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:

imagine falling for the most obvious spy of all time on bumble ??? (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.

No matter how many times we do it... 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.

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:

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!

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

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:

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)

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).

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:

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.

feedback from the team 🥹

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

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

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

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

the Abundance book release is March Madness for land use zoning policy nerds

i am somehow first in line to borrow the single copy of "Abundance" at the san francisco public library

remember Bard?

can confirm, ChatGPT 4.5 is quite good at what it does:

One of the most common questions I get from other founders is “how should I hire our first VPE?” It took lots of trial & error for me to answer that question, and I wasn’t able to easily find this information online. But with some mentorship, I figured it out and hired someone fantastic.

one of those days when vibe coding goes too far...

all of management can be summed up by two questions: - what’s your goal? - have you talked to that person?

if you worked for 18F and you want to continue working on free, easy, accessible tax filing (or if I can do anything at all to help you find a new gig): contact me - my DMs are open!

want to start making Government more Efficient TODAY without having to work for a certain Department? jobs dot columntax dot com

who is building the equivalent of 1Password for Operator?

i love reading unsolicited reviews like this from real people who can file their taxes in under 10 minutes using our software and call it all-caps FANTASTIC!

switching like this between IC Software Engineer and Manager actually seems like the perfect career path ??? being a manager makes you a better IC and visa versa

the real Premier 1K status is actually spending time with your friends and family and not between a United Clubs in Newark and SFO

“executive coaching” was a good rebrand to get men to go to therapy

it's important to remember during this zuck rebrand era that: - facebook is a terrible product that tricks baby boomers into liking AI slop content - instgram is a time suck and anyone who wants to accomplish anything important in life tries to minimize their time on it

got an absolutely quintessentially perfect top HN comment on this blog post

not today, satan!

seeing an in-person NFT art gallery is the equivalent seeing one of those covid floors circles: reminiscent of a bygone ZIRP era

there’s something incredible (and maybe slightly disconcerting) about getting on a plane built pre-9/11 and has flown ~5 times a day for the past 25 years. truly incredible engineering

i’ve asked every uber/lyft driver i’ve had for the past 4 years how they filed their taxes last year 😅

i mindlessly pass on more deal flow each week (just because founders are coming to me to chat) than most professional VCs see in a year

not today, satan!

airbnb is hiring interns again we are so back

I totally forgot about it, but someone just reminded me I made an Anki deck for the book Designing Data-Intensive Applications @intensivedata and...people left really good reviews!