SETH WERKHEISER FROM The Social Media Escape Club had me on his live chat yesterday. We discussed writing techniques, the ongoing Saturn-Neptune bardo, making the exodus from social media, Tim Apple, Cambridge-Mead pink-colored notepads. Also the galley for my Jeffrey Dahmer serial-killer romance novel and my history working for CBS and FOX. We also touched on my podcast Fame Whores and the amount of porn on Twitter (well, I broached that topic 😭). Enjoy. And thank you again, Seth!
And Now, This:
I’m coming up on my fifth year on Substack, so I want to talk a bit about what I’m trying to do for you with this newsletter and video series.
WOODRUFF is the product of a lot of reading, thinking, listening, interviewing, researching, staring at the wall—writing, deleting, rewriting, editing, etc.—to put together a compelling newsletter or video for each of you four or five times a month.
In my four + years on Substack, I’ve never asked for money. I consider requests like that a turn-off and tacky. My thinking is that if something is of quality, folks will pay for it of their own volition. This is a sensible theory, but it is also unrealistic and naive in a world where people have been trained to think that if something appears online, it must be or should be free to access. Those days are no more.
Think about how many fucking paywalls you hit nowadays while trawling the net. It occurred to me the other day that our population is now divided between people who can pay for the truth (or at least vetted, legitimate writing and reporting) and those who can’t and thus fall into the lair of clickbait and tabloid-inspired hysteria. No wonder Trump was re-elected.
Good writers put you, the reader, foremost in their mentation while writing and editing their work. They think about your time, interest level, and, most importantly, whether their creation is entertaining. And, to me, entertainment is everything in reading and writing. Not in a Barnum and Bailey way, but in a genuine way, where you feel enthused and informed and happy to have read something. Even if it’s about a depressing topic, to me, even that sort of writing should be entertaining.
Consider the word’s etymology: ‘Entertain’ is from late Middle English: from French entretenir, based on Latin inter ‘among’ + tenere ‘to hold.’ The word originally meant ‘maintain, continue,’ later ‘maintain in a certain condition, treat in a certain way,’ and ‘show hospitality.’ That’s the key to me, right there: to show hospitality. But also to hold something together from chapter one to the conclusion. That’s a whole other art form in writing—maintaining a piece’s integrity and you, the reader, along with it.
Presently I maintain a level of variety within the newsletter—a combination of free content and paid. But as I’m heading into 2026, I will place more content under the paid rubric for my readers who ‘get’ what I do here each month and wish to support the effort. I will also be moving more of my content on Substack into group meetings and Zoom talks. I want to create an astrological ‘node’ that is relaxed, intimate, and, yes, entertaining. To offer, what Seth called in our talk yesterday, “more realness.” And I’d love for you to be a part of that community.
Finally, consider this interesting statistic: The price for a paid subscription to WOODRUFF is about the same as a cappuccino, beer, or glass of wine (if you drink cheap wine) at your favorite watering hole. It is all pretty manageable and affordable.
Love,
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