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Applied AI Use Cases and Frameworks, Portfolio Theory and Decision-making in an Uncertain World
How can you use AI to better invest your time and money in an uncertain world?
Hi, I’m Taylor. Since 2008, I’ve been interested in developing better ways for thinking and acting in an uncertain world.
Right now, that question has led me deep into AI. I’m building a personal and team operating system on Claude Code — designing skills, memory systems, and agent workflows that turn a CLI into something closer to a second brain with agency. I’m writing about what works, what’s hype, and what this shift means for how knowledge workers actually think and operate.
Right now, I invest and advise founders running early stage startups and small businesses. Before this, I ran a multi-strategy hedge fund for five years with a focus on building absolute return portfolios incorporating trend following and long volatility. I also wrote a book, The End of Jobs, about how technology is reshaping careers.
What You’ll Find Here
1-3 long-form essays per month and a monthly newsletter with the best books, articles, and podcasts I found this month.
Some themes you should expect:
How to apply AI to your work. I’m currently deeply immersed in AI tools and particularly CLI tools like Codex and Claude Code. I write about what’s actually working for me, what the emerging OS layer for knowledge work looks like, and how to approach it to get the most of it for you and your work.
How to be a better investor. I research and write about investing with a focus on optimizing after-tax total return through portfolio construction. This means less stock picking, more topics like risk management, trend following, ergodicity, and the Kelly criterion.
Decision-making under Uncertainty. Think OODA loops, complex systems, antifragility. The mental models and frameworks that help you make better bets with incomplete information — whether the decision is about a portfolio, a business, or your career.
The Interesting Times is a monthly digest of the most interesting things I find on the internet, typically centered around these same topics: investing, technology, and decision-making strategy.
If you’re interested in diving in, here are some of my best essays:
What This Is NOT
I know I have all the keywords in here, but this isn’t a trading signals newsletter or an AI hype feed. I only publish when I have something worth saying which you should expect to me 1-3 times per month.
Why People Read This
The people who stick around tend to share a specific disposition: analytically minded, they care about getting decisions right, and they’re suspicious of ‘conventional wisdom’ that hasn’t been stress-tested or thought through. They often work in finance, tech, or run their own businesses.
About Me
I’ve been writing online since 2012 and have 150+ published essays.
Professionally: I spent Five years running a hedge fund, a decade of consulting with founders and have media mentions in NBC, Inc, and the Financial Times.
Personally: I live in Austin, Texas with my wife, our toddler, and a dog named Paddy who told me to tell you that you really should subscribe if you like milk bones or head scratches. (No, I am not above pandering with cute photos of my dog, sue me).
