British newspapers in the mid to late 2000s were strange places. We knew there was this thing called the internet and that it was coming after us but it all seemed far away, mystical, silly, impractical and not entirely serious as a threat to the mighty news business of chopping down trees and printing words on paper. I can still remember the day at Scotland on Sunday in 2005 when the hotshot designer (Mark) called us over to show us something called You Tube, which had been invented that year. In Scotland calling someone a tube is not a compliment. Back then saying “you tube” in a Glasgow bar might get you chibbed (that is hit violently). An online start-up called You Chib would have had only niche appeal outside Scotland.

But that day we crowded round the computer screen to see this thing called You Tube. It was like a DVD or video player, only on a computer with no need to put in a CD-Rom thingy. You just typed in and clicked and there it was on your screen. A man on a skateboard carrying his cat, or something. This would obviously never catch on, we said. How much of a market could there be for skateboard and cat videos when we already had established high-quality brands such as “You’ve been Framed”? Honestly. Those crazy Californians.

But what else is from California? The Beach Boys. My colleague Chris Deerin asked Mark to see if there was any footage of the Beach Boys, one of our favourite bands, on this You Tube thingy. And there it was almost in an instant. Grainy footage of the young Beach Boys getting around or singing about surfing, which only one of them could do to a proficient level. Surfing that is, rather than singing, which they could all do brilliantly.

Fast forward several years, and I had moved to the Telegraph in London. First I was on the Sunday Telegraph, working for one of my favourite people, Patience Wheatcroft, which was terrific fun. But I think it is fair to say that the internet posed a particular challenge to Sunday newspapers. The entire ethos by definition is different. The internet is about instant gratification, speed and the erosion of hierarchy. Sunday newspapers take a week to produce, hopefully with scoops, and then they land with a pleasing thump on the doormat, to be dissected at leisure. It ostensibly makes a certain sense to say that the Sunday journalists should pitch in to the internet operation on Tuesday when they are “seeing contacts”, but the moment this starts to happen the peculiar quality of the Sunday newspaper experience has been weakened and eroded. Many Sunday newspaper journalists feared the internet more than most. With good reason.

In late 2007 I moved across to the Daily Telegraph, where my then boss, and now friend, was ahead of most of us in realising the scale of what the internet was doing to the news business and what would be required to respond.

Newspaper journalists are often terrible at change. For all that we take to task businesses, banks, generals, politicians, football managers, actors, charities and civil servants over their alleged failings and inability to get with it, we’re generally bad at getting with it ourselves. We went into newspapers because we loved newspapers – the gossip, the thrill of news, the pubs, the physical process of thundering presses – and now we were forced to contemplate the possibility that what had earlier in the decade seemed comfortingly far off, the replacement of newspapers with online outlets, was here already. The internet had destroyed the newspaper classified ad business and was changing reader habits with alarming rapidity.

We had to attend a lot of company meetings to discuss the revolution hitting media. Journalists would have to write for online too, and launch their own online TV shows, while blogging and vlogging what they had for breakfast. Although the mood was kept upbeat, one could not shake the feeling that we executives were giving the media equivalent of a lifeboat demonstration or drill, staying calm in order to ensure that the passengers did not get spooked, panic and tip over the vessel.

It was explained in these meetings that we were on the cusp of great change and opportunity in journalism but it would require us to adapt. Quite a lot people were adapted right out of the door.

And new people arrived to freshen the place up. Newspapers, or British newspapers, and that is never more true than during a period of great transition need a smattering of wildcards and unusual characters to add personality and unpredictability. This might be a social diarist with a fear of leaving the house, who makes up for it by wielding a wicked pen that punctures the pomposity of the powerful. Or it could be a lazy lush of a reporter who does as little as possible for a week and then writes at five minutes notice the most extraordinary colour piece during an unfolding disaster. It’s a weird business. And the more it has become built around young graduates, like wot I woz once, rather than drawing from local papers and oddball corners of the nation’s life, the less varied and in touch with the country it has become. But that’s another story.

Right. I put Milo Yiannopoulos in the headline and I should probably get on with it and explain why. There is a connection.

Today, Milo is a superstar of the pro-Trump parts of the media and a Breitbart bad boy who has become infamous for his internet antics. Attempts to have him barred from American universities, where he delivers his anti-Islam and pro-Trump routine, have attracted considerable publicity in the US and here. Now he stands accused of endorsing (he denies this) paedophiles who want to have relationships with young boys. There he has gone too far, almost certainly for the Trump White House and possibly even for his fans in the nut job paradise that is the internet. Even before the latest row there was controversy over the invite extended to him to address CPAC, the US annual forum in which distressed and baffled mainstream conservatives look for ways to connect with and understand the outside world.

I must say that whenever I see Milo on television causing fights and being a chancer I feel partly responsible. I was one of the executives at the Telegraph that could have halted his emergence, or at least tried to put him off journalism, but did not.

Back in the late 2000s Milo was just another conservative blogger trying to get noticed, and there the Telegraph – hungry for innovation – could help. Actually, it was apparent fairly quickly that he was something unique. Not only did he arrive at the Telegraph full of ideas, excessively confident at a young age about how he could become a king of the web, and us his vassals. He also had an interesting or unusual personal history. Although he had been to Cambridge, I think, there was talk of him being someone who should not be crossed. Who was this bloke? What was his name? What on earth was he wearing? He appeared to revel in the speculation.

In the olden days he would have been rejected or sent to work on the diary or in Telegraph features making the tea and fighting with the other interns. That way he might learn the trade or be booted out.

Not in the internet era. Milo quickly found a home at Telegraph blogs, where the blogs editor, Damian, was a bit of a digital visionary. Damian not only understood the journalistic fundamentals. He has a flair and energy that was perfectly suited to trying to get the stuffy old Telegraph to grow instant comment or what were then known as blogs. Damian encouraged the bloggers to range freely across politics, theatre, life, religion and music and to within reason not be afraid of controversy.

Telegraph blogs took some stick, both internally and externally. I don’t know what it was like for the readers. We writers absolutely loved it at its peak. It took me a while to plunge in, encouraged by contributors such as Dan Hannan. What a pure delight blogging was in that period. At its best it allows the writer to play with formats, and to meander in ways that would never be allowed in a 750 word piece commissioned and written to order for the pages of a newspaper. Blogging has its drawbacks and limitations. But, and I can only speak personally, the intensity, volume and scope for experimentation, all encouraged by Damian, made me a better writer.

Milo had plans for Telegraph blogs. Lots of plans. And suddenly, for a brief period, he was the Telegraph’s visionary guru handing out internet kool aid to us baffled and sceptical hacks and to the seriously talented people then in charge of the site. He was parachuted in to meetings with the company’s leaders where he mapped out his vision of a Telegraph at the forefront of a millennial media revolution.

This all sounds ridiculous now. Hell, it was ridiculous then. But it was before we had all realised that Facebook and Google were not our friends. They were going to suck up all the ad money and kill all but those with the sense to charge for quality content. We didn’t know that then. Anyway, the ferocious pace of change in media at that point, and the need for novelty, for an answer, any answer, meant that a character like Milo (a charismatic conservative chameleon) could walk right in.

With hindsight, I failed miserably in my responsibility as comment editor and should have made a stand. I was not alone in this. Quite a few other experienced executives thought the Milo for clicks experiment would blow up but we agreed in the pub that there was no point being near the scene of the explosion.

It wasn’t long before the first bangs were heard.

The greatest strength of blogging or online comment is also its greatest weakness. While it allows for a free flow of ideas and energetic debate, to get scale there has to be a lot of content which means it is by necessity more lightly edited. This should force the writer to think about legal and ethical responsibilities because there are fewer lines of defence. There were reader comment sections to contend with too, where congregated upstanding genuine readers and assorted ne’er do wells sitting at home in their underpants.

But that need for speed and the demand for a lot of content in blogging means that you need people to stay on the right side of the boundary marked controversy. Just over the border roams a posse of media lawyers eager to get you to the High Court, and even experienced writers stray.

Milo was wild. Under the guise of “optimising our social assets” he set about causing maximum outrage and seemed by turns furious, energised and amused by any criticism. Online he seemed to pick fights with absolutely everyone. Stephen Fry was a target, I remember, and Fry made the mistake of responding, which was exactly what the fame-hungry Milo wanted. The search for clicks and attention was remorseless and rather awe-inspiring in its horrible way. When Twitter arrived it was veritable catnip to a controversialist on the make.

What really caused concern was the capacity his allies outside the building had to fight back in nasty fashion against anyone who crossed or questioned the self-styled guru and supposed intellectual renegade. The tone was horrid and unappealing. Like Ayn Rand, only even less humane and less forgiving.

Critics of Milo in the comments and on social media were savaged late at night. It was all pretty unpleasant and not at all what had been envisaged when the Telegraph attempted to inject some digital energy into its operation. As a result, after one explosion too many that I cannot mention, there was an investigation into what had gone wrong. Those of us who had thought it would go wrong could not say so afterwards because we had not said so to our bosses in advance. Undertakings of better monitoring were given. Youthful exuberance on Milo’s part, and the enthusiasm of his emerging fanbase, was blamed. Round everyone went for a further spin on the internet merry go round.

The overall effect of the episode was part denouement of a satirical novel written by Tom Sharpe and part spoof comedy Bruno, the Sacha Baron Cohen vehicle.

After I left the Telegraph for other pastures, there was a subsequent controversy involving Milo supervising a groovy tech competition called Start-up 100 or something, that was run through one of his companies, it is alleged. There was a row about paying for hotel bookings and deposits for an awards ceremony. The paper eventually paid up to avoid embarrassment, I am told. Milo left and founded something called Kernel, a tech website which is still the subject of debate.

Next stop for Milo? The rest you know. He attached himself to Steve Bannon and Breitbart, enjoying a reinvention as a crusader for Trump and crucifier of the “safe space snowflakes” or irritant to people with basic good manners and a sense of decorum and respect for others. Today’s row will either propel him to new heights, with defenders likely to call the attacks on his comments about paedophilia “fake news”, or it will finish him and his Simon & Schuster book deal in the US.

And me?

I have had various adventures in the media since, culminating in the launch last summer of Reaction, the site you are reading now. Alongside writing a weekly column for The Times, I edit Reaction. We’re a small team on Reaction, but dedicated to providing quality commentary and analysis on politics, democracy, technology, culture and ideas. Part of the inspiration is that original spirit of the best of the “non-clickbaity mainstream media tries the internet” thing that Telegraph blogs did so well before they blew it up.

As of last week, in order to expand Reaction and to try to build something where a wide range of good writers can be paid properly, we introduced paid membership.

You can subscribe here, for only 75p per week. Get my weekly newsletter and much more besides, including member-only events. It is early days and we won’t get as many clicks as Milo. But that’s kind of the point.