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I'm a software engineer and entrepreneur focused on modern web technologies and AI.

Here's an ongoing autobiography, which also shares the story of my by-the-bootstraps "unschooling" education: now the subject of a chapter on grit and resilience in the bestselling book Mindshift by Barbara Oakley.

An angel investor once described my core soft skill in the role of founder or early team member as: "The ability to perceive exactly what needs to be done. And then to do it."

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In the past, I coined the term "Startup Cities" as co-founder of StartupCities.org and a startup spinoff, both of which focused on why startups should build cities. I now write about Startup Cities at StartupCities.com

I've won several awards for economic research and have been published or interviewed in Virgin Entrepreneur, a16z's Future.com, The Atlantic's CityLab, Foreign Policy, and in academic volumes by Routledge and Palgrave MacMillan.

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AI Empathy

It's long been a joke in engineering that some people have "Machine Empathy" or what Dilbert once called "The Knack". Basically, the ability to "think like the computer." I think there's something related but different now: "AI Empathy."

Dilbert, who has "The Knack"

Machine empathy was an ability to visualize and intuit how computers work at lower levels. Great engineers have this (which is one reason why non-technical vibe coders seem to struggle more than engineers who vibe code).

But AI Empathy is different. It's more like empathy for a human:

  • Does this agent have the tools it needs to accomplish this task?
  • Have I made clear "what good looks like"?
  • Are there unresolved questions we should talk about?
  • Is the problem clearly broken down or a pile of vague mush?
  • Are there docs and context around the agent so it can find the path to a solution?

This is very close to how a good engineering leader structures tasks for their team.

I can't help but wonder if AI Empathy develops more easily in a certain type of mind, perhaps not the same type of mind that found Machine Empathy easy to grow.

Jul 06, 2026
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