I love using TripIt, but is Pro worth the price?

Without a doubt, TripIt is one of the best online travel tools I’ve come across. With very little effort, TripIt creates consolidated travel itineraries including air, hotel, and car, enabling automatic calendar integration and sharing. They even introduced an iPhone app, putting the itinerary, along with helpful links to maps and flight tracking, right in your pocket whether online or off. The company cleverly combs forwarded confirmation emails from just about every travel company and web site, extracting the pertinent bits.

I’ve become a TripIt ambassador, inviting all of my co-workers and close friends to join in. But free services have their limits, and I have long wondered how TripIt would monetize their business. The company has been partnering with airlines (like Virgin America) and airport shuttle services, but partnerships don’t keep the lights on. Eventually the company would have to find a way to make money.

The answer arrived in my inbox this morning. TripIt is introducing an optional “TripIt Pro” version which adds automatic monitoring of itineraries, notifying if your flight is delayed, for example, as well as mobile alerts. This version will cost end-users $9.95 per month (once the trial period ends).

Although I love TripIt, I’m not sure if this upgrade is worth nearly $120 per year. Airlines already send alerts of delayed or cancelled flights to my phone via email or SMS. I trust that TripIt’s alerts will be more uniform and helpful, but I doubt they’ll be that much better. For now, I’m holding off on TripIt Pro.

The company does have plans to add alternate flight options in the future, which might start adding serious value. If they can say “go to the Delta counter within the next 10 minutes to get re-booked to Boston” I’d be all over it! I’d also like to see better integration with Exchange and iPhone calendars than the current simple ICS subscription. But let’s think bigger than this.

As a frequent flier, I’d love it if TripIt could help manage my airline and hotel mileage accounts. What if it suggested ways of maximizing their value, keeping track of upgrade “stickers” and the like? What if the company monitored the latest mileage promotions? I’d also love it if they included airport tips, like which restaurant at Chicago O’Hare serves edible food (Maccaroni Grill near gate K2) and where to find a power outlet (in the outermost corridor between E and F). TripIt already points to SeatGuru’s amazing aircraft information, but how about integrating this information right into the itinerary? And I’d love to see a combination of TripIt and Kayak!

What do you think? What can TripIt add to make its Pro service worthwhile to the frequent flier?

© sfoskett for Stephen Foskett, Pack Rat, 2009. | TripIt Goes Pro To Monetize Travel Itinerary Management
This post was categorized as Apple, Personal. Each of my categories has its own feed if you'd like to filter out or focus on posts like this.

iPhone OS 3.0 is coming, offering enhancements for enterprise Exchange ActiveSync

As the release of iPhone OS 3.0 nears, I set out to discover how the new OS changes the iPhone’s ability to synchronize data with Microsoft Exchange servers using ActiveSync. What follows here is my deductions so far, and is of course subject to change when the new OS is released!

For the most up-to-date information, see my iPhone Exchange ActiveSync Guide!

This post is part of my series focused on integrating the iPhone with Microsoft Exchange using ActiveSync:

• iPhone OS 3.0 information:
  1. First Look: iPhone 3.0 And Exchange ActiveSync Integration
  2. How To Subscribe To Internet Calendars In iPhone OS 3.0
  3. How To Access LDAP Directories In iPhone OS 3.0
  4. iPhone 3.0 Exchange ActiveSync: Better But Not Perfect
• How To Set Up iPhone Exchange ActiveSync
1. A Few iPhone Exchange ActiveSync Gotchas
2. Can the iPhone Sync With Multiple Exchange Servers?

New ActiveSync Features

1. iPhone OS 3.0 allows users to create meeting invitations! Finally, right from the phone, you will be able to set up meetings, select invitees, and send invitations. Initial reports are that this functionality is definite and fairly complete.
2. Enhanced mail search includes contacts, messages, and even mail still on the Exchange server! This is a huge and welcome addition. No longer will you be frustrated that the iPhone didn’t download that one important message from last month, and no longer will you have to scroll around trying to locate it! This is integrated into the new Spotlight screen: Flick left from the home screen and you’ll be able to search email, contacts, calendars, and all other phone content! But Spotlight only searches message metadata, not message content.

New Related Features

1. The calendar app supports CalDAV and ICS calendars as well as ActiveSync, making it much easier to use Google, Yahoo, and TripIt calendars. But these probably will not be integrated and synchronized with the ActiveSync calendar, leaving you in multiple-calendar hell.
2. Peer-to-peer contact exchange using BlueTooth seems certain. Since the iPhone gracefully integrates on-phone changes with ActiveSync contacts already, this will be a welcome way to build out one’s Exchange address book.
3. Cut, copy, and paste are definitely in, and will work in the mail, contacts, and calendar apps!
4. The mail app now supports landscape mode, with its larger keyboard.
5. A new API for email within applications would be compatible with Exchange, allowing a new family of corporate apps and possibly mitigating some of the missing features. I can imagine someone developing a far more feature-packed email client which embeds the native email client and extends its support to public folders, for example.
6. iPhones running 3.0 appear to allow automatic on-demand connections to VPNs. Again, not specifically an ActiveSync feature, but this would make the process of accessing a firewalled Exchange server more friendly.
7. OS 3.0 supports LDAP servers. Although this is not an ActiveSync issue per se, it could allow a workaround for the single-ActiveSync issue (which remains). LDAP contacts would make the basic IMAP email connection with a second Exchange server somewhat more tolerable. But it’s not yet clear if LDAP contacts are all that functional in 3.0, or whether they’ll make the cut at all.

Bad News

1. The iPhone will remain limited to full ActiveSync with a single Exchange server. Although you are free to establish as many IMAP connections as you like, including connecting to Exchange with IMAP, you cannot use more than one ActiveSync service. However, as noted above, 3.0 does include LDAP support so at least the contacts from your second Exchange server might be accessible.
2. Still no notes sync (with Exchange). Although iPhone OS 3.0 does allow synchronization of notes with Apple Mail for Mac users, it does not appear to support Exchange or Apple’s own MobileMe over-the-air services.
3. Spotlight does not include full-text search of mail messages. Although it’s nice to be able to search through everything on the iPhone, and even content on the Exchange server, you still have to remember the sender, subject, etc.
4. Battery life is poor with Exchange ActiveSync push and the new push notifications enabled. iPhone push battery life has been a problem for quite a while.

As the iPhone OS 3.0 release nears, I will keep my eyes open for enterprise Exchange ActiveSync features and post them here. Subscribe to my Apple feed for up-to-date details!

© sfoskett for Stephen Foskett, Pack Rat, 2009. | iPhone 3.0 Exchange ActiveSync: Better But Not Perfect
This post was categorized as Apple. Each of my categories has its own feed if you'd like to filter out or focus on posts like this.