The trick is to do these things without coming off artificial. If Microsoft or Apple tried this, it would backfire, though Apple could do many things MS can't because of their known focus on the end user.
Memorable and authentic is a win. Memorable and fake is poison. Unmemorable is the dead pool.
The weird thing is that today I could far more easily believe Microsoft doing something like this than Apple. When I think of how present-day Apple conducts itself, I think of cleanliness and sterility all the way. Microsoft, on the other hand, has been trying to be a bit more "goofy" since around Windows 7.
Ah, Derek Sivers. He is a very inspiring person, I really recommend reading his website. I particularly loved his piece about the person who was his inspiration, Kimo Williams[1]. I regret I haven't stumbled upon this earlier, before I realized the lesson myself.
I see "standing out" as being nothing more than the most extreme version of yourself.
This guy brought out a nice side of his personality with that e-mail, and his personality is seemingly very great. I'm glad this worked for him, I wonder what other spaces could apply this "personal touch" trick?
I do this with my 'Out of Office' messages. I personalise them to the reason for my absence, and normally throw in something quirky - very much in line with my personal and business positioning. The responses I receive are amazing!
Here's my most recent example, to explain it better:
I am currently in Belgium on leave, and will return on Wednesday 9 May. I will respond to your email, if appropriate, next week - if your message is urgent, please contact ...
If the rest of your day was planned based on my response, then you now have some time on your hands. Here are three time-filling ideas, based on my trip:
1) Watch the film In Bruges, while I am actually in Bruges. We'll both have a great time - me, alas, without Ralph Fiennes
2) I will be in Antwerp, host of the 1920 Summer Olympics. It will be the 7th Olympic Host City I have visited - spend some time counting how many you have seen.
3) I will be visiting the European Parliament in Brussels. If you really need to fill some time, please solve the Eurozone crisis (and remember to write down your answer).
I've just looked through my old emails from cdbaby I can see that when I received that email in 2007 I instantly forwarded it to several friends. It clearly worked.
I would be annoyed if I got this email present-day, but in the past, in a world of online retailers trying to seem "authentic" or "legitimate" by being excessively formal, it would have been a breath of fresh air.
That the tone of your correspondence (and the little things in general) matter is a timeless message.
But what exactly that tone should be is a constantly shifting matter of style/perception.
Memorable and authentic is a win. Memorable and fake is poison. Unmemorable is the dead pool.