Canisius Rozario left a multi-billion dollar company managing 300 people to become employee number 12 at Collide. The CTO role at a seed-stage startup came with anxiety, stress, and constant noise about every new AI tool dropping daily. But it also came with the opportunity to build something real in an industry that solves actual problems, where bad answers don't just cost money, they kill people. Chuck and Canisius break down what it actually takes to go from a ChatGPT wrapper to enterprise-grade AI infrastructure, why oil and gas professionals are more impressive than tech bros, and how they're building models trained specifically on petroleum engineering exams. The team went from six months to build a pilot to days, and they're just getting started.

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00:00 - How Jimmy's dad helped recruit the CTO
03:25 - The recruiter pitch that almost missed the mark
05:27 - Why a 2.5 hour Sunday call changed everything
08:21 - Learning AI by building it in the hardest vertical
11:27 - The most important hire Colin ever made
13:09 - Recruiting AWS, Microsoft, and Candy Crush engineers
17:03 - From miniature model to actual infrastructure
19:15 - Why clients ask "what's your software stack?"
21:14 - The upside-down map incident on day three
24:02 - What startup anxiety actually feels like
27:05 - Why shiny object syndrome kills execution
29:07 - Six months to a month to weeks to days
31:22 - Oil and gas people are the best on the planet
35:25 - Controlling drill bits thousands of miles away
37:33 - The rubber meets the road next three months
40:15 - Building platforms clients can build on
43:00 - Principal-to-principal sales versus employee sales
47:13 - Team breakdown: the superstars running 100x faster
51:20 - Jazz and the haunted Skirvin Hotel story
53:32 - Training models on petroleum engineering exams
55:36 - Zero critical vulnerabilities on penetration testing

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Why Collide's CTO Left a Billion Dollar Company to Join 12 Employees