Earlier this year I wrote about our AI-powered wealth manager — a setup where my wife and I sit down once a quarter, fire up an AI agent in the terminal, answer a series of questions about our accounts and goals, and walk away with a prioritized list of things to act on. It caught our estate-planning gaps before we left the country, found us thousands in Roth-conversion tax savings, and forced us to actually look at our asset allocation.
The thing is, every time I described that workflow to someone, I got the same reaction: “That’s cool, but I could never set that up.” They were right. A terminal, a carefully constructed prompt, a directory full of markdown files — none of that is something a normal person should have to build just to get competent financial guidance.
So my wife and I decided to productize it. Today we’re launching Alistair, an AI financial coach.
Traditional financial advisors charge about 1% of your assets under management. On a $1M portfolio, that’s $10,000 a year — and for that you’re often getting a quarterly phone call and a PDF of pie charts. Meanwhile, most people who can’t justify that fee are left to figure out investments, taxes, estate planning, and retirement on their own, usually by Googling in the dark.
We’d built something for ourselves that filled that gap, and it genuinely worked. The only problem was that it lived in a terminal and required a lot of setup. So we wrapped it in a web app and made it accessible to anyone.
Alistair is CFP-level financial guidance across six domains — investments, tax, estate, retirement, risk management, and insurance analysis — available whenever you need it, not four times a year. Ask it about portfolio construction, tax-gain harvesting, RSU strategies, beneficiary designations, Social Security timing, umbrella coverage, whatever. It meets you where you are and gives honest, actionable answers.
We built this from a place of not wanting to hand our entire financial life over to yet another app. Alistair never links to your bank, brokerage, or any financial institution — no connections, no logins, no account access, ever. You describe your finances in your own words, upload a document, or share a screenshot. You decide what it knows. Everything you share is encrypted at rest and in transit, and we never sell it or use it to train models.
Competent advising for less than a cup of coffee. Alistair is $4.99/month, with a free tier to get started and a 7-day Pro trial — no credit card required. Advisors charge 1%. We don’t.
If any of this resonates — or if you’ve been meaning to get your financial life in order and just haven’t — give it a try at heyalistair.com. This is the workflow we’ve been using on ourselves for our own money, now with a front door on it. I’d love to hear what you think.