Archive
Every essay, kept in order.
The full archive grouped by year, with every piece still linked back to its topic.
2025
Fifteen DollarsThere is a slide that appears in pitch decks now. On the left, the old model: a subscription fee. On the right, the new model: a percentage of value created, uncapped, aligned with outcomes. 'We don't charge for seats,' they say. 'We charge for results.' I think this argument is wrong.
The CompressionSometime around 2015, there was an office in a WeWork. The walls were exposed brick. The desks were reclaimed wood. They were building a website for a premium dog treat brand. The project would take four months and cost $180,000. And then, very quickly, a large language model learned to do most of it.
The Curious Case of Living to 175The longevity people think we are going to live a very long time. They might be wrong. But they might be right, and if they are, certain things follow that nobody seems to want to talk about. Female fertility has a biological clock. Male fertility does not. This asymmetry exists now, but stretch the lifespan to 175 and leave the fertility window where it is, and something strange happens.
The Hole Does Not Care What You Try to Fill It WithArtists have always enjoyed calling businesspeople greedy. The suit is the villain. The creative is the hero. The suit wants money and the creative wants meaning, and these desires are understood to be fundamentally different in character, one craven and the other noble. This seems worth examining.
E-Commerce Reporting is Anti-AccountingAll e-commerce platforms will tell you you've made a certain amount in 'Sales' but especially in today's world of cross-border commerce, it's not sales at all. It's a mess of liabilities, pass-through charges, and fees that would make any accountant wince.
What Each Side In the Remote Work Debate Won't AdmitThe remote work debate has calcified into tribal identity. Both sides have developed elaborate ideological frameworks to support their positions. Both sides are lying about what they actually believe.
The Seven Archetypes of Founders and CEOs: A Field Guide for Co-Founders and Early EmployeesBefore you join a startup or accept that co-founder offer, you need to understand what type of leader you're dealing with. The difference between a Value Maximizer and a Lifestyle Architect isn't just philosophical—it's the difference between 80-hour weeks and asynchronous Slack messages from Bali.
Bodies Not Boats: Why Your Company Is More Organism Than VesselEveryone talks about getting your team 'rowing in the same direction,' but companies are more like bodies than boats. Your kidneys filter toxins while your heart pumps blood—different jobs, same organism.
What is work?The old world had clear roles: the mason, the monk. The capitalist, the clerk. The new world does not.
The Pricing Leak Crisis (Startup Case Study #2)When their internal pricing strategy document accidentally went to 3,200 customers instead of 3 executives, CEO Melissa had to choose between damage control and radical transparency.
The Two-Deck Dilemma (Startup Case Study #1)When Maya discovered her co-founder was maintaining two different financial models—one for investors, one for banks—she had 72 hours to decide whether to sign the Series B term sheet that could save or sink their company.
A Field Guide to Entrepreneurs: Species, Habitats, and EvolutionFrom garage tinkerers to Twitter philosophers, mapping the entrepreneur ecosystem across four decades of creative destruction.
The benign mediocrity of AI responsesIt's the second day of 2025. Commercial consumer-facing AI has been around for over two years. Here is a fundamental problem with AI chat.
Before we learned to look downThe last time I truly learned a city's anatomy was fall 2004, those four months at UVic when I owned nothing with a screen. No laptop, no cell phone, not even a hand-me-down Nokia.
The journey from Liberia to NosaraThe journey from Liberia to Nosara is a kind of prelude—a two-hour stretch of road that forces you to leave behind any neat, tidy expectations you had about Costa Rica.
The Thenar EminenceIn everything, there's this mechanical feeling—a patterning you almost never think about, unless you force yourself to. Life, it turns out, is governed by these little, unnoticed forces and movements that pile up in the background.