I’m not sure what it is about me & ad firm Crispin, Porter Bogusky. I’ve been running into them pretty consistently since back in my Startup 1.0 days, and not just in the “Crispin seems to be everywhere lately” way. Just the other day, I saw that Crispin won Microsoft’s ad business here in Seattle which will put me in close proximity to them once again.

I first met Jeff Hicks and creative director Alex Bogusky back in Atlanta in the mid-90’s when we were launching the brand and Web site for VirtualBank. I think the agency had something like $20mm in billings back then. That’s a long way from the over $1b they do today. My companies have worked alongside or near CPB at Virgin Atlantic, BMW and EarthLink.

Their attitude then, as now, is what some might call “smart ass” but others label as “cheeky.” These are the guys who brought you “Subservient Chicken” and say you should “Wake up with the King.” They also handled the anti-tobacco “Truth” campaign, the launch of the BMW Mini and the highly viral “Simponize Me” Web site.

I can’t say I’ve always been enamored with their style. They produced the viral videos for a “Block of the Day” site that my Startup 1.0 company developed for EarthLink. It was like pulling teeth to get the videos past sophomoric penis jokes. Funny once, maybe…But 20 different spins on the same joke?

Still, CPB has always been in the enviable position of driving their clients; not vice-versa. They’ve done some amazing things that every ad-type dreams of being able to actually sell-thru to the client. The Virgin Atlantic spoof porn video comes to mind as one example.

But the general M.O. for a brand choosing CPB these last few years seems to be a brand in trouble. Burger King fell on some challenging times not long ago that put their very existence in question. EarthLink is still struggling to find a strategy as their dial-up cash cow starts to get a lot thinner. And we all know about what those “I’m a Mac, I’m a PC” ads have done to Microsoft’s image.

Hopefully, CPB can deliver a nice little shine to the new Microsoft I’m seeing here in Seattle. The company really is shaking things up lately, and my house will certainly be worth a lot more if Microsoft funds itself in a new hiring boomlet. I guess I’ll be staying tuned, as they say…