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AI First

A collection of 4 posts
The AI Replacement Framework: What to Automate vs What to Hire
AI First

The AI Replacement Framework: What to Automate vs What to Hire

I almost hired a $120K/year senior developer in Toronto. Instead, I spent $50/month on AI tools and $3,200/month on two developers in India. The result? 5x the output at 1/10th the cost. Here's the framework that saved me $80K and taught me the
Dec 2, 2025 7 min read
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Why We Fired Our Happiest Customers
AI First

Why We Fired Our Happiest Customers

We had 254 active contractors. They loved us. Real usage. Good retention. Genuine appreciation. We fired them anyway. The Decision That Didn't Make Sense In October 2025, we sunsetted SimpleDirect Financing—our embedded lending platform for home improvement contractors. Six years of building. 13 lender integrations. Tens of
Nov 28, 2025 5 min read
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Why I Run Every Decision Through 3 AIs
AI First

Why I Run Every Decision Through 3 AIs

I don't trust any single AI. Not because they're bad. Because they're biased in ways you can't see until it's too late.
Nov 27, 2025 5 min read
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Capital, Code, and Audience: The New Framework for Building in the AI-First World
AI First

Capital, Code, and Audience: The New Framework for Building in the AI-First World

The old playbook is dead. For years, we've been told the same story: raise millions, hire 20+ people, move to San Francisco, burn $500K/month, and hope you find product-market fit before the money runs out. That worked when information moved slowly, when you needed physical proximity to
Nov 20, 2025 9 min read
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