Speaking to the dead; AI projects defended; BookTok influencers: Newsletter 10 September 2025

Newsletter 110. Dead people I once knew are still making me smarter — and kinder. Plus, debunking the MIT study about failed AI projects, the Anthropic piracy settlement on hold, three people to follow, and three books to read.

I see dead people

I’m older than most of you. Retirement age (but I’m not retiring).

As a result, I know some people who’ve died. I was close with some of them.

We don’t talk about death. It’s a taboo. People don’t want to think about their own mortality and the limited lifespan of their loved ones. They’d rather pretend it doesn’t exist.

That’s a shame, because it is inevitable for each of us and everyone we know. Some of us will know love. Some of us will achieve success. Some will have a bunch of close friends, and some will only have a few. But all of us will die.

When I think about the people I knew who’ve died — you can say “passed” if you want, but I prefer to be clear and just say “died” — anyway, when I think about them, there is of course sadness. But there’s also a presence, my own version of who they were that lives forever in my mind and comes to me when I want to think about them, or am reminded of them, or at random other times. Often, that happens in dreams.

Here’s a dream I had last night. I was at a hotel walking around when I stumbled into a wedding. It turned out it was the wedding of my best friend from childhood and adulthood, Josh Friedman. I’d apparently been invited but decided not to come since it was his second marriage, but in the end I happened upon the wedding at random. In the weird dream logic, his second marriage was to Amy, the same woman he’d been married to his whole adult life. I had been the best man at his wedding, and he at both of mine.

I got a chance to talk to Josh for a while at this event and it was a warm and friendly conversation like we’d never been out of touch. It made us both feel good. I told him I was happy for him and Amy, and I was.

Josh was only 57 when he died in 2015 — has it really been almost ten years? — but I think about him from time to time. He was as nice a guy as has ever existed, and I was lucky to be friends with him. I can hear his voice and remember how he thought about things. It was weird to see him in my dream, but not uncomfortable or sad. Why would two old friends talking be sad?

In my mind there is a version of my dad, who died three years ago at age 89. Whenever I had a decision or at triumph or a setback, I would talk to my dad. I try to live my life the way my dad lived his, and the way I love and interact with my wife and children reflects what I learned from him. I had 64 years to share this life with him, which I got a lot out of. He’s still there for me when I need him, and I still think of what he would say about what I was doing. He was proud of me, and would still be, and that matters.

I think about Bill Bluestein, my mentor at Forrester Research, who taught me a whole lot about thinking, writing, and being bold. He was only 44 when he died 24 years ago, but he made a big impression on a lot of really smart people. My best clients tell me that they can hear my voice coaching them when they are writing. That’s high praise, because it’s like Bill: I can hear his voice when I write. (“Don’t equivocate! It’s better to be wrong than wimpy.”)

When you’re 67 years old, lots of your friends are going to die in the next 20 years. I probably will, too. You can’t escape.

But you can get to know them and what makes them special so you can cherish it and keep it after they’re dead.

Maybe that’s why I write so much. When I’m gone, you’ll still be able to hear my voice. I hope it helps you. If it does, even for a moment, it was worth it.

News for writers and others who think

You may have read about the MIT study that showed that a disappointing 95% of AI projects fail. But as Christopher Penn perceptively points out, “Folks, if you haven’t worked in enterprise companies, it takes 6 months to get a damn coffee machine approved from procurement. A software development project that meets regulatory, compliance, legal, and security standards takes 6 months just to have the FIRST input call. . . . in a 6 month period, when most projects take 3-5 years, 40% of enterprises adopted general use LLMs like ChatGPT and 5% of firms accelerated years-long projects to get them done. In enterprise software and computing, that is a BLISTERING pace.” That’s the appropriate perspective.

Although Claude owner Anthropic says it settled its case with the authors whose pirated books it trained on, the judge in the case rejected the settlement. Both parties now need to work harder on the details of how they will distribute the $3,000 settlement per pirated book.

Jane Friedman talks about how AI affects editors, even if they don’t use it. Most notably, you’ll be dealing with AI-generated content (and messes) from writers and publishers.

Shel Holtz, SCMP writes a heartfelt remembrance of the writer Shel Israel, whose voice we can all still hear even though he’s gone.

Apparently, in the romantic fiction market, according to The Bookseller, “the line between influencer and creator is becoming increasingly blurred.” Editors are “increasingly finding their authors online” or favoring writers with a large social media following. Sounds like a questionable way to find writers to me, but hey, I’m no romance novelist.

Three people to follow

Jeffrey Bussgang, investor, author, startup expert

Liz Faber, English professor helping students use AI appropriately in writing

Adam Grant, legendary author delving into how people really think

Three books to read

Useless Etymology: Offbeat Word Origins for Curious Minds by Jess Zafarris (Chambers, 2025). A useless book I absolutely have to have. How about you?

Coming Up Short: A Memoir of My America by Robert Reich (Knopf, 2025). One of America’s most influential liberals explains how he got that way.

Smart Brevity: The Power of Saying More with Less by Jim VandeHei Mike Allen and Roy Schwartz (Workman, 2022). Write with punch.