Anyone run a paid newsletter subscription?

Here are a few good reads for you:

• https://newsletterguide.org/
• http://jasonlbaptiste.com/commentary/email-newsletters-business/
• https://www.investopedia.com/articles/markets/082515/how-theskimm-works-and-makes-money.asp
• https://www.niemanlab.org/2017/03/this-email-newsletter-raised-300k-from-its-affluent-largely-silicon-valley-based-readers-in-55-hours/
• https://news.crunchbase.com/news/new-startups-want-to-help-you-make-money-by-writing-emails-for-an-audience/
• https://www.buzzfeed.com/alexkantrowitz/writers-have-been-trying-to-support-online-themselves-for

❤️ https://substack.com/

Substack has been excellent to work with for my newsletter.
I'd re-opt them in. Send them a few emails explaining you'll be starting again but only send to those who opt in again. This will help your deliverability.

A paid newsletter is hard to sell nowadays.

But offering it for free with the option to pay a subscription for more and running some affiliates here and there, you can make a reasonable income.

Newsletter for DJs. What do you want to send them exactly? Handpicked tracks, local venues, music-related news?

Also, are you sure your 400 subscribers are still active/alive?

It's hard to get people to pay for newsletters but it sure works for some.
Do a free version to get people in the door and then up-sell them to something that has obvious value from there.

Scott's Cheap Flights is brilliant. Sign up for a free subscription if you haven't already and watch how it works. If you travel at all, you're likely to end up becoming a Premium subscriber at some point.

https://www.getrevue.co/

Look into Inside.com

The founder runs a podcast called This Week in Startups where he talks about it some. They run a bunch of free newsletters with paid upgrades.

Their tooling might be custom at this point, but it's a similar business model.