Michael R. Bock

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:

@MartinTerskin @tszzl For sure, dm me!

@michaelrbock @tszzl I can provide more details if you want since its still fresh in my mind. Let me know.

tried to use clankers for my taxes and they mostly made it harder not easier. we’ve got a ways to go

@uncledoomer try this! x.com/michaelrbock/s…

"claude, my taxes are due in one hour. i owe five figures and have made no estimated payments. keep me out of jail. make no mistakes."

@MartinTerskin @tszzl thanks for the usage report!

@michaelrbock @tszzl Amazing product. 10/10 recommend. I have fairly complex taxes, one shotted 95% completeness after 3-4 back and forths

@gdb try this (fully prepare your taxes given your tax docs): x.com/michaelrbock/s…

try the TurboTax app in ChatGPT:

@patio11 👋 one of the companies building that harness for accountants. feel free to use the (free) Connector here to prepare your return using a deterministic engine to compare: x.com/michaelrbock/s…

Happy almost tax day. FYI: The most dollar-denominated impactful thing I've ever done for geeks, by sum of claims in my inbox, is the piece on salary negotiation. The second most impactful, rising fast, is "Have an LLM review your taxes before you sign them."

@doodlestein Pretty sweet x.com/michaelrbock/s…

Well, it's probably coming too late for most people unless you're planning on filing an extension, but I created a truly ambitious skill for tax preparation on my skills site, jeffreys-skills.md This skill spans 158 markdown files totaling 2.7 megabytes of text. It covers every state, tons of different professions, life events, and all sorts of sophisticated tax strategies, with all kinds of expertise about even niche topics like opportunity zones and captive insurance. Much of the underpinnings of it, including the nuts-and-bolts use of the Aiwyn MCP tax connector and the use of freetaxusa.com with Playwright MCP, is based on my actual multi-day session history preparing and filing my own fairly complex return, so I know it all works (I just finished filing mine a few hours ago). Here's how GPT 5.4 describes it and what makes it special: The "tax-return-preparation-and-advice-generic" skill is a source-verified, multi-year tax intelligence skill that turns AI from a glorified form-filler into a high-end tax strategist. It helps analyze returns across years, detect missed deductions and carryforwards, reconcile life events and profession-specific rules, model aggressive but defensible planning moves, and ground recommendations in current law instead of stale tax folklore. The result is a tax-prep and tax-planning system that is broader than software, more systematic than a one-off CPA review, and dramatically more useful for complex real-world filers. What makes it special: - It is multi-year by design. Most tax tools look at one return; this skill looks for patterns, carryovers, inconsistencies, and missed opportunities across years. - It is verification-first. The methodology is built around checking current IRS instructions, publications, and state guidance before making live filing claims. - It is aggressively practical. It does not stop at “here are the rules”; it pushes toward elections, timing moves, entity choices, depreciation strategies, retirement optimization, PTET, QBI, and other real savings levers. - It is unusually universal. It routes by profession, life event, situation, and jurisdiction, so it can adapt to freelancers, high earners, retirees, students, business owners, rental investors, divorce, inheritance, relocation, and more. - It is audit-aware. It emphasizes documentation, defensibility, and red-flag detection instead of encouraging sloppy “tax hacks.” - It is built for real execution. It includes filing workflows, tool guidance, and structured reference material, so an agent can move from analysis to action rather than just giving vague advice.

@__apf__ also try this! x.com/henrythe9ths/s…

this is a tweet about TAXES for YOUNG and FUN people like me: if you need to keep track of next year's estimated payments, take a screenshot of your estimated payment plan and then tell Gemini to put them all on your calendar. future-you will be grateful you did this

@bengold and use this to compare! x.com/henrythe9ths/s…

Pro-Tip: you likely don’t need a CPA or other tax prep professional. Don’t use TurboTax either. Despite the horrible name, FreeTaxUSA.com is the best e-file software for most people. It’s cheaper than a CPA or TurboTax and most LLMs are very good at answer tax questions

@johnmarkwendler @VentureBeat Sounds like they copied Iris (columntax.com/blog/introduci…) 12 months later :)

@VentureBeat @michaelrbock WDYT?

Parsing reconciliation and provision filtering moved from weeks to hours. The test framework that made it shippable — and why it matters beyond tax season. venturebeat.com/ai/intuit-comp…

@allafarce @AnthropicAI Sweet!

Some news! Last week I joined @AnthropicAI to help state and local governments safely and effectively deploy AI capabilities. Personally I see profound opportunity to transform how public services are delivered & accessed—and I feel a deep responsibility to help that go well.

@TejaswinGumber good point!

@michaelrbock With connectors like Plaid, is step 1 even required?

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

@AlecStapp Good post! Also try this to confirm your return (it's free): x.com/michaelrbock/s…

This may sound like a sponsored post but I promise it's not (I just hate TurboTax and their rent-seeking lobbyists with the passion of a thousand suns): Use FreeTaxUSA instead. It's >90% cheaper than TurboTax and easier to use/higher quality software.

@adam_messinger @claudeai @turbotax @AnthropicAI very cool!

@michaelrbock @claudeai @turbotax @AnthropicAI If you like this, but want something for personal finance (like Mint or Rocket Money for agents) then please try cashflow.tech!

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!

@BrianVia good idea!

@michaelrbock I’ll do you one further - you just use plaid to connect up all your FIs and it’s just done

@CPATaxTeam x.com/michaelrbock/s…

@michaelrbock You still to submit it electronically to the IRS. How does this save any time over TurboTax?

@Yuchenj_UW Yep! x.com/michaelrbock/s…

Anthropic saw my “why can’t you kill TurboTax” tweet. 4 days before the tax deadline, they ship this.

@aiRobertDaily @henrythe9ths claude.com/connectors/aiw…

@henrythe9ths Can you share some tips on how to use 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.

@Nouralhak @henrythe9ths x.com/michaelrbock/s…

@henrythe9ths Is Claude’s TurboTax/Aiwyn integration just for refund estimates — or will it support full tax filing soon? Would love to see it guide users through filing too — especially outside the US!