As I stood at the back of the converted church hall, waiting to take my place on stage, I looked down and noticed that a small china cup had appeared in my hand. It was half filled with coffee and I had no idea how it had got there, but I took a huge gulp from it anyway, in the hope that it would be strong enough to wake me up.

I am resolutely not a morning person.

The reason for my exhaustion was partly due to the fact that I’d been having trouble sleeping, with the terrifying reality of our fundraising situation and the prospect of Kudocities launching in a couple of months whirling around my head and keeping me awake into the early hours. But mainly it was due to the fact that, the previous night, I’d been on a second date.

Twenty-six years old, blonde, American, smart and funny, Karen had recently arrived in London to read Middle Eastern Studies. Being new in town she’d signed up to the test version of Fridaycities after seeing a link to the site on the popular London blog Londonist.com. She had created a profile in the hope of making new friends and, as was expected for new members, she had also uploaded a photograph.

I had always had a strict policy when it came to meeting women on the Internet: I didn’t do it – wouldn’t do it – not ever. No matter how many of my friends told me that times had moved on and that ‘all kinds of people find partners online now’, it still smacked to high heaven of desperation. I mean, honestly, how mentally unstable does a pretty girl have to be that she can’t go out into the real world and find a boyfriend? What part of her personality is so hideously off-putting that she would have to hide behind a computer monitor? And it’s just as sad for men – if you don’t have the confidence to approach a girl in a bar, or at work, or on the train or anywhere else for that matter, how goofy are you going to be when you have to have an actual first date?

Online dating was for losers.

And then Karen signed up to Fridaycities, created her profile and uploaded her picture. And she was fucking stunning. So much so that I sent Matt, who runs Londonist.com, five hundred Kudos to thank him for directing her to the site. I convinced myself that making contact with Karen wouldn’t be Internet dating at all: she hadn’t signed up to Fridaycities to find a boyfriend, although she had flagged herself as single in her profile; she just wanted to make some new friends in a new city.

The truth was, if she was half as hot in real life as she was in her profile picture, then she was well worth abandoning my golden rule for. If things went well, I could always tell my friends I’d met her in Starbucks. I decided to drop Karen a line, in my guise as a Fridaycities staffer welcoming a new member, using some of the interests she’d listed on her profile to spark a conversation. This plan would turn out to be more difficult than I’d hoped: when I looked at her profile I found that the only interest she had listed was ‘coffee’, which struck me as slightly narrow-minded. I told her as much in my email and she sent back a funny reply informing me that actually she liked many, many things other than coffee and if I was really interested I should ask her about them.

I was really interested.

As we emailed back and forth it soon became clear that we had lots of things in common: our politics, our sense of humour, even our musical tastes. A few weeks earlier I’d been mocked mercilessly on the site for asking whether any of the other users would be going to see Canadian band Barenaked Ladies, who were due to perform a gig in Hammersmith. Karen revealed that she, too, was a fan of the band and that we should definitely go to see them together when they were next in town.

Before I knew it, it was 4.30 the next morning; we’d been emailing back and forth all night and had then moved on to Instant Messaging. Karen was great, and I was slowly becoming fascinated by her. But I couldn’t ask her out. Absolutely not. For two reasons…

1) I’d met her online. She could be a total freak. I had my golden rule.

2) She was basically a taller, less Anglicised Savannah.

I mean, who was I trying to kid here? Here was this girl – this blonde, American, funny, smart girl – and I’d decided in less than six hours that I wanted to go out with her. Meanwhile, I was spending all day every day with Savannah – the one-time love of my life – before she went home every evening to her live-in boyfriend and I went home to my empty flat. You don’t have to be the sharpest tool in the psychological box to work out what was going on in my head.

But, I told myself, Karen wasn’t exactly like Savannah. For a start, she was taller. She liked coffee, while I knew for a fact that Savannah preferred tea. She was from Pittsburgh (Go Steelers!), not California.((I’m aware one is a city and the other is a state.)) She was single. God, the two of them were almost polar opposites. And, anyway, there’s nothing wrong with having a type.

But I still didn’t know anything about this girl. And I’d still met her on the Internet.

And yet. And yet.

Suddenly my Instant Message software pinged, heralding the arrival of another message from Karen.

Karen (4:45 a.m.): So, you should probably ask me out then.
12.1

Our first date was incredible: exactly like they’re supposed to be in the movies. We began with dinner in a Polish restaurant near Knightsbridge before going on to her friend’s birthday party near Carnaby Street before ending up at the Roxy, an indie club near Tottenham Court Road where we kissed for the first time to the sound of ‘99 Red Balloons’ by Nena. At just after 2.00 a.m., finding myself briefly alone at the bar, I took the opportunity to send Karl a text message. He was the only one who knew where I was (I’d considered telling Savannah, ostensibly to warn her that I might be late to work the next day, but really in the hope it would make her sickeningly jealous). Of course Karl’s first reaction when I’d told him about Karen was to roll his eyes: ‘Of course you’re going out with her; she’s exactly like Savannah.’ But what did he know? The text I sent from the bar simply read,
‘ Smitten.’

For our second date, we ‘d gone to the theatre to see a new comedy show based around the international arms trade. What better way, I reasoned, to appeal to her political side (Middle Eastern Studies!) while also introducing her to the British sense of humour? What I hadn’t anticipated was the fact that the show would be one joke after another full of obscure British references – references to members of the shadow cabinet, to long-passed storms in Westminster teacups, even to children’s television shows of the early 1980s. I had to spend the entire interval and much of the rest of the night explaining to Karen – at enormous length – why Antonia de Sanchez was funny, or what an emu might be doing on a roof with a TV aerial. But, despite the slightly odd topics of conversation, we had a great time, ending up back at her place which is where, after about an hour’s sleep, I’d woken up less than forty minutes before I was supposed to be on the other side of town, speaking on a panel about the future of social networking. And to make things worse, I was supposed to be meeting Savannah there.
Oh God. How the hell was I going to make it in time? And, more importantly, how was I going to stop grinning long enough to actually speak?

12.2

I crashed through the doors at the back of the hall with minutes to spare, to be met by a far from impressed Savannah.

‘Good night?’ she asked, raising her eyebrows towards the church roof. After my first date with Karen, I’d decided to come clean with Savannah about what I was doing, figuring it was better coming from me than her reading about it on my Fridaycities profile. I’d expected her reaction to be positive – for months I’d been trying to convince her, subtly and not so subtly, that we should get back together. After all, we were spending most of our time with each other and everyone who saw us – cab drivers, people in bars, people in meetings – assumed we were a couple from the way we flirted and bickered. But every time Savannah had rejected me, saying there was no way she and I would ever get back together, especially now we were working together.

But instead of being pleased she actually seemed hurt: ‘So all that stuff about us getting back together was just bullshit was it?’ she asked.

I protested: ‘But you told me there was no way on earth we’d ever get back together.’

‘There isn’t.’

‘Well, okay then.’

‘Okay.’

Back in the church hall I knew she knew I’d come straight from Karen’s. It was strange, really; a pathetic part of me wanted her to be horrendously jealous that, after almost two years of me hinting that I wanted us to get back together and being rebuffed every time, I was finally moving on. But an equally pathetic part of me wanted exactly the opposite: for her to think that my dates with Karen didn’t mean a damn and that she only had to say the word…

I’d seen this kind of behaviour before, of course, and I realised to my horror what I was doing. I was acting like every ex-girlfriend I’d ever complained about – convincing myself that I was falling for someone new just to compensate for not having what I really wanted.

‘Yeah, it was okay, ‘ I lied. ‘I didn’t get home till late and then forgot to set my alarm.’

‘Sure.’

‘No, really.’

‘Drink your coffee. You’re on in two minutes. You slut.’

The event was the New Media Knowledge Forum, an annual conference to discuss the hottest trends in new media, which of course this year could only mean one thing: social networking. Throughout the day a whole host of panels and presentations had been scheduled. There was a debate on how the mainstream media should use social networking, featuring representatives from the BBC, Channel 4, the Guardian, Yahoo! among others. There was a keynote speech by Nic Brisbourne about how actually to make money out of the social media, all ending with a free-wheeling, wine-fuelled panel on ‘future gazing’ where the audience would get a chance to grill a selection of the day’s speakers on what the future held for social media. The highlight of the day, though, was the early morning keynote speech by Jason McCabe Calacanis, the founder of a new search site called Mahalo.

Calacanis had gained fame – infamy is perhaps a better word – during the first boom as the publisher of the Silicon Alley Reporter, a must-read trade publication covering the Manhattan new media community (the so-called Silicon Alley, a sort of homage to northern California’s Silicon Valley). Calacanis was a famed party animal and the Silicon Alley Reporter would often feature reports from glitzy new media gatherings, leading one New York magazine to describe him as the ‘yearbook editor of Silicon High’. Calacanis rode out the dot com boom by selling the Silicon Alley Reporter and founding a pure Internet media company called Weblogs, Inc. Much like Nick Denton’s Gawker empire, Weblogs, Inc. specialised in publishing ultra-targeted blogs for various niche groups (gadget freaks, film nuts etc…) in the hope that advertising dollars would follow closely behind. The difference between Gawker and Weblogs, Inc. was that Gawker chose to roll out a relatively small number of sites and concentrate on building them each into major brands, while Weblogs, Inc., created dozens and dozens of sites – fifty in its first year of operation – in the hope that a few would be successful. Between Calacanis and Denton, similarity had bred contempt and it wasn’t long before the two men became mortal foes, with Calacanis poaching blogger Peter Rojas from Gawker’s gadget site, Gizmodo, to join his own, Engadget.

One of Calacanis’ closest friends was once quoted as saying: ‘Jason would never stab you in the back. He might stab you in the face, though.’ It’s not clear if the friend was speaking metaphorically: Calacanis holds a black belt in Taekwando.

Watching the situation from this side of the Atlantic, Robert Loch’s view on the Calacanis/Denton debate, and their constant sniping at each other, was slightly more to the point: ‘I just wish Jason and Nick Denton would stop whining and sleep together so the rest of us can get some peace.’

I had never met Calacanis but knowing that he was a sworn enemy of Angus’s old pal Nick meant I was keen to see his keynote. But, sadly, by the time I rushed in, he’d already left the stage. Ah well, I would have to catch up with him at the after-party which, befitting his status as visiting foreign dignitary, was being held in Calacanis’ honour back at Adam Street.

But first I had business to attend to…

12.3

‘The next panel is called “The Upstarts”: Does Social Media Have Long Legs to Match its Long Tail?’

The event ’s organiser, Mike Butcher, took to the stage and introduced our panel. Mike was a famously outspoken dot com journalist and he and I hadn’t always seen eye-to-eye. A couple of years earlier we’d had a very public spat after he wrote an article accusing me of using my Guardian column for blatant self-promotion (he was absolutely right, of course, but there was no need to draw attention to it). Given our history, I was quite surprised to be invited to take part at all, but since the spat we’d run into each other a couple of times and had made up. He’d (sort of ) taken back some of his nastier comments and I’d called him a wanker. All was well again.

His introduction continued as I took my seat behind a long table containing a row of microphones and lots of little bottles of water. I poured the contents of one into a glass and drained it in one gulp. God, I was exhausted.

‘ The panel will talk about whether or not the entities being created at the moment – sites like Trustedplaces.com (another local review site, and a competitor to WeLoveLocal.com) and Fridaycities, whatever Fridaycities is…’
He couldn’t resist. Wanker.

Aside from Mike, the only person on the panel I’d met before was Walid Al Saqqaf, the Parisian co-founder of Trusted Places. Although, like WeLoveLocal, Trusted Places was technically a competitor, we’d decided to restrict our competitive urges to regular Mojito-fuelled games of table football in Walid’s favourite French bar, Cafe Kick. Walid would beat me to a pulp every time. It was embarrassing, but I was honing my skills and one day I’d beat him. Or at least he’d surrender – he was French, after all. The other panellists included Phil Wilkinson whose site, Crowdstorm, aimed to bring people together to share information and reviews about products they want to buy either online or on the high street. Next to him were the Internet consultant Jemima Gibbons and Justin Davies from Buddy Ping, which was a mobile social network for people on the move. I immediately thought back to our mobile-obsessed VC; maybe I should introduce him to Justin.

With all the panellists introduced, Mike took a deep breath and asked his first question, directed at Walid.

‘Walid, you’ve recently raised money. How much was that?’

It’s always the first question.

Walid happily explained how Trusted Places had raised half a million pounds in angel funding (which was true: they had, the bastards), and that they were using it to develop Trusted Places’ personalisation features and also to develop a mobile version of the site.

In my head I edited our Word document, adding the line

Kudocities: the mobile version.

Gulping down my second glass of water, I braced for Mike’s first question aimed at me. I was sure he’d be unable to resist either pitting Walid and me against each other, or somehow making me defend Fridaycities.

‘I have two questions…’

Or maybe he’d do both.

‘First, how do you differ from Trusted Places? Are you basically the same?’

He obviously wanted me to say Fridaycities was far, far better than this two-bit (well-funded) pretender, but I wasn’t going to play his game. Instead I took exactly the opposite tack, pouring praise on my friend Walid and explaining how we each offered a different spin on a similar idea to users. In fact, I went on, we expected many users to be members of both Fridaycities and Trusted Places.

Take that, you cocky little git.

But, of course, I couldn’t resist adding: ‘It’s worth pointing out, though, that Fridaycities is about asking about anything at all, not just about restaurants and bars.’

And then came Mike’s follow up.

‘And how do you react to people who say that there’s an element of flash in the pan to all of this social networking business?’

‘Oh, that’s simple…’

Pause.

‘I ignore them.’

The audience laughed, and so did the panel. I’d dodged a bullet. But in reality, every single person in the room was, like me, laughing more out of nervousness than anything else. We were all in a constant state of terror about that very question. What if social networking was just a flash in the pan? What if, despite the hundreds of millions of people flooding to MySpace and Bebo and Facebook and the gazillion niche social network sites, it was all just a fad – like the hula hoop or Tab Clear? What if, while we were all rewriting our business plans to become social networks, Internet users found some other kind of site to get excited about. None of us had any way of knowing – given that none of us knew anything at all. All we could do was laugh about it – and cross our fingers tightly behind our backs.

One thing that the whole panel could agree on was that local social networks – that is, networks based around the users’ physical location – were the future. People were hardwired to be more interested in people on their doorstep than people halfway around the world. And if the Internet really was all about sex, then statistically it’s much more likely that you’ll be able to have sex with someone in the same town or city as you than halfway across the world. I found all of this hugely comforting; yes, there was still a huge chance that what we were doing would turn out to be a flash in the pan, but at least we’d be one of the brightest flashes. For a few seconds, I felt what I thought was a flash of confidence. It might just have been the coffee finally kicking in.

By the time the floor was opened up to questions, I was surprised at how amicable the proceedings had remained – particularly as several of us on the panel were competitors. All that changed when a stocky American in the audience stood up, not to ask a question but to make an observation:

‘I just want to say, as an entrepreneur from the US…’

Uh-oh, I thought to myself. He sounds like an activist at a TUC conference. ‘As a Marxist single father, I just want to say…’

He went on: ‘People in our industry are delusional. Instead of saying “why can’t something happen?” we say “why might it happen?” and I think that’s an asset.’

Ah, the old ‘entrepreneurs should be dreamers first, pessimists last’ argument. It was a stereotypically American viewpoint, and apparently we in the UK were letting the side down. He explained.

‘You guys need to listen to me. Last night I went to a networking dinner over here and I was surprised and depressed at how quick everyone is to kick each other and be cynical. And the press is so cynical about stuff. I wouldn’t want to be an entrepreneur here, because you’d get your ass kicked. I’d want to go to the US.’

Well, fuck off back to the US then, you smug Yankie cunt, I thought, suddenly feeling the same overwhelming urge to defend our national honour that I felt every time Walid put another little plastic baby football past my defender and into the back of the net. How dare he come over here and lecture on being positive?

‘Wait a minute…’ I interrupted, incensed. ‘I really have to defend British cynicism here. That cynicism is what makes Britain such a wonderful place to live in.’

‘Yeah!’ The audience – 99 per cent cynical Brits – were with me, too.

But the American was having none of it. ‘Yeah, but there are parents who use that attitude towards their kids and they turn out neurotic.’

I really couldn’t help myself; he’d left himself wide open.

‘I think you’ll find we have fewer therapists over here than you do in America.’

Big laugh, even a smattering of applause this time. And then, as the other panellists weighed in, too, I swear I could hear the first swells of ‘Land Of Hope And Glory’ in the background. Sensing a full-scale diplomatic incident was about to erupt, Mike stepped in to move things along. ‘There’ll be a fight later on in the car park, ‘ he joked.

At least, I think he was joking.

I felt pretty good about my performance on the panel. I might have damaged the special relationship ever so slightly, but, given that I could barely keep my eyes open, I was pretty damned pleased with myself for putting the lippy little fucker in his place. Hopefully it would get a mention in the press coverage of the event, giving Fridaycities a much-needed publicity boost. What with that and the news that local social networks were the future, I could go home and get some sleep before the party.

With Jason Calacanis in attendance, I had some serious schmoozing to do later. I only hoped he wouldn’t hold the fact that I’d bitch-slapped one of his countrymen against me. Nah, he’d probably find it funny – judging by his spat with Nick Denton, Calacanis was as cynical as they came.

Savannah was less than impressed by my new-found national pride.

‘You really get off on stuff like that, don’t you?’

‘What? I was just fighting Britain’s corner.’

‘No you weren’t. You were playing to the gallery and you know it. You’re such a bloody child sometimes.’

She was clearly still jealous about my date with Karen. That was the only explanation.

12.4

The after-party began at eight o ‘clock the following evening at Adam Street, although describing it as a party isn’t entirely accurate. Mike had restricted the invitations to just the speakers and panellists and a smattering of other web luminaries. The aim was to give everyone the maximum opportunity to mingle with each other and to meet the guest of honour – which suited me down to the ground. By a total coincidence, Robert was hosting a networking dinner in an adjoining room so I knew the soiree would get a lot more crowded later on. Savannah and I had an hour at most to track down Calacanis, sell him on the idea of Fridaycities and convince him to introduce us to his wealthy Silicon Alley mates so they could invest in us. Hell, if we did a good enough job, maybe he’d invest himself. What was it that idiot American had said at the conference? ‘Dream more’? Okey dokey.

But first I had to work out which of the dozen or so people in the room was Jason Calacanis. I cursed myself quietly for missing his keynote speech, but fortunately Angus was on hand to help me out.

‘ Which one’s Calacanis?’ I whispered.

‘He’s around here somewhere, ‘ he said. ‘Come on, I’ll introduce you. But then you’re on your own. Remember: be nice to him; be impressive. He’s very important.’

‘10-4, chief!’

‘Jason, have you met Paul and Savannah from Fridaycities?’

Jason McCabe Calacanis turned round and smiled.

Oh. Shit. Of all the arrogant, stocky Americans, in all the audiences in all the fucking world, why did I have to bitch-slap the important one? Shit, shit, shit. Un-be-shitting-lievable. There was only one grown-up way to deal with a situation like this: suck up like a vacuum cleaner…

‘Hi, Jason, nice to meet you! I just wanted to say I really, really enjoyed your keynote speech yesterday – you made some really interesting points, ‘ I lied, praying that he wouldn’t ask me any questions about a keynote speech I hadn’t even heard.

‘Thanks very much, ‘ he said, ‘I think it went pretty well. So, where are you guys from? Fridaycities? What’s that?’

Oh thank God, he hadn’t remembered me. No, wait a damn minute here! He hadn’t remembered me! He hadn’t remembered a single word I’d said about Fridaycities or presumably anything else I’d said on the panel. And I know for a fact he was in the same room because I’d spent five minutes arguing with him. But not a flicker of recognition.

The bloody smug Yankee cu… But Angus’s words were ringing in my ears. Be nice. Be nice. Be nice.

‘Let me buy you a drink. Savannah will tell you all about what we’re doing.’ He graciously agreed to let me buy him a double whisky- ‘Scaatch on the rocks’- and I ran off to the bar, leaving Savannah to begin the pitch.

‘Hey, buddy, what can I get you?’ asked Andreas, Adam Street’s head barman.

‘A double Scotch on the rocks for my new friend, a beer for Savannah and I’ll take a rum and Coke. Actually make it a double.’

‘Tough day?’ asked Andreas.

‘Ask me again in an hour.’

The main bar at Adam Street is, I swear, one of the wonders of the modern world. Andreas is a walking, talking encyclopaedia of cocktails and the menu is packed with his inventions, including the most recent addition: the Bobby Loch.

Late one evening Robert – who practically lived at Adam Street before he moved into Mr Rong’s – had convinced Andreas that, as he spent so much money at the bar, it was only right that he had his own cocktail on the menu. He saw himself like a member of the Rat Pack who would insist that the pianist played their signature song whenever they walked into their favourite bar. Adam Street didn’t have a pianist, but it did have Andreas.

The next time Robert came in, he was served the very first Bobby Loch – a variation on the Zombie, but even more potent with at least two extra types of rum thrown in for good measure. To give you an idea of how strong that is, you need to know that the Zombie is one of the strongest cocktails there is. Invented in the 1930s by a restaurateur called Donn Beach, it’s served in a tall glass containing fruit juice, various liqueurs and a whole lot of different types of rum. Beach invented it for a friend of his who was about to go to San Francisco on a short business trip. His friend drank three of the things before leaving and on his return complained that the drink had turned him into a zombie for the entire trip. Which is perhaps not surprising, given that it has the same alcoholic strength as seven normal cocktails.

And, incredibly, the Bobby Loch was even more potent than the Zombie. In fact, so potent was it that Robert and I would order them whenever we were with friends who weren’t heavy drinkers. He and I had developed a pretty good tolerance for them over time, but even we couldn’t drink more than two without the room starting to spin. Three, especially after wine with dinner, and it was Goodnight Vienna.

Having already insulted the guest of honour, the night was starting to look like it might yet turn into a Bobby Loch night. But that would have to wait – I only had about forty-five minutes of schmoozing time left.

I wandered back to Jason and Savannah and, although Jason was talking animatedly, I could tell the schmoozing wasn’t exactly going according to plan. Calacanis didn’t seem really all that interested in hearing about Fridaycities, but, on the other hand, he was clearly absolutely fascinated by Savannah. In fact, he was busy telling her about his summer house. This, it should be noted, is the man who told the New York Observer in 2000: ‘I can’t tell you how many propositions I get, it’s absolutely insane… My life is surreal. I’m not used to women liking me… it’s depressing to think they like me for my Rolodex, or for what I can do for their dot com.’ The article was entitled ‘They’re Single, Ambitious, Worth Millions, But Can New York Women Download Their Megabyte Egos?’

I caught the tail end of their conversation: ‘You really should come over to visit some time. You can stay in my summer house. And of course you can bring your boyfriend. Do you have a boyfriend… ?’ I plonked down his drink and sat on the stool that was between them. It was the only grown-up course of action.

‘One double whisky on the rocks, ‘ I smiled sweetly, through gritted teeth. I couldn’t really blame him, of course – Savannah was looking particularly hot that evening and, anyway, he was a married man. There was no reason for me to dislike him over some harmless flirting.

‘He’s a bit… much, ‘ said Savannah as Calacanis disappeared to make a phone call.

‘Do you think?’ I replied. ‘I hadn’t noticed.’

‘Oh, for God’s sake, you can’t possibly be jealous.’

‘Jealous! Don’t be stupid. Why on earth would I be jealous of a multi-millionaire describing his fucking summer house to …’ Before I knew it I was raising my voice.

‘To what? Your business partner?’ She silenced me with a raised eyebrow. Busted.

‘Well, I just think we should be trying a bit harder to network.’

‘Actually, I’ve got his business card and I told him I’d send over some information about Fridaycities.’

‘Well … uh … that’s good …’

One Bobby Loch, please, Andreas.

Not long after, Robert’s dinner spilt out into the main bar. Suddenly the room was packed. It had been one of the better attended Internet People dining events and I recognised at least a couple of the angel investors and VCs who had suddenly appeared. At a stroke, the combined net worth of the room had increased considerably, which could only mean one thing – we were about to witness a subtle, but definite, dick-swinging competition.

‘Who wants a drink?’ shouted Calacanis over the hubbub. ‘My round. Paul?’

I ordered a dark rum on the rocks; Savannah the same, but with Coke.

‘Are you sure you don’t want a man’s drink, Paul?’

Oh yes, I thought, rum, the drink of choice for Hunter S. Thompson, Ernest Hemingway, pirates … and girls.

‘Double Scaatches for everyone, ‘ he shouted, to no one in particular. ‘Hey, Paul, you don’t mind getting them in do you?’ He threw his Amex card across the table at me; it landed on my lap.

Be nice. Be nice.

‘Sure, no problem, ‘ I replied, hissing under my breath at Savannah, who was smirking away: ‘You’re really enjoying this aren’t you?’

‘I don’t know what you mean.’

Evidently revenge for my second date with Karen was a dish best served on the rocks. I scooped up the red Amex and stomped over to the bar. ‘Fifteen double whiskies, ‘ I said, before suddenly realising what I was holding in my hand. A multi-millionaire’s Amex card. How often does that happen? For a glorious moment, an image flitted across my mind: a press release, headed: ‘Fridaycities secures first round funding from Jason Calacanis’ credit card:

City-based social networking site today announced the closure of its angel round, with an undisclosed six-figure investment from Jason Calacanis’ American Express card. The deal was announced to industry journalists today, and will be announced to Calacanis in about thirty days.

Heh. But, no, that would be slightly too much revenge for some harmless flirting and a bit of macho grandstanding. Instead I shouted back over to Andreas who was lining up the whiskies. ‘Actually, can you stick a couple of rum and Cokes on that order as well and two – no – make it four Bobby Lochs? Just leave them in the bottle for now – I’ll get them later when we’ve finished these.’ The least the cheeky fucker could do was pay for Savannah’s and my drinks for the rest of my night.

Later on, after Calacanis had left to go back to his hotel, Angus asked me how the networking had gone. I rolled my eyes. ‘He’s a dick.’

‘Really? I thought he seemed decent enough. Why do you say that?’

I explained about the flirting, which carried on even after I’d told him Savannah and I had once been a couple (at which point, incidentally, he’d smirked at Savannah and expressed surprise that she’d dated below her league. Which may or may not be a fair point); then there was the stunt with the drink; and just the fucking arrogance of the man.

‘So, you don’t like him because he does exactly the same kind of things as you do, but with fifteen million times better credit?’

Yeah, that was about the size of it.

But at least the free drinks took some of the sting out of that particular unpalatable truth.

12.5

My encounter with Jason Calacanis gave me good reason to stop and take another look around at where my life had taken me, or perhaps where I’d taken my life. I’d had my first book published at twenty, been a ‘latter-day Jonathan Swift’ at twenty-two, a Guardian columnist at twenty-three, the Managing Director of a book publishing house at twentyfive, and now … and now … having given it all up in search of YouTube-founder levels of fame and fortune I was … essentially nowhere. Speaking on panels at the pleasure of former adversaries, dating a girl I wasn’t in love with and in love with a girl I wasn’t dating and spending all my time schmoozing and pretending to like people in the hope they’d give me some money. I couldn’t have been more depressed at what I saw in the mirror of my career – I was succeeding backwards.

I had spent the last two years trying to be a big-shot business person and it had so far come to nothing. Jesus, I couldn’t even get arrested in this town.
Things couldn’t be any more depressing.

And then I got arrested in this town.

Chapter Thirteen: ‘Banged up’…