The only kind of people you can target with this offering are wannabe entrepreneurs.
Anybody who’s serious about this is going to pick info products, courses and guidance, probably expensive ones, and likely very specific to the current problem they are facing.
The only people who’d want to read generic advice on various entrepreneurship related topics are people who are thinking about it, want to stay in the loop, but don’t actully want to to commit.
These people are likely to be very price sensitive and even $97 a year would feel a lot to them (this is comparable to premium YouTube wich can presumably fill any future entrepreneur with enough content to keep indefinitely busy).
You would need something very specific - either an underserved niche, or a very special voice, or a crazy amount of credibility to make this work. I imagine someone like Alex Hormozi can charge that for a paid newsletter, but he’s super famous in these parts and has been putting out quality original content for many years.
I voted maybe, but after thinking and writing this out I now lean towards a pretty strong no.
This is essentially a marketplace of relationships, similar in a way to a dating site. Every marketplace has an easy side (demand) and a hard side (supply). For heterosexual dating in the West the easy side is usually men and the hard side is women.
In order to make this work, you need density of users in a specific location, which immediatly points to certain ways of marketing it. If, for example, you set up a booth at every entrance to the Central Station in New York and try to get everyone coming in to install the app, you might get enough density to create some connections (especially since people tend to spend some time there). Same for malls, airports (although harder because of border partol and the gate system).
But this will only work if you’re physically present to get a significant number of people to install the app who are going to remain in close proximity to one another for a while. A rave or a dancebar might work too.
It will be impossible to create this density by marketing online and expecting a high enough percentage of random people to have the app installed (unless you have 100’s of millions of VC dollars to invest in marketing - and likely even then).
So it’s not a bad idea, but executing it will require intense local focus. If you haven’t read The Cold Start Problem, give it a look. It discusses this in depth and has examples from Uber and Tinder on how they made it work.