Hello Ev. In regard to monetizing content. Forbes became the leading revenue magazine in America (I was publisher) for 3 reasons: 1) Brand was relevant. We called Forbes the “Capitalist Tool” at a time when anti-Vietnam turned into anti-business. 2) Credibility: we called a spade a spade. 3) Entertaining: we made business reporting more like biographies, and that brought in the best writers.
So for Medium…my humble suggestion is within 10 years your brand will be able to charge $150 per year. The challenge is between now and then.
Three ideas: 1) Medium is a talent agency for writers (and video/podcast, etc.). You need celebrities on the platform. Have a debate between Nassim Teleb and Danny Kahneman. Charlie Rose interview. 2) Engagement: Medium has convening power. Start a thought leadership event series. 3) Start a print version. Sell ads. Place it in lobbies and airline waiting rooms.