The Upgrade: A Cautionary Tale of a Life Without Reservations (40 page)

It was only when I got past all of that nonsense that I started to understand the place. But only started.

It would be ludicrous for me to suggest I understood a damn thing about Vegas after just a month there. Socrates once said, “I am only wise insofar as what I don’t know, I don’t think I know.” And that’s how I felt at the end of my trip: my 33 days in Las Vegas had only taught me how much I don’t know about Las Vegas. And, as it turned out, the end of my month in Vegas was only the start of a far, far longer relationship with the city.

I’ll get back to the Vegas story in a moment, but first an interlude to talk about a girl.

Her name was—and is—Molly and she was—and is—a flight attendant for Virgin America. We met on a flight from San Francisco to New York when, like a dick, I tweeted a message about how “hot” the girl making the pre-flight safety briefing was. I’d been sober for nine months by then, but apparently I was still capable of acting like a jackass, particularly when it came to pretty girls. To make matters worse, by some weird twist of something one of my fellow passengers on the flight happened to follow me on Twitter (proving my point that you never know when someone is watching) and decided it would be funny to share the message with the girl in question.

By rights that kind of behavior should get one booted from a plane, but—as I discovered—Molly has much more effective, and appropriate, strategies for dealing with people like me. A few moments later, she was crouched next to my seat. “Just so you know,” she said, “we can see Twitter too.”

Busted.

Except not really. An hour or so after landing, I was notified that@friendlyskies was now following me on Twitter. I followed back, of course. And sent her a direct message. You know, just to apologize for being a dick. Maybe she felt bad for embarrassing me on the plane;
maybe it was the accent—but for some reason, direct messages soon turned to emails, emails to texts and finally to dinner.

My first date with Molly was possibly the most difficult of my adult life. I’d never really been someone who goes on “dates”—preferring instead the British approach of going to a bar, getting drunk with a girl and—rarely—waking up with her the next morning.

Sitting across from a beautiful, smart, funny flight attendant—even writing this I still have no idea why she’d said yes—I realized this was the first time in a decade that I wouldn’t be able to blame booze when I inevitably struck out with an amazing woman.

“Should have started with a plainer girl,” I thought. Why make it harder on myself.

Another interlude. I promise all these threads will join up in a moment.

Two years ago, on the night of my thirtieth birthday, I was writing a weekly column for Mike Arrington’s TechCrunch. Sarah was working there too. It was the perfect gig, and I stuck with it—even when, nine months later, Mike decided to sell the company to AOL for just shy of thirty million dollars. On the night the sale was announced, Sarah called. It was late and she was crying. “This is the end of TechCrunch,” she said.

And she was right, of course. It’s rare for any company to survive an acquisition without losing its personality—and AOL is notorious for fucking up the businesses it buys. “The killer of all things good” is how one disgruntled founder described them. By sheer force of Mike’s personality, TechCrunch remained intact for almost a year. Even AOL’s subsequent acquisition of The Huffington Post—which installed Arianna Huffington as the new editor in chief of all AOL “content properties”—didn’t screw things up too badly. Mike had received assurances that TechCrunch would remain editorially independent from AOL and so Arianna was forced to accept that she was ring-fenced out of our one tiny corner of the Internet.

But then, finally, it happened. Mike decided that, with all his newfound wealth, he’d quite like to set up an investment fund—CrunchFund—to invest in technology startups, including some of those we wrote about at TechCrunch. That was all the excuse Arianna needed: citing the extreme conflict of interest of an editor investing in companies he covered, she forced AOL to make a choice: either Mike goes or … well, that was really the only side of the ultimatum. AOL had acquired Huffington Post for $300 million dollars, and TechCrunch for less than a tenth of that. Arianna was too valuable to anger, Mike was ousted and Arianna took over TechCrunch, installing a New York-based puppet editor to do her bidding. I resigned on the same day—Mike had been too good a friend for me to stick around. Sarah left shortly afterwards, followed by the site’s former CEO, Heather Harde. An “implosion” was how
BusinessInsider.com
described it.

Another first: the first time in my life I’d resigned from a gig rather than being fired.

And so let’s draw together those threads.

 

December 2011
. A year and a half after that first date with Molly. The date which, despite my excruciating attempt to explain why I wasn’t drinking while trying not to sound like a mental patient, lead to a second and a third. It also lead to a whole string of other wonderful, and terrifying, new experiences: her meeting my friends, me meeting her friends, her meeting my parents, me meeting hers, our first vacation together. All things that, in other words, my old self would have dismissed as unbearably domestic and dull but which, when experienced with Molly, made me absolutely sure that getting sober was the best decision I ever made. Would ever make.

(Molly’s sitting on my bed at the Plaza as I write this. She says “hello.” The fact that I’m sharing that shows just what a thoroughly unbearable couple we’ve become. Really, you’d hate us.)

 

Four months after my resignation from TechCrunch
. Freshly unemployed, and despite having literally written the book on why I should never again try my hand at entrepreneurship, I put together a business plan for a new publishing company. One that would specialize in producing magazines for ereaders and tablets like the iPad and the Amazon Kindle. In other words, platforms where readers have shown themselves willing to pay a modest cover price for the kind of real writing and reporting that the free, ad-supported web struggles to support. Some commentators have described the venture, somewhat inaccurately, as a “fuck you” to the celebrity-driven, ad-supported Huffington Post. Our first publication: a topical news magazine, with jokes, is due to launch later this year. Our first investor was, of course, Mike Arrington’s CrunchFund.

Our second investor is Tony Hsieh, CEO of clothing retailer Zappos—which was sold to Amazon in 2010 for close to a billion dollars. Tony is the last character of this story. During my month-long Vegas trip, he was the first local to email me a warm welcome to the city, offering to give me a tour of the new corporate campus that Zappos was building downtown.

After years of hemorrhaging tourism—and money—to the Strip, Downtown Vegas was in desperate need of regeneration. Seeing an opportunity to build a city, as once he’d built a company, Tony decided to relocate Zappos from the suburbs of Henderson to the former City Hall building downtown. In doing so, he’d bring thousands of young, reasonably affluent employees to the area—regenerating it at a stroke. The campus is due to open in 2013 but already work has begun on the restaurants, bars, coffee shops, retail stores, apartments—not to mention parks, schools and libraries—that all of those thousands of new residents will need.

What I quickly realized as Tony showed me around Downtown Vegas was that the area was becoming one giant start-up. A place into
which entrepreneurs were flooding, and where any idea that might attract more people and “energy” to the once beleaguered part of town was welcomed with a warm hug.

That first trip to Downtown Vegas wasn’t enough to convince me to move there, of course. Even sober, I was having far too much fun traveling the world, promoting my book and scooping up lucrative hotel review commissions on both sides of the Atlantic.

Still, after a brief trip to London for my book launch, I did come back to the city, to explore some of Downtown’s classic hotels like the Golden Nugget and the Golden Gate. And then, after a jaunt to LA to visit Ruth, I was back in Vegas again. The first of Tony’s investment projects—two new restaurants—were ready to open, and I didn’t want to miss out on seeing what was effectively the launch of his city “startup.” It was when I resigned from TechCrunch and instinctively booked a flight “back” to Vegas that I realized San Francisco was no longer my hub of choice. My new publishing company would be based in Downtown Vegas, and so would I.

If there’s a spiritual home of the hotel dweller, surely it’s Las Vegas. And what bigger way to prove that I really am finally immune to the siren call of alcohol—the drug which had helped me do so much career damage in the past—than to set up shop in a place where the stuff oozes out of the ground and runs down the walls?

So that really is the end of the story. It’s smart to be wary of memoirs where the endings are too neat—the protagonist really does get dry, he really does meet a perfect girl (on a plane!), he really does move to the mecca of his particular specialism (a place to which, by the way, his perfect girl’s job brings her several times a week), and he really—truly—is a completely changed man.

There’s only one way to know for sure, I suppose. Next time you’re in Vegas, head downtown and look me up. I’ll be the one living happily ever after.

T
here are so many people to thank and so few pages left in which to thank them, but first an important disclaimer:

Everything you’ve read in this book is true, to the best of my recollection. It is impossible to overstate, though, how much alcohol I consumed in the past few years and so it’s inevitable that my recollection is more than a little fuzzy in places.

Wherever possible, I’ve checked the stories with the people involved or with the official police record. I’ve also relied on the half-dozen notebooks that I filled during my travels, plus emails, blog posts, Twitter updates and all that stuff. Inevitably, though, there will still be mistakes.
Mea culpa
. Email me at [email protected] and I’ll be sure to fix them in any future printings.

In almost all cases I’ve used real names for people featured in the book. A couple of names have been changed where I’ve wanted to avoid embarrassing people, particularly girls who have been misguided enough to become involved with me. There are no composite characters though: everyone in the book is a real person …

And so, to the thank-yous …

Thanks firstly to every single person who agreed to allow me to write about them. In particular, Michael Smith, Michelle, Zoe Margolis, Scott Rutherford and Ruth Fowler.

A special additional thank you is due to Eris, Hannah and Kelly. I still have no idea what you saw in me, but I’m glad you saw it, however briefly. I’m ridiculously grateful that we’re still friends.

And a very special thank you to Molly Choma. Sobriety may be its own reward, but you make a pretty amazing bonus prize. I love you.

Thanks also to those who were fortunate not to have been included in the book, but without whom much of it wouldn’t have been
possible: Oli Barrett, Richard Moross, Sarah Bee, Stuart O’Connor—and in particular Olivia Hine for always having a better idea.

Thank you to Charles Arthur and Michael Arrington for being the two best editors in the world. Your patience, support and encouragement are appreciated more than I can say.

Speaking of patience, thanks once again to my parents for continuing to hide their disappointment at the path their eldest son has chosen for his life. I owe them everything.

Thanks to my agent, Robert Kirby at United Agents, my editor at W&N, Alan Samson, for believing that I had a second book in me—and Gary Baddeley at Disinformation for believing that Americans might want to read it too. I have no idea if you were right, but here it is.

More than any of the above, though, thank you to my best friends, Robert Loch and Sarah Lacy. There simply aren’t the words to thank you for staying with me for the ride, even when I threatened to swerve off the road. Without you I’d be dead, emotionally and probably literally. This book is dedicated to you both.

Follow Paul Carr on Twitter:
@paulcarr