If ebooks aren't your jam, create tools instead. I don't recommend a one-or-the-other approach, necessarily, but if you have more development talent than writing talent, this may be a more attractive option for you. These tools can be valuable enough to some of your website visitors that they'll trade you their email address for a free demo of the product you built. Then, for your first email, ask them what they thought of the tool. It's the perfect icebreaker.
Emails triggered by milestones, like anniversaries and birthdays, are fun to get -- who doesn't like to celebrate a special occasion? The beauty of anniversary emails, in particular, is that they don't require subscribers to input any extra data, and they can work for a variety of senders. Plus, the timeframe can be modified based on the business model.
Dynamic segmentation – As alluded to earlier, you can’t just send out a generic message to everyone on your list. While basic demographic data can be used to segment your list, that’s far from taking the dynamic approach. Automation tools can help you segment your list as they go through the funnel, allowing you to send personalized messaging depending on their actions and behaviors.