The Upgrade

No sense in burying the lede: I’m still sober. As I write this, the counter of ispauldrinkingagain.com is ticking towards 800 days. The public self-shaming has worked, so far, and I haven’t had a drink in twenty-four months. Even today, the support of friends and strangers steadfastly refused to subside even though, honestly, I struggle to remember what all the fuss was about alcohol. Much of that is down to the clear and present benefits of sobriety. Six months after quitting, I’d dropped 42 pounds in weight and was walking ten miles a day. A lack of hangovers gives you that kind of energy, and time. And once you start to feel better, you’re driven to eat better and walk further and … well … not drinking is addictive too, it turns out. Two years sober and I’m in the best shape of my life, and I’ve never been so happy. I’ll get to a couple of the other reasons for that happiness in a moment. But before that, let’s tick off the hotel question. Four years after giving up my London flat am I still living a nomadic life in hotels?

In hotels, yes. Nomadic, slightly less so.

I’m writing these words from the Plaza Hotel in Downtown Las Vegas. I love the Plaza, not just because it’s a nice hotel with large rooms available for $50 a night, but also because, like me, it figured out a way to profit from the thorough hiding dealt out to the hospitality industry by the global financial meltdown.

One way or another, every city in America was affected by the bursting of the housing bubble, but Vegas—a city where risk is encouraged, and frequently rewarded—felt those effects harder than most. Before the crash, house-flipping had become something of a local sport, with first-time buyers and existing homeowners snapping up new houses and condos as fast as they could be churned out across the limitless desert land surrounding the city. As house prices continued to rise, the buyers would “flip”—and flip again—their property, using the proceeds to buy more and more and more real estate, despite having no real idea who would ultimately live in all these houses. It seems remarkable now—or fitting, perhaps—that even the inveterate gamblers of Vegas didn’t realize that no lucky streak lasts forever. The bubble burst, the flips turned to flops and the entire town went broke. Get into a Vegas cab today and there’s roughly a one in three chance that the driver will be a former construction worker—lured here by the plentiful building jobs and, of course, the cheap housing. And now they’re trapped, paying off an underwater mortgage—or flat-out homeless. Commercial property suffered too, albeit on a grander and more tragi-comic scale. A couple of miles south of the Plaza lies the 75 percent completed shell of the Fontainebleau hotel. Even unfinished, it’s an impressive sight: a 69-story, 3,889-room tower of shimmering blue glass. But the cranes are no longer moving; the recruitment center across the street has stopped hiring. For the time being, the Fontainebleau is destined to remain a $2.9 billion building site—the banks having refused to make good on the final chunk of loans needed to complete construction. Finally, three months ago, the Fontainebleau’s owners auctioned off all of the hotel’s unused fixtures and fittings. Seeing the opportunity, the Plaza bought all of the room furniture, paying pennies on the dollar. Which is why I’m sitting in the newly refurbished Plaza, on a $400-a-night chair, at a $400-a-night-desk, next to a $400-a-night bed, all for less than fifty bucks.

Why I’m in Vegas—particularly Downtown Vegas—is a slightly longer story: one that began as a direct result of the book you’re holding. Last May, I decided that it would be fun to spend an entire month here, staying a single night in each of the hotels that line the Strip.

“Ugh. That’s the worst idea I’ve ever heard.”

It would be fair to say that Sarah didn’t share my enthusiasm for my trip. Moreover, it turns out her opinion was shared by the majority of my American friends. “You’re an idiot,” said another, when I explained my brilliant plan. “Are you fucking kidding me?” wondered a third.

Even my insistence that the trip was “for work” fell mainly on deaf ears, except in the case of my friend Kate, who snarkily enquired if that meant I was planning on becoming a prostitute. Why else would I want to move to Sin City for an entire month?

Actually, Kate wasn’t far off the mark: the naked commercial truth was that my UK publisher—in the form of my new “publicity manager,” Jess—was badgering me for idea on how we could promote The Upgrade in the old country.

“I could spend a month dicking around in Vegas hotels and writing about them,” I suggested, without really thinking through how much work that would actually entail. “And this will be my first visit to the Strip since I stopped drinking. Thirty days sober in Vegas might actually kill me.”

Jess’s reaction to the idea went way beyond mere professional approval: she was positively bouncing with excitement, while also seething with jealousy. British people who have never been to Las Vegas really want to go to Las Vegas: Jess’s enthusiasm and envy were shared by every one of the Brits and other Europeans to whom I mentioned the plan. My friend James from London promptly canceled all of his meetings and booked a plane ticket to join me for a week.

I’d expected a mixed reaction, but not one so neatly divided along nationality lines. My non-American pals couldn’t imagine a more fun place to spend a month than Vegas, while my American buddies would rather put their eyes out with the blunt end of a cocktail umbrella than set foot in the Bellagio or the MGM Grand.

So what gives? Why do so many Americans turn up their noses at Vegas, while we foreigners can’t get enough of it?

For a start, Americans’ familiarity with Vegas has matured into the mother of contempt. Forty years have passed since Hunter S. Thompson and his “Samoan” attorney jumped in their red shark and began the journey that would forever brand Vegas as the global center of decadence and depravity. In the four decades that followed the publication of Fear and Loathing, Las Vegas has swollen unrecognizably wider and taller and brighter and costlier and pornier. Compared to Thompson’s bleak and gritty Vegas, today’s Strip is like Disneyland—if Disneyland doubled its prices and paved its streets with badly-Photoshopped hookers.

Hollywood hasn’t helped: 2010’s most popular movie—The Hangover—told the story of a gaggle of man-children who travel to Vegas and nearly drug themselves to death. Indeed, every single Vegas-based movie or TV show from the last couple of decades—Fear and Loathing, The Cooler, Showgirls, Leaving Las Vegas, Honeymoon in Vegas and every episode of CSI: Crime Scene Investigation—has delivered broadly the same message: Vegas will mess you up good. And certainly my own history with the city would appear to bear that out.

Then there’s the mounting economic argument against celebrating Las Vegas. Writing on The Daily Beast, Meghan “Daughter of John” McCain blamed Vegas’ reputation as a den of reckless abandon for the fact that her father is no longer able to visit—lest Democrats accuse him of possessing poor judgment.⁵¹

Why, then, are we foreigners still drawn the place? Aren’t we supposed to be the cultured ones? Well, yes. And that’s sorta the point: we love Las Vegas for precisely the same reasons that we love America. The town is the living, breathing embodiment of the phrase “only in America.” Frankly, no other country but the USA would have the solid brass balls required to build the place; to see a patch of desert and declare “what this place needs is a bunch of casinos, hookers and a big, glass, Egyptian-themed pyramid with an American flag suspended from the ceiling!”

Sure, the Chinese have the money and the love of gambling, but they lack the showmanship: there’s a reason the Triads have failed to produce their own Sinatra. The Saudis love to waste their oil money on giant playgrounds surrounded by sand, but their squeamishness over booze and naked women takes them out of the running. Europe? Please. The Germans lack the sense of humor; the Spanish would never get it finished, we Brits don’t have the space—and the French? Two words: Disneyland Paris.

No, Vegas is as quintessentially American as a teenage kid pleasuring himself with an Apple Pie, and in the past half-century or so it has grown to reflect all of the best and worst of the land of the free. The impossibly beautiful women; the love of risk-taking and the life-changing consequences those risks can bring; the sense of well-pack-aged fun; the really freaking amazing weather. Hell, the town even has its own Statue of Liberty, just like the one that has beckoned so many immigrants to a new life on these shores. Except, of course, the Vegas version has its own roller coaster. Tired and huddled masses? Not any more!

In a final ironic twist, while various American editors were interested in commissioning me to write a one-off piece about my trip, it took the Greek-born founder of what is now the content arm of America Online to see the full potential of the adventure. “You have to write a daily diary, daahling!” cried Arianna Huffington in that way she does (she really does). “And take this Flip Cam! Get video!” God bless you Arianna: the American Dream is you.

My plan was to start out in LA, where I’d rent a suitably American car, and drive three hours across the desert until I hit the Sahara hotel—the one-time home of the Rat Pack that was now just weeks away from closing permanently after a lifetime of service. From there, I’d just follow the best deals along the Strip, writing about whatever fun occurs along the way.

More importantly though, I wanted to spend the bulk of my trip away from the bright lights. To meet some of the people who work and play in Vegas, with no less hubristic a goal than to figure out what modern Vegas can tell us about the state of the American dream.

I wanted to spend one day with a Vegas cop, and another with some kind of sex worker (“FOR WORK”). I wanted to find God in a casino chapel and ask a real-estate expert to explain why the Vegas housing market is so screwed that people have to live in storm drains. I wanted to meet someone who lives in a storm drain. I also wanted to get married to a cocktail waitress dressed as Elvis, shoot an assault rifle, jump off a building and talk to fat people in the Burger King at the Luxor. God, I hate the Luxor, but I’d lay money that some interesting stories pass below its stupid pointy roof. And one more thing: 5 percent of Las Vegans are members of the Church of Latter-Day Saints—maybe, finally, I might meet a fucking Mormon.

Thirty-four days later and, of those lofty goals, I’d achieved precisely two. I’d spent a downlifting afternoon in the company of two foreclosure lawyers who painted a picture of the greed, misfortune and human stupidity that was neither limited to the bankers nor the punters. And, yes, I’d finally met a Mormon: a spa consultant who invited me to join her for a “couples” massage treatment that she had designed for the Cosmopolitan. Four hours naked with a sexy female Mormon: done and done.

My final few days on the Strip were a curious whirl of press—TV, radio, magazines, newspapers of various stripes—all of whom asked the same question in a different way: how has 33 days in Las Vegas changed my opinion of the city?

As I stood outside Caesars Palace, being interviewed by Fox5’s Elizabeth Watts, it occurred to me that there’s probably no other city on earth in which a man wanting to stay an entire month would constitute headline news. But Vegas, of course, is unlike any city on earth: it’s a place where, so the popular narrative goes, out-of-towners like me fly in in our millions, drink our body-weight in alcohol, accidentally fuck a hooker and go home with enough “crazy” stories to get us through the rest of the year.

Embarking on the Vegas trip, I expected—and received—a lot of cynicism from Las Vegas locals. Blogs with names like Vegas Chatter and Vegas Tripping crowed that I wouldn’t last a week let alone a month. And I get it: for people who call Vegas home, the idea of yet another journalist coming to their town and living out a Hunter S. Thompson fantasy on the Strip might be cause for rolled eyes and cynical sighs.

Hell, even people who were professionally obliged to be nice to me weren’t. Most hotel PRs on the Strip flatly declined to meet with me. On the few occasions when I wrote negative reviews of hotels or shows, the reaction was swift and, well, mental—Criss Angel’s publicist spent half an hour on the phone railing against the “inaccuracies” in my review of his show (“You said that Criss is a ‘douche’—he isn’t” / “Actually, I said he dresses like a douche. And he does.”) while somewhat-sinisterly insisting that she’d hate for one negative review to ruin my relationship with the Cirque du Soleil “family.”⁵²

I’ve dealt with a lot of big city PRs in my life and I’ve never, ever seen the kind of defensiveness I experienced in Las Vegas. Maybe they’re just not used to being asked actual questions, I thought. After all, the city’s most high profile entertainment “journalist” is Robin Leach: the guy who used to host Lifestyles of the Rich and Famous—a man who, had he been present for the killing of Osama bin Laden, would have felt compelled to praise the man’s history of charity work.

For the longest time I was baffled. The locals distrusted me—until they met me at least—the PRs hated me and the media couldn’t understand what the hell I was doing spending so long in their town. What could I do to please these people? And why on earth would Las Vegas of all places—a city that prides itself in crazy behavior and not giving a fuck—act so defensively and insecurely when faced with an unpaid blogger from—gasp—The Huffington Post?

Again, it took me an embarrassingly long time to figure out the answer. For a start, let’s once and for all dismiss this myth that Las Vegas is a crazy place where “anything goes.” It isn’t. It’s a place where almost nothing goes, especially if it’s likely to offend Jesus. Gay people can’t get married; and most chapels flat-out refuse to even perform civil ceremonies for (as one wedding chapel worker put it) “those people.” Strippers can’t get fully naked where alcohol is served. Escorts can’t ply their trade or get health benefits. The mannequins in the lobby of the Mirage wear pasties for fuck’s sake. Pasties! But—ooh!—at least you can smoke in casinos.

Rampant capitalism—and a bedrock of religion—do that to a place: filing the edges off the fun and distilling everything down to its most efficient money-making core. There’s no profit in anarchy; you can’t spend money when you’re unconscious. And why on earth would you want to frighten away the Bible Belt Republicans? They’re the ones with all the cash.

Let’s also dismiss that even more prevalent misconception—particularly amongst us outsiders—that Las Vegas is a big city that doesn’t give a fuck. It most certainly is not. Las Vegas isn’t a big city, but rather a small town which—thanks to a confluence of legislative, geographical and historical events—happens to attract billions of dollars of tourism revenue each year, centered around a single street that mostly lies just outside city limits. Oh, and it very much does give a fuck.

To be clear, when I say Vegas is a small town, I don’t mean it’s a big city with small town attitudes; I’m mean it’s actually a small town. A place where, away from the Strip, you can’t walk into a bar or a coffee shop without bumping in to someone you know by name. A place where the arts scene is confined to two or three blocks, but where a passionate group of local business people and culture-lovers bust their asses every day trying to help it grow. A place where the mayor gets elected time and time again with 85+ percent of the vote, despite his fondness for organized crime, and no one being sure what he actually does. A place where the next mayor will be the old mayor’s wife. A place where foreclosures hit hard, unemployment is amongst the highest in America and where the education budget is being slashed. Again.

Once you realize all of that, suddenly everything else starts to make sense. The distrust of outsiders—particularly reporters; even bloggers—isn’t because the people of Las Vegas are mean; in fact everyone I met was as warm-hearted as the people I’ve met in any town in America. It’s because every month another journalist or filmmaker comes into their small town and writes the same story, or makes the same movie.

Those writers mention the wedding chapels (ho ho ho), but not the museums; they meet the “larger than life” mayor but not the people actually building businesses and raising families here. And then they fuck off and leave the good people of Las Vegas to continue worrying about their mortgages, or their kids’ schooling or their jobs. And that includes the PR people who—as one admitted under promise of anonymity—don’t want to get fired for “allowing” a rogue journalist to write something bad. “We’re used to controlling the story,” said my source, “we give them a comp and they write what we tell them, and everyone’s safe.”

Me not wanting a comp during my trip (uncharacteristically, I paid for all but three of my rooms—I wanted to see what the hotels were really like, not some sanitized media version) wasn’t a positive sign, it was a red flag: I was up to something. And no one ever got fired for saying no. Furthermore, in a small town, no good can come from negative reviews: when tourism is the lifeblood of a place, every show has to be AMAZING, otherwise—oh God, oh God—people might stop coming.

But of course, the cynics were right weren’t they? Read back the above paragraphs and there it is: the hit-job they feared. Silly old small town Vegas, with its silly terrified people—and clever old me coming in and cleverly understanding what makes the city tick.

Except that’s the precise opposite of how I came to feel about Las Vegas.

I came in to the city with all the swagger of a Strip-striding weekend tourist, ready to confront the place based on my misconception of its size and self-confidence. I wasted a huge amount of time being confused by the defensive attitudes I encountered and being surprised by the culture, the arts scene and how friendly everyone was when I finally got to speak to them.

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.”

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.