co-founder @columntax (acq). prev @waymo @pioneerdotapp @google. see my popular tweets using this side project i made: toptweets.by/@michaelrbock

Joined November 2009
880 Photos and videos
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1/ After 5 years, I’m proud to share that @ColumnTax has found a new home. We’ve been acquired by @AiwynAI. I couldn’t be more sure this is the right move for our business, tech, and team. These pics are the moments we started & sold the company:
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Here I am about to lead a Product Review meeting (and I'm not nervous at all). I know it's going to go well because I forced my reports to write a Problem/Solution Review doc. The best AI Product & Engineering leaders are using Problem/Solution Reviews to ensure their team is actually building the right product instead of just building software for the sake of it. At some point in my company's lifecycle, we scaled the number of projects we were working on to the point that I could no longer lead every single one. As co-founder and head of Product & Engineering, this was a big transition. I reached out to folks I knew and was lucky to get an amazing template. It helped me ensure we kept building the right things, even as I was managing more. The template was so helpful that I wanted to memorialize it for other founders and Product & Engineering leaders:
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Michael R. Bock retweeted
Replying to @michaelrbock @tszzl
Amazing product. 10/10 recommend. I have fairly complex taxes, one shotted 95% completeness after 3-4 back and forths
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Michael R. Bock retweeted
Thanks for this. I used it and it works insanely well.
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I've worked on tax software for the past 5 years This is very obviously the future tax filing UI (no more spending hours on TurboTax): 1. drop your docs (or open Claude Cowork in your tax docs folder) 2. your tax return is done 3. there is no (3). that's it
Tax season is here and a connector is all it takes to make @claudeai way more useful. Checkout what we just shipped: Connect TurboTax or Aiwyn Tax (formerly Column Tax) to Claude to estimate your refund, see what you may owe, and get a better understanding on the forms before you file.
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Michael R. Bock retweeted
Replying to @zachweinberg
I was shocking impressed, I gave it my return last year and all my docs. It actually caught some things I missed last year. Pretty sweet tool! For anyone with W2s and 1099s/1098s this should be a no brainer to use. I wonder how long till it can do complex 1065 returns
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Michael R. Bock retweeted
I checked this against my 2025 personal tax return and it was the exact same. I have fairly complicated taxes. If you have a regular w-2 job this is a no brainer. By next year this should be handling 90% of all tax cases.
AI to prepare your tax returns for free. claude.com/connectors/aiwyn-…
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Michael R. Bock retweeted
AI to prepare your tax returns for free. claude.com/connectors/aiwyn-…
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I've been working on tax software for the past 5 years. This is the last year anyone will have to pay for TurboTax. You can try it yourself today: - add the Aiwyn Tax connector inside of Claude (link below) - give it access to your tax documents (W-2s, etc.) - ask Claude to prepare your tax return ...and that's it!
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i think i accidentally broke Gemini ??
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1/ OpenAI just launched GPT-5.4 Pro, their premium model at 12x the API cost of standard GPT-5.4. $30/M input tokens, $180/M output vs. $2.50/$15. I ran TaxCalcBench on Pro. The result: exactly tied with standard GPT-5.4 12x the price, 0% improvement But the full story is more nuanced:
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3/ This is the inference scaling story in one chart. You can either pay 12x more for a model that's better "out of the box", or give the cheaper model a bigger thinking budget and get the same result. For tax computation, thinking time fully substitutes for model premium. The ceiling is the same.
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4/ GPT-5.4 Pro launched this week with impressive headline numbers: 89.3% on BrowseComp, 83.3% on ARC-AGI-2, and native computer use. On tax? Same ceiling as standard. The gap between Pro and standard narrows to zero when both models are allowed to think deeply. Updated rankings (strict): GPT-5.4 Pro: 62.75% <-- new (tied #1) GPT-5.4: 62.75% Opus 4.6: 52.94% Gemini 3.1 Pro: 49.02% GPT-5 w/ Search: 41.67% GPT-5.2 Pro: 41.18% Sonnet 4.6: 37.25% Gemini 3 Pro: 36.27% Opus 4.5: 36.27%
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This is actually genius: a Chrome extension that allows you to drag across your Google calendar and then paste your free times as perfectly-formatted text!
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Oh wow, things move quickly: GPT-5.4 at xhigh thinking just hit 62.75% (up from 56.85% yesterday):
1/ The rivalry between OpenAI & Anthropic continues: GPT 5.4 is now the best model in the world at filing taxes (better than Opus 4.6)! We Just ran TaxCalcBench on GPT-5.4. 56.86% of tax returns computed perfectly. That's #1 overall: the first model to break 55%, surpassing Claude Opus 4.6 (52.94%). OpenAI reclaims the top spot. Updated leaderboard:
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1/ The rivalry between OpenAI & Anthropic continues: GPT 5.4 is now the best model in the world at filing taxes (better than Opus 4.6)! We Just ran TaxCalcBench on GPT-5.4. 56.86% of tax returns computed perfectly. That's #1 overall: the first model to break 55%, surpassing Claude Opus 4.6 (52.94%). OpenAI reclaims the top spot. Updated leaderboard:
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3/ Some context on what just happened: Medium thinking GPT-5.4 matches Gemini 3.1 Pro's best result (49.02%) exactly. But high thinking adds another 8 points on top. This is the biggest single-model jump we've seen from a thinking level increase. Compute allocation matters a lot here.
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4/ Updated rankings (strict -- every line must be correct): GPT-5.4: 56.86% <-- new Opus 4.6: 52.94% Gemini 3.1 Pro: 49.02% GPT-5 w/ Search: 41.67% GPT-5.2 Pro: 41.18% Sonnet 4.6: 37.25% Gemini 3 Pro: 36.27% Opus 4.5: 36.27% Eight months ago, 32% was SOTA. Now the top model is nearly at 57%. The trajectory keeps accelerating.
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