Apologies for the totally over-the-top headline but I was looking at two different stories this morning, which at first blush don't have much in common but seem connected in some way. The first is a story in the Observer about "Why the iPod is Losing Its Cool", and the second is about a conference in San Francisco later this month called the "Future of Web Apps" featuring - among others - Michael Arrington. So how are they connected? Well, they're both leading, lucrative brands in their respective industries with a huge amount of influence and little competition. The iPod is still the MP3 device to own despite efforts by Dell, Creative Labs, etc., while Arrington is arguably the King of Web 2.0 given TechCrunch is regarded as the arbiter of all things Web 2.0. Arrington's status as king was confirmed last month when Business 2.0 magazine had a photograph of him on the cover in a story about the business of blogs. What separates Arrington from many people in the Web 2.0 crowd is he's a true, dyed-in-the-wool entrepreneur with the energy and drive to aggressively seize a huge and fertile opportunity. Steve Jobs is doing the same thing with the iPod by pumping out new iPods just to make sure competitors don't grab a market foothold. But - and this is a big but - at some point even the strongest brands can lost some of their zest. Maybe the Observer story, which talks about declining sales and a consumer "backlash", is a true depiction of the iPod but maybe it just reflects the idea consumers are always looking for the next new and shiny thing because even cultural icons like the iPod become to lose some momentum over time. The same thing could perhaps be applied to Arrington, who is seemingly everywhere and anywhere within the Web 2.0 world given his expanding empire (blogs, consulting gigs, start-ups, parties, conferences) Don't get me wrong, TechCrunch does a great job of covering the Web 2.0 landscape and it clearly continues to have a large following (96,312 FeedBurner subscribers). At some point, anyone/anything starts to lose some freshness. Perhaps it's the need to have new voices or maybe I'm sitting way too close to the "Web 2.0" fire that Arrington helps fuel. Will I stop reading TechCrunch? No. Are there any indications Arrington is losing his mojo? No. In a sense, Apple and Arrington face similar strategic challenges: maintaining their market leadership positions while, at the same time, keeping their brands vibrant and vital. No doubt, it's a nice problem to have.