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.

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.

I had a few encounters with Microsoft lawyers that were, in a word, scary. But in a good way. Every time I worked with them, they were hardcore on following the law, and I greatly appreciated and respected that. 

A Microsoft engineer (the awesome .Net Perf architect, inventor of the phrase “Pit of Success”, and now Distinguished Engineer Rico Mariani) recently told me he used Copilot to script a way out of a laggy system. He was delighted. The story triggered a memory from the early days of PowerShell when my diplomacy was clearly … pre-operational.

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:

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!  

In response to my blog Welcome to the Room, Davor Vukovic asked the question:

I might be mistaken, but don’t the required resources result from defining a theory of success (i.e., the solution)? My understanding is that you first define a plausible theory of success and then evaluate it against the available resources, not the other way around; then adjust.