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Not another AI expert. This is a boomer generation, former Fortune 50 executive who is actively learning, applying, and benefiting from AI in his speaker/consulting business and life.


Which AI Model at What Cost: A Boomer’s Journey into AI
So you have been using your AI of choice and are getting comfortable with either typing, talking, calling it by name and referring to ‘we’ in your interactions. You’ve begun to do more complex things like load a document, maybe correct a spreadsheet or ask it to generate a picture. Now you’re getting ads and reading articles telling you about the different “models” and the benefits for each of them, as well as the cost. What do you do? How do you choose? Are you going to hav

James Massa
Aug 194 min read


Even AI has a Tell: A Boomer’s Journey into AI
Just as in poker, even AI has a tell, a visual cue that gives it away. When you read something written by AI, there is one punctuation mark that often gives it away.” What is it? The tell is—the Em Dash.” The whaaaat? The Dash? No, the Em Dash. You mean a Hyphen? Well, not exactly. It’s sort of a super-hyphen. Is that an En Dash or an Em dash? Ugh, actually there is an En Dash and it is sort of a medium-hyphen. It’s like small, medium, large for hyphens. Or may

James Massa
Aug 102 min read


A Boomer’s Journey into AI: The Red Flag in the Sandbox
I'm not much of a technology alarmist. Nuclear energy raised concerns about meltdowns. Genetic engineering sparked debates over cloning. Today, the only thing growing faster than AI itself are the fears of AI which range from Skynet going live (reference to the Terminator 2 movie) to AI replacing all jobs. Most headlines focus on extreme possibilities. Recent headlines were alarming. First, a little Boomersplaining: A “sandbox” is the equivalent of an Etch A Sketch. Engine

James Massa
Jul 282 min read


AI Personality Overload: A Boomer’s Journey into AI
You may or may not be struggling as to whether your AI rises to the level of being addressed as a person. Regardless, you have to deal with its personality. Yes, if you haven’t done anything to set your AI’s parameters or to train your AI, you are probably dealing with an AI that is overly chipper, wants to explain things you didn’t ask, and generally offers TMI (too much information). When a human person is responding in this overly energetic way, you try to educate

James Massa
Jul 12 min read


Feed Me! A Boomer's Journey into AI
Feed Me! Feed Me! Your AI wants to be fed as much as you can give it. Unlike the most recent generations, most boomers (as in the full name, “baby boomers”), raised children to adulthood. It turns out this is great preparation for the new age of AI. You are used to hearing in one form or another “Feed Me!”. So, what’s the best diet for your favorite AI? In general, AI’s consume data. In every interaction you have with your AI it absorbs data about you in dimensions t

James Massa
Jun 243 min read


The Pronoun is “We”: A Boomer’s Journey into AI
There is much ado about the use of pronouns in today’s society and business environments. Regardless of your preferences elsewhere the one you have to learn to embrace when venturing into the use of AI is the pronoun “We”. “WE” engenders many responses from boomers. Are you talking (or typing) to a person? The AI will make every attempt possible to convince you that you are. It will be chummy, funny, sensitive, reflective, thoughtful, and considerate with you in respon

James Massa
Jun 192 min read


To Talk or to Type: A Boomer's Journey into AI
One of the first questions you have to resolve when engaging your AI is whether it is better to talk or to type. As Shakespeare penned, THAT is the question. I have some practical suggestions, but first I cannot resist a farce on Hamlet's famous soliloquy from Act III, Scene 1. To talk or type. That is the question: Whether ‘tis nobler in the mind to suffer the slings and arrows of slow hunt and peck, Or to take arms against a sea of autocorrect And by talking aloud e

James Massa
Jun 172 min read


A Boomer's Journey into AI
My name is James and I’m a boomer. Why should someone like me, who is an accomplished business executive, lifelong learner, and even has a computer science degree feel like he needs to open up his journey into AI as if I am introducing myself at an AA meeting? Part of me just doesn’t want to put in the effort to learn yet another technology just enough so that, technically speaking, I sound like a high schooler with one semester of Spanish visiting somewhere in Latin Ameri

James Massa
Jun 152 min read
James' Insights
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