Where is technology’s critical culture?

The industry, the media, and the ‘five little questions’.

A few weeks ago, a startup founder for a pretty mundane app called Need tried to get the attention of a tech journalist at the San Francisco Chronicle by sending her a swag basket. In it, there were oysters, tequila, a vibrator, and some lubricant. The package had nothing to do with his business, a question and answer app, but he wanted to get the writer’s attention. Apart from the blatant sexism of his choice of swag, where did he get the idea that being incredibly creepy would be read as anything like a respectful request for media coverage?

Last month, the anonymous-message app Whisper, billed as “the safest place on the internet” found itself in hot water. They’d been involved with some stories covered by The Guardian, so the paper arranged a visit to talk about an official partnership. Instead, the journalist discovered that Whisper has tracked people who have specifically selected the (allegedly functional) feature that disables location tracking. Not only that, but they’ve shared that information with authorities. There’s a lot more to it, of course, but when they learned what Whisper was doing, they changed their minds on the partnership and reported what they learned. Because that’s what journalists are supposed to do.

Whisper’s founder accused The Guardian of getting its facts wrong. Whisper’s Editor-in-Chief Neetzan Zimmerman (formerly of Gawker) called the reporting “a pack of vicious lies”, and claimed the paper would regret it. Where did Whisper get the idea that it was cool to tell tech journalists what you’re really up to, and then assume that they’ll keep your secret even after you cross an ethical line?

Two weeks ago, Ireland’s WebSummit ran a Google Hangout called “How to Hack a Journalist”. PR advice helps startups get coverage that’s appropriate for them, and it helps journalists be more efficient and informed. There’s a place for straightforward business news, just like there is for sports scores, the weather, and parliamentary proceedings. Giving the underdog a break isn’t terrible, but at some point, a scaling company ceases to be The Little Startup That Could.

How cosy is too cosy?

This week, the tech world, along with journalists, politicians, celebrities, and sports stars, descends on Dublin for WebSummit. It’s 20,000+ people coming to Ireland with the intention of having a good time — so of course, it’s a good time.

At something like WebSummit, hundreds of journalists will be beamed in and out of the city. They’ll have a good time, and they’ll write about the good time they had. That’s part of the story, sure. But how many will indulge a little critical curiosity about how the company behind it has scaled so quickly, or ask the many exhibitors and attendees if they really feel it’s been a good return on their investment? The Guardian, usually pretty good at critical coverage, are media partners — will they ask questions about the deals that go down at this event that calls itself “Davos for Geeks”, or just report the good news?

As a writer, you often have to make nice to get a story, and that includes hanging around events and being pleasant, but it’s too easy to start feeling like it’s intrusive to dig into the dark side of someone you’ve just had lunch with, especially when those people still see themselves as scrappy little Davids trying to take down the big ogre Goliath. Nobody wants to pick on the underdog.

Last year, Elon Musk’s visit to a Dublin nightclub made the Irish national news. He was interviewed on the WebSummit stage by Enda Kenny, the leader of the Irish government, who asked him for advice on the digital economy, and offered Shannon, in the west of Ireland, as a base for his Space X missions. Even though the internet met the tone-deafness with fitting mockery, and even though the bombastic silliness of the event is well-recognised, apart from a few softball questions about gender imbalances on stage, it was largely covered in the media with straight reportage. This year, Enda Kenny is helping the WebSummit’s founder ring the NASDAQ opening bell. David isn’t winning; he’s just become Goliath.

Criticism does happen, but it doesn’t get very far. Food critic Jay Rayner tweeted his annoyance with WebSummit’s failure to pay speakers, and called the organisers “an ill-mannered lot”. Commenters on the piece on Broadsheet.ie see the company in less than a positive light. The Irish Times’s Karlin Lillington wrote two years ago about some of the data protection issues in the company’s marketing, but that didn’t get much traction. Even now, if you want your personal data removed from their database, it will cost you a processing fee, and you must do it in writing. (And it used to cost even more.)

From the Web Summit’s terms of service page.

The pseudo buddy-buddy emails written in an over-familiar tone are kind of endearing when you’re a few people working out of a shared office, but at some point, success is no longer an unlikely victory over the monster. It’s not really Davos for geeks, if it ever was, it’s Davos for people who also go to the regular Davos.

It’s not just WebSummit. In a discussion at TechCrunch Disrupt, Fab founder Jason Goldberg talked about the company’s recent ‘pivot’ into lifestyle brand Hem. I’m curious about (read: a little suspicious of) how they kept their billion-dollar valuation, fired most of their staff, and changed everything about the company, including the name, offering, market positioning, and physical location. But there wasn’t any follow up. Earlier this year, a picture of AOL’s “digital prophet”, Shingy, riding on a wrecking ball at a Mashable party at SXSW seemed to sum up most of the worst elements of the industry in a single image.

It’s hard to cover an area with the necessary intimate knowledge without letting your intimacy with that world affect how you write, or letting your snark about some techbro riding on a wrecking ball derail what are actual, serious questions. But that’s the job, to get your story without falling in love with your subjects nor becoming too distracted by how not-serious it all seems once you see it up close. But this is serious money, and these companies have serious impact.

The “five little questions”

With tech, there’s a huge crevasse where the critical culture should be. In part it’s because old media doesn’t really understand tech. Producing critical reporting or investigative stories in the conventional press is hard. There aren’t a lot of resources, and the editors don’t generally understand the area. Most of them are still too busy getting their heads around their own technical platforms and dismissing social media as a silly thing for kids.

On the other hand, the new media companies covering tech are often tech companies themselves. The big ones try to disclose any interests they have in companies mentioned, but they’re not exactly likely to subject themselves to structural analysis. You’ll find critical pieces in Valleywag, but the business model of Gawker Media and other online-only outlets makes it a tough space to research and produce the in-depth reporting we need. Some of this is because hatchet jobs and snark make better clickbait, even if it’s mixed in with real, in-depth, quality writing, as it is on BuzzFeed. But that’s not the whole answer.

If you ever wonder why a story in an online outlet seems a little too enthusiastic, or why a teacup storm just won’t die, search the relevant companies on Crunchbase, where you can look up startup funders and founders. Who shares investors? Who is on whose board? It’s never been easier to find out who writes cheques to whom. It won’t give you answers, but it might help you ask a few more questions about the real relationship between the Davids and the Goliaths. It’s never seemed more like a missed opportunity, even among all the useful business and development wisdom, to ask questions more probing than “How did you get to be so awesome?”

The late Tony Benn, in his outgoing speech to the British House of Commons in 2001, mentioned that when you meet a powerful person — and one of his examples is Bill Gates — you should ask them ‘five little questions’, as he calls them: “What power have you got? Where did you get it from? In whose interests do you exercise it? To whom are you accountable? And how can we get rid of you?”

From inside the industry, it’s obvious why it seemed okay for a startup founder to send sex toys to a journalist, or why another would be genuinely shocked that a reporter broke the wink-and-nod code of confidence that, whether by design or default, is enabled every time a glass is raised. Everyone wants to take down a Goliath. Nobody wants to admit they are one.

The whole startup narrative is based on a scrappy gang of youngsters out to better the world. When they celebrate huge deals forged in late-night drinking sessions at an event that costs four figures just to attend, it becomes, not just an equating of the value of business with shareholder value or investment rounds, but a bit of David-and-Goliath theatre.

Most media outlets, at least the ones that even pretend to be serious, cover businesses with at least a squinting critical eye, but when it comes to tech startups, all a company has to do to get sympathetic coverage is present itself as the underdog. But if you ask Tony Benn’s five little questions of the powerful people in the tech industry, or even ask those with a moderate amount of power, the answer to every single one is ‘the investors’. In other words, Goliath.