The Upgrade: A Cautionary Tale of a Life Without Reservations (26 page)

Another factor in reducing my rate was the fact that it was the eve of the winter solstice: Iceland’s shortest, most miserable day.

No one said that writing a book about living in hotels would always be sunshine and roses.

In the six months since
Bringing Nothing to the Party
had been published, my life had changed immeasurably.

I’d gone from being Paul Carr, the failed businessperson, loser in romance and struggling journalist, to Paul Carr, the failed businessperson, loser in romance and struggling journalist who had written a funny book about it.

That sounds like a tiny change in circumstances, but the effect had been dramatic. Two days after the book arrived in stores, I received my first piece of feedback from a total stranger: a woman called Ellie who had read it in one sitting, on a train journey from London to Edinburgh. Ellie had some questions, most of which concerned my relationship with my ex-girlfriend.

Up until that moment—and I realize how ridiculous this sounds—it simply hadn’t occurred to me that anyone would read the book. And it certainly didn’t register with me that many of the people who did read it would be total strangers. Thousands of total strangers, reading about my life.

Just before I left London after the launch, the head of a PR agency invited me to lunch. She wanted to pay me a small fortune to talk to her staff about how to use the Internet to make their clients look good, presumably on the basis that if I’d been able to—what was it Mil said?—partially fake a sensitive side, then my secret would probably work wonders for their clients.

We arranged to meet at her office and the first thing I saw when I walked in was two neat stacks of my book—maybe ten or eleven copies in all—sitting on her desk. I must have cringed when I saw them because the agency head immediately apologized—“sorry, I meant to hide those before you arrived. I’ve bought a copy for everyone in the company to get them up to speed with your story. Those are the spares.”

And so she had—I met maybe half a dozen of the agency’s employees and every single one of them had reached a different part of the story. “You’ve just left The Friday Project,” “you’re hanging out at Adam Street,” “you’ve just split up with …”

At lunch, every time I mentioned a friend by first name—Robert, Zoe, Michael—the agency head knew exactly who I meant. The guy with the apartment in Soho, the outed sex-blogger, the tousle-haired candy guy.

It’s hard to explain how that feels—meeting a group of people for the first time who already know everything about you including your friends, your arrest record and the tragic-comic circumstances in which you split up with your ex-girlfriends.

Flattering, in a way, that they’d cared enough to keep reading. But also fucking terrifying. I suppose bloggers like Zoe must feel like that too, but it was genuinely new to me: I’d always been careful not to talk about anything on my blog that affected me emotionally, but for some reason I hadn’t applied that filter to the book.

I’m not really sure why I felt more able to express myself honestly in print than online. The closest I’ve come to an explanation is that when I write online I get instant feedback in the form of emails or people posting comments. This drives home the fact that lots of people are reading and so makes me more likely to steer clear of touchy subjects. When I write for print, though, there tends to be a decent-length gap between writing and publishing, making it much easier to forget that there’s a real audience. Because of that, I tend to write books with one person in mind; either an actual person or a fictitious reader.
⁴³

It probably makes for pretty arrogant prose (my fictitious person always gets my jokes, no matter how “in”) but it’s the only way I can avoid being crippled by uncertainty about what to include and what to leave out. The problem with that approach is that it makes it really
fucking weird when someone who isn’t that reader corners me and tells me that they’ve read the book. It wasn’t meant for them. It was meant to be a private conversation, between me and my fictitious reader.

But here’s the even weirder thing. After a few weeks, the weirdness—those daily surprises—had started to feel normal to me. The idea that my life—failures, fuck-ups and all—was literally an open book. I’d even got used to people I’ve never met feeling qualified to psychoanalyze me.
⁴⁴
Being aware that everyone knows all the embarrassing details of my life became incredibly liberating.

For a start I stopped giving any thought to the consequences of telling the unvarnished truth on my blog; the more terrible the confession, the more people tuned in, and subsequently bought the book. The same was true with my drunken behavior in the months that followed the book launch. I’d always been a dick when drunk, but there had been consequences to that dickishness the next day: people who met me while I was drunk tended never to want to see me again.

But after the book was published, all that changed: it didn’t matter how outrageously I behaved, or how offensive or arrogant I acted, people would just laugh. “You’re such a dick,” they’d say, “just like in your book.” The weirdest example of that was when an editor from the
Guardian
had asked me to write a weekly column about my drunken travels through the world of technology. Or, more accurately, when I told an editor from the
Guardian
that I was going to write such a column, and he agreed to pay me for it.

Before the book, I’d had to beg for every single newspaper commission I got, and even then most of my ideas were turned down. But a few weeks after publication, I was ego-surfing for my own name on Google and I noticed that Charles Arthur, the paper’s technology editor, had written about me.

He’d read
Bringing Nothing to the Party
on holiday and had subsequently read a post on my blog about me crashing a major Internet conference, getting blind drunk and setting up an impromptu drinking party in a promotional double-decker bus in the middle of the conference center. It was a story of dickish behavior by any metric you care to use—I was eventually ejected when I decided to set fire to a straw hat—but, for Charles, it had made hilarious reading.

In his review, he likened me to Hunter S. Thompson, which made my now spiraling ego nearly burst out of the top of my head. I emailed him, thanking him for the review and telling him, in effect, that it was his lucky day. I had an idea for a weekly column about my “gonzo adventures at technology conferences around the world” and I’d chosen the
Guardian
as my outlet. Amazingly he said yes.

We decided to call the column “Not Safe For Work,” both as a warning about its content and also as a reference to the fact that I had been fired from every job I’d ever had, including an earlier stint as a
Guardian
media columnist.

Since starting the column, I’d been traveling non-stop, visiting a new place almost every week and waltzing into just about any conference, festival, party or event I liked.

For the first time in years, I could use the
Guardian
’s name to get me into things, and not be lying. I went to Paris for LeWeb, Europe’s most prestigious Internet conference, where technology entrepreneurs and European leaders come together to educate each other about how the world works. It’s a two-day event, but unfortunately my deadline fell at the end of day one.

Unfazed, I simply wrote 1000 words about how I’d found the venue
too cold, the speakers too boring and the Wi-Fi connection too spotty to bother sticking around. The correct response of Loic and Geraldine Le Meur, the husband and wife team who organize the conference, should have been to ban me from the event for life. But I was
that guy
: the technology columnist from the
Guardian
who got drunk, went to conferences and insulted everyone, so, instead of adding me to his
liste noire
, Loic invited me to come back the following year as a speaker.

Readers, too, who had every right to feel short-changed by my half-assed review that failed to cover a single minute of the scheduled program, instead emailed me in their droves to say how brilliantly irreverent I was. Incredibly, rival conference organizers even emailed me to invite me to tear apart their conferences.

I made my second trip to San Francisco for TechCrunch 50, an annual conference organized by
TechCrunch.com
, the world’s most influential technology news site. Entrepreneurs from around the world flock to the conference to pitch their business ideas to a panel of experts and investors. The best pitch is awarded $50,000 and is also heavily promoted on
TechCrunch.com
. The promotional attention is actually worth more than the prize money, given how TechCrunch is essentially the news site of record for Silicon Valley.

But instead of actually covering the conference, I decided to rent some space above a bar and put on my own event. Called Smack My Pitch Up, the idea of the event was for entrepreneurs—and anyone else who felt like it—to come on “stage” and pitch the worst idea they could think of, to a panel of drunks. The event was a huge success, and my reputation as a traveling drunk was further assured.

Next I headed to Las Vegas for BlogWorld, an in-no-way-dorky-sounding event that brought together bloggers from across the world for a couple of days of … well, I actually have no idea. I didn’t in fact attend the conference. Robert and I had just decided to fly in for two days of sponsored parties.

An added bonus of BlogWorld was that Sarah Lacy was in town, hosting a promotional event for her book. Since our evening at Homestead the previous April, we’d kept in touch by email, regularly comparing notes on book sales and the weirdness of sudden semi-infamy.

Since her South by Southwest interview, and the subsequent publication of
Once You’re Lucky
,
Twice You’re Good
, Sarah had been on a non-stop book tour—appearing at industry events, doing readings and generally being celebrated as the person who wrote the definitive book on Silicon Valley. Amusingly, whereas a few months earlier she’d been the interviewer at Mark Zuckerberg’s keynote in Austin, now she was frequently the star of the show—being paid thousands of dollars to share her wisdom with attentive crowds.

I wasn’t quite at the stage of being paid thousands of dollars to share my wisdom—largely because I had none—but, thanks to my column, I was certainly enjoying a growing level of online infamy for my irresponsible behavior.

The inevitable meeting of worlds—Sarah’s increasingly successful professional one and my increasingly successful unprofessional one—came at BlogWorld when I was invited to a party at the MGM Grand, hosted by a Silicon Valley PR man called Brian Solis. Sarah was guest of honor. I, of course, had spent the entire day of the party drinking champagne in my hotel room, diligently not covering the conference.

By the time I finally arrived at the MGM Grand, I was blind drunk; the kind of drunk which can only end in disaster. The party was outdoors, around a gigantic swimming pool. I remember staggering through the door and slumping down on a banquette underneath some kind of fabric tent. Waiters were milling around, carrying trays of champagne, but I decided to order an entire bottle for myself before thinking better of it.

“Make that two,” I slurred instead. Given that bottles of house champagne were $250, it’s probably a good thing that Robert arrived when he did.

“He’s probably had enough,” said Robert, cutting off the disappointed waiter, who had just been cheated out of—at least—a $100 tip.

“You’re trashed,” said Robert.

“That I am, Robert. And I’m getting paid for it,” I said.

“You’re also going to really piss Sarah off. This is her party.”

“Oh, shit, you’re probably right” I said, reaching for the half-empty glass of champagne that someone had left on the table.

“Has she realized I’m drunk?”

“I imagine so. You spoke to her when you came in,” he said; “you told her she looked nice and then asked where Sarah was.”

“Oh,” I said. “That’s not good.”

“No, it’s not. Seriously, mate, you have to go somewhere and sober up.”

“I’ll be fine.”

I necked my glass of champagne as Robert walked away. A couple of minutes later I saw him talking to one of the bouncers. Two men in black suits with plastic wires trailing from their ears appeared either side of me.

“Sir, can we speak with you for a moment?” said one. “Just over here,” said the other, guiding me forcefully by the arm toward the exit.

As we neared the door, my drink-addled brain finally figured out what was going on. I saw Robert watching from beside the pool.

“You bastard,” I shouted, “you asked them to throw me out? Are you serious?”

“It’s for the best, mate,” he shouted after me as I was forcibly ejected onto the Strip. “You’ll thank me in the morning.”

“Like fuck I will—you fucking bastard. Judaaaaasss …”

Of course, I did thank Robert in the morning. Not only had he ensured I’d been thrown out of the party before I’d drowned myself in the pool—or debt—he’d also spent half an hour smoothing things over with Sarah.

She’d been, quite reasonably, upset at me turning up drunk in the
first place, let alone having to be thrown out, but Robert had explained to her that I was just being “Drunk Paul”—which is how he’d started referring to my most epic drunken behavior. I was still a nice person when I was sober and, given this was a one-off incident—in Vegas of all places—Sarah should probably give me a pass, he argued. Just this once.

Fortunately Sarah and I had become good enough friends by this point that she agreed, although my behavior would still cost me an apology lunch, champagne and a promise not to drink for the rest of the time she was in town.

I agreed and, if anything, the incident actually made us even better friends, in the way that only twenty-four hours of groveling apologies can. Still, I knew I’d dodged a bullet: Sarah was one of the few people who didn’t find my drunken behavior hilarious.