At 14, I started my personal finance ledger.
I packed takeout at my uncle’s restaurant on the weekends. At the end of each night, he pressed a fresh twenty into my sweaty palm, plus a fresh Coke pumped from the soda rail gun. I shoved that bill deep into my pocket until I got home, slipped it into my wallet, and updated the ledger (college-ruled looseleaf in a black 3-ring binder) with a new line.
My friend, Peter, measured his twenties in video games (he needed three shifts to buy one). Unlike Peter, I was a good first-gen immigrant. I wasn’t saving for something as frivolous as a game. The point of saving wasn’t to buy something, but to watch number go up.
I’m more sophisticated about money now. But in the rawest, most primal sense, I’m still very much that 14-year-old boy. Number up was good. It meant security, status. It means I’m doing the right things and am therefore worthy of respect and love.
And if number go down? Heaven forbid. It means loneliness, losing your house, and abject failure.
When Amy and I first moved in together in LA, the financial system evolved into an envelope system. This was a sophisticated one. It involved several envelopes, stacks of bills I cleaned curry and fish sauce from the Thai restaurant where I waited tables, and a pile of receipts I punched into a Google Sheet. I also used Mint. That was 2012.
YNAB came the same year. Then we went to a spreadsheet, Personal Capital, Tiller, Kubera, then Monarch.
Most years, the target was saving 25% of take-home pay. Was I hitting it? Probably, mostly. But with money landing from a few different places, and apps that couldn’t tell a business transfer from an investment, “probably” was as close as I could get.
In 2026, I paired Monarch with the system I run in Claude Code. This is the best I’ve ever had (and it’s only getting better).
🤖 What Claude Code (plus Monarch) does for my finances
Six things:
1/ The monthly review. I run this during the first week of the month. It takes 10-15 minutes and answers four questions: Am I hitting my savings rate? What are the red flags? What am I spending money on? Anything I can optimize for next month?
2/ The review with Amy. Every two months, this takes about 20 minutes. It uses the same data but leads with progress toward what we’re building together (retirement, paying off the mortgage, a house in Ireland) and it ends with three questions: What else should we be spending on? What else should we be saving for? What do we spend on that we don’t care about?
3/ Forecasting. Every month I tell it what changed (new client, a distribution coming, a big one-off) and it re-runs the year. I get one number: the projected surplus or deficit at year end, and how it moved since last month.
4/ Investing. Once a quarter it answers one question: do I need to reallocate?
5/ Taxes. Estimated expenses for the year, what’s deductible, and the questions for my CPA. It runs all of this in a few turns (versus taking up 3-4 weekends of me trying to wrap my head around everything).
6/ Burn rate and savings rate. These are the two numbers I care about most. What does it cost to run this family for a month, and what fraction of take-home actually got saved.
💼 Why is this SO valuable with a Portfolio Career?
When I had one employer, the money question was mostly answered before it even hit my checking account. My employer withheld taxes and handled 401(k) deductions. I took home the white meat, twice a month, and it was always the same number.
A portfolio career is amazing. BUT… it tears all that apart like a starved vulture. You’ve got clients paying on different cycles, or paying late. Money that’s mine on paper but not mine to spend. And nobody withholds anything for you, so you have to mind your taxes and retirement contributions and sort the irregularities as they pile up.
Yes, all of it is figureoutable. Nothing on its own is going to trip you up, if you’re careful. What isn’t easy is figuring it out while you’re working two jobs, raising a family, and dealing with a leak in the house that has you hanging quart containers beneath your windows as water drips from the seams in the sill. Meanwhile, the baby’s teething and definitely not sleeping and none of the kids want to eat your chicken and sweet potato hash so you’re ordering out… again.
That’s the challenging part. That’s what AI actually helps with.
🚀 How to get started
Before anything else, you want to know where your money is going. That’s the whole job of the prompt below. This is one you can run tonight.
(I’ll walk through my full stack below, but if it’s over-engineered for you, start with this.)
First, export last month’s transactions from whatever app or bank you use (almost all of them give you a CSV). Then paste this into whichever chat model you already use.
You are my monthly money reviewer. I'm pasting a CSV of last month's transactions from [app or bank]. Columns are [date, account, merchant, amount, category].
My take-home income last month was [amount]. My savings-rate target is [25]% of take-home, where "saved" means money moved to savings, investment, or retirement accounts. These accounts are mine, so money moving between them is a transfer, not spending: [list your account names]. Payments to a credit card are transfers, not spending; the spending is the card's own transactions.
Do this, in order:
1. Classify every row as one of: income, spend, savings or investment, tax payment, transfer between my own accounts, or unclear. Show me the unclear ones as a list and stop until I've answered.
2. After I've answered, give me one line: my savings rate last month versus my target, and the gap in dollars.
3. List red flags: any spend category more than [30]% above the prior month if I've given you one, any single transaction over [amount], and any account with zero activity that normally has some.
4. Show the top ten spend categories with totals, and mark each one as recurring or one-off.
5. Give me a next-month playbook: three to five concrete moves, in order, each one sentence.
Never invent a transaction or a category I didn't give you. If a number can't be computed from what I pasted, say so instead of estimating.
When it works, you get a short list of transactions it wasn’t sure about, then the four answers in order, then a playbook on what to do next.
⚙️ How my financial system actually runs
Everything starts in Monarch. Every account we own reports into it, so there’s only one place to pull from.
Here are the skills I run:
1/ Pull money. Claude pulls a fresh snapshot from Monarch, classifies every transaction, checks my totals against Monarch’s, and shows me whatever it couldn’t place. I answer, it turns my answers into rules, and it runs again.
2/ Monthly review. Opens with net worth and what’s liquid versus what’s tied up in the business or the house, then the four questions I mentioned above. Then it asks me what changed (new work, a distribution, a big one-off payment?) and re-runs the year. Ten to fifteen minutes.
3/ Quarterly review. One question: do I need to reallocate? It shows drift against my targets, how I’m pacing toward the retirement contribution limits, and which goals are on track. It’s only allowed to suggest where new money goes.
4/ Tax prep. Reads the year’s documents, surfaces deductions, flags what a Philadelphia S-corp owner has to get right (the distributions, the local business taxes), and writes one summary for my CPA.
🧰 The stack
Here’s the stack of apps and tools my family uses for our personal finances:
-
Monarch Money for aggregation
-
Claude Code running my whole financial system
-
Roam for the running notes, decisions and the questions I want to ask next time
-
Google Docs for my old finance journals and reviews with Amy
-
A CPA for taxes and expert advice and anything I can’t or shouldn’t be doing myself
-
Gusto for payroll, because an S-corp has to pay its owner a salary
-
Carry for the Solo 401(k)
-
Vanguard for the rest of my investments
-
Checking accounts and credit cards, more of both than I’d like to admit, but I keep them around for different reasons (beyond the scope of this post)
💰 How to get rich
Having a great financial system is great for tracking, but tracking isn’t the same as growing. In other words, yes, I think you should have a system and I think this is a great one, AND you also have to focus on getting rich. Getting rich is outside the scope of this post, but here’s what I’d recommend you read. So read these books, and do it in this order (I’ll explain why):
1/ I Will Teach You to Be Rich by Ramit Sethi – Always my go-to recommendation for someone getting started in their financial journey. Ramit sets you up for success. This is where you learn all the blocking and tackling (e.g. credit cards, getting out of debt, which savings account to open, etc.) Note: I worked at I Will Teach.
2/ Psychology of Money by Morgan Housel – This book is a perfect follow-up to Ramit’s, diving into why we handle money the way we do. It’s super insightful about the weird ways our brains work when it comes to money and risk, showing you how to make better financial decisions. If IWTYTBR is the block and tackling, then this is the mental game of personal finance.
3/ The Millionaire Fastlane by MJ DeMarco – I didn’t love this the first time I read it. It gave very Rich Dad Poor Dad. But on the second and third reads, the ideas here changed how I think about diversifying income sources.
4/ Quit Like A Millionaire by Kristy Shen and Bryce Leung – This one has a strong FIRE vibe (Financial Independence, Retire Early), which isn’t for everyone. But even if retiring early isn’t your goal, it’s packed with straightforward tips on how taxes work with different investments. Useful as you dive deeper into exploring how you want to design an investment portfolio.
Work in this order: Read Ramit’s book. Then implement your version of this financial system. Then read the rest of the books.
🤝 When you’re ready, here’s how I help you land your next job:
My Land The Interview Resume Service: Stop getting ghosted and start getting interviews. I hop in and show you exactly how to fix your resume, LinkedIn, and cover letter. No more wondering why your applications disappear into black holes. Just marketing materials that work.