. Include special prizes for Microsoft employees or ex-employees to submit videos. Invite Google and Apple employees to join in on the fun.

Get a panel of judges like Ze Frank, Robert Scoble, David Pogue, Walt Mossberg or other respected Internet characters and bloggers to judge the contest.

Proudly admit on Daily Show and your Vista media tours that you are listening to users and show some self depreciating humor as you showcase the funniest user videos about the death of Clippy. Leverage the fact that you HAVE LISTENED TO USERS and gotten rid of an annoying pest. Hire a few joke writers for Bill and get the online community laughing with you.

Stephen Colbert is the master of this with stunts like his Green Screen Challenge.

Microsoft, please let us know you made a huge mistake that took 10 years to correct and publicly bury Clippy’s annoying head in a mass of funny, community generated laughs at your own expense. It’s not the death of Clippy, but rather the lost opportunity to be authentic with your users that hurts me.

With a few of the generally positive reviews of some of the features of Vista and Office 2007 you could milk a fun challenge like this for plenty of positive press and good laughs to support some of your media spending. You could engage the community instead of having us all blog about how weak your marketing is. Move the discussion away from Apple’s funny pokes at you, to your own confident self effacing pokes at yourself.

Make it easy for me to like you. I’ve worked with some of great people in Redmond including a lot of the senior executive team. There are a lot of smart people at Microsoft and say what you will about them, they work hard to release good products. They may not be cool, but the do run a large percentage of the worlds computers for more reasons then they generally get credit for.

I’ve also bitten into enough worms in my long history with Apple (Can anyone say Newton?) that I’m not a religious fan one way or another. I don’t view Apple ads as telling me I’m an ‘dullard’ for using Windows. I view them as funny because they all have an element of truth. Most people in Redmond know this. Bill knows this. We all knows this. That’s why they work and people like them.

I don’t need Bill analyzing the factual basis of the parody. I need to see him joining in and laughing harder at himself to make me like him and his company on an emotional level.

Even though it was media scripted and kind of self serving but at Microsoft’s developers conference, Bill’s been coached on being funny and laughing at himself before.

Unfortunately even when I go to find this video to show off a case where Microsoft laughed at itself I can only find a fan copy on YouTube. I know Google owns it, and Windows Media Player is nowhere to be found, but your customers look for video on YouTube and you should get any video that helps your image up there ASAP. Don’t just leave fan versions, it shows you don’t love me.

Hell any decent creativity on how to leverage Bill being on the Daily Show could have included him showing the dance scene from the end with him and John Heder on a Vista machine. Bloggers everywhere would have played the clip and laughed with Microsoft. (Comedy Central’s removal of clips from YouTube makes it hard for me to compare, but I’m sure there have been more views of his mishap on the Daily Show then the 160k views of the Napoleon Dynamite clip on YouTube)

I’m a big fan of my Tablet PC which I’ve had for 2yrs (until it’s graphics card went kaput right in the middle of writing this blog post - it’s on it’s way to Toshiba to be repaired and I spent Sunday trying to mount my hard drive in VMWare on another machine to access all my stuff easily - Arrgh…), and I also enjoy the Macintosh computers and Apple devices I have. I have 7 computers between my office and my home. I have spent hundreds of thousands of dollars in Microsoft software licenses throughout my career, at my various companies and at home. Yes I am now using open source for all my development projects - but I am still using your software and tools happily in many places and probably will for years to come.

Why do you make it so hard for me to defend your brand?

A Valentine Gift Emerges - I will work for Love

Instead of upgrading to Vista or Office 2007 I spent the day writing this blog post and thinking about the differences between big and small marketing. Authentic and mass marketing. Hugh’s gift of humor and Microsoft’s annoying blunders.

Bloggers work for love in most cases and that is what caused me to spend my day working on this instead of upgrading. Love. I realized what Hugh’s lesson and Microsoft’s failure to engage me could teach me and I realized how to help someone I love.

Amidst writing this blog post, an idea for a gift for Kelly emerged (in addition to the stuff I bought her at Stormhoek Swag and the mandatory chocolate).

My girlfriend is a massage therapist and does organic body & skin treatments. She has a small business and has been working really hard lately doing promotional brochures, coupons and trying to build her clientele.

She is eager for my help in teaching her how to use the Internet to market herself better but I end up not always finding the time beyond just helping her writing a few brochures. She tries her best (and has done a great job) learning desktop publishing tools and wants my help to be able to market online better, but she doesn’t want to bother me given how busy she knows I am. (She hates to bother me with her small business when I’m busy with the ‘big’ family businesses - but that doesn’t make her work or business not important to both of us).

So for Valentines this year, thanks to Hugh’s inspiration I am giving her a book of coupons I created for lessons on online marketing and helping her build her own little global microbrand. I’ve included items like,

  • How to set up and create an email newsletter for your clients
  • How to use Google Reader and Technorati to track content and industry news for your customers and networking
  • How to use Meetup and Upcoming to organize informational and promotional educational events
  • How to setup a database of her customer visits with email reminders and CRM systems
  • and of course….if and when she would like how to setup a blog and an intro course to blogging.

This is going to take some time out of my schedule, but it’s quality time that I’m happy to spend with Kelly and will be the best Valentine gift that I could give her. [Personal Note: Happy Valentines Day Baby - I didn't want to wait until Valentines to post this, and she reads my blog, so I'll have to add some surprise element for this week]

So now Microsoft may have to wait a bit longer for me to upgrade and play with their new toys.

Other people who love me more are competing with you for my time, and I’m sorry to say that you just don’t know how to say I love you - so for now I bid you adieu….

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