Michael R. Bock
@michaelrbock.com
co-founder of Column Tax // michaelrbock.com
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
if you put gun to my head and ask me to explain the difference between a "Topic" and a "Description" in Slack...tell my family i love them
April 16, 2025 at 11:21 PM
if you put gun to my head and ask me to explain the difference between a "Topic" and a "Description" in Slack...tell my family i love them
one under appreciated benefit of Waymo is the time it estimates a car will arrive before you book is always exactly corrrect vs. Uber which seemingly uses an RNG to estimate
April 13, 2025 at 4:08 PM
one under appreciated benefit of Waymo is the time it estimates a car will arrive before you book is always exactly corrrect vs. Uber which seemingly uses an RNG to estimate
in the UK do they call cookie banners "biscuit banners"?
April 10, 2025 at 8:50 PM
in the UK do they call cookie banners "biscuit banners"?
the first person to get an AI coding assistant to reliably work inside of JetBrains IDEs will be a billionaire
April 4, 2025 at 4:51 PM
the first person to get an AI coding assistant to reliably work inside of JetBrains IDEs will be a billionaire
Claude Code outputting the total cost at end of each session is one of the worst Product decisions i've ever seen a company make
March 25, 2025 at 3:50 PM
Claude Code outputting the total cost at end of each session is one of the worst Product decisions i've ever seen a company make