The WSJ reports that Apple is looking to hire high-level cloud experts to help guide the company’s cloud strategy. This is an encouraging move, because a fresh vision is exactly what Apple needs if it’s going to pivot from offering device-centric user experiences to network-centric user experiences. The very best way to get that vision, and to turn iCloud from a “me too” version of Google Apps into something uniquely compelling in its own right, would be for Apple to buy fistfuls of great startups that could super-charge iCloud with one or both of the following characteristics:

1. iCloud should give users the ability to do something they already do in a better, more fun, or more convenient way.
2. iCloud needs a network effect, such that iCloud users will routinely say to non-users, “Hey, even though you don’t own an Apple product, you still need to sign up for iCloud so that we can do this particular thing together.”

To that end, I’d like to suggest that if Apple is serious about developing a cloud strategy that isn’t doomed to failure, it should “think different(ly)” about its approach to product innovation and buy both Hipmunk and Tripit. Before you take to the comments to tell me to put down the crack pipe, hear me out.

Travel as the new “email, contacts, calendar”

Right now, iCloud’s lineup of web-based contacts, email, calendar, and storage doesn’t cut it because there are many fantastic, non-Apple ways of doing these things. Contrast this to Gmail’s launch, which innovated by offering webmail users the killer feature of gigabytes of email storage. Gmail was just plain better than Hotmail and other free webmail services, and users switched in droves.

Even though Gmail started out an engineer’s side project, Google is serendipitously riding the service’s success right into the enterprise. And now, the webmail service has become the proverbial camel’s nose under the enterprise tent; if Google Apps has a future in the enterprise then it can thank Gmail’s generous storage quota.

My point is that in order to gain traction with users, Apple should quit trying to replicate Gmail, and instead it should try to replicate Gmail’s recipe for success: just take something—anything, really—that users are already doing, and offer them a much better way to do it on your servers. Hence the Hipmunk suggestion.

Hipmunk has set out to build a better flight search engine, and searching for flights is something that everyone does at some point. So if Hipmunk is succeeding, then why not spend some of that giant cash pile to buy them and integrate them into iCloud? Make me sign up for an iCloud account in order to use Hipmunk, and then try to entice me to some of the other iCloud services by, say, automatically adding my Hipmunk-booked flights to my calendar. Or maybe integrate Hipmunk and Siri directly so that the latter can act as a travel agent for the former.

While Hipmunk would address the “better mousetrap” suggestion above, Tripit could give Apple the network effect that a cloud service needs in order to scale. I initially signed up for Tripit because my friends were on it and wanted to connect with me to share itineraries; now I use the service to plan all of my travel. Again, Apple could make an iCloud login mandatory for Tripit, so that everyone who signs up for the service in order to connect with a friend ends up with an iCloud account.

Ultimately, an Apple purchase of Hipmunk and Tripit may or may not be the right move, what I’m really trying to suggest that Apple do is to make the fundamental mindset shift that web technologies demand if they’re going to be taken on their own terms. As a product company, Apple is used to pouring large amounts of money into a few very large bets, and that’s a great approach for physical devices. But the cloud gives you the opportunity to make lots of smaller bets so that you can cut the losers and iterate the winners into something massive. Apple just hasn’t shown any signs that it “gets” the latter approach. So regardless of whether the company actually takes my suggestion and buys two travel startups, Apple should encourage its newly hired cloud execs to make lots of small, quirky bets, and then see where the winners take them. Leave the “hero product” mentality to the devices side of Apple, and let a million flowers bloom on in the cloud.