Thriving in Ambiguity

Sam Altman promised GPT-5 would be “more reliable, with a lower likelihood of hallucinating.” But after trying it myself — like asking it to turn a photo of my daughter playing softball into anime (and it gave her two gloves) — I’m left asking: is this really progress?

In this episode of Thriving in Ambiguity, I break down:

• Why GPT-5 feels like a necessary but rushed release

Dynatrace just changed the game. 🚀

I wasn’t even planning this episode—I’m in the middle of my series on the Dynatrace Platform—but last week, Dynatrace dropped a huge nugget: Gen 3 is here, and AI is at the forefront. I couldn’t wait to break down what this means for IT teams and share real-world examples of how AI is transforming what’s possible.

In this episode o...

What do you get when you combine 16 monitoring tools, constant war room calls, and app chaos? For Kroger, it was a nightmare—until they flipped the script with Dynatrace.

In this episode of Thriving in Ambiguity, I walk you through Kroger’s real-world transformation, featuring insights from Jay Cotton, their lead performance engineer. You’ll hear how their “Captain America Team” ditched the noise, tamed ...

Welcome to Thriving in Ambiguity, the podcast where we break down complex tech—ideally without losing our minds.

In this first episode of our Dynatrace series, I’m diving into Infrastructure Observability, the foundation of proactive IT operations. And we’re starting with a real-world nightmare: TD Bank, a $1.4 trillion financial institution, found out abou...

Welcome to Episode #17 of Thriving in Ambiguity — the podcast where we cut through the chaos of modern tech without losing our minds.

This week, we’re talking observability — not the buzzword version, but the real deal. From my days in the war room to what I’ve learned working with state agencies, Fortune 100s, and SaaS-heavy stacks, I’m breaking down:

• Why traditional monitoring is br...

Welcome back to Thriving in Ambiguity, the podcast where we break down the complexities of technology — ideally without losing our minds.

In this episode, we dive into a story you definitely haven’t heard before: the secret link between Stark Industries, the rise of J.A.R.V.I.S., and the unexpected tech platform that made it all possible — Dynatrace.

Is it fi...

Welcome to Thriving in Ambiguity, the podcast where we unpack the complexities of technology—ideally without losing our minds. In our new series, Anonymous or Not: Crazy Stories in IT, veteran tech leader Steve Mancini shares jaw-dropping, hilarious, and sometimes uncomfortable real-world stories from over 20 years in IT.

From bizarre security loopholes to inappropriate laptop di...

Just returned from the NASCIO 2025 Mid-Year Conference in Philadelphia, and there’s a lot to unpack. In this episode of Thriving in Ambiguity, I delve into the key takeaways from the event, shedding light on the evolving landscape of state IT leadership.

Key Highlights:

• Cybersecurity remains the top priority for state CIOs, marking its 12th ...

A tragedy no school ever expects — and the hard lessons we learned too late.

In this episode of Thriving in Ambiguity, I share the real story behind a crisis at Howard High School that changed everything. As the IT Director at the time, I thought we were ready. We weren’t. And today, I’m revealing what we got wrong — and what you must get right before it’s too late.

In this episode:

• Why the best technology isn’t enough without...

AI isn’t just disrupting industries—it’s coming for companies that move too slow.

In this no-fluff episode of Thriving in Ambiguity, I sit down with AI strategist and keynote speaker Chris Carr to pull back the curtain on what’s really happening behind the scenes with generative AI. Spoiler: it’s not a “someday” problem. It’s a right now problem.

Here’s what we break down:

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