#26 Newsletter? More like OLD letter!

It's a fair question! 

When I started this thing, my goal was simple: see what happens.

Early in my career (like first-week early), I met the founder and then-CEO of a data storage business. He wanted to show me his new data center, even though it wasn't really necessary for me to write him a few inspiring emails. 

At one point in the tour we stopped on a catwalk above the most massive silently spinning thing I've ever seen. I mean literally, I’ve never seen such a large mass of anything move so quietly. It had to be many tons, moving too fast to see, and it must've been on million-dollar bearings greased by God himself. 

The CEO explained it spun so perfectly with so much weight that, in a power failure, its momentum would run the data center until the gas-powered generators kick on and take over. 

What I can't forget about that moment is he didn't even care about the spinny thing.

It was just equipment he bought from someone else. The way my heating system is neat, but I’d rather tell you about the stairs I designed and made. For him, the real magic was in his server racks. He could talk about that (and did) for hours.

I remember realizing if I could help mind-blowingly smart people just blow other people's minds as much as they do mine, then those kinds of C-somethings would eventually seek me out and I’d have a career I enjoy.

(It’s so damned simple in hindsight.)

Writing for other people in some form or another has been my chosen profession for almost 2 decades. And during all that time, I've been shown a million or more big silent spinny things. And I don’t mean (just) failover systems for data centers.

I mean I’ve gotten to work directly and hands-on with the methods, mindsets, and mistakes of a lot of very interesting people. 

People with a very high ratio of 🤯 to 🥱.

That's why we're here. 

Or, at least, that's why I hope YOU are here. My goal with this newsletter has been to share a few of the mindblowers (or the lessons I’ve taken from them) that I’ve always found pretty handy. I think 🤯 —> 🔧.

The reason I am here might be a little different.

I keep calling this newsletter an experiment, because it is. I just wanted to see what would happen!

I wanted to see what would happen if I wrote in my own voice. I had to figure out if I even had one! I wanted to see if I could write a newsletter that AI can't yet replicate (it can't; I test it on most issues).

I wanted to see if anyone actually finds this stuff as useful as I have. I also wanted to see if I would be comfortable in the spotlight, which is not typically my style.

Finally, I wanted to have fun, and I am. Writing anything is always fun for me. I wrote 15 clauses in a contract yesterday, for someone else's lawyer, and enjoyed it. (I also really enjoy winning slow and painful fights.)  

But this has been a different kind of fun.  

Under a cottonwood tree at the bottom of a canyon with rapids above and below and hundreds of miles to go—what the hell ARE you doing?

Answer: operating outside of your comfort zone is either fun, or fear. And that’s the difference between still living and already dying.

But that’s all foo-foo. Here are 4 communications and content lessons I've learned in this experiment so far.

I’m tired of this popular criticism of AI:  "LLM's are just really fancy auto-complete." 

First, it’s true. LLM's work by predicting the most probable next word based on patterns they’ve learned analyzing vast amounts of text data.

But here's what the cynics misunderstand: HUMANS ARE ALSO just really fancy autocomplete. Especially when writing.

This is why you hear proponents of manual writing frequently explain that writing is a process of thinking.  Because it is! 

Just like an LLM puts a word after a word, so do you. And then you see it there and think to yourself, “wow, that’s what I think.” Or “wow, I don't think I think that?” “Maybe I think something else, I’ll clarify it.”

You do this constantly, and yet none of us do it enough.

Hence, the first lesson of this newsletter that you might find useful: 

Lesson 1: Writing is essential to the health of your thinking. I don’t mean mental health. I mean your athletic fitness solving new problems. That matters because health has market value.

This newsletter, unlike all of the newsletters Publera is paid to write or operate, is written fresh, every week, with no backup bank of content, no calendared process for editor handoff (surely you've noticed my typos), no A/B testing, no click optimization, and no fucking shit. It's just me and the keyboard, with a deadline. 

I knew going in this would make it more fun for me. But now I am also convinced it’s led to a better product.

You know that feeling you get in a grocery store aisle? When you notice how many of the foods for sale are so utterly processed, even the processes by which they arrived there on the shelves? It's just processed food from an industry of process, and it’s so abundant? That's your email inbox right now.

I believe in the near future of content marketing, someone is going to find and nail the farmer's market model. It will have low scale and high ROI.

Lesson 2: Giving away your expertise for free might be stupider than we think.

Conventional wisdom says to give away 80% of what you know for free, and people will pay dearly for the remaining 20%. That is actually true, and also my experience with this letter.

However, this experiment has left me unconvinced it’s such a wise strategy. 

First, it screws the buyers. Earlier in this experiment, I wrote an issue with very clear steps to solve a specific problem. Later, a client who reads this newsletter (and gave me permission to call her out), hired us to solve that exact specific problem.

I just sent her a google doc version of the newsletter issue. She and her board were not only thrilled but weirdly SURPRISED when they solved the problem precisely as I’d outlined. (I could not bring myself to invoice.)

What this calls to mind is what I've always called "the ten dollar free couch." 

If you put an old couch on the street for free, no one will take it. But if you put a cardboard and sharpie sign on it that says “$10”, some college kid will have it on the roof of his Honda in 20 minutes.

You might not get your $10, but you got rid of your couch and he's watching football on that thing for 4 years, crying when he gives it away after graduation.  

(Actual example. Big thanks to my grad school housemate Tom Neeley for an insight that got a nasty couch out of our house and made Facebook billions of dollars in 2012.)

In this sense, I have done you all a disservice with my weekly rambling, simply by not charging you money for it.

Second, the "lead magnet" theory of content marketing was developed prior to LLM's. It could be a dumb-ish idea now.

Example: I can take 3 years of spam from Legal Zoom and stuff it into an LLM that generates a perfect email strategy AND the content for it. Meanwhile, my rising local attorney happens to be a good friend in need of an utterly average content marketing system, and I don't have time to make him one by hand. 

In fact, with the average efficiencies and scale we have in newsletter operation (not rocket science), I could build an entire nationwide agency that does this and requires less than 5 hours of my time per week. And whether I told you all this or not, some kid almost certainly will do this. And she should!!

So watch what you're leaking in the lead magnets, folks. It’s 2025.

Lesson 3: Get weird!

One thing I've enjoyed about these emails is I get better engagement, feedback, and outreach when I veer from the beaten path a little. When I let my "weird brain" shine (as I’ve called it in the decades before it was vogue to discuss one's mental architecture). 

Life is way too short to be serious all the time, and it’s usually a bad idea anyway.

In 1974 Daniel Kahneman published the paper that would create Behavioral Economics–the field of study that says, essentially, the least rational thing you could possibly do is expect people to think or behave rationally.  

The same is true of communication. Perfectly structured PowerPoints persuade no one outside of a conference room. Outlines and highly structured, even bulleted, paragraphs (I'm looking at you ChatGTP), are NOT the gateway to changing people's minds.

Humans are weird. It takes finesse, risk, and originality to move them.

So if you want to persuade humans, or maybe just enjoy being one more, you've got to embrace a less rational structure in all forms of your communication. 

And that is the most rational decision you could ever make. 

4. Bonus lesson: Negative feedback is incredibly tough to earn.

I am used to writing for C-somethings, and a key fact of their job is almost everyone has an opinion on how they should be doing it. They constantly hear negative feedback. 

Other people have YouTube channels for their podcast or content. It's really easy to get negative feedback there! (joke in links section). 

So I assumed it would be easy for me to solicit tough feedback from all of you.  But that’s not been the case.

Instead, I get decent engagement on the ending poll, with nearly 100% "Super Handy!" in 26 issues. I suspect I’m not actually that good, and you all are just observing my grandmother's rule, "if you don't have something nice to say, don't say it." 

The only real negative feedback I’ve been able to discern is when people read less or unsubscribe. I yearn for more detail.

But again: we’re in the grocery aisle of your email inbox. And the feedback we give to 99% of all the products in a grocery store: we just don't buy it. 

Life in the inbox is strange indeed. 

So if you're still reading, thanks for hosting me in yours. Truly. And if there’s anything I can do to make the final 26 issues better for you, let me know.

The glass is half empty, but that’s why we filled it.
Jesse

PS: LINKZ! 

• Totally irrelevant: Margot and Lilly have had this bath toy for a while, and it still amuses me every night. I have no idea why it’s so pleasant and have seriously contemplated mounting one at our kitchen sink.

• Wikipedia might be the largest mansplaining platform on earth (although without some serious model adjustments Chat GPT will soon take that crown), but YouTube is still the king of negative feedback.

• If you haven’t read any Kahneman, here’s the book that changed my life. While he probably never says the word “communication” once, it might be the single most important thing you could read to better understand how (and why) to move people.

• The first single-boat expedition down the Green and Colorado is a wild story of perseverance. Holmstrom even climbed from the canyons to mail letters to his mom, which he wrote every day. His death years later is wilder and remains and unsolved mystery with the FBI. Here’s a good-but-hard-to-find book if you want a long adventure/mystery read.

• SONG OF THE WEEK: With a chorus that croons “oooooo, we’re halfway there!” this was obviously going to be the song today.

PSSSSSSS:  The share link. Send this one to your young friend who wants to start a newsletter agency for lawyers. (Actually, send that friend to me??)