Category: InternetCategory: Internet

I got to talk with Frederick Woodruff (Woodruff, The Dahmer Diaries, and Fame Whores) about how he started working on the web, running his popular Woodruff astrology newsletter, writing a book, his podcast, and so much more. Enjoy!

What percentage of your Substack subscribers have a ★★ or lower activity rating? For me, it’s 65%. Maybe I’m a horrible newsletter writer and that’s why no one reads my publication?

Or maybe Substack greased the wheels to drive subscriptions and give the illusion that they’re a coveted source of enthused readers? This is straight from the social media playbook as detailed by Cory Doctorow’s concept of Enshittification:

First they lure users onto their platforms, then attract businesses who might profit from this newly formed public, and then finally squeeze both for their own profit. Tech giants lure users in with convenience and then degrade their services over time, draining profit at the cost of user experience. In the meantime our public squares have turned somewhere between the mall and a dumpster fire, that is unfit to deal with the problems of our times.

I was looking for a free place to start a newsletter back in 2021. The Recommendations feature rolled out in early 2022. I got lots of subscribers from that! Then Substack Notes came in April of 2023 – like Twitter, but “nicer!”

The subscriptions flowed like water, like a fire hose!

Until it didn’t. I used to get 25+ new sign ups a day, but as you can see above (that 65% of my email audience if dreadfully unengaged), what did that really get me?

(more…)

Stop posting and invite three of your biggest fans to connect.

Resist “getting out the word” to everybody, and reach out to three key contacts.

The element of “this might not work” brings clarity by way of tension, while waiting for an algorithmic break reduces your work to a scratch-off lottery ticket.

​Join me (Seth Werkheiser) for a 90 minute interactive workshop on the endless decisions that come with running a newsletter in 2025.

​Should you import your list to Substack?
What should you put in my welcome email?
Which analytics even matter?
Should you switch platforms?
What the heck is SPF/DKIM/DMARC?!

​Instead of writing, we’re getting lost hours in CSV files and platform settings instead of actually connecting with your readers.

Wednesday, August 27 from 12:30 PM – 2:00 PM EDT

Get more info here: https://lu.ma/uqrfb65q

In today’s Mini Escape Pod Zoom call, a member was talking about leading virtual co-working sessions. They had a sales page set up with their Square Space site, and (to avoid having to upgrade their Square Space plan) they linked out to Gumroad for payments.

They had an email list of 700 people, which is a great place to start! I suggested they also reach out to some people personally, too, since not everyone reads every newsletter, and it’s good to just directly invite people to things you’re starting (I did this initially with my Escape Pod Zoom calls back in 2023).

They brought up maybe paying for some classified ads. Spots that are relatively cheap via assorted email newsletters, and usually a good “customer fit” for this sort of thing.

The only thing I cautioned was to figure out their own invite / newsletter flow first.

Figure out how to get a few people to go through their paid process first. Get a few customers into the flow first, and make sure things are moving smoothly before injecting any paid traffic into the system.

The last thing you want to do is spend money on a “leaky” sales process.

UPDATE 8/14/2025: Just wanna stress that there’s a lot of talk about funnels, and paid ads, and “driving traffic” on the internet, especially wrapped about making sales. That’s sort of what I’m talking about, but at a much slower level. We don’t need to “drive” 1,000 people to our sales pages right away. Heck, if we get 10 people to click over, that’s great. And that’s what I’m talking about here. Get 10 people to your sales page. Maybe two sign up. Hey, that’s a 20% conversion rate, and in internet terms, that’s good. Sure, you’ll learn more from 100 people to visit, but start with 10. Be content with learning on a monthly schedule, not an hourly one.