The examples of Trello and Jira are specifically problematic, because their history says otherwise: Jira built its considerable market share and brand awareness without a free plan of any kind, offering instead just a short-term trial license; I remember just a few years ago that the price of admission was thousands of dollars per server, and yet here it is. And Trello comes from the other direction, having been entirely free of charge at launch and only latterly monetizing.
The broader problem with this example is that the companies in question evidently don't value information, and have instead relied on personal hubris, which speaking as a longtime service provider is itself a red flag for "problem customer", and if not quite the horrors depicted in the article then certainly on that spectrum.
All of which illustrates that talking to anyone who self-describes as an "influencer" is generally a net negative, unless you're in the FMCG category. Influencers demanding freebies is something to be abhorred, and there is no equivalence here to seeking high quality professional advice.