When I discuss some of the wilder ideas from the first wave of dotcoms with Totally Wired readers, several examples never fail to make the conversation. Pets.com paying $20 to ship $8 bags of cat litter coast-to-coast for free, is one: AllAdvantage.com’s notion of paying web surfers by the hour, with a bonus for any friends they referred, was another. In the latter case, the idea was that details of public surfing habits would be valuable enough to marketeers to offset the cost of paying geeks to stay indoors. Stupid, huh? Well, yes, but…

In the months since the book was published in hardback (just UK, I’m afraid, the US gets a paperback to coincide with the new UK edition in May), I’ve found myself developing an unexpected sympathy with those dodos of Web 1.0. Indeed, something small reminded me how far from resolving the problems they tried to tackle with such reckless brio.

A few months ago, I was asked to write a piece for the Sunday Times on an innovative project called ‘Sonic Journeys’. The essence of Sonic Journeys was to take interesting walks – or in one case, a train journey in Devon – and ask composers to soundtrack them. Downloaded for free, the soundtracks could then be played on a traveler’s ipod or phone, changing the experience in interesting ways. The one I’d been asked specifically to try was by Adrian Utley of Portishead, a musician I’ve admired since seeing his band at the Roseland Ballroom in New York back in ‘97, at Croft Castle in Herefordshire.

Among its ancient woods, Croft Castle boasts what is thought to be the oldest tree in Europe, the Quarry Oak, reckoned to have been alive when William the Conqueror invaded Britain in 1066. I loved the experience and enjoyed writing the piece, even standing about in the rain while the photographer posed me with the gnarled old Quarry Oak. Then on Sunday 18 October it hit the streets and the ether. Lovely. Except that I quickly realized something was missing, something which I should have foreseen, but hadn’t.

I started out writing for newspapers at The Guardian and still have friends there. For the past five years or so, I’ve been telling them ‘You have to stop giving this stuff away: I know what it costs to get the information on your pages, the effort to takes to interpret and present it, and if you don’t charge, you’ll have to stop doing it.’ Sure enough, the magazine journalism I grew up with and still have a romantic attachment to is all but dead in the UK, because it’s expensive and expendable. More will obviously follow, which is ok until it starts hitting the quality of news, which is patently now happening.

So when Rupert Murdoch announced a pay wall at The Times and Sunday Times, I applauded, thinking that someone had to make a stand for content and the skills which go into producing it. The ideal of unmediated information has a punishing downside in the form of unreliability and the time it takes to sift the sea of data: I love social media, but there are times when I yearn for someone to tell me what I need to see, in exchange for me getting a wodge of my time back. For this, I would pay, I thought, so surely others would too.

Then I saw what happened with the Sonic Journeys piece, as it hit the streets, but not the ether. By which I mean that the piece had no echo, it simply stopped where it was, because no one could forward or tweet it or engage with it online, unless they were one of the few behind the paywall. And I was surprised at how much I missed this – not so much the connection, but the engagement, and by how arid the experience seemed without it. The pay wall: I’m not sure I think it can work anymore.

So it turns out that we’re no nearer resolving the problems Josh Harris and his peers were trying to find all kinds of creative ways around in the late 1990s. An effort which suddenly looks to me much braver and more pioneering than it did back then. So as more time passes, I find that my respect for them grows.