Michael R. Bock
@michaelrbock.com
co-founder of Column Tax // michaelrbock.com
It's amazing that Oura ring independently knows I recently sold the company I founded:
January 22, 2026 at 4:40 PM
It's amazing that Oura ring independently knows I recently sold the company I founded:
Here's what I was doing in 2016:
January 20, 2026 at 3:18 PM
Here's what I was doing in 2016:
Claude Opus 4.5 (w/ Claude Code) is known as the best coding model today, but which model is the best at filing taxes?
We, at Column Tax, tested the latest crop of frontier models and here's how they stacked up on TaxCalcBench:
We, at Column Tax, tested the latest crop of frontier models and here's how they stacked up on TaxCalcBench:
January 7, 2026 at 3:50 PM
Claude Opus 4.5 (w/ Claude Code) is known as the best coding model today, but which model is the best at filing taxes?
We, at Column Tax, tested the latest crop of frontier models and here's how they stacked up on TaxCalcBench:
We, at Column Tax, tested the latest crop of frontier models and here's how they stacked up on TaxCalcBench:
i made an app: "Wrapped Wrapped" that tells you about your year in Wrappeds:
- how many apps sent you a Wrapped
- which Wrapped has the most stats
- which Wrapped you viewed the most and for how long
download link in the next post 👇
- how many apps sent you a Wrapped
- which Wrapped has the most stats
- which Wrapped you viewed the most and for how long
download link in the next post 👇
December 25, 2025 at 3:55 PM
i made an app: "Wrapped Wrapped" that tells you about your year in Wrappeds:
- how many apps sent you a Wrapped
- which Wrapped has the most stats
- which Wrapped you viewed the most and for how long
download link in the next post 👇
- how many apps sent you a Wrapped
- which Wrapped has the most stats
- which Wrapped you viewed the most and for how long
download link in the next post 👇
1/ After 5 years, I’m proud to share that Column Tax has found a new home.
We’ve been acquired by Aiwyn.
I couldn’t be more sure this is the right move for our business, tech, and team.
P.S. these pics are the moments we started & sold the company:
We’ve been acquired by Aiwyn.
I couldn’t be more sure this is the right move for our business, tech, and team.
P.S. these pics are the moments we started & sold the company:
December 16, 2025 at 3:21 PM
1/ After 5 years, I’m proud to share that Column Tax has found a new home.
We’ve been acquired by Aiwyn.
I couldn’t be more sure this is the right move for our business, tech, and team.
P.S. these pics are the moments we started & sold the company:
We’ve been acquired by Aiwyn.
I couldn’t be more sure this is the right move for our business, tech, and team.
P.S. these pics are the moments we started & sold the company:
imagine falling for the most obvious spy of all time on bumble ???
(a friend sent me this screenshot, I'm married 😅)
(a friend sent me this screenshot, I'm married 😅)
November 3, 2025 at 4:40 AM
imagine falling for the most obvious spy of all time on bumble ???
(a friend sent me this screenshot, I'm married 😅)
(a friend sent me this screenshot, I'm married 😅)
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 the horizon.
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 the horizon.
October 29, 2025 at 1:48 PM
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 the horizon.
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 the horizon.
No matter how many times we do it...
I always get nervous before a big announcement (coming tomorrow!)
I always get nervous before a big announcement (coming tomorrow!)
October 28, 2025 at 4:25 PM
No matter how many times we do it...
I always get nervous before a big announcement (coming tomorrow!)
I always get nervous before a big announcement (coming tomorrow!)
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.
Glad to hear the founder whisper networks are still sharing this knowledge around.
October 23, 2025 at 3:35 PM
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.
Glad to hear the founder whisper networks are still sharing this knowledge around.
1/ GPT-5 is worse than Gemini 2.5 Pro at filing your taxes (but it's really close and they both can't do it yet)
we proved it via our tax calculation benchmark:
we proved it via our tax calculation benchmark:
September 18, 2025 at 5:38 PM
1/ GPT-5 is worse than Gemini 2.5 Pro at filing your taxes (but it's really close and they both can't do it yet)
we proved it via our tax calculation benchmark:
we proved it via our tax calculation benchmark:
I got married last month.🤵♂️👰♀️
Here's what it taught me about B2B2C tax software:
Just kidding :) but I do really recommend getting married to the love of your life with all your friends & family around!
Here's what it taught me about B2B2C tax software:
Just kidding :) but I do really recommend getting married to the love of your life with all your friends & family around!
September 17, 2025 at 2:00 PM
I got married last month.🤵♂️👰♀️
Here's what it taught me about B2B2C tax software:
Just kidding :) but I do really recommend getting married to the love of your life with all your friends & family around!
Here's what it taught me about B2B2C tax software:
Just kidding :) but I do really recommend getting married to the love of your life with all your friends & family around!
no one had even heard of git worktress before claude code
August 13, 2025 at 8:49 PM
no one had even heard of git worktress before claude code
amazing ChatGPT Agent Mode use case: find & validate coupon codes without having to test them yourself
August 3, 2025 at 7:08 PM
amazing ChatGPT Agent Mode use case: find & validate coupon codes without having to test them yourself
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:
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:
July 23, 2025 at 3:17 PM
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:
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:
this is the wildest cold twitter dm opener i've ever received
July 21, 2025 at 11:17 PM
this is the wildest cold twitter dm opener i've ever received
this is what founder <> founder private text messages look like (and what makes the job so fun)
July 21, 2025 at 2:05 PM
this is what founder <> founder private text messages look like (and what makes the job so fun)
why is everyone complaining about a GPU shortage if it turns out you can just buy them on amazon ;)
June 21, 2025 at 3:48 PM
why is everyone complaining about a GPU shortage if it turns out you can just buy them on amazon ;)
1/ I’m working on tax filing software, and this caught me by surprise: an engineer just open sourced the IRS's Direct File project (now that it seems likely the current administration will shut down the program for next year).
June 5, 2025 at 4:02 PM
1/ I’m working on tax filing software, and this caught me by surprise: an engineer just open sourced the IRS's Direct File project (now that it seems likely the current administration will shut down the program for next year).
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:
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:
May 29, 2025 at 3:17 PM
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:
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:
i don't think most people fully appreciate just how much of modern startup software was built by Hack Reactor coding bootcamp 2014 - 2016 grads
May 15, 2025 at 5:47 PM
i don't think most people fully appreciate just how much of modern startup software was built by Hack Reactor coding bootcamp 2014 - 2016 grads
spotted: a BMW delivering laundry. it's so over. we are absolutely heading into a recession.
April 27, 2025 at 2:47 PM
spotted: a BMW delivering laundry. it's so over. we are absolutely heading into a recession.
feedback from the team 🥹
April 24, 2025 at 5:16 PM
feedback from the team 🥹
this is insane branding for smoothies
April 24, 2025 at 4:28 AM
this is insane branding for smoothies
as sad as it is, there are a few reasons, as a company operator, you need to immediately fire someone:
- illegal activity
- lying
- harassment
- creating a Slack Canvas instead of a normal document
- illegal activity
- lying
- harassment
- creating a Slack Canvas instead of a normal document
April 17, 2025 at 8:24 PM
as sad as it is, there are a few reasons, as a company operator, you need to immediately fire someone:
- illegal activity
- lying
- harassment
- creating a Slack Canvas instead of a normal document
- illegal activity
- lying
- harassment
- creating a Slack Canvas instead of a normal document