Protopia
Writing by Curtis Duggan — Essays on technology, startups, philosophy, and the human experience in the age of AI.
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What Each Side In the Remote Work Debate Won't Admit
The 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 Employees
Before 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 Vessel
Everyone 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 Evolution
From garage tinkerers to Twitter philosophers, mapping the entrepreneur ecosystem across four decades of creative destruction.
The benign mediocrity of AI responses
It'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 down
The 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.










