Be Curious, Not Judgmental

Ruminations and musings about healthcare AI, technology, and strategy

  • The Humbling Math of Health AI: Why ChatGPT Can’t Grade Your Heart Yet

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    During my time at Apple, I developed deep respect for the engineers and data scientists working on algorithms for the Apple Watch. Watching them develop features like irregular rhythm detection for atrial fibrillation gave me an appreciation for just how hard this work is. The Apple Watch generates continuous, high-frequency data streams: heart rate sampled throughout the day, HRV measured during sleep, motion data at sub-second intervals. The sheer volume… Read more

  • The Hyphen Is the Story

    The Hyphen Is the Story

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    My mother photocopied a Harvard application when I was three years old. She didn’t know any other American college by name. Just this one: the best one, the one that could justify what she and my father had left behind when they came from South Korea with a baby and a handful of certainties about survival. That photocopy lived in our house like a contract I never signed. It said:… Read more

  • Dear Tim

    Dear Tim

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    Tim Cook steps down as Apple’s CEO on September 1, 2026, and John Ternus takes over. Many of the recaps of the Cook era will lead with the iPhone, services, and the trillions of dollars of market cap. Far fewer will take seriously the claim he made to Jim Cramer in January 2019: “I believe, if you zoom out into the future, and you look back, and you ask the… Read more

  • The Patient Will See You Now

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    For two decades, technology has expanded patient agency over information. Search put medical knowledge in the browser. Wearables put physiology on the wrist. LLMs put explanation on demand. All of that mattered, but none of it changed where medicine begins. Patients became better informed participants in institutional care. They could read more, track more, and ask better questions. But the choreography around the patient stayed the same. The system initiated.… Read more

  • AI Jevons Paradox: Why AI May Create More Work, Not Less

    AI Jevons Paradox: Why AI May Create More Work, Not Less

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    The prevailing narrative about AI and white-collar work is a displacement story: AI learns a cognitive task, the humans who perform that task lose their jobs, and the only question is how fast it happens. Software engineers are the canary. Lawyers and accountants are next. Eventually, the thinking goes, most knowledge work gets automated away. There’s a problem with this narrative. It mistakes the death of a role for the… Read more

  • LumiHealth: What Building a National Health Game Taught Me About Behavior Change

    LumiHealth: What Building a National Health Game Taught Me About Behavior Change

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    A toast to the program I built at Apple with Singapore — and a case for why wellness is infrastructure, not a nice-to-have. Tim Cook once said, “If you zoom out into the future, and you look back, and you ask the question, ‘What was Apple’s greatest contribution to mankind?’ It will be about health.” I used to think about that line often when I worked at Apple. And it… Read more

  • The Blinking Cursor Returns: Finding My Childhood in the AI Agent Era

    The Blinking Cursor Returns: Finding My Childhood in the AI Agent Era

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    There’s a cursor blinking at me from my terminal. White text on black, minimal, waiting. It reminds me of sitting in front of my Commodore 64 decades ago—same patient expectation before the first keystroke. I’m 10 years old again. The weird part is: the command line is back—not because UX failed, but because intelligence makes friction survivable. The agent is the new GUI. Why AI Agents Bring Back the Command… Read more

  • When You Upload Your Medical Records to AI, Who’s Actually Protecting Them?

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    Forty million people ask ChatGPT health questions every day. This week, OpenAI and Anthropic made it official: connect your medical records, sync your Apple Health data, let the AI see your full health picture. The product pitches emphasize encryption, privacy (as I explored in health privacy in the AI era) controls, and promises not to train on your conversations. Here’s what they don’t mention: your conversations with ChatGPT or Claude… Read more

  • A Year of Talking to Computers

    A Year of Talking to Computers

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    I built four iOS apps in the last month. Orbit, a personal CRM Visit Notes, an AI scribe Mosaic, an Apple Watch explorer Curator, a photo album app They’re not masterpieces. They’re real enough to be useful, real enough to be a little embarrassing in places, and real enough to teach me (again) that software is mostly an endless series of small decisions. I’m still slightly surprised that this is… Read more

  • Your Gut is a Value Function

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    Tim Cook once said the most important lesson he learned at Apple was to listen to his gut. That stuck with me, mostly because I had to learn it the hard way myself. Early in my career, I thought “trust your gut” was code for “I don’t have the data.” But over time, I learned to listen to my gut, just like Cook describes doing at pivotal points of his… Read more