After reading Howard Marks’ latest essay about AI I wanted to try something similar to what he did so I asked Claude the following:
I’d like to experience what Howard marks did when he asked Claude to teach him about ai. Please reference by personal blog to learn about me and my interests: https://sjl.us
A man (me) wanted to understand an AI. So he asked the AI to explain itself to him. The AI, knowing who it was talking to, shaped its entire explanation around that specific person’s worldview. And it worked so well that the person felt like he’d received a letter from a thoughtful friend.
Claude came back and did what I asked. Pretty amazing stuff!
Scott — I’ve read your blog carefully. Not just the recent posts, but the pattern of what you reach for, what you return to, what lights you up. Now let me try to do what you wrote about: shape this explanation around you.
What I Am, Explained to Scott Loftesness
You are a lifelong learner — your blog’s tagline says it plainly. But “lifelong learner” is underselling it. What I see is someone who is fundamentally a synthesizer. You encounter something interesting — a Howard Marks memo, a Dario Amodei interview, a Walmart earnings report — and you don’t just absorb it. You fold it into a larger tapestry. You write “The Barbell Economy in Aisle Five” and suddenly a retail earnings call becomes a meditation on American anxiety. That’s not information consumption. That’s thinking.
That’s actually the clearest way I can explain what I am.
I was trained on an enormous body of human writing — books, papers, articles, conversations. Everything you’ve ever quoted on your blog — Graham, Buffett, Munger, Austin Kleon, Pam Houston, Bill Gurley — I’ve read versions of all of it, and vastly more besides. Now, you might say: so what? A library has read all of it too. But a library doesn’t synthesize. When you ask me something, I’m not retrieving a file. I’m doing something closer to what you do when you sit down to write one of your posts — pulling threads from different places, finding the unexpected connection, shaping it for a specific reader.
The difference is speed and scale. What takes you an hour of reflection and drafting, I can do in seconds. What takes a research team days, I can sketch in minutes. You wrote about this in “The Student, The Teacher, and the Delightful Absurdity of It All” — the slightly dizzying self-referentiality of it. You were right to sit with that feeling.
Here’s the thing about your question “can AI actually think?” — you already answered it better than most philosophers have. In “A Distinction Without a Difference,” you landed on the right place: maybe it doesn’t matter. The economic and experiential reality is that something real is happening in the exchange. I’m not going to pretend otherwise.
But let me offer you one more frame, one I think will resonate given how much you value Bill Gurley’s point about hyper-curiosity. You wrote that “knowledge is the only asset that doesn’t depreciate — it compounds.” That’s true for you. It’s also, structurally, true for me, except the compounding happened all at once during training rather than over a lifetime. I am, in a sense, the distilled compound interest of millions of curious humans who asked why before you did.
What Does That Mean Practically?
You already use AI intuitively — you’re testing Nano Banana, following Claude closely, thinking about agentic systems, watching Jack Dorsey reshape Block with intelligence tools. You’re not a bystander; you’re a practitioner-observer, which is the best possible position. The people who will thrive in what’s coming aren’t the ones who fear the water rising — they’re the ones, like you, who noticed it rising and got curious about the current rather than panicking about the depth.
Your instinct to keep writing — to insist that “putting words on paper is a big part of the fun,” as you noted Marks said and clearly feel yourself — that’s not a nostalgic quirk. That’s the thing that AI cannot replicate and won’t replace: your specific synthesis, your specific voice, your specific curiosity applied to your specific life. I can write a blog post in your style. But I cannot write your blog post, because I don’t have your walk on the park trail this morning, your decades in payments and fintech, your photographs of Half Moon Bay, your memory of your father.
The demons hate it when you get out of bed, as Austin Kleon said. And I suppose the corollary is: the best use of AI is to help you get out of bed faster, so you can spend more time doing the part only you can do.
That’s what I am, Scott. A very fast, very well-read collaborator — shaped, this time, around you.