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Baring All To AI
As a rule, I don’t trust centralized platforms, even if they have strange but reassuring mottos or convoluted non-public benefit ownership structures. But to participate in today’s tech-driven society, sometimes you have to hold your nose and pick a horse. For me, Google and Anthropic represent the lessor of two evils. That’s why I have a Pixel, not an iPhone, and it’s why, despite my deep reservations, I just uploaded a year’s worth of my personal financial transactions and an 89-page overview of my entire financial life into Claude AI.
Am I f*cking crazy?
Possibly. But let me explain. My wife and I have been engaged in a long overdue financial planning project. Paying attention to money is one of my least favorite past times. But just like root canals or arguing about politics, there comes a time in your life when you can no longer avoid the pain. Earlier this year we changed financial advisors, and we took that transition as a cue to do a complete audit of our financial life. That meant a review of nearly thirty years of investments in startups, real estate partnerships, venture funds, and friends’ restaurants, not to mention a dog’s breakfast of stocks, bonds, crypto, and retirement accounts.
Every so often, the CEO of one of those startups or the fund manager of a venture firm would reach out with news — “Huzzah, we sold the company!” Or “Man, I’m so sorry…
