
🛡️ Chief Product Officer @SolveCyberRisk 💷 Ex VP/GM (Growth, AI Banking, Open Finance, App UX) @nubank 📌 Ex VP Ads & Shopping @Pinterest 👍 Ex PM Ads @Meta
Philadelphia, PA
Joined March 2009
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11/ As I've thought about this, I think a few things jump out:
A) A CPA's edge was information asymmetry. Clients either didn't have the time and/or the skill to check the work. I just checked 20 years of it for $137.
Value != moving numbers from a PDF to software.
12/ cont..
B) If you're a CPA and you'd rather start from a structured JSON of a client's full history than a folder of PDFs, I want to talk to you. You're the CPA of the future!
Taxes still run on people trying to push PDFs into software. That's nuts.
13/ cont...
C) And this is probably the most it will ever cost. All in, about $7 per year of all of my returns supporting docs at API prices, and it only gets cheaper from here.
Add a few dollars to fill in the tax returns themselves.
The ROI speaks for itself!
08/ How it works:
- classify every file from its first few pages (~$10 for all 820)
- pull each year into one JSON: ~38k values in all, headline numbers mapped by meaning so 2006 and 2025 line up
- check every carryforward: does what left year N match what showed up in year N+1?
09/ Taxes are complicated, though. The model raised 87 flags that were "high" on the first pass, and later de-prioritized.
What fixed that was downloading all of my IRS transcripts. My record keeping was inexact, so they closed 84 flags without me answering anything.
02/ Who were they? H&R Block, then TurboTax, then four CPAs. At every switch the new preparer got last year's return and a stack of PDFs. None of them looked further back than that (and I get it!!), and information was lost.
05/ But, as I said... there were some big misses. Esp this year.
The draft leaving off extension payments I'd already made, so it said I owed a lot when I was actually due a refund. Missing a ~$2.4K state refund and two gift tax returns I had to file. (Luckily, fixed all of these!)
04/ To be fair, most of the 20-yr misses were small. Expenses entered 2x. A daycare listed 2x under two names. Stuff like that. Nobody ripped me off, but there were *some* big misses.
I was paying for someone to keep the history straight, while they looked one year at a time.
My wife and I have ~50 kinds of plants in our yard: boxwoods, lilies of the valley, hollies, dahlias, hydrangeas, tulips, daffodils, etc etc.
We used to wing it. Then we tried a spreadsheet (lasted maybe a month?)
But now that we can just do things, I built an app for us.
Built it with Claude, Supabase and Expo. It’s side-loaded on both our phones, not in the App Store. Took less than a day total, maybe ~1 hour of ACTIVE time working on it (Claude Code + Remote Control).... some of that while between errands. And have been using it for months.







