How AI Helps (and Doesn’t Help) with My 70k Reader Newsletter

Welcome to the Scarlet Ink newsletter. I'm Dave Anderson, an ex-Amazon Tech Director and GM. Each week I write a newsletter article on tech industry careers, and specific leadership advice.

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AI has been changing the tech landscape dramatically over the last few years. I’ve been repeatedly asked about how I use AI, or how I think AI could be used today in writing and social media.

That’s certainly difficult to answer in the limited text space we have available in a newsletter. But I’m going to take a swing at it. And since I just finished my article (scrolled back to the top to make this note), I’ll say that this one turned out to be quite the doozy. It took me a good amount of AI usage, testing, etc.

Four disclaimers:

1. For my examples, I will use Claude and ChatGPT. I’ve used various AI models, and I currently think Claude and ChatGPT are the most likely to return useful results. So I’m using them for my examples because it’s easiest. I don’t plan to compare Claude and ChatGPT because that’s not the point of this article. Each example will just be from one of them randomly.

2. I’m quoting anecdotes, not data. I’ve spent many hours prompting various AIs. So many hours. At various times they’d give better or worse results. I’m looking to show a typical response, not the best or worst.

3. AI changes all the time. I try using AI essentially any time a major release happens because their capabilities are changing so quickly. So if you read this in 12 weeks, it’s possible that things have changed.

4. Success for me means a substantial savings in time. If it takes me 5 minutes to prompt AI to save me 7 minutes, it’s not worthwhile. And if I prompt it, and then have to re-write it regularly, again, it’s not a success. Or if it takes me 12 hours to create my own self-trained AI to save me 5 minutes, it really is unlikely to be worth my time. So my version of success is a slam dunk, “I save a ton of time”.

I have a request for any readers who feel they’re better at AI and AI prompting than I am. Can you look at my requirements, and get better results than I do? I’d love to hear from you in comments or over email.

What is my writing business?

Let’s start from the product requirements point of view.

I write a paid newsletter article once a week. My articles are purposefully evergreen, meaning that they’re almost never time sensitive. An article I wrote in 2022 should be relevant now. Which is a key data point for understanding my social media strategy.

Every Monday, around 6 something AM, my newsletter is sent to around 70k people. Everyone gets a portion (30-50%) of an article, and a few thousand of those people pay me monthly / annually to read the full article. (Thanks everyone!)

I get new readers through two main methods of discovery:

1. Substack has a recommendation feature. Other newsletter writers recommend my newsletter, and people end up subscribing (for free or paid). I don’t go out of my way to make this larger, although I’ve seen newsletter writers optimize this more than I do.

2. Social media posts, primarily LinkedIn (for me). I could write a very long post about what I’ve learned about social media. But the primary takeaway is that my newsletter slowly shrinks if I don’t write social media, and slowly grows if I write social media. So it’s my controllable growth lever.

This means that my work consists of two major bodies of work. An article and social media to advertise the overall newsletter.

My writing work, and where I could potentially apply AI.

Let’s break down those two bodies of work into the more precise elements.

1. Idea Generation

Every dang week, I need to come up with an article idea. Seriously, it’s no joke. I’ve had great coffee meetings with someone, where I jot down enough article ideas for a few weeks. At other times, I spend most of my writing time brainstorming. Once I have an idea I like, the writing itself tends to take less time than thinking.

Personally, the ideas come from a mix of just thinking about the past while staring at a wall, reading Reddit posts on the various CS related Subreddits, emails / comments from readers, and discussions with real life people.

2. Article outline

Once I have an idea, it immediately begins to break into an outline in my head. Funny enough because writing outlines in school felt like a waste of time. Turns out it’s not a waste of time at all. As a side note inside a side note, one reason that outlines are useful is to ensure that an article idea is a fully fleshed idea worth writing 3k+ words about. More than once I’ve had a good idea, and realized that it’s more of a 750 word idea. Which might work for social media, but not my newsletter.

The structure of the article might be a narrative story following a timeline (A Day in the Life of a Senior Manager at Amazon). Or it could be a listicle (12 Things I Learned in Big Tech). Or it could be some version of (without a cute name for it) an educational article (How to Both Embrace and Defeat Imposter Syndrome).

3. Article body

The most obvious part of the writing process is filling in that article outline with content. I sit there, and type. Thankfully, this is the part I like, and believe I do well. Including the typing. I’ve always been good at typing.

I also insert in a couple of personal photos, but that’s barely work. It’s mostly looking through our photo collection randomly, and attaching a couple of photos that strike my fancy.

4. Article quality control

I’m listing this just to explain that I don’t do much of this. For philosophical and practical reasons, I try not to do much post writing editing. I write, I usually skim the article, and then I publish. For my style of article, I want it to be natural, and not overly edited.

5. Social media content generation

I need one to six+ paragraphs written for each social media post. Each post needs to include text, and a link to a corresponding/relevant article. My general social media strategy is to make useful social media posts. When a reader finds them useful, they’ll like/share on social media, increasing my post visibility. They also might click through to the article, and pay to read the whole thing. Which is where the money comes from.

I wrote software which gives me a list of random archive articles (my content is purposefully evergreen as I mentioned) to write content for. Therefore, my main work is to turn a previously published article into a social media post.

I’d say that social media content generation is the hardest work that I’m not interested in doing. I’d rather just write articles, but it’s critical for me to write high-quality content on social media, or my newsletter slowly declines. Which is why this section of the AI section below is the most important (to me).

My overall thoughts on using AI and this article.

I enjoy writing, and I do this as a hobby. Having AI write my articles for me would defeat the purpose. So that’s not something I’m interested in at all.

However, I’m not against using AI to help with other aspects of the work involved.

For the purposes of this article, I rate the usage of AI from 1 to 10. As a (usually) data-driven person, I’d love to tell you the exact criteria by which I’ve rated AI usefulness. Except I can’t. Because in all cases it’s extremely subjective.