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AI Skilling, Once a Sprint, is Now a Marathon
A winner-takes-all mentality marked the early days of ChatGPT. The major AI labs were all openly chasing Artificial General Intelligence. An AGI breakthrough would supposedly kick off an intelligence explosion. This in turn would trigger a chain reaction of recursive self-improvement; whoever got there first would be forever uncatchable. Generative AI research was positioned as…
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Reading Recap: December 2025
White Fragility by Robin Diangelo I was a bit intimidated by this book, but it turned out to be much gentler than I thought it would be. Terms used to talk about racism in the contemporary United States have different definitions than what I grew up with. I think it is often these new definitions…
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Tools of the Trade
Reading physical books is a different experience than reading digitally. It is a more human connection to the author’s work. You can view the progress as your bookmark takes its many steps through the pages. The bookmark itself can contribute to your individual experience. When I think of certain books, they take me back to…
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A Mustache is all you Need
Add one to your profile picture, drop your pronouns, and change your name to something masculine, and your LinkedIn posts will become 200+% more visible. I am seeing this claim trending on LinkedIn recently and find it concerning. Not because it exposes gender bias in LinkedIn’s recommendation algorithm, but because the claims are not backed…
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GPT Chat’s Path to Profit: Models, Competition, and Adversarial Uses
The models behind GPT chatbots will continue to improve, but they are good enough today. Everything we discussed in the previous sections (1, 2, 3, 4) is possible with the technology that exists today. Model capabilities and personality do play a role in retaining users on a given platform. Trying to win the fight for…
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Reading Recap: November 2025
Pedagogy of the Oppressed by Paulo Freire I had this one on my list for a long time. Some good insights on how to evolve the student-teacher (manager-direct) relationship. Overall, I found it a bit long winded and intellectual. I think reading this with a discussion group vs solo would probably have helped. The Code…
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GPT Chat’s Path to Profit: Jailbreaking the App Store
AI Agents are a broad and often confusing topic. As we continue thinking about monetizing consumer GPT chatbots, let’s focus on AI Agents’ ability to take actions. Many people have seen agents that operate like a human using a computer or a browser. These are a useful demonstration of what will be possible to automate,…
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GPT Chat’s Path to Profit: Modalities and Mobile
The conversational nature of GenAI chat lends itself to voice modalities much more naturally than web search engines do. Speaking a keyword query and having results URLs read back to you feels very stilted. Search is a discrete action and doesn’t carry state from one search to the next. A voice conversation with a search…
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GPT Chat’s Path to Profit: Advertising
Advertising is coming for GenAI consumer chatbots. In part 1, we looked at the parallels between web search and information retrieval with chatbots. Chatbots already have a rich collection of user data that can be leverages for ad targeting. Let’s take a look at how they can build an advertising platform to monetize usage. The…
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GPT Chat’s Path to Profit: Web Search
Consumer-facing GPT chatbots will inevitably start to monetize their products. Cost pressures from burning through cash and the high costs of inference may accelerate this change. But even without the cost pressure, it seems unlikely that tech companies will leave any potential profits on the table. The standard game plan for tech companies providing “free”…