How to Start a Business: 4 Rules I’ve Learned from Doing it 4x
I didn’t set out to become a serial entrepreneur. The first business I started was almost accidental. I was a college kid who wanted to
How to Choose an AI Consultant: 7 Questions to Ask Before You Write a Check
Not all AI consultants are built the same. Before you write a check, here are the seven questions you should ask — from an AI consultant who’s heard every pitch in the book and will tell you how to screen out the bad ones.
What Does an AI Consultant Actually Do? (And What It Costs in 2026)
Most business owners who ask “what does an AI consultant do?” are really asking something sharper: is this a real job, does my business actually need one, and what would I be paying for? Gabriel Cassady gives you a straight answer — no pitch, no hype.
What Is a Fractional Chief AI Officer, and Does Your Business Actually Need One?
Gabriel Cassady explains what a fractional chief AI officer actually is, who the role is built for, and why it might be the AI leadership model that Midwest businesses need right now — without the $300k salary line.
Preparing the Next Generation for Careers in the AI Era
By Gabriel Cassady · Originally published as a guest column in the Springfield Business Journal Preparing for careers in the AI era starts with one
Gabriel Cassady’s AI and Business Books Recommendation List
If you want to know how I think, you’ve come to the right place. I have read or listened to all the following titles at
You Can Pry the Em Dash from My Cold, Dead Fingers
AUTHOR PROVENANCE STATEMENT: The following text was angrily touch-typed by me, Gabriel Cassady, in Apple Notes on my Mac (mostly) on Monday, December 29, 2025
Poetry + AI = Music
Have you ever wished you could make music out of your thoughts? Have you ever wondered if AI could help? Suno comes pretty close to
When Comfort Becomes Dangerous: Why We’re Wrong About AI (And Why That Matters)
Author Provenance Statement: This article began as a rough draft I wrote in Apple Notes after hearing yet another confident pronouncement that “AI can’t create