There are plenty of opportunities to bet against many of these markets, some more direct than others.
To bet against the Canadian housing market, for instance, you could look at shorting vulnerable financial institutions (Canadian banks and lenders with exposure to the Canadian housing market). You could also look at the Canadian dollar, which could conceivably fall if there's a housing crash.
Private startups are obviously a more difficult target, but you should consider that the types of events likely to push the private startup market into meaningful decline would in most cases also be bad news for publicly-traded tech companies as well, and you can short just about all of these. There are numerous advantages to targeting publicly-traded companies (liquidity, availability of information, in a major market correction there will be forced selling, etc.).
On the second point, the correlations between hyped startups and established software vendors often isn't that strong. It doesn't necessarily need a major crash for markets to decide that Uber actually isn't worth 40% of the current global taxi market.
Indeed in some cases there's the distinct possibility the correlation goes the other was and profitable public incumbent tech providers will benefit from the loss-making VC-funded upstart unicorns in their market crashing and burning
When folks talk about the desire to bet against the private IPO bubble, they're thinking about a broad, significant decline that affects lots of companies, not the downfall of a specific company. Realistically, this type of broad, significant decline is unlikely to happen without a major correction in the public markets.
So long as the public markets are seen as being strong and stable, it's unlikely that the small, relatively illiquid market for private tech companies will correct itself.
Canadian banks are in good shape though, they weathered the 2008 storm easily. Mortgages are limited to 25 years in Canada and you need some 20% down IIRC.
I do think there is a housing bubble, especially in Vancouver, but it's not clear to me how one could bet against it. And there always the chance that the prices are sustainable, they are positively mild compared to Zurich or Tokyo or San Francisco.
You can get a 30 mortgage, as long as you have 20% down (so you don't need CMHC insurance).
The real reason why shorting the banks won't work is that with less than 20% down the CMHC insures that the lender will get their money back. For thenon-insured mortgages, the banks can also go after other assets since all Canadian mortgages are recourse loans.
To bet against the Canadian housing market, for instance, you could look at shorting vulnerable financial institutions (Canadian banks and lenders with exposure to the Canadian housing market). You could also look at the Canadian dollar, which could conceivably fall if there's a housing crash.
Private startups are obviously a more difficult target, but you should consider that the types of events likely to push the private startup market into meaningful decline would in most cases also be bad news for publicly-traded tech companies as well, and you can short just about all of these. There are numerous advantages to targeting publicly-traded companies (liquidity, availability of information, in a major market correction there will be forced selling, etc.).