Searching for California Casual Chic


A note from Greg the Frequent Miler: In November 2017, Barclaycard offered to send me on an all-expense-paid first class trip to California to learn about the new Uber credit card. Their goal was clearly to butter me up to write good things about the card. Conflict of interest? Absolutely. Was I interested anyway? You bet — it sounded awesome. Plus, there were no explicit strings attached. In other words, there was no requirement for us to write about the card or the trip, or anything else for that matter. Since we had already written good things about the Uber card, I figured that the conflict of interest issues were actually pretty small. But neither I nor Nick could go since it overlapped with FTU Chicago. So, instead, I forwarded the invite to author and photographer J.M. Hoffman. To-date, for Frequent Miler, Joel has published several destination guides under the heading “You’ve gotta see this”: Australian Wildlife, Melbourne and Sydney, and the Florida Everglades. Now, Joel adds a few lighthearted stories about his all-expense-paid Uber-adventure. 

And, for the record, I would have been equally at a loss for how to dress “California casual chic,” but at least I know who Katy Perry is…

I was told to dress in “California casual chic,” so right off the bat I had a problem, because I’d never used those three words together.

My destination was Los Angeles, for a three-day weekend of tier-one experiences highlighting the vast rewards at the finger tips of Uber card members. (Yes, I lifted that misleading phrase directly from the promotional material sent to me by Uber and Barclaycard, who paid for my extravagant trip to announce the launch of their new Visa card.) I suspected, however, that those top-notch experiences were designed for people who know how to dress in California Casual Chic, not for people like me who wear New York Whatever’s Convenient.

My All-Expenses-Paid Suite at the SLS Hollywood

And that was before I knew that I’d be joined in Los Angeles by such elegant “influencers” as Christie Ferrari, PhD, who reaches hundreds of thousands of followers on Instagram; and Kimia Kalbasi, who is going to win a prestigious award one day for her innovative photographic sense. I, on the other hand, didn’t even know that “influencer” was a job.

Even my hotel, the fabulous SLS Hollywood, reminded me of where I was, with a mirror-shelf in my room displaying an SLS-branded fan next to a solitary die (for luck). I bet that was California Casual Chic. I bet Snake Girl watching over the hotel billiard table was, too.

Snake Girl in the SLS Hollywood

And let’s be clear about something else: When Uber throws a party, they go all out. Our first cocktail hour — just one of many, and longer than an hour — featured drinks crafted with liquid nitrogen. And you don’t want to be ill-dressed at a magic-potion party.

Magic-Potion Cocktails at the Uber Launch Party

Then it was off to the exclusive Catch LA for dinner in a private dining room specially redecorated with prominent branding.

In fact, it turned out that our program offered a well-rounded, careful balance each day of breakfast, lunch, and dinner (roughly two hours apiece), plus copious drinks, of course, including cannabis cocktails in at least one spot:

Cannabis Cocktails at Gracias Madre

That kind of grueling schedule leaves precious little time for other events, so our only true destinations were a wine-tasting “safari” (outdoor zoo) in the stunning Malibu hills and a show by LCD Soundsystem at the famous Hollywood Palladium. (“LCD Soundsystem” is the name of a band, not, as I first thought, the technology they use.)

Lauren Bowling at Malibu Wine Safaris

We also had an afternoon pool party at Katy Perry’s old residence in the foothills overlooking Los Angeles, where stars like Kevin Hart and Laz Alonso dropped by to see and be seen, and the singer Wrabel dropped by to sing. (And by “dropped by,” I mean they were paid to show up.)

Pool Party at Katy Perry’s Former Residence
Wrabel Gives a Private Sunset Performance

So there I was, spending thousands of dollars of other people’s money on dozens of hours of eating and drinking, of seeing and being seen, and of acting like a VIP:

My Ride for the Weekend: A motorcade of these custom-decorated SUVs drew stares as Uber brought us to each new destination.

On one hand, this weekend clearly wasn’t for me. I’d never heard of LCD Soundsystem. I didn’t know who the stars who dropped by were. I didn’t even know who Katy Perry was. (Turns out she’s pretty famous, at least to judge by her 68+ million followers on Instagram.) When I go on safari, it’s not to Malibu wine country but to the African bush. I’m not a big drinker. And I had never used Uber!

On the other hand, I did have a blast, in spite of my I-go-on-safari-in-Africa snootiness. And while I didn’t sign up for the Uber card, I have started using Uber from time to time.

Still, the finances of the card nagged at me. Why did they spend so much promoting it? How could they offer 4% cash-back on dining without charging an annual fee? Wouldn’t they lose money on each dining transaction? And why didn’t they offer 4% cash-back on Uber rides? I’m still working on those. In the meantime, Harvard’s Scott Kominers has a few thoughts.

And as for California Casual Chic? Well, it turns out the SLS Hollywood has some samples conveniently painted right there on the elevator wall. So I took a selfie with them.

I blend right in, don’t I?

Selfie With Pretend People who are California Casual Chic
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