Chuck Yates (@nimblephatty)

Why Most CIOs Are Quietly Praying for Retirement — And the Few Who Aren’t Are About to Get Very Rich I had a moment this week where I was sitting across from a Director of IT and it hit me — this poor bastard has the toughest job in the entire company. The business folks get to be full-time dreamers: “Hey, can we automate this? Can the AI just know what to do? Can it walk my dog while I’m in this meeting?” Meanwhile he’s over there thinking about data security, system reliability, whether some employee is gonna click on an email that says “You’ve won a $1,000 Walmart gift card!”, whether Ukrainian hackers are going to steal their customer data at 2 a.m., and whether his entire team is about to get replaced by three interns and ChatGPT — all while knowing none of this stuff actually works the way the brochures promised. And here’s the part that makes me feel for the guy — for his entire career he’s been rewarded for keeping the machines running and not getting fired. Now we’re asking him to suddenly become a profit center, to be out over his skis with AI initiatives. It’s like telling the hall monitor he’s now responsible for running the company’s underground poker game. Did I just compare our AI software to an underground poker game? Yeah, probably not the best analogy, but hang with me here, I’m rolling. Meanwhile the C-suite is over there wondering why nothing’s happened yet, completely oblivious to the fact that they’ve spent twenty years brutally punishing IT for not playing defense. Hell, I know CIOs who got fired because Windows 95 sucked. The real kicker is how to even get started. Our philosophy has always been to start small — automate one workflow, prove it works, and then compound fast. Smart in theory. In practice, with a big organization, that feels like bringing a birthday candle to a forest fire. The C-suite doesn’t get excited about incremental. They want to see something that actually moves the needle. So you’re stuck trying to thread this ridiculous gap: build something small enough to actually work, get real user adoption, and make sure the vendor isn’t full of shit. Honestly, I don’t envy that seat one bit. At Collide, we’re committed to being real partners with the folks actually doing the building. I’ve got serious scar tissue from getting fired for not being “openly collaborative” with other oil and gas companies on well spacing back in the shale days, and I’m never making that mistake again. We’re gonna share what we learn, educate when we can, and actually listen — God knows we have a lot to learn too. Truth is, my tech guys are dying to find some partners in crime — and I really gotta stop with the crime analogies, I swear that’s not what we’re doing here — because they get all excited explaining the latest and greatest AI breakthrough and I respond with the technical sophistication of a man asking if his rotary phone has Bluetooth. Sip slowly, my friends.

I thought my ex-wife really hated me… until I started selling energy software. Holy shit. I’ve had longtime friends and former portfolio companies look me dead in the eye and say, “You’re not gonna pull that crap on me, are you?” It’s been brutal. Turns out oil & gas operators have been lied to, nickel-and-dimed, and screwed over so many times they’re now full-blown once-bitten, twice-shy survivors. So we did something that feels kinda corny: we wrote an actual Customer Bill of Rights. Want to see the 8 commitments we’re making — including the one where every customer gets my and Collin’s cell phone number? Link in bio / comments. Sip slowly ☕