London startup blog The Kernel could face closure from enforcement of a high court order for £16,853 against its parent company Sentinel Media, whose sole director Milo Yiannopoulos has been embroiled in rows for months with former contributors who have gone unpaid.

Non-payment of the debt could mean the forced winding-up by a court-ordered administrator of Sentinel Media, whose only obvious assets are its web domain, kernelmag.com, and the income from its mailing list. The mailing list itself is not an asset unless it can be shown to have been properly collected under the Data Protection Act.

Yiannopoulos is also being investigated by the criminal investigations team of the Information Commissioner's Office for failing to register Sentinel Media under the Data Protection Act – despite running a paid-for mailing list since the site went live in December 2011. Failing to register where required would be a criminal offence with a maximum fine of £5,000, for which the directors of a company are personally liable.

The £16,853 order is being enforced on behalf of Jason Hesse, who was The Kernel's editor for several months last year before leaving in May. He won an unopposed claim for unpaid wages and unfair dismissal in January. A high court order for enforcement was made on 20 February.

Sentinel Media is said to owe at least £10,000 more to other former contributors and co-founders, and other sums to photographers who said Yiannopoulos, its editor-in-chief, used their work on The Kernel without permission or payment.

Hesse's case was not opposed at any stage, and he received no communications from lawyers representing Sentinel Media or The Kernel, despite Yiannopoulos having claimed to a Forbes blogger in December 2012 that "I've sunk about £50,000 into the Kernel so far, I think, most of which has gone on lawyers … I don't know whether I should be proud of the fact that we spend double on lawyers what we do on editorial."

Hesse told MediaGuardian: "Milo never paid me a penny for the work I did as editor, nor for the three months of hosting bills I paid for The Kernel, nor for the money I lent to him personally. Why he thinks he can just get away with it is beyond me. I hope that the high court's order will help him finally understand that it isn't his choice to decide whether or not he wants to pay me; it's the law."

Two other former writers, Margot Huysman and Mic Wright, say they are still waiting for a balance of about £4,000 each to be paid. Yiannopoulos paid each of them about £1,000 at the end of October and, they say, promised further payments each month – but those were not forthcoming. When Huysman complained of the non-payment on Twitter, he sent her emails saying "You've already made yourself permanently unemployable in London with your hysterical, brainless tweeting, by behaving like a common prostitute and after starting a war with me, as perhaps you are now discovering" and implying he had a salacious picture of her from a party that he would publish if she persisted in complaining.

The threat proved baseless; Huysman has since worked at two other major UK publications, including the Sunday Times.

By the end of the summer of 2012 both Wright and Huysman had left, complaining about being unpaid. A number of other writers and photographers, including Willard Foxton, Sean Anderson and William Hanson say they are owed smaller sums ranging from £100 to £500. One of the original co-founders, Stephen Pritchard, a journalist who helped set up the site and lent £3,000 interest-free for 12 months on the proviso of repayment in January 2013, was told by Yiannopoulos that he would "have to look at the accounts" about repayment and told not to discuss the debt.

Hesse commented: "His refusal to pay those people that he'd hired is simply unacceptable, though in hindsight, I don't believe he ever had the money to pay me or Margot. It certainly would be interesting to see the company's accounts."

The site's only known source of income is from its "Nutshell" mailing list, for which subscribers pay £5.50 per month, ostensibly for a weekly mailing. But it has appeared only irregularly since the end of November, leading to complaints and demands for refunds from some. Concerns by its previous email provider Groupspaces that the content could leave open to a joint libel action is understood to have forced it to seek another provider.

A number of people who signed up for a novel-writing challenge in January reported having their names and emails added to those who received an edition of the Nutshell in February, without having given their consent.

"The Kernel had the opportunity to write about real issues in the London tech scene, which is one of the most vibrant and exciting technology development spaces globally," commented Steve Karmeinsky, an entrepreneur and angel investor who has frequently been the target of sniping by Yiannopoulos. "Unfortunately, rather than that, it morphed into a celebrity/gossip magazine; rather than being the Economist of the sector, it was very much the 'National Enquirer'. Further, it became just a mouthpiece for Milo Yiannopoulos to write nice things about his friends."

In a statement, Yiannopoulos said: "We do not know what the purpose of, or motivation for, the Guardian's latest fishing expedition is – though we can guess – but the company remains in good health, with ambitious plans for 2013. We have no further comment to make on private financial matters, nor on any malicious, baseless attempts to bring our directors, employees or associates into disrepute."

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