In this situation, do you hire someone to negotiate with or for you? I'm thinking the intention here was to sell the company for $10 million and that came across as a threat because of the language that was used. You would not record the call [1] and then publish it if you actually were blackmailing them for $10 million. I'm not faulting the guy here at all, I just think it comes down to lack of experience in dealing…
It's certainly a strange call. Hey, you want to charge me $20 million per year, so why don't we make it easy and you just pay me $10 million to go quiet? It's really confusing. He wants Reddit to pay $10 million so he isn't "loud" with API usage? He wants them to buy and takeover the app? He's wants a payment to shutdown? Is he even serious about any of this? I get the impression he lacks the confidence to ask for a…
Him not rabble rousing their user base against them would have been the benefit.