People will only value your solution if they value their problem. If they don’t think their problem is that big of a deal, they won’t pay for you to solve it.
1. Most people trying to sell a paid newsletter as an offshoot of their free newsletter struggle in part because they're approaching it the wrong way.
Let me explain...
2. What most creators do in this situation is their paid newsletter is basically the same as their free newsletter but includes additional issues or bonus content in some way that's not available in the free newsletter.
They sell "more."
But...
3. Almost nobody wants "more" - even of a newsletter they love!
Most people don't want extra emails in their inbox or extra "content."
And they especially don't want to pay to get more similar stuff that requires their attention.