Ugly deals often look ridiculous right before they look inevitable.

Would you have invested?

Go back to 2013.

A PE firm is looking at a majority stake in a Canadian outerwear brand at an implied valuation of about C$250 million. The business is doing roughly C$200 million in annual sales. It is known for one thing: expensive winter jackets. Made in Canada. Premium price point. Highly seasonal demand. Limited product breadth. Plenty of people could look at that and see a niche business with cold weather exposure and fashion risk wearing a parka.

The red flags were not hard to find.

One category.
One obvious season.
A high ticket product most normal people do not need.
Questions around how far the brand could travel outside its core base.
And the usual private equity anxiety attack around whether a niche premium label is a real platform or just a good few years in a favourable market.

The thesis, though, was interesting.

The brand had authentic heritage. Real product truth. Genuine scarcity. A growing following in markets where the cold weather story travelled. And a management team that understood premium positioning and brand discipline.

So at entry, this is what you were really betting on:

That a business built on premium parkas was not too narrow.
That seasonality would not cap the upside.
That scarcity and brand discipline would matter more than category breadth.
And that a company dismissed by plenty of people as too niche could become something much bigger once professionalised and scaled.

A lot of people would have passed.

Too concentrated.
Too fashion-adjacent.
Too dependent on one hero product.
Too easy to sound clever while saying no.

The outcome?

The company IPO'd in 2017 at about C$1.8 billion. The shares surged in their market debut, and the business that looked like a very expensive coat company turned into one of those deals everyone later pretends was obvious.

That is the game.

The ugly deal is often just a category people have not learned how to respect yet.