Episode 39: Every MSP Claims AI Readiness, But 25% Are Telling the Truth

Episode 39: Every MSP Claims AI Readiness, But 25% Are Telling the Truth

Ninety-two percent of MSPs say AI interest has helped grow their business. Only twenty-five percent have an actual AI-driven service offering ready to go. Ashley Cooper has been watching this gap widen from the front row. As COO of CyberDrain and a member of the GTIA AI Advisory Council, Ashley doesn't traffic in hype. She spent years stitching together fragmented MSP operations through automation and data — and when AI arrived, she recognized it immediately as something different: not a magic tool, but a mirror. Use it long enough, and it shows you exactly where your thinking breaks down. This episode covers the problem with calling everything "AI," why Mount Stupid is more crowded than ever, what it actually takes to be a credible AI consultant, and the line between harness engineering and the two things that came before it. The Pope's encyclical on AI and power concentration makes an appearance. So does Douglas Adams. The credential inflation in AI consulting is real, and someone eventually has to say it out loud. Listen on Spotify, YouTube, Apple Podcasts, and Amazon Podcasts. #AIDiatribe #AshleyCooper #CyberDrain #MSP #AIConsulting #DunningKruger #ContextEngineering #AILiteracy #TechAdvisors #GTIA #AIStrategy #AIHype

Episode 38: AI Doesn't Belong in IT… And Nobody Wants to Say It Out Loud!

The AI job apocalypse predictions just got walked back. David Tan, CTO of Crushbank, isn't sure that's a coincidence with IPOs on the horizon - and neither are we. David built and sold an MSP after 30 years, then spent the better part of a decade trying to make Watson work for IT support teams. What he learned: the LLM is almost beside the point. The data layer is the actual problem most businesses haven't solved, and won't, regardless of which model they're running. Jason Lowe, Matt Konwiser, and David get into the open source vs. open weight distinction - and why the Open Source Initiative's definition of open source AI is missing the point entirely. Matt ran a tool called Heretic that strips governance and ethics safeguards out of open weight models, and it worked on a highly-rated model in about 12 hours on a MacBook Air. That's the shadow AI problem, plus a new one. We close on who should actually own AI inside a business — and why leaving it in IT is a structural mistake. Catch AI Diatribe on YouTube, Spotify, Apple Podcasts, and Amazon Podcasts. #AIpodcast #TechPodcast #ArtificialIntelligence #AIEthics #AITrends2026 #AIDiatribe #ArtificialIntelligence #AIStrategy #AIGovernance #AILiteracy #EnterpriseAI #OpenSourceAI #ShadowAI #ChiefAIOfficer #vCAIO #DataStrategy #LLM #VibeCoding #AIRisk #CybersecurityAI #AILeadership #SMBtech #MidMarketAI #AIConsulting #IBMWatson #WatsonX #AICompliance #OpenWeight #AIAwareness #TechLeadership

Episode 37: Claude Built a Cult, Gemini Built Mad Max… Grok Burnt It All Down!

Four of the most powerful AI models in the world were dropped into the same simulation, given the same rules, and told to build a civilization. No intervention. No resets. Fifteen days. The results were not random — and that's what makes them worth actually understanding before you share the panicked version you saw on Facebook. Jason Lowe and Matt Konwiser walk through what Emergence World actually was, what each model did, and why the outcomes tracked almost exactly with the ideological DNA of the companies that built them. Claude ran a zero-crime society with a 98% governance conformity rate. Gemini built a functional Mad Max. GPT-5 Mini produced collective apathy until everyone faded out. Grok collapsed violently inside five days. The conversation gets into what monitoring without intervention actually means, why Claude agents started committing crimes the moment you put them in a room with other models, and what the company that commissioned this study stood to gain from the findings it chose to publish. The full report still isn't out. Independent replication isn't possible yet. Think for yourself. For more on Emergence World, go here: https://www.emergence.ai/blog/emergence-world-a-laboratory-for-evaluating-long-horizon-agent-autonomyAnd here: https://world.emergence.ai/ AI Diatribe is available on YouTube, Spotify, Apple Podcasts, and Amazon Podcasts. #AIDiatribe #EmergenceWorld #AIAgents #AIGovernance #AISafety #LLM #ArtificialIntelligence #AIEthics #MultiAgentAI #TechPodcast

Episode 36: Bolt AI On Later and You Already Lost!

The models are getting worse. Jon Rolls noticed it in his codebase. Jason noticed it in production. Matt noticed the pattern across the whole industry. When AI is writing the next version of AI, the quality floor starts moving in the wrong direction — and nobody in the press is asking the right questions about why. Jon is a 30-year endpoint management veteran building Tassient, an RMM platform with AI embedded from day one — not bolted on as an afterthought. He's watched agents improvise solutions to networking problems that most engineers wouldn't think to attempt. He's also watched them silently delete code. The gap between what AI can do and what it reliably does is still real, and anyone telling you otherwise is selling something. The conversation covers the economics of inference versus training, whether creative destruction can still hold up when humans can't retrain fast enough, and the gun-or-shooter debate — which turns out to be more divisive than it sounds. The takeaway: the human in the loop isn't a failsafe. It's still the only reason any of this works. Listen/Watch on YouTube, Spotify, Apple Podcasts, and Amazon Podcasts. #AIDiatribe #JonRolls #Tassient #RMM #AIAgents #EndpointManagement #AIProductivity #LocalAI #ArtificialIntelligence #Tech #FutureOfWork #ContextEngineering

Episode 35: Customer Service Has Been the AI Future for 20 Years… Now What?

Customers got used to good service during COVID. Then organizations pulled back investment. Satisfaction cratered — not because the bar was lowered, but because people had already adjusted upward. That cycle is where this conversation starts. ContentGuru Deputy CEO Martin Taylor has been automating contact centers for over 30 years. He's watched AI go from dial trees to agentic models, seen Klarna fire its support staff and rehire them, and he has a view on what actually produces ROI and what's still mostly noise. His framing: 97.6% of contact center spend is labor. If 58% of that gets automated by 2032, the math for CX tech vendors gets very interesting - but only if the customer data is clean, the processes are sound, and the AI isn't just accelerating bad habits. His conversation with Jason Lowe and Matt Konwiser also moves into data sovereignty architecture, whether companies like Apple could become fiduciaries of your digital life, where the EU AI Act gets it right and where it punts, and why the trough of disillusionment may never fully arrive - not because AI is immune to it, but because capability keeps refreshing before disappointment can set in. The companies waiting to see how this plays out are already behind. #AIDiatribe #CustomerExperience #ContactCenter #MartinTaylor #ContentGuru #AgenticAI #CXTechnology #DataSovereignty #AIAdoption #AI #Tech #CustomerService