From the Red Carpet: TripIt Goes Hollywood

Remember when travel used to be elusive and glamorous?  Well, although the glitz of cargo ships and luxury rail has largely faded and traveling is now more of an everyday activity, it can still occasionally wow you. Case in point: the TripIt team’s recent trip to New York for The Webby Awards.

The 15th Annual Webby Awards - Cocktails

Image courtesy of The Webby Awards on Flickr

Of course, I should start by saying what an honor it was (and is) to have won the Webby for Best Mobile Travel App.  TripIt makes some of the highest rated and ranked apps for iPhone, iPad, Android, and Blackberry, so we already know that travelers love our apps.  But receiving recognition from the industry leaders who vote for the Webbys – people like David Bowie, Matt Groening, Richard Branson, and Harvey Weinstein – is an extra thrill.

But this trip was also about the thrill of attending a real-world red carpet event, including fancy parties, celeb sightings, paparazzi – the whole deal.  I attended along with TripIt co-founders Gregg Brockway and Andy Denmark (and their spouses), plus Amy Jackson, who heads PR for TripIt.  While some of them tried to play it cool, I admit I was a tiny bit star struck.

Internet Week 2011 Webby Award Cocktails

Image courtesy of Yahoo Advertising on Flickr

It started with the Sunday-night cocktail reception at the Boom Boom Room, the swank bar/club on the top of the Standard Hotel in NYC’s Meatpacking district. The main “celebs” here were other Webby winners – people who are well-known among the Silicon Valley / digerati crowd, but not exactly famous.  We did catch a very brief glimpse of Adrian Grenier (star of HBO’s Entourage), but the next famous person (albeit not quite as well known) was the husband of celebrity stylist Rachel Zoe, Rodger Berman.  Of course, I can’t help but think that the biggest stars in the room were TripIt’s very own gang, pictured here.

Internet Week 2011 Webby Award Cocktails

Internet Week 2011 Webby Award Cocktails

Internet Week 2011 Webby Award Cocktails

Images courtesy of Yahoo Advertising on Flickr

But the big guns weren’t until the next day when we attended the main Webby Awards event at the Hammerstein Ballroom.  We emerged from our taxi only to be approached by tourists asking us what all the buzz was about across the street at the Hammerstein.  When we told them it was the Webby Awards, they said “the what?”  A subtle reminder that this red carpet was largely for tech geeks, but that just helped set my expectations for the event a bit lower than they had been.


And that’s probably why I was so excited to immediately “run into” Lisa Kudrow on the red carpet as we entered the ballroom.  Oh, and that’s Brooke Shields she is talking to (she never turned around, so I had to settle for the back of her head).


Once inside, we spotted many other celebs from afar or presenting on stage.  The list included Grenier, Marlon Wayans, Dan Savage, Christiane Amanpour, Anna Wintour (for the record, I don’t think she was wearing Prada), Daniel Radcliffe, and Antoine Dodson.  The highlight for me was Wintour’s five-word acceptance speech for’s award:  “Sometimes, geeks can be chic.”  The crowd seemed to love Dodson’s live rendition of his famous YouTube video for “hide your kids, hide your wife.”

And in case you missed our five-word speech, here’s “Because getting there shouldn’t suck,” in all its glory:

After the main awards, we headed over to club Hiro at the Maritime Hotel for the after-party.  I guess celebrities go to bed early (especially on this Monday night!) because the only one we saw there was Grenier – yes, he gets around!  Not only did we see him, but we boogied right next to him on the dance floor for quite a bit.  It’s a miracle we even saw him through the fence of models towering over him.

Meanwhile, our colleagues in San Francisco celebrated by watching the live streamed awards at Mighty. It was truly a bicoastal affair.




So there you have it.  It was a fun experience I will remember forever, and a great reminder that travel can still be fun, exciting, and even a little bit glamorous.  Given the popularity and rave reviews of our new iPad app, I have a feeling this may not be TripIt’s last visit to the Webby Awards.

And next time, I’ll be sure to get Brooke Shields’ picture from the front.

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