Shamelessness is acting without embarrassment and countersignalling is deliberately downplaying because you're so confident you don't need to prove yourself.
Using the example from the article, another person who comes to mind besides Paris Hilton is Trump. He uses countersignalling as a strategic tool, and sloppiness as a Swiss knife. The followers of both Paris and Trump interpret that sloppiness as confidence and authenticity, which is why it's so effective. And to pull off being deliberately sloppy, you need to be shameless.
Put another way: if you buy, be very ready to sell fast, and very confident that you can gauge when a market turns.
Pretty hilarious to use “assume every person on the planet signs up for their highest tier individual offering” as a basis for criticizing a firm's valuation as too low (obviously, if that analysis suggests a firm’s valuation is too high, it would be a powerful argument, but...)
> Given their current product offerings, I really don't see a way they could ever justify a $300B valuation unless they get everyone on the planet to subscribe to their $200/month plan.