I’ve got a friend who is well known for always dressing in a highly elegant manner. We often share an office, and she spends a lot of time commenting on the fact that, sartorially, I look like a scumbag. Luckily Gabby and I are great friends so I’ve never taken offence at the comments. She’s right, I’ve never really worried about clothes and my usual go-to involves whatever item of New Zealand-made Cactus kit is closest to hand in the morning.

So it’s safe today to say that, when it comes to fashion, I’m entirely out of my element and not really capable of commenting.

That said, I have noticed a certain penchant amongst a certain class of young entrepreneurs. That penchant is to be seen wearing expensive Gucci loafers. The practical and financial implications of Gucci loafers are confusing to me. If you had to design the least practical yet most expensive piece of footwear possible you would be hard-pressed to come up with anything better than a pair of Gucci loafers

Nonetheless, they would appear to be the badge of honour amongst a certain subset of our startup founders and I’ve noticed a positive correlation between Gucci loafers and talking a big game. I’ve also noticed an interesting inverse correlation between said shoes and actual entrepreneurial success.

Recently I’ve been thinking of Gucci loafers is I read of the acquisition of one high-flying start-up by another. Unfiltered was the creation of Jake Millar an exceptionally young, exceptionally articulate, and exceptionally confounding young man.

Millar famously turned down a $40,000 scholarship to study law and instead decided to start up a company that would make its gazillions filming videos of well-heeled business people for the edification of those who can but aspire to be similarly heeled. Millar saw some measure of success raising many millions of dollars and having such luminaries as former Air New Zealand CEO Rob Fyfe and former Saatchi and Saatchi global head Kevin Roberts joining him on his journey.

I have to be honest and say that I never quite understood the proposition of Unfiltered. There are no shortage of videos of these sort of individuals espousing their opinions on seemingly every topic and why an individual would pay a subscription to watch said videos when they are generally available for free on YouTube, is a total mystery to me.

No matter what logic would suggest, as is sadly the way with the start-up ecosystem, Millar and the industry’s and measure of success was how much money the business raised and by this metric they were doing swimmingly. Far be it from me to suggest a connection between moneyed types, their insatiable desire to see themselves in the media, and investment decisions but for whatever reason many of these lauded and credible business leaders invested in the Unfiltered platform

Fast forward a few years, some very snappy suits and a notorious party at the Kim Dotcom mansion and you have a situation where the company had burnt through the majority of its cash with nothing to show other than some very expensive (and very empty) champagne bottles a big catering bill, and a few self-aggrandising videos.

Not to worry because where one Gucci loafer wearing founder fails, there is always another one to step into the breach.

Enter from stage left Jamie Beaton, another exceptionally young, exceptionally articulate, and exceptionally confounding founder. In Beaton’s case, it was Crimson Education, a business that was started to help smart kids get into US Ivy league colleges, pivoted slightly to be focused on providing tutoring for young students, and has humbly moved on, it would seem, to the simple job of reinventing education in its totality.

Crimson decided to buy Unfiltered, and I used the word “buy” in the loosest sense. A price tag in the tens of thousands of dollars for a company which has raised many millions isn’t what I would term a purchase, rather at best it’s a fire sale.

Crimson is, apparently, going to use all of that Unfiltered ego-boosting content to give its student clients some motivation and aspirational goals to strive towards.

Now I have my own views on the Crimson business, but I’m also well aware that Beaton has quite a litigious streak so I will refrain from using terms such as Ponzi scheme. Suffice it to say I think Crimson could be a great little tutoring business that could really make a difference to students lives. it is not, however, a multi-hundred million dollar enterprise that is going to change the world no matter how many John Keys, Julian Robertsons, or Kevin Roberts Beaton drags out.

Maybe my leg of sartorial knowledge is mirrored by a dearth of understanding of the entrepreneurial space. Maybe in years to come, I will be forced to eat my words and kneel down in reverence to the Gucci clad feet of people like Jamie Beaton and Jake Millar.

I suspect this is not the case, however, and I will continue to progress in my own unfashionable way as far from the Gucci Emporia and the entrepreneurs that frequent it as humanly possible. Even if it results in ongoing ribbing from Gabby.

Ben Kepes

Ben Kepes is a technology evangelist, an investor, a commentator and a business adviser. Ben covers the convergence of technology, mobile, ubiquity and agility, all enabled by the Cloud. His areas of interest extend to enterprise software, software integration, financial/accounting software, platforms and infrastructure as well as articulating technology simply for everyday users.

  • Thank you for asking the same question I’ve always pondered. Why pay for a bunch of videos when You Tube is free! Furthermore, what is the difference between Oompher and Unfiltered? It strikes me he used his sale proceeds (my taxes) to set up an identical concept to the previous one! And while I’m on, what has the government department he convinced to buy Oompher actually done with it?

  • Janine Manning |

    I’ve been working with Jamie since he was a teenager, and ‘Gucci loafer wearing founder’ does not come to mind as a phrase to describe him. It’s a long bow to draw a parallel between Jamie/Crimson and Jake/Unfiltered.

    It always surprises me how some NZ commentators, armed with little knowledge, can so casually tap out such mean-spirted ‘observations’. Take a look at the quality of Crimson’s shareholders on Companies Office – they have undertaken full DD before investing, but you seem to think you know something they don’t? Your (imagined) views on Crimson do a disservice to the 500 employees of a successful NZ company, who are growing and scaling a global business. Many of our employees are young, ambitious Kiwis; working hard and making a difference in a NZ company that has been audited each year by a Big4 firm with a clean slate.

    Note: Kevin Roberts is not a Crimson shareholder and never has been.

    • Hi Janine. There were a fair few Theranos shareholders (not to mention board members) that waxed similarly about what Elizabeth Holmes was doing. Now, I’m not equating Jamie with Elizabeth (she channels STeve Jobs better than Jamie does) but I reserve the right to have my opinions and share those same reckons.

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