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Strategic Abandonment: JGSD Does Not Mean Doing Everything

July 28, 2026

You’ve committed to embracing The Terrible Ten. You’re going to push through the messy first attempts. You’ve internalized the JGSD mindset. You’re going to stop planning and start shipping.

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AI Legal Risk: Summary and Board Takeaways

July 28, 2026

AI can accelerate legal work, but it can also accelerate legal mistakes.

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Stop Talking About It: Just Get Shit Done

July 27, 2026

You’ve been in three meetings this week about the same initiative. There’s a Miro board with 47 sticky notes. Everyone agrees it’s important. The Slack thread has 200 messages.

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From 10 to 1,000: How Repetition Becomes Second Nature

July 23, 2026

You survived your first 10 attempts. The skill that felt impossibly foreign now feels merely difficult. You can execute without panicking. You know what good looks like, even if you’re not there yet.

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Practical Rules for Safe AI Use: Use AI Like a Junior Assistant, Not Like a Private Vault

July 23, 2026

Use AI like a junior assistant, not like a private vault.

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The Terrible Ten: Why Your First 10 Attempts Must Suck

July 22, 2026

You’re three slides into your first executive presentation. Your voice cracks. You forget your transition. The CFO is checking her phone. You can feel yourself sweating through your shirt.

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Lawyer-Client vs AI-Client Privacy: Privacy in an App Is Not the Same Thing as Privilege in Court

July 21, 2026

Privacy in an app is not the same thing as privilege in court.

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The Board-Level Case for Open Source Security Operations: Why Your Next SOC Shouldn't Come with a Subscription

July 17, 2026

Over the past month, I’ve published a technical series on building an AI-powered Security Operations Center using open source tools. The question I keep getting from board members: “This is interesting for homelabs, but what about enterprise?” Here’s the business case.

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The Pattern of Sanctions: The Issue Is No Longer Whether AI Hallucinates; It Is Whether Legal Teams Have Controls

July 16, 2026

The issue is no longer whether AI hallucinates; it is whether legal teams have controls.

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How to Build Your Own Personal AI Agent: A Step-by-Step Guide for Non-Technical Leaders

July 15, 2026

A personal AI agent is not “a chatbot with a nicer UI.” It’s an assistant that can do multi-step work for you—collect information, draft outputs, and sometimes take actions across tools. Done well, it saves time and raises your AI literacy. Done carelessly, it becomes a privacy and security liability.

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Hallucinated Legal Citations: One Fake Citation Can Turn Into a Real Disciplinary Problem

July 14, 2026

One fake citation can turn into a real disciplinary problem.

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Your First AI Experiment as a Board Member: Low-Risk, High-Learning

July 13, 2026

The fastest way to build AI literacy is to use AI yourself—but do it in a way that is safe, low-stakes, and educational. The goal is not “to become a power user.” The goal is to understand where AI helps, where it misleads, and what controls matter in real life.

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