It's a strategy as old as time, but it's a strategy that usually fails. Spending a lot of money on customer capture only works when customers are actually solidly captured. Most markets have fairly heavy competition and customers will only stay captured as long as there is no substantial cost to staying captive.

Take Uber as an example: yes they've raised prices to become profitable, but not to the insanely profitable levels they could if they had a true monopoly. People will stay on Uber when the competition is still at a roughly equivalent price, but will switch if Uber raises its prices enough.

Uber Eats is different, since its a 3 sided market where the cost is paid by the restaurant rather than the user.

AI appears it's going to be more like Uber the car service. Claude can charge $200/month, but charging $2000/month seems unlikely to work. I'm sure many would be willing to pay $2000/month if they had no alternative, but there are alternatives.