The Latitude59 start-up extravaganza held each year in the Estonian capital, Tallinn, has over the last nine years developed a reputation for innovation, speculative thinking and, quite simply, being cool. This year’s event, running from May 31 to June 1, had all the ingredients for more of the same, plus one artificial additive that turned the whole thing a bit sour. That bland yet unpalatable ingredient was His Royal Highness the Duke of York, better known as ‘Airmiles Andy’ to his disloyal subjects for his renowned love of all-expenses-paid trips to exotic locations.

Tallinn might not be particularly exotic, nor particularly expensive to reach – even a business class ticket would barely dent the £43mn Sovereign Grant from which HRH is remunerated for whatever it is he does – but he was a very peculiar choice as ‘keynote speaker’ to open Latitude59. After all start-ups, and particularly Estonian start-ups, are supposed to be about young, visionary entrepreneurs competing in a meritocratic manner to access seed money that will allow them to make the world a better place.

So who better to get things going than a middle-aged, ponderous aristocrat who has never operated a start-up and has a history of hanging around with dictators and badmouthing “f*****g journalists, always sticking their noses in”?

His ten-minute keynote at Latitude59 did not disappoint, in that it was extremely disappointing. It began with HRH revealing he had just become the latest recipient of an Estonian e-residency card, but rather fluffing an attempt to make a joke out of it. “This is a wonderful gift of e-residency (pause). It’s slightly annoying (pause) that I can’t be more flexible (pause) about my residency (pause) in more general terms (polite tittering),” he quipped.

Effective public speaker he is not. If you can imagine a slightly over-inflated yet compressed version of Prince Charles, you have some idea of his physical appearance. And while his oratorical style – if a series of painful sighs can be described as such – is superior to Charles’ in clarity, it is inferior in vocabulary. He lacks both the comic delusions of his elder brother and the thespian delusions of his younger brother Edward, coming across as someone who would probably rather be elsewhere, provided the ticket is first class and can be put on expenses.

The rest of the ten-minute ramble, roughly half of which was pauses, included such insights as that education is important, that Estonia is great (but you already knew that) and that his job description is “to support British prosperity”, whatever that means. He did however have the consolation of being presented with a goody bag containing a chipmunk facemask, which one hopes will make it into his official declaration of benefits accrued.

Estophile Ed

Estonia has made effective use of its e-residency card scheme over the last year with Prime Minister Taavi Roivas popping up like some proactive political Scrappy Doo on countless US chat shows and Euro websites promoting it. The actual benefits of holding a card are limited, but as a marketing exercise it has been a genuine coup.

Card number one was issued to renowned Estophile Edward Lucas – a smart move, as it guaranteed that he would immediately write about it. Since then Ban Ki-Moon, all US chat show hosts interviewing Roivas and various other people regarded as good PR have had cards forced into their wallets, creating a blaze of publicity along the way.

And now Prince Andrew, an individual with a reputation that is hardly one most would aspire to. “There are some advantages in the connections that I have,” he said at one point in a moment of inadvertent candour, referring not to peddling influence in the Old School Tie manner or operating in a world of Central Asian authoritarians where kickbacks are to be had, but in his current role as the head of a start-up organisation called ‘PitchAtPalace’, which “offers the chance to get your tech business idea in front of a global audience of influencers who can catapult it to the next level”. It is quite likely some of his ancestors had experience of catapults, trebuchets and other manners of siege engine, so perhaps he has finally found his niche.

The rest of his advice to start-ups consisted chiefly of statements well beyond parody or self-awareness. “Start-ups need to understand that money doesn’t grow on trees,” he warned, a state of affairs happily not applicable to the Sovereign Grant, which is guaranteed by law never to pay less in any year than it did the previous year.

If the Duke of York is the new poster child for E-stonia, then one has to consider if the concept is at what start-up culture calls a “jumping the shark” moment. For those not familiar with the term, it refers to an episode of US sitcom “Happy Days” in which The Fonz jumped over a shark on water skis, instantly transforming the hitherto charming and funny show into a toe-curling embarrassment forever. It signifies the moment at which something good turns irredeemably awful.

Awarding ‘Airmiles Andy’ (at least it’s better than ‘Randy Andy’ as he was known before that) e-residency may not be actual jumping the shark, but it is perilously close; at least dancing with the dolphin, or possibly even prancing with the porpoise.

Sources in Estonia suggested to bne IntelliNews the decision to create the royal e-resident might have a simple but astounding explanation: that no one bothered to Google him. In the world’s leading-edge online country.

But luckily, Prime Minister Roivas was on hand to offer an instant alternative to the now uncool e-residency scheme. After watching HRH mumble his way through an unconvincing pitch for London as a place to start a business (“Coming to London is probably a stepping stone”), Roivas sneakily signalled to conspirators and the words “fastEST, strongEST, cleverEST” flashed onto a giant screen.

“Hehe... and modEST.” chuckled Roivas.