This is a really good question.

Here's the tricky thing -- your free list is the marketing channel for your paid product. So it often helps if the free list is quite large (100k+).

BUT some, like @JayCoDon, make the jump earlier. Some insights from when we interviewed him 🧵...
When to go paid:

"I originally wasn't going to go paid at all, but I kept hearing from people saying that what I was offering was too valuable."

So, around 950 subscribers he "flipped the switch," charging $200/yr and offering a 50% discount for early sign ups.
On Pricing:

"I was gonna charge $100... Because everyone was charging $100/yr...

[But] if someone takes 1 idea from me and applies it to their business that's worth a lot more than $100. So literally, I think the day before I launched, I changed the 1 to a 2, and that was it."
Conversion rates:

By the time we'd interviewed him ~9 months after going paid, his free list had almost tripled in size, and ~9% converted to paid.

Based on other data I've seen, 9% conversion from free to paid is very high. What helps:

-Niche audience
-Utility content
What's utility content?

When @bradwolverton interviewed @danoshinsky he said the best newsletters are built around 1 of these 4:

Identity - Who you identify as (cat people, etc.)
Service - Info people want
Utility - Info people need
Personality - e.x. @APompliano & others
To sum up:

-Free newsletters market your paid newsletters. If you go strictly paid, you need a new marketing channel

-Pricing/timing aren't always a science. Experiment.

-If you're putting out great content that serves a need you don't need a huge list.

-Also, charge more ;)
If this was useful, be sure to follow me, our lead editor @bradwolverton, and @HatchKolby

We developed hundreds of pages of research on the newsletter industry, and are emptying our notebooks here on Twitter.

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More from @damn_ethan

20 Aug 20
@theSamParr and @TheHustle got access to #GPT3 from @OpenAI. I fed it the first few lines of Moby Dick, then let it rip. It wrote some beautiful prose about the freedom of life at sea, then went on an insane tangent about how whales are like Holland cheeses. Thread below.
First, a few lines of the intro written by the (human) author, Herman Melville, which I input into the system:

"Call me Ishmael. Some years ago...(1/5)
...never mind how long precisely having little or no money in my purse, and nothing particular to interest me on shore, I thought I would sail about a little and see the watery part of the world. It is a way I have of driving off the spleen and regulating the circulation...(2/5)
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