What a lovely question. Top of mind for us, too. Our first Guide, on Equity Compensation, is entirely free. Think of it like our public sandbox. For now, we're thinking all future Guides will be available for purchase (one-time payment and you get digital access + updates). The first Guide we'll launch for purchase is The Holloway Guide to Raising Venture Capital (https://www.holloway.com/g/venture-capital/about), which we're hoping to have out in June. This post is an excerpt from that.
We'll also be posting more on our blog, like this post, to build up awareness of what we're up to. Our policy internally is that if we're going to post content to promote one of our products, though, it needs to be helpful to readers on its own. It can't just be content marketing junk to get you to click.
So, fingers crossed. We're making a bet on people being willing to pay for what we're creating!
You guys certainly have product market fit for the free articles (atleast using HN as a proxy) :)
Curious to see if the same reception is there for the paid content, especially given that the topics you cover have a lot of free articles and videos (e.g.: YC has an entire library of it).