I’ve been thinking about this a lot myself. For the most part, what I’ve done is tried to decide what’s the one thing I’m ultimately selling. In my case, it’s a book and some additional resources that are directly related to it. Then, everything else I create around it is free and chalked up to marketing regardless of the cost/effort to create it. In many cases, it’s sharing bits of content from the paid products. Depending on the variety of things, I could see having maybe two or three things that you sell, but too many things, and it’s just too much to keep up with.
Here’re the thoughts that come to mind In your case. (Take it with a grain of salt, of course.) With Ruby Tapas and your books, you have closely related materials. I would try to get them all onto a single site where they help promote each other and could be bundled. (What if pre-paying for a year also gave people a free copy of your books?) Then, as long as everything else you published and given away for free had tasteful mentions of the products that you sell, they’re just really targeted marketing. Another consideration is that I only charge for things for which I want to provide support. When something is free, there’s no obligation or burden to answer emails that are way off base.
So you ideally end up with several funnels that all include a large dose of great free content. That could be an email course with five hand-picked popular tapas that you convert to text with code samples. They’re valuable by themselves, but they’re just a small subset. Or maybe there’s an email course that’s a high-level overview of Exceptional Ruby.
Here’s how I’ve decided to layer it. For context, these decisions all revolve around my book and ultimately promoting it.
Since I’m working on a second edition of the book, and it’s a big update, I’ve simply published the first edition for free in a Medium publication. I’m also trying out some new topics as posts there as well.
I’m extending that Medium publication into new territory by interviewing other SaaS founders. Instead of bundling these into a package, I’m publishing the interviews on the Medium publication. I’m a little less sure about this approach because I’m also paying for transcriptions. (~$45 for each transcription) These end up long, and I have to manually edit and make some corrections on the transcripts, but it feels like the right thing to do.
Quick References/Cheat Sheets. I’ll be creating these to go with the book in a package since they add value and, if I do it right, provide great summaries for after someone has read the book. So these by themselves aren’t as useful without reading the book. So while I could give them away, I feel like they’re too directly related to the book.
Email Courses. For now, I’ve got an email course that condenses the first 25% of the book into a series of emails. It’s useful all on its own, but hopefully, after reading them, people are excited to read more. Once all of the aforementioned interviews are published, I’ll turn that into a free email course as well. When I do that, I’ll probably cherry-pick some select quotes and topics and include a link to the videos. The cliff notes will hopefully give people enough information and context to decide if they want to watch the full 30-40 minute interview.
Slide Deck. Slide decks are great ways to provide quick overviews of things in a visual and condensed manner. They let someone get the 60-second overview of a topic in a way that’s useful, but it also helps lead into an opportunity for them to learn even more by buying the relevant book.
Spreadsheets. In my case, there’s a spreadsheet that goes with the book. It’s useful enough on its own, but it’s also a key piece of the package because it can save someone so much time vs. setting up their own version. Since the value is so much higher, it’s something that feels justified being paid. I am, however, thinking of smaller portions of the spreadsheets that I could replicate and share via Google Sheets. These would be very focused, but still useful outside of the context of the book.
Ultimately, I think the best approach is to find ways to give people as much value as possible outside of paid products, but make sure that it’s easy for them to make the connection to the paid products. I’m personally against email gating. I’d rather just put it out there an include a “Hey, if you liked it, you can support it by…” callout. In these cases, the key is just to make sure that everything that gets produced ties back into the full ecosystem.
Hope that helps!