Fellowship at Harvard Law School

I’ve always had a stone in my shoe about being a college dropout.  As such, I never imagined I’d be walking into Harvard Law School as anything other than someone who needed directions to MIT. I’m an engineer. I build systems. I’ve spent my career building things that work — reliably, predictably, and without prayer-based assumptions about what’s happening underneath.

Five weeks into retirement, I realized I’m constitutionally incapable of watching the most important conversation in the world go sideways without doing something about it.

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Another Scary Microsoft Lawyers Incident or Don’t be on the Wrong Side of Antitrust

I’ll never forget the day the world stopped. I picked up the phone and heard: “Hello. This is LCA. I’m calling to inform you that you are the subject of a formal investigation into anti-trust violations.”

At that point, everything got blurry. I think I forgot to breathe for a few minutes. I was in shock.

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Fixing the Windows Syntax Boof-a-Rama

When I put together the core concepts of PowerShell, I was committed to solving the boof-a-rama that is Windows CLI syntax.  Prior to PowerShell, any developer that got at least a ‘D’ in a course on parsing was allowed to inflict their damage on the user community.  This incoherence caused a great deal of confusion as users struggled to navigate at least four distinct syntax groupings:

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Product Market Fit is Math

I have a lot of conversations where teams toss around the concept of Product Market Fit (PMF) like it’s a vibe. We all pretend to get the gestalt of it, but usually, we’re just guessing. Here are explanations my teams have used over the years:

Is your Hair on Fire?You have PMF when the customers are buying the product as fast as you can make it—or usage is growing as fast as you can add more servers.

How would you feel if you could no longer use this product?If at least 40% of them answer “very disappointed,” you have reached the threshold. Anything less means you are building a toy, not a necessity.

Since I got involved in angel investing, I learned the cold truth from my fellow investors:  PMF is MATH!  

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Welcome to the Room

A lesson in leadership by Satya Nadella

When I was Promoted to Technical Fellow, I was “invited to the room”, joining Microsoft’s other Senior Executives.  It was really something. Achieving the Senior Executive status is often mistaken for a comfortable reward, a final destination with enhanced perks and support. A more  fitting analogy is reaching the NFL Super Bowl. You are now part of an elite team where nothing less than peak performance is acceptable. As the Navy SEALs put it, “The only easy day was yesterday”. You can feel that energy when you walk in the room. 

I didn’t know what to expect but what I got changed my worldview and my life.

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The AI Finance Golem

Bad things happen when you are grounded in the real world.  Ergo, in systems architecture, we constantly look for feedback loops. Negative feedback loops provide stability (like a thermostat). Positive feedback loops provide amplification, but without a governor, they inevitably lead to system runaway and collapse.

You know the story of the Golem of Prague? The Rabbi builds a protector out of clay. It works great until it doesn’t. In engineering terms, the Golem failed because it lacked a governor—a negative feedback loop. In systems architecture, positive feedback loops without governors don’t just grow; they run away and tear themselves apart. That is exactly what it appears we are building with this circular financing of AI where capital flows from Big Tech balance sheets into startups and immediately flows back as revenue.

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