The Upgrade: A Cautionary Tale of a Life Without Reservations

by Paul Carr

  Part of me knew that meeting Sarah Lacy was a bad idea. What if she’d decided to look up my blog after Robert had spoken to her? I’d already pissed off one woman in the past twenty-four hours. But, then again, after South by Southwest, I’d actually taken the time to read some of her BusinessWeek columns: they were insightful, funny and annoyingly well written, and from Robert’s description she definitely sounded like someone I’d like to meet. I’d just have to suck it up, go to the barbecue and hope she didn’t stab me with a steak knife.

  804

  ‘You Brits are actually far less offensive than people in the US.’

  Saying that out loud was Sarah Lacy’s first mistake, given that she was talking to me and Robert. She’d arrived at the barbecue a few minutes after us, and Robert had immediately dragged me over to say hello. I mumbled a few apologies about my South by Southwest post, which – to my relief, but also slight disappointment – she still hadn’t read, but she dismissed my pathetic arse-kissing, saying that the abuse she gets from US commentators was far worse than anything I might have said. Having read some of that abuse, I agreed with her.

  Still, though, Robert had taken her comments about our inability to offend as a challenge. I forget the joke he decided to tell but I know the punch line was ‘it’s lucky your party trick isn’t a doubleheaded blowjob’. I know this because Robert insisted I video the exchange on my digital camera, but by the time I’d figured out the video setting I was only in time to record the punch line and Lacy’s response. We were hoping for an on-camera ‘that’s inappropriate’. Instead all we got was loud laughter, and a concession that – OK – some Brits could be more offensive than Americans.

  I liked Sarah Lacy. Her wedding ring – and constant references to her husband – had helped me to ignore the fact that, yes, she was astonishingly pretty and instead concentrate on how much we had in common when it came to work. She told me how ‘everyone’ in London had insisted that we meet, on the grounds that ‘you’re apparently the British version of me’. But she also admitted that, from the other reviews she’d heard from my ‘friends’, she had been expecting someone far drunker.

  ‘You should have seen me yesterday,’ I said.

  ‘Well, how about later this week? Robert told me you have a book out about London entrepreneurs, and my book about their San Francisco counterparts is out next month. Let’s get a drink one afternoon and compare notes.’

  Back at my hotel – while I waited for Eris to come over so I could take her for the world’s most grovelling apology dinner – I wrote an email to Hannah.

  From: Paul

  To: Hannah

  I met Sarah Lacy today. She’s not a cunt. In fact she’s great. I feel like a traitor – I’m sorry.

  The reply came back almost instantly.

  From: Hannah

  To: Paul

  Oh, Paul, you haven’t fallen for her have you?

  ‘No!’ I replied, ‘I mean, only in so far as I fall for every American woman. But for once my crush is purely professional. She described me as the British version of herself, and I think she might have a point. I have a feeling we’re going to be friends.’

  ‘Dammit,’ wrote Hannah, ‘I nearly met her in London but everyone kept saying how nice she was and I couldn’t bear it. Now you too. I suppose I’m going to have to start liking her too.’

  805

  I’d arranged to meet Sarah in Homestead, a bar in the Mission district that serves bowls of unshelled peanuts with the beer and encourages you to drop the shells on the floor. A huge dog wanders around picking up any stray nuts and every so often an old woman ambles in from the street, pushing a shopping cart, selling tamales with hot sauce.

  I was twenty minutes late and, when I walked in, Sarah already had a beer in front of her, lined up next to a shot of Jägermeister. Yep, the American version of me, I thought.

  ‘Hey!’ I said, nodding at the full glasses in front of her. ‘I assume you’re OK for drinks?’

  ‘Well, seeing as you’re so late, you can get me a martini. Olives.’

  The American version of me, who triple-fists drinks.

  ‘So, I should probably start by telling you what I wrote in my blog post …’ I put our drinks on the table, ‘but if I do, I’d rather you didn’t punch me on the nose.’

  Knowing that she doesn’t ever read stuff that’s written about her, I could have kept my mouth shut. But for that same reason, I had to tell her – if only to apologise properly for it. By now I was feeling crushingly bad about the whole thing.

  ‘Of course I won’t punch you on the nose. I’m pretty unoffendable by now. But also I really don’t want to know. I don’t read stuff online because if I did it would upset me. What you wrote is a matter for you and all of the other people who have decided they hate me despite having never met me.’

  Ouch.

  It was a reasonable point, and it instantly made me feel even worse. I was just another chump on the web who tapped out hate from behind a screen. Just because I thought of myself as a professional writer didn’t alter that fact. Lacy had a contract for BusinessWeek, her own weekly video show on Yahoo.com and had been invited to appear on stage at South by Southwest, while I sat in the audience talking shit on a blog.

  ‘I’ll probably take it down,’ I said. What a coward. What a fucking hypocritical coward.

  ‘You shouldn’t,’ she said, ‘you should leave it up. You wrote whatever you wrote, and you should stand by it. To be honest, Geoff – my husband – cares more than I do. He actually does read this stuff and you can imagine how he felt sitting at home in San Francisco while people wrote on the Internet that they wanted to rape me.’

  ‘Oh, you saw that guy then?’

  ‘Geoff told me about it. There were several people saying stuff like that.’

  Jesus. I thought about girls who I’d cared about – my most recent ex in particular – and wondered how I’d feel if someone had said that about her. Then I thought about how I’d feel if some dickhead blogger had written a transcript about her flirting with Mark Zuckerberg. None of it was funny any more.

  We talked a bit more about the interview – even though she was understandably bored with the whole subject – and it was interesting to hear some context. How Zuckerberg had insisted on her being the one to conduct the interview and how, apart from a couple of guys who had heckled, they’d both actually come off stage thinking it had gone reasonably well. It was only afterwards when people told them about the Twitter backlash that they’d realised how controversial the whole episode had been.

  The conversation finally moved on to less awkward subjects, especially as we had more drinks. After an hour or so, Eris came to join us – my apology dinner, but more so Robert’s damage limitation, had worked, and she’d decided to give me another chance.

  The three of us talked until closing time, comparing the difference between entrepreneurs in our respective countries, and with Sarah sharing her thoughts on friends of mine she’d met in London, including Robert, Michael and Michelle. We talked about writing and how, despite our similarities, neither of us could do the other’s job. I was too much of an egotist to write about other people without putting myself at the centre of the story, and Sarah was too interested in business and billionaires to pad out her work with self-aggrandising bullshit.

  At one point we ended up talking about unicorns and specifically whether eighties cartoon heroine She-Ra rode on a magical winged unicorn (as I insisted) or just a bog-standard magical winged horse (Sarah’s recollection). Before we knew it, a wager was made: if I was right, Sarah would give me the advance copy of her book that she had in her bag, inscribed with a message of my choice. If she was right, I had to send her a copy of my book on publication, again with a custom message written in the front.

  Robert was right: Sarah was fun.

  As Eris and I headed back to my hotel for the last time, we held hands. It felt nice, but we both knew this was probably the last night we’d spend together.
I only had a week left of my visa waiver and I’d been advised by friends who knew the system to understay slightly so that immigration didn’t get suspicious on my next visit: people who stay for exactly three months look like they’re abusing the system.

  I’d bought myself a few extra hours by switching my return flight so I was flying directly from San Francisco rather than having to go back via New York, but still I was leaving in the morning. I felt sad at having to leave a city I’d fallen in love with, but such was the life of a nomad. The most important thing was that Eris and I were parting on good terms; a minor miracle after my ridiculous behaviour a few nights earlier.

  I was also glad to have met Sarah. I looked down at the copy of Once You’re Lucky, Twice You’re Good sticking out of my bag. Of course I’d been right about the winged unicorn and, as agreed, Sarah had written an inscription in the front: a confession that, rather than me being the British version of her, she was the American version of me.

  ‘Dear Paul, I am the American version of you – and that’s all I can ever aspire to be. Your friend and doppelgänger (I WISH!) – Sarah Lacy.’

  Your friend. That made me smile. After all the shit I’d written about her, I was ending my trip with a new friend. I promised to keep in touch by email and she promised (grudgingly) to look at my blog and keep track of my nomadic adventures.

  ‘So where next?’ asked Eris.

  ‘Spain, apparently,’ I replied.

  It was Robert’s idea. The more time he’d spent in San Francisco, hearing details of my travels that I’d conveniently left off the blog – Michelle and Jonesy, the lost night in LA, the hooker with the braces – the more jealous he’d become that he hadn’t been along for the ride.

  ‘I want to live like you,’ he said.

  ‘But you live in a penthouse in Leicester Square. With a hot tub on the roof.’

  ‘Yeah, but you live in hotels and get drunk with hairdressers in bedsheets and fuck disabled girls in LA.’

  ‘She wasn’t disabled … wait, how did you …?’

  ‘Michael told me.’

  By the end of the week, Robert had made a decision: like me, he wasn’t going to renew his lease. Like me, he was going to pack a few things into a suitcase and become a nomad. ‘I’ve spoken to Scott and we’ve agreed that I can do everything I need to do on the road, as long as there’s wifi. In fact, Scott’s probably going to join us for a bit too.’

  ‘Us?’

  ‘Oh, yes,’ he said. ‘I knew there was something I meant to tell you – we’re going to Spain.’

  Chapter 900

  Oh Deary Me

  ‘If you’re feeling kinda tedious

  If life is seriously mediocre

  Here’s how to get that adrenaline flowing

  Just step aboard a Boeing, going … high!’

  Early May is still supposed to be the off-season in Spain, but high in the mountains of Andalucía the sun was so hot that I could feel its heat against my bare legs. And not just from above: it was hot enough to radiate off the patio, and up through the bottom of the hammock.

  I adjusted my sunglasses and listened to the sounds of the mountain. We were an hour in any direction from the nearest town so really the only sound to hear was the goats. Every day a farmer led a couple of hundred goats, each wearing a small bell, down the steep path at the end of our driveway. We never saw or heard the goats returning at the end of the day, leading us to assume that they were being herded to some kind of goat pie factory. Poor old jangly goats.

  And that’s all I could hear: just the soothing sound of two hundred goats ambling to their deaths, the ringing of bells, the occasional sound of the farmer shouting something in Spanish.

  And then, suddenly, one other sound.

  Louder than the goats.

  The unmistakable sound of Robert having a blazing row with an award-winning Hollywood actor about the price of an ornamental goose lamp.

  901

  Almost a month had passed since Robert had made the decision to give up his London lease and join me in living the life of a high-class nomad. We’d joked that with just me travelling it was an adventure, but with two of us we had the beginnings of a club. The ‘Kings of the Road Club’ we’d called it.

  With two of us spending all of our free time – which is to say all of the time we were awake – thinking about the logistics, we’d come to some interesting conclusions about the possibilities of nomadic living. Robert in particular had taken it upon himself to see how much further my arbitrary £50-a-night budget could be pushed. Realising that I knew hotels better than he did, he’d focused on other types of accommodation: and the fruits of his research tasted delicious.

  Rob had discovered that, for most of the year, there were hundreds – thousands, even – of luxury villas lying empty, all over Western Europe. During the summer months these places – with their heated swimming pools and tennis courts and hot tubs and breathtaking sea views – rented for as much as £4000 a week as holiday homes for rich people. And yet, between September and June, they sat empty, abandoned and unloved – but still available to rent. If you didn’t mind the fact that it was slightly colder than normal, or that you had to stay outside of normal holiday time, then owners were more than happy to rent them out for a few hundred pounds a week simply to justify keeping the heating on.

  The deals were incredible, as was the range of places available. On just one website – Owners Direct – so called because it allows the owners of the villas to rent directly to people, without paying agency fees – Robert had found a twelve-bedroom château in the French Pyrenees for less than £1000 a week in the off-season. Twelve bedrooms! If we could find more people to join the club and split the rent, that worked out at £12 per person per night. But even that paled in comparison to the next place: for a few hundred pounds more, we could rent an entire hamlet, complete with fifteen houses and its own shop.

  Or, to put it another way, if three people split the rent they could rent their own village for less than I was paying for my one-bedroom flat in London. Every day my inbox would slowly fill up with emails from Robert with subject lines like ‘This place has its own beach!’ or ‘Why would a house need a private race track?!’

  Eventually he’d settled on a three-bedroom villa in an isolated village called Valle de Abdajalis. High in the Andalucían mountains, surrounded by breathtaking scenery and crystal-clear lakes, the villa had an outdoor hot tub and a mountainside patio with a barbecue and its own bar – and it was less than an hour from Málaga airport. More importantly, it was available until June for the off-season price of £420 a week. If Robert and I went halves on the rent, we’d be paying £210 a week. Or £30 a night, which included weekly cleaning and wifi. EasyJet flights from London were less than £60 return, and we could hire a car for £10 a day. Even with transport, it was still under my £50-a-night budget. The decision took me about thirty seconds to reach.

  But Robert’s thinking hadn’t stopped there. With an extra bedroom, he’d realised that we could offer weekend breaks to our friends in London for, say, £200 for two nights, and cut our weekly rent in half at a stroke. He’d sent out a group mail to his personal and business contacts and had so much interest that we could have filled the place every weekend, and lived there ourselves rent-free, for a year. As a cheeky bonus, he’d added the fact that ‘guests would be expected to fill the fridge with food and booze’. That would take care of our weekly shopping bill, too.

  Our plan was to take the place for two months at first. Robert had work to do on the business plan for his new venture and I had final edits to finish for Bringing Nothing to the Party, ahead of its July publication.

  Working in hotel rooms was one thing, but sitting in the mountains of Spain, miles from anywhere, I truly appreciated just how much the Internet had changed how – and where – it’s possible to work. With only my laptop and my mobile, I was just as connected to the world up a mountain in the middle of nowhere as someone working from an office in
London. But unlike the office worker, I could choose at any time to close my laptop and switch off my phone and instantly be on holiday. Rather than having to make time to work before I could relax, I could spread both of those experiences throughout the day. Half an hour’s work – in the hammock, of course – then a beer and a splash in the hot tub, then another half-hour’s work. After the first week I realised I was actually working for more than eight hours a day some days, every one of them productive.

  I had also become an expert in the emerging art of hammock working. For the first few days I was a struggling amateur – trying to balance my laptop on my stomach as I lazed in the hammock. My neck and wrist soon told me where I was going wrong. Over the next week of trial and error I narrowed down the three most comfortable positions for hammock working:

  Position one: the yogi

  Trying to work whilst lying flat is crippling to your productivity and your neck. For a start, you’re liable to fall asleep, which is a bad idea if you have a laptop balanced precariously on your stomach a few feet above a concrete patio. With the yogi position, you sit upright, in the centre of the hammock, with your legs crossed. The sides of the hammock just touch the edges of your knees. The yogi is actually the least comfortable of the three positions, but it has the benefit of being only a stretch away from lying down. If you’re a fan of spontaneous snoozes, this is the position for you.

  Position two: the sideways yogi

  Of the three positions, the sideways yogi is the most suitable for long stretches of work. Your posture is exactly the same as the yogi, except that, instead of facing forwards, you turn sideways. The benefit of the sideways yogi is that it allows you to swing gently back and forth as you work, and also provides more support for your knees. Experts at the sideways yogi can position their beer just slightly behind the hammock so that it is retrieved on the back swing, swigged on the forward apex and then returned on the next back swing. Warning: after six beers there is every chance you will fall backwards on to the patio and almost snap your spine.