Michael R. Bock
@michaelrbock
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co-founder @columntax. prev @waymo @pioneerdotapp @google @udacity. see my most popular tweets using this side project i made: https://t.co/fdDI6ikNJ0
San Francisco, CA
Joined November 2009
Thrilled to share we've raised $21.7m for @ColumnTax to scale up our fundamentally new tax filing product https://t.co/Zy2jtZx9wA It's been so much fun building the first-ever IRS authorized tax filing API with the amazing team here
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How will we know that AI has really “made it”? The task that most exemplifies our ability to automate knowledge work is “doing your taxes”. At Column Tax we’re now within line of sight to fully automating taxes. We started the company at the perfect moment, with LLMs just on
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No matter how many times we do it... I always get nervous before a big announcement (coming tomorrow!)
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The blog post in question: https://t.co/lavuMHp0Hv
Let me know what you think: https://t.co/5LfaoWzPG8
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Positive review of my most popular blog post: "Hypothesis Sheets - how to navigate and exit the idea maze with a (good) startup idea". Glad to hear the founder whisper networks are still sharing this knowledge around.
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Iris deep dive blog post: https://t.co/1flptpZAR5
1/ Tax is a special domain: it requires 100% correctness (you don’t want to compute someone’s taxes incorrectly!) So we’ve had to build lots of custom infrastructure to deploy AI agents. It’s working. We’re now able to build our tax engine much faster than traditional methods:
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This timeline has been pretty amazing to live through: - ChatGPT: released Nov 2022 - Devin (first coding agent): released Dec 2024 - Claude Code: preview Feb 2025, GA May 2025 That means Iris (Column Tax's tax development agent), which we wrote about publicly for the first
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Our project to test if AI can file taxes yet (they can't) made it to the front page of Hacker News, and all of the comments were constructive and none snarky! I consider that a huge win on multiple fronts! This project has been a labor of love for me & Column Tax: this data set
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Not many companies are hiring early-career folks right now. But when someone blows you away in the interview process, you take a bet on them. And sometimes those bets pay off in a big way! That's Yeahwon:
Meet Yeahwon Lee, Software Engineer at Column Tax. 💻 Based in Los Angeles, CA, Yeahwon joined Column Tax in September 2023 and in just over two years, she’s already helped millions of taxpayers simplify their filing experience.
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Lots of parallels between @simonw's "Designing agentic loops" blog post (published this week) and our original AI tax development agent blog post (published back in May!) on how we build Iris, a coding agent specifically for a domain (tax) that requires 100% correctness.
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OpenAI just released a new benchmark for economically-valuable tasks, GDPval (great name!) and personal income tax return preparation is one of the examples. It's cool to see the model companies catch on to the importance of testing AI's ability to file taxes, similar to
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I've spent thousands of dollars testing AI models on real-world tasks & inadvertently learned the nuances of the major model APIs. Here's an unordered list of things I've stumbled upon via TaxCalcBench (testing models' ability to calculate tax returns) about the OpenAI,
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AI is making the human part of tax filing more important, not less. More than half of Americans file with a tax professional each year, and that share has grown over the last five years compared to DIY filing. AI will streamline data entry and repetitive tasks, but it won’t
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4/ next up? adding tool use (code execution & web search) to see how that helps models calculate tax returns also testing Claude Opus 4.1 and GPT-5 mini & nano follow here:
github.com
Code & data for TaxCalcBench. Contribute to column-tax/tax-calc-bench development by creating an account on GitHub.
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3/ GPT-5 is impressive in many ways especially because it's knowledge cutoff is still September 2024 but it's not the leader in tax calculation today (even with maximal test time compute)
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2/ back in July, we published the first-ever eval for US personal income tax calculations https://t.co/Vpz5DCH0Io
1/ Can AI file your taxes? Not yet. We tested the latest frontier models and the results were full of catastrophic errors. Letting AI do your taxes would mean IRS rejections, audits, and penalties:
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