7. Summer 2025

Heard on THE RANDOM FOREST:

“The insights were a little off - like the taste of artificial sweetener. Not the real sugar.”

“Punctuation isn’t a rule - it’s a style choice. Like leaving the bottom of your cardigan unbuttoned.”

Editor’s Note:

I’m grateful for the friends and readers who kept this newsletter alive during my career change. It’s been an amazing first six months at Palo Alto Networks, and I’m excited for all the opportunities I’m getting to head up CFO Program Ops there.

On the personal side, I’ve been building out THE RANDOM FOREST backend to generate brand new content from THE RANDOM FOREST archive through a custom SLM. Visit my website to check out my demo of the small language insights model. Slim for short. It generates insights through a combination of three key AI patterns: Human interaction, recognition and hyperpersonalization. The name was inspired by Jim Croce’s lyrics about a kid who get hustled at a pool hall, but returns the next time to win back what he lost:

You don't tug on Superman's cape
You don't spit into the wind
You don't pull the mask off that old lone ranger
And you don't mess around with Slim

Highlights:

After a busy first half of the year between work and family commitments, we're finally taking some vacation, and even going to a couple concerts next month - Girl Talk and Lady Gaga. I was re-listening to some songs to get amped up, and came across a lyric I love in Dance in the Dark: “Find your freedom in the music… find your Kubrick.” It’s the modern equivalent of the call to action in Rilke’s Archaic Torso of Apollo: “You must change your life.” Art imitates life - Rodin’s sculptures influenced Rilke’s own art. Like Tony Bennett to Lady Gaga, what started as a distant appreciation of the elder artist became a mutual influence on each other’s art later in life. For those of you familiar with The Day of the Jackal, you’ll recognize the homage. I preferred the book, but the Peacock show is really good - my wife and I have been watching it when the boys fall asleep. But I digress.

Speaking of digressions: I find that the kind of freedom Lady Gaga is talking about is a type of digression to the way of operating I find myself in most of the time, most of the days. The "to-do" list - a seemingly endless scroll of tasks and obligations that weigh me down before my day begins. In starting a new job, where I have the high-quality problem of always having more demand for what I do than time in the day, I started to change how I think about that list. Like that alternate title from Dr. Strangelove: "I stopped worrying and learned to love" that I can do a lot. I can’t do it all, but I’ve traded my to-do list for a can-do list.

"To-do" implies obligation debt - a constant race against the clock. "Can-do" shifts the narrative toward gratitude and opportunity in each item. This subtle change in perspective transforms the mundane into the meaningful, allowing me to find a sense of agency and even joy in the day-to-day. It reminds me of the Zen koan: Before enlightenment, chop wood, carry water. After enlightenment, chop wood, carry water.

That got me thinking. What's the point of all the AI? More output in less time sounds good. But once we get more productive, what will we do with the extra time or output? Will we fill that time with more work, more efficiency, more output. Or will we make space to pursue something deeper, and more authentically human? More connection, more affection, more reflection.

This brings me to an unexpected experience that happened to me recently, when technology failed but human interaction prevailed. The BART train system experienced one of its recent outages when one of the stations caught on fire and damaged the power grid. Trains were halted and re-directed, and people were stranded in stations that didn’t have internet or cell service - not knowing what to do. Then something interesting happened. We started talking to each other. We figured it out. We got to where we were going. And in the process, we got to know each other. A PE teacher late to finals. An engineer who rides a scooter the last mile to work.

Stranded together, we shared stories and speculated about the fire. We were forced out of our individual digital bubbles, and into a shared human experience. It was messy and inconvenient, but it was real. A reminder that despite all our advancements in technology, face-to-face spontaneous human interaction can’t be replicated. Like that great scene in Good Will Hunting: Sean tells Will he can’t learn anything from him he can’t learn in a book - unless he wants to share something about who he is.

We’re in a world where AI can summarize, analyze and generate content from vast digital libraries. I personally taught myself how to generate content 100% autonomously - no more meetings to perseverate over the placement of the words on the slides. But what I prompt AI to generate still comes from my experiences. When our son got stung by a bee for the first time, my wife got answers from Gemini on what to do to make it hurt less. But we held him, and helped him and talked to him about how it felt. When he said it “itched,” we knew he meant it stung. I used NotebookLM to see: Could an AI-generated podcast grok the intention of my newsletter? The insights were a little off - like the taste of artificial sweetener. Not the real sugar: “Why do you think the author links these seemingly off-topic moments?”

There’s a different type of intelligence at stake. It can work together with AI, but the goal is important to define. In AI, goal-driven systems require us to define what we’re trying to achieve. Dionne Warwick sung it best: “What’s it all about?” First, I do think it’s about more, not less. An “and” operator, not an “or.” In a recent interview with author Kathryn Schulz about her new memoir Lost & Found, Ezra Klein talks with her about how our lives are an endless series of “and.”

I’m not a techno-optimist, but I’m not an AI pessimist either. I’m a realist, and a humanist. With more efficiency and more output comes more opportunity for experiences. With more experiences, comes real intelligence that artificial intelligence can’t replicate. Qualities like taste, instinct and style. My readers know I don’t use oxford commas. I can run Deep Research on all the cases where the absence of a comma created literary or even legal uncertainty. But punctuation isn’t a rule - it’s a style choice. Like leaving the bottom of a cardigan unbuttoned.

We have permission to embrace the messy style that comes with being human. The freedom that you can skip a to-do, a button or a comma.