My first thought was what everyone is saying here sounds like time to make a different bet.
But, since you asked for advice on being the difference you want to see at the company:
You should put some time on his calendar and have a crucial conversation. He’ll respect your questions and insight. If not, that’s a further sign that maybe it’s time to move on. Just say what you said in this post, maybe a little softer. See if you like what he says.
You could write up a product spec for the MVP that you think people want and recommend that you heads down crank that out. He probably has that on his mind since the board is demanding a revenue plan.
I wouldn’t worry about empathy right now, just get in there and talk. You’ll find what you need to be empathetic about. But, at the same time, he’s a CEO and should be held to a high performance bar.
What are your usage metrics? Especially your returning users. How long and regularly do your users get on the site?
If you don’t have regularly returning users and don’t plan on meaningfully changing the site, then I’d either sell ads or go build a related product/paid version and advertise it for free on this site.