From Cybersecurity to Vending Machines: How Justin Krakow Built On Point Amenities with AI

Justin Krakow spent 15 years in cybersecurity, most recently at Dell, before deciding the work had become a checkbox exercise that no longer fit. After leaving in October 2024, he and his family — wife and three kids, ages 10 to 17 — built On Point Amenities, an AI-driven vending business in Castle Rock, Colorado, inspired by Japan's far more expansive vending culture. In this conversation, Justin talks about why he chose vending over more obvious small-business paths, how he's using AI to handle inventory, sales tax complexity across jurisdictions, and margin analysis in an industry still running on spreadsheets and guesswork. He also shares how he's built AI into his personal routine — tracking sleep, energy, and focus to manage effects from his military service — and what he tells AI when it starts to drift off track. We close with where the business is headed over the next six months and what running it as a family actually looks like day to day.