On Angel Investors, Mid Life Crises and Gucci Loafers

I am the epitome of uncool. While others drive nice cars and wear fancy clothes, I’m in an old Subaru with a quarter million kilometres on the clock and still wearing a pair of prototype Cactus shorts that should have been retired years ago. It’s probably a lack of confidence that I could actually pull it off but, whatever the reason, I’ve never been drawn to trying to be part of the hoi polloi.

As far as I’m concerned, I’m just a random guy trying to make his way through life and struggling with all the sort of stuff that other people struggle with. So I don’t really get bling or eye-candy, especially not when it’s around the neck, wrist or arm of someone who really should know better. The chances of me being seen wearing a Rolex, a pair of Gucci loafers or an Armani suit are somewhere south of zero.

This idea of people needing to look “cool” was bought up the other day by a buddy who had seen something I wrote about the recent demise of the Unfiltered business. Suffice it to say, Unfiltered was a marginal kind of an idea that was, on so many levels, driven by the egos of its founder, investors, board members and other stakeholders and it only took a few years and a few million dollars for the world to see that the emperor really didn’t have any clothes on.

In my article, I pointed to the alleged bad behaviour of the founder and his penchant for living the high life. I made a slightly in-jest remark about his predilection for Gucci loafers and was faced with a barrage of criticism suggesting that somehow, by critiquing his dress sense, I was succumbing to some kind of -ism or other.

I was kind of confused that anyone would take it this way, but, for the record, I don’t really care what someone wears so long as they pay for it from their own pocket and it doesn’t get in the way of them actually doing, you know, their job.

But this whole theme of needing to look cool works the other way around as well. What I mean by that is that I am perturbed at the well-heeled and well-respected business people who invested in this business. Someone who has run an airline or a global marketing business should, you’d think, have the business acumen to be able to actually assess a venture.

And then I had a realization. Some of these investors have no need or desire for the business they invest in to actually make a financial return. For them, the investment is designed to make them look cool. It sits alongside the Armani suit, Rolex watch and Gucci shoes they potentially have sitting in the closet and is used to build up a veneer or credibility.

Compete in the Coast to Coast? Tick. Make a million bucks a year? Tick. Be named as a high-profile investor in this week’s coolest startup? Tick.

The chap whom I was talking to, himself an industry insider and hence unable, or unwilling, to say so publicly, suggested it was similar to the fat Russian oligarch with a 20-year-old girlfriend on his arm: for sure it might be true and enduring love, or maybe it’s something else altogether.

I was reminded of an event I attended a few years ago in which a bunch of early-stage founders pitched to a room of investors. At the table I was seated at was a middle-aged corporate type who was loudly telling those around him of the investment success he’d seen over the years. On his arm was a woman who must have been 20 years younger than him. Now tell me I’m jumping to conclusions but I couldn’t help but wonder if his approach to startup investing was similar as his approach to relationships – whatever it takes to look cool.

I’m going out on a limb here and I’m sure my comments will be criticised by many, but I can’t help but wonder if many investors would rather self-aggrandise by investing in ventures that have little or no market validity but look “cool”, than actually supporting real businesses that actually make a difference to the world.

Startup Rolexes – who would have thought that they are a thing? (And, for the record, if you want to wear a Rolex, please don’t let me stop you.)