I think this is an important point. Startups trying to make privacy ‘cool’ need to pay more attention to branding. While I love DDG, the name and the whole flavor of their site will necessarily limit their reach to technical people.
In terms of popular media, I thought Mr. Robot did a pretty good job of making privacy/security tech seem sexy, even if the main character is usually bypassing it.
Here’s a good example: https://youtu.be/i9CBKGLVCME
If these things caught the sparkle in customer's eyes, we'd all know it by now.