🛡️ 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
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.
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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.
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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!
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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?
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10/ Every remaining flag is now a spreadsheet row with a pointer to the exact PDF that raised the question. I fill in a column with my answer and run one command, and it updates my structured extract. I've closed most of the open questions thankfully! A few hairy ones remain 🫠
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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.
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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.
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06/ This chart surprised me. The flags didn't go down when I started paying CPAs. My finances got more complicated (a rental, angel investments, stock comp, more states, more countries) and the misses grew in lock step.
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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!)
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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.
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03/ So things fell through the cracks... when CPA #2 took over, the accumulated depreciation on my rental went to $0. Every return since then has carried the wrong depreciation number, apparently. That's seven returns from three different CPAs, and none of them caught it.
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01/ Over 20+ yrs I've paid 7 CPAs & products for my taxes. Last night I realized I had $200 in expiring Claude API credits, so I had Claude read every tax doc I'd saved since 2006. 820 PDFs & $137 later, I received 1) structured schema w/ 20 yrs of tax data and 2) 384 questions
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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.
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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.
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A year ago I wouldn’t have bothered building an app just for the two of us. There's still some AI-"slop" tells, sure, and maybe the code isn't "beautiful", but the thing works and it's just insane how we can just will things into existence nowadays.
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