Your Chatbot Can’t Keep a Secret — Can You?
Your chats with a consumer AI app are postcards, not sealed letters. What free, paid and business plans really do with them, and a five-minute privacy check-up.
Same Technology, Different Planets — Is AI Really Just a Smarter Google?
Most people judge AI from a free chatbot, while a small sliver hand agents real work. For asset owners, that gap can cost twice, and the fix is better judgment, not more enthusiasm.
A Money Coach at the Kitchen Table: ChatGPT Connects to Your Bank — Now What?
ChatGPT can now read your bank, card and brokerage accounts and act as your money coach. It is impressive, convenient, and not a fiduciary. What changed, and what to check before you click “connect.”
This Is Not a Drill: What Anthropic’s Mythos Means for Asset Owners
An AI model held back from release because it is too good at finding software flaws is a siren, not a test. For family offices, with large fortunes and small teams, here is what to do before next quarter.
A month building an AI analyst: three lessons that weren’t on my list
After a month, my AI analyst was better at spotting its own improvements than I was, the cheap model was often the right one, and its memory belonged in files, not chat.
My Newest Colleague Is a Lobster — And It Monitors 197 Funds Before Breakfast
Two weeks, plain-English instructions and one stubborn space lobster: what it took to build an AI agent that watches 197 funds, and why it should never get the master keys.
The 2025 Private-Markets Playbook: Why the Easy-Money Era Is Over (and That’s Good)
Cheap debt and rising valuations no longer do the work in private equity. The next decade’s returns will go to managers who improve businesses, and investors who can tell the difference.
The Invisible Tax Stealing Your Retirement
A 1.8% fee on my first retirement statement looked harmless in 1998. Over 30 years, a fee like that can take around 40% of your final wealth. Here is where to look for it.
The Magic Show Problem: Why Your Private Equity Returns May Feel Like an Illusion
A street magician turned $20 into $100 for my son. A private equity fund’s headline IRR performs a similar trick. The numbers to ask for instead.
What My Local Pizzeria Taught Me About Private Equity’s Biggest Myth
Our favorite pizzeria lost its magic once it got famous. Most top-performing fund managers do too. Why past rankings are a poor guide to picking the next winner.