My posts

Random thoughts on AI and metadata

The Hidden Tax Penalty Killing Bootstrapped Startups

Nov 3, 2025

The Hidden Tax Penalty Killing Bootstrapped Startups

Three years ago, when we started making profit as a bootstrapped startup, I was stunned by how little money I could reinvest in my own company compared to a funded competitor. We paid ourselves 20% of the profit and paid 40% in taxes and reinvested the rest i.e. 40% into our business. Meanwhile, a VC-backed competitor could show losses and invest 100% of the revenue plus the $10 million or $50 million they raised from investors. In this essay, I'll show you how screwed up the incentives are for bootstrapped companies and what we can do to fix this.Real numbers from my startupLet me s
From Lossy to Lossless Reasoning

Oct 31, 2025

From Lossy to Lossless Reasoning

In my last post, I argued that code generation is not only used by AI coding tools like Cursor. It is the kingpin behind reasoning and all that is built on top of it (from agentic AI to AGI itself). For example, if you ask AI how to position a 13-foot ladder to reach exactly 12 feet up a wall, a reasoning model like GPT-5 uses the pythagorean theorem to calculate the answer: 5 feet from the wall. There are two ways it can do this:Code generation mode (Tool use): Generate math.sqrt(13*13 - 12*12) and use Python as a tool to run it and return 5.Pure reasoning mode (No tool use): If you ask GPT-5
Reasoning Is Not Model Improvement

Oct 23, 2025

Reasoning Is Not Model Improvement

How tool use became a substitute for solving hard problemsWhen OpenAI released o1 in April 2024 and called it a "reasoning model," the industry celebrated a breakthrough. Finally, AI that could think step-by-step, solve complex problems, handle graduate-level mathematics.But look closer at what's actually happening under the hood. When you ask the latest model, ChatGPT-5 to multiply two large numbers, it doesn't calculate. It generates Python code, executes it in a sandbox, and returns the result. Unlike ChatGPT-3, which at least attempted arithmetic internally (and often failed), ChatGPT-5 de
If you think Eight Sleep's AWS outage is bad...

Oct 22, 2025

If you think Eight Sleep's AWS outage is bad...

Wait for AI to fold you like a taco!
Your startup has to be a surveillance state to automate jobs

Oct 16, 2025

Your startup has to be a surveillance state to automate jobs

Last week, in one of the OpenAI DevDay interviews, Sam Altman said he expects zero-person startups in years to come. Meanwhile, OpenAI's support agent seems to be struggling to answer correctly. I ran into trouble while finetuning its model to invoke MCP calls consistently. So I asked that question on email and the support agent came up with all sorts of wrong answers. I was about to give up when an OpenAI engineer jumped in and fixed it. He spoke to his MCP team and told me that finetuning MCP calls are not supported yet and asked me to use tool calls instead. So why is it that the AI of the
Build a Cannon to Kill a Mosquito

Jun 11, 2025

Build a Cannon to Kill a Mosquito

At Guesswork, we are a team of four engineers with no background in sales or marketing. So, we had to figure out a way to get customers without relying on any of those skills. That led us, through trial and error, to a surprising approach: we call it "Build a Cannon to Kill a Mosquito." Using this methodology, we’ve acquired over 4,500 customers. In my talk at Lean culture, I explained how we did it, and why this counterintuitive strategy works especially well for technical founders. This is a summary of that talk.Three Startup ArchetypesMost startups fall into one of two categories:Technology
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Founder & Developer - Guesswork.co

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