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Are You a Risk Taker? Look Down!


Blog by Arnold Shuchat | October 9th, 2022


I just got back from the 2022 IOI Summit Conference which was all about the future of real estate technology. But before I post anything about the technology side of the event, I want to deal with the elephant in the room and say what must have been nagging at the back of some attendees' minds, depending upon their year of birth, and, sorry ladies, but I think this is a man thing. I only heard one comment on this topic but something immediately clicked in my head: it wasn’t just me.

I am not a fashionista. I am a down to earth guy struggling with Whistler/Blackkomb Mountain’s definition of a senior. So when I packed my lightest possible version of comfortable clothes for this overnighter, a debate raged in my head about the appropriate level of “executive” footware having regard to image, comfort, style and traditional business “oxfords”. I opted for comfort and chose the purest reflection of my defiant persona eschewing that Harvard/Bostonian look for my grey canvass Sketchers. 40 years ago, this would have been the cause of a negative job interview. I am not sure how these would go down today.

I am pleased to report that for the most part, I felt like I had arrived at a venue of like-minded souls. The western caste system of black oxfords for business was in a sense a reverse caste system at this venture capital event. Generally speaking, if one was employed by someone else and NOT a shareholder of a corporate attendee, there was a greater probability of the traditional black oxford; a kind of bondage to tradition that reflects perhaps a personal statement about one’s risk tolerance in life. It makes sense. If one isn’t going to step over the line and take a personal wardrobe risk, why would a career or startup risk be any easier?

The startup gang however, those entrepreneurs circling the waters in the pitch battle for funding from the “oxford” wearers… now that’s another story. One might think that attire fit for a traditional job interview might be fitting. That hypothesis could not be further from the truth! Head over the Champ’s Athletic store for a pair of red converse high tops if you really want to show the folks with the dough how much you care about what the king wears; ditto for the T-shirt choice!

From a sociological standpoint this whole observation makes so much sense. Those dreamers, thinkers and wonderers who shared their dreams and visions with us from the conference stage are looking to the future. Their entire collective DNA is based on “what if?” And, the oxford wearers, everyone else in the room and the rest of civilization need them.

So in conclusion, if you have ever wondered where you were on the risk/entrepreneur spectrum, perhaps start by taking a look straight down. Would you wear a pair of red Converse high tops to work tomorrow?

It was a great conference and we are now beginning to experience what was technological fantasy just a few years ago being possible today.

Where do you go to see the future?