Articles, Thoughts, Perspectives
and interesting nerdy topics on technology & AI
Deep dives and honest perspectives on AI, agentic systems, and enterprise architecture — for leaders and builders who want the thinking behind the technology, not the hype.
115 articles
Your Team Is Already Using Shadow AI. Put It to Work.
Your team is already using AI. You just don't know which parts.
2026-09-04
AI Governance
The Build/Buy Decision Is Now a Three-Way Door
The build vs. buy decision used to be two doors. Now it's three, and most teams are still walking through the wrong one.
2026-09-02
Strategy
Curiosity Is the Only Skill AI Can't Take From You
AI is getting better at almost everything we once thought made us valuable. But there's one thing it can't give us: the desire to know.
2026-08-31
AI
The Five Signals Every AI System Must Emit
Most AI systems in production are running blind, and the operators don't know it until something catches fire.
2026-08-31
AI
Stop Measuring Developer Productivity. Start Measuring Decision Velocity.
The most dangerous metric in software engineering right now is not a bad one. It is a distracting one.
2026-08-28
Leadership
AI Doesn't Make Developers 10x Better — It Makes Organizations 10x Smarter
The 10x developer narrative is the most persistent myth in software engineering. The idea that a single exceptional person can be worth ten…
2026-08-28
AI
The New Skills Every Engineering Leader Needs
The skills that made you a successful engineering leader five years ago are not the skills that will make you successful five years from…
2026-08-28
Leadership
Technical Leadership in the Age of Autonomous Agents
Leading software teams was always about managing people who wrote code. You hired engineers, you set direction, you reviewed output. The…
2026-08-28
Agentic AI
Why Documentation Is About to Matter Again
Documentation has a reputation problem. It is seen as overhead — something you write because you have to, not because it creates value. The…
2026-08-28
AI
The Rise of AI-Native Engineering Organizations
Most engineering organizations are treating AI as an add-on. They layer it on top of existing processes. They buy tools that promise AI…
2026-08-28
AI
Shadow AI Is an Organizational Problem, Not a Security Problem
Every week, another set of tools gets blocked. Another AI policy gets written. Another security team sends a memo about the dangers of…
2026-08-28
AI Governance
The Engineering Leader Is Becoming an Intelligence Amplifier
For the last twenty years, engineering leadership has been about getting scarce information to the right person at the right time. You…
2026-08-28
Leadership
Escalation Systems That Scale: When Human Review Doesn't Become a Bottleneck
Well-designed escalation doesn't add friction. It concentrates human attention where it matters most.
2026-08-26
Agentic AI
The Ballot Tracking Debate Is Really an Engineering Problem
The Supreme Court put mail-in ballot tracking back in the news — and the real question underneath is an engineering one: chain of custody for a secret ballot.
2026-08-25
Architecture
Governance That Scales With You: How Mature Organizations Keep Their AI on Track
Governance is rarely the thing that breaks first — and that's exactly why it's the thing that breaks most often.
2026-08-24
AI Governance
Designing AI Systems That Stay Useful Even When They're Partially Wrong
Most production AI is directionally right but imperfect — here's how to design systems that stay useful when they're partially wrong.
2026-08-21
AI
The Hidden ROI of Reducing AI Rework
Almost every enterprise AI system has a hidden cost that doesn't show up in any dashboard.
2026-08-19
Strategy
Business Continuity for AI Systems: What Operators Need to Know Before Something Goes Wrong
We design AI systems for their best moments. We test them on sunny-day scenarios.
2026-08-17
Agentic AI
When AI Should Override Human Judgment
Most conversations about AI governance focus on one direction: humans override AI.
2026-08-14
AI Governance
The Moment a CTO Stops Reading the Code — And Why That's No Longer the Right Fear
The old fear about CTOs losing the code is outdated — AI made understanding faster than reading.
2026-08-12
AI Leadership
The Developer Is Dead. Long Live the Developer.
The 7 stages of developer grief in the age of AI — from denial to the new craft.
2026-08-10
AI Leadership
Don't Automate the Org Chart
What 350 leaders, two days of building, and one leadership legend reminded me about the future of organizations.
2026-08-07
Leadership
Domination — A leadership gathering AND AI HACKATHON
350 leaders, 60 days of AI upskilling, and an in-person hackathon — with John Maxwell in to speak. The technology is easy; the people and process have to change too.
2026-08-06
Leadership
How AI Operator Roles Evolve in the First Year of Production
One of the most rewarding patterns I've observed in enterprise AI isn't technical at all. It's human.
2026-08-05
Agentic AI
Setting Confidence Thresholds That Earn Trust in Production
One of the most practical decisions an AI team makes is also one of the most overlooked: "At what confidence level should this system escalate to…
2026-08-03
AI
The Biggest AI Risk Isn't Connected AI. It's Unconnected AI.
Isolation feels safe but creates blind spots — Shadow AI is the real enterprise risk.
2026-07-31
AI Governance
The Metrics That Actually Tell You If Your AI Is Healthy
I've reviewed a lot of AI dashboards. Most of them are measuring the wrong things.
2026-07-29
Leadership
The Foundation AI Can't Build For You
Everyone is buying AI. Almost nobody is preparing for it. The ten foundations that determine whether AI succeeds at scale.
2026-07-27
AI Leadership
The Token Limit Nobody Talks About
Your brain has a context window — and great leaders manage it like an engineer.
2026-07-24
AI Governance
The Corporate Parody Albums Are Out
Four corporate parody albums and a single, 48 tracks total — written in two nights with AI, out under artist WanderingCTO.
2026-07-15
Life
The AI Kept Working. That Was the Problem.
Most operational AI failures begin with success: a system that keeps going when it should pause.
2026-07-10
AI Governance
Your AI Pilot Succeeded. That's Why It Failed.
The quiet failure rarely looks like a failure — the pilot works, then it stops moving.
2026-07-08
AI Leadership
Your AI Is Wrong Most of the Time. That's Fine If You Design for It.
Directionally correct outputs that are wrong in acceptable ways are perfectly usable — if the workflow survives imperfection.
2026-07-07
AI Governance
The Number That Decides Whether Your AI Actually Works (And Nobody Sets It)
The threshold that determines your autonomy rate — and the least-examined parameter in the system.
2026-07-06
AI Governance
Your AI Governance Is Already Broken. You Just Haven't Noticed.
Governance drift: the gradual erosion of constraints that starts well and ends badly.
2026-07-03
AI Governance
AI Isn't Saving Your Team Time. It's Just Changing Where the Time Goes.
AI systems don't eliminate work — they relocate it. The dashboard shows savings; the team feels rework.
2026-07-02
AI Leadership
The Hardest Skill in Enterprise Tech Isn't Technical. It's Making Decisions With Incomplete Data.
The request for certainty is almost always a disguised request to avoid the decision.
2026-06-29
Leadership
Your AI Will Fail. Your Operators Won't Know How to Run Without It.
The hidden dependency of AI-augmented workflows — and the black start capability every organization needs.
2026-06-26
AI Governance
Trust Your AI Less. It Will Work Better.
Visible uncertainty builds more durable trust than confident silence.
2026-06-24
AI
Your AI Works Great. Your Human Review Queue Is the Real Crisis.
The math of escalation is the most overlooked constraint in AI system design.
2026-06-22
AI
Your AI Is Lying to You. It Just Can't Say "I Don't Know."
Most AI failures come from systems that were never allowed to admit they were unsure.
2026-06-19
AI
What Happens When a CTO With Severe ADHD Stops Trying to Fix His Brain and Starts Building Around It
The scaffolding nobody sees — and what AI became for a brain that thinks in webs, not lines.
2026-06-19
AI Leadership
Your AI Strategy Isn't Failing—It's Just Too Small
Most AI strategies aren't failing.
2026-06-04
Strategy
Build vs Buy vs Hybrid: What Changes When AI Writes the Code?
The build vs. buy debate isn't new — but agentic AI and AI-generated code are rewriting the answer.
2026-06-01
Speaking
Designing for AI Fluency Across the Organization
Most organizations approach AI fluency as a training problem.
2026-06-01
Org Design
Standardizing AI Patterns Across the Enterprise
Most enterprises don't struggle with AI ideas.
2026-05-28
Architecture
AI as an Operational Multiplier, Not Just a Productivity Tool
Most organizations start with AI as a productivity tool.
2026-05-25
Leadership
The New Build vs Buy Decision in the Age of AI
Build vs buy has always been a core technology decision. AI is changing the answer—but not in the way many expected.
2026-05-21
AI
Designing AI Workflows That Get Better Over Time
Most AI workflows are designed as if they are static. Define the use case.
2026-05-19
AI
Where AI Creates the Most Enterprise Value
Most AI strategies start with visible use cases. Customer-facing features.
2026-05-14
Strategy
Building an Internal AI Platform Teams Actually Want to Use
Most enterprises invest in internal AI platforms with centralized models, shared infrastructure, and standardized access. However, many struggle…
2026-05-12
Architecture
AI Talk / Panel Discussion — Prologis Innovation Event
Honored to be part of the annual innovation event hosted by Prologis in Charleston — the future of industrial transformation through AI.
2026-05-11
Speaking
Designing Your First AI-Native Operating Model
Most organizations treat AI as an add-on rather than a fundamental shift in how work gets done. While early AI adoption delivers quick wins…
2026-05-06
AI
You Don't Need More AI Use Cases—You Need Fewer That Actually Matter.
Most enterprises don't have an AI shortage—they have too many AI ideas. Every team maintains a list of initiatives to automate, improve, or…
2026-05-05
AI
OnCon Icon Awards 2026 — Technology Professional of the Year
Named to the OnCon Icon Awards 2026 Technology Top 10 during my time as CTO at Ashley.
2026-05-01
Speaking
From Copilots to Capability: Turning AI Into Real Enterprise Leverage
Most enterprises have moved beyond initial AI introduction, with copilots now widespread across email drafting, document summarization, coding…
2026-05-01
Strategy
The AI-Augmented Workforce: Redesigning Roles, Not Replacing Them
The conversation about AI and employment typically begins with the wrong question: "How many jobs will this replace?"
2026-04-28
Org Design
AI Made Your Teams Faster. It Also Exposed How Slow Your Decisions Really Are.
AI is delivering on its promises. Work executes faster—outputs generate instantly, analysis completes in minutes, responses draft in seconds.
2026-04-25
AI
AI Escalation Paths: The Missing Layer in Most Automation Programs
Enterprise automation programs are missing a critical design element: structured escalation pathways for handling AI uncertainty.
2026-04-22
Agentic AI
From Data to Decisions: Where AI Actually Changes the Game
Most enterprises have invested heavily in data infrastructure—dashboards, reports, and analytics platforms—based on the assumption that better…
2026-04-19
AI
The First 12 Months of AI Maturity: What Actually Changes
The first year of AI adoption rarely looks the way organizations expect.
2026-04-16
AI
"Human-in-the-Loop" Is Too Vague for Enterprise AI
"Don't worry—we'll keep a human in the loop."
2026-04-13
AI Governance
Auditability Without Gridlock: Designing AI Controls That Operators Will Actually Use
Most organizations agree on one thing when it comes to AI:
2026-04-10
Agentic AI
Governance is Not About Slowing AI Down. They Are About Making It Usable at Enterprise Scale.
A lot of AI initiatives stall for the wrong reason.
2026-04-07
AI Governance
AI Isn't the Constraint Anymore. Your Organization Is.
For years, the story was simple: We don't have the technology yet. Now we do.
2026-04-04
Org Design
Turning Principles Into Practice: How to Build AI Systems That Hold Up in Production
Most organizations do not fail at AI because they lack intelligence, models, or ambition. They fail because the system around the AI never changes.
2026-04-01
AI
Kill Switches, Not Apologies: Operational Control in Agentic AI
Apologies don't stop systems. Kill switches do.
2026-03-27
Agentic AI
Escalation Is Not Failure
Escalation is often treated as a breakdown in execution. Something went wrong.
2026-03-25
Agentic AI
Designing Decision Boundaries for AI Systems
Every AI system makes decisions. What varies—often implicitly—is how far those decisions are allowed to go.
2026-03-23
AI
Trust Is a Throughput Constraint
Throughput doesn't slow down when systems can't act. It slows down when people don't trust the output.
2026-03-22
AI
Autonomy Without Ownership Is Just Drift
Autonomy without ownership isn't speed. It's drift.
2026-03-19
AI
What Breaks First: Models or Workflows
When AI systems fail in production, the immediate instinct is to look at the model. Was the data insufficient?
2026-03-17
AI
Constraints Are Not the Enemy: What The Goal Teaches Us About Scaling AI
In The Goal, Eliyahu Goldratt dismantled a common assumption: that making every part of a system more efficient will make the system itself more…
2026-03-14
AI
Why Confidence Beats Correctness in Organizations
In most organizations, confidence outperforms correctness long before anyone notices a problem. This is not because people prefer to be wrong, but…
2026-03-11
Org Design
From Hallucinations to Incidents: How Confidence Escalates Risk
If it sounds right, will anyone stop it?
2026-03-09
AI Governance
Who Decides When Humans Are Wrong?
When AI challenges authority instead of automating it
2026-03-07
AI
When Intelligence Refuses to Perform
Why the smartest systems don't try to be impressive
2026-03-05
AI
From Intern to Operator: When AI Becomes Part of the Org Chart
Most AI doesn't arrive with authority. It arrives quietly — as a helper, an assistant, an accelerator.
2026-03-03
Agentic AI
Designing AI Systems That Are Allowed to Say "I Don't Know"
The quiet failure rarely looks like a failure.
2026-03-01
AI
The Cost of AI That Doesn't Know When to Stop
Unchecked AI doesn't just make mistakes. It compounds them.
2026-02-28
AI
Why "Human-in-the-Loop" Is Not a Governance Strategy
"Human-in-the-loop" sounds responsible. It signals caution.
2026-02-25
AI Governance
Where Progress Gets Lost
So I have a number of my leaders send a weekly update - not to me, but to THEIR teams. Make sure to motivate, communicate, and help change minds.
2026-02-16
AI
Who Owns AI Risk: The CTO, Legal, or the Business?
AI risk doesn't announce itself as a single failure. It emerges quietly — in handoffs, assumptions, and gaps between teams that all believe…
2026-02-12
AI Governance
What Happens When AI Disagrees with Your Best People?
The hardest AI problems aren't technical. They're organizational.
2026-02-09
AI
AI as a New Layer of the Stack (And Why No One Owns It Yet)
AI didn't arrive as a feature.
2026-02-06
Architecture
The Myth of Autonomous AI: Why Humans Should Never Leave the Loop
"Human-in-the-loop" is often framed as a safety net.
2026-02-03
Agentic AI
Data ≠ Information ≠ Knowledge ≠ Decisions — Why AI Blurs What Organizations Can't Afford To
One of the quietest failures in enterprise AI isn't model quality.
2026-01-31
Org Design
From Meaning to Control: Why AI Needs Guardrails, Not Just Models
Every generation of technology has its "oh no" moment.
2026-01-28
AI
Why Meaning Has Always Been the Hard Part of AI // Ontology, Semantics, and NLP
Why Meaning Has Always Been the Hard Part of AI, and how we got here.
2026-01-26
AI
The AI Maturity Curve in Manufacturing: From Automation to Infrastructure
Manufacturing has always been a proving ground for technology.
2026-01-25
AI
AI Systems vs AI Features: Why Architecture Beats Demos
Core truth: Demos win funding. Systems win production.
2026-01-23
Architecture
Agents, Agentic Systems, and AI Workflows
What the Differences Really Mean — and Who Should Be Building AI
2026-01-22
Agentic AI
The First 90 Days of AI for Tech Teams who haven't started with AI yet...
Most AI initiatives don't fail because the technology is bad.
2026-01-21
AI
From Hallucinations to Incidents: How Confidence Escalates Risk (v2)
Wrong answers are a problem.
2026-01-19
AI Governance
Why Manufacturing Will Lead Enterprise AI (Not Silicon Valley)
Physical constraints force better AI design
2026-01-19
AI
Perfect Data Is a Myth. Operational Data Is Reality.
In manufacturing, changing master data isn't a cleanup task—it's an operational event.
2026-01-16
AI
What Comes Next Is Different: Why Agentic AI Must Move Beyond Loops and Into Systems
We're seeing eye-opening results from systems that run models in tight loops—retrying, iterating, and pushing forward until something works. In…
2026-01-16
Agentic AI
Speaking & Sessions
My Sessionize speaker profile — talks, sessions, and the speaking record as a CTO.
2025-08-18
Speaking
Six Days in China: High-Tech AI Advancements Outpacing American Innovation
Speed, scale, and strategy — and why the U.S. must treat AI education, automation, and rare earths as musts, not shoulds.
2025-08-18
AI
American Horrorplex: #1-Ranked Haunt in Kentucky
WHAS11 on the Horrorplex being rated #1 in Kentucky by Scare Factor.
2024-10-15
Life
American Horrorplex: Louisville's Spookiest Thrill
The haunt I co-own, previewed by WLKY — 80 actors, humble beginnings, and the season ahead.
2024-09-23
Life
Bungee Jumping in Macau: Dive Head First
233 meters off the Macau Tower — when you realize you have a once-in-a-lifetime opportunity, just dive head first.
2024-07-21
Life
How AI Is Transforming Software Development
A panel of leaders at the Rally Global Cross-Sector Innovation Conference on how AI changes the craft — and why the reframe matters more than the tools.
2023-08-31
Speaking
El Toro + Starburst: Query Performance at Scale
350B data points a day, 300% query performance improvement, and $5M in savings on the El Toro data lake.
2023-06-01
Architecture
Fostering Curiosity in Data Engineering
A guest post on the Starburst blog — six ways to foster curiosity in data engineering and drive real results.
2023-03-22
Writing
He Gave Me a Severed Hand With His Contact Information on It. Let Me Explain...
A staffing pro sent me a severed hand with his number on it — and it turned out to be the best sales lesson I've seen.
2021-05-19
Life
Existential Flexibility: Short-Term Sacrifices for Long-Term Success
It's not about being the best — it's about being your best. A Code PaLOUsa 2020 talk on long-term success, sustainability, and growth.
2021-05-05
Speaking
Code PaLOUsa Speaker Interview Series — Richard Teachout
A 2020 interview on how online advertising works, leadership, and the haunted house — plus the talk I gave that year.
2020-07-02
Speaking
Standing Out in the Tech Industry
A remote Code Louisville session during COVID — standing out in tech, from a CTO's seat.
2020-06-18
Life
Wanted to Share Something We Sent From the Asylum Haunted Scream Park to Our Huge Cast
President Evil Bunny's address to the Asylum cast at the start of the pandemic.
2020-03-14
Life
Working Remote: Tips for Leaders and Teams Who Don't Usually Work Remote (and Even Those That Do)
Written during COVID — how leaders and teams suddenly working from home can actually make it work.
2020-03-13
Leadership
Cookie-Free IP Targeting: The HostingAdvice Interview
A 2020 HostingAdvice profile of El Toro — why cookies were crumbling and IP targeting was the answer.
2020-01-02
Speaking
El Toro Podcast S1 E13: Halloween Hustle, Bourbon, and Haunted Houses
The 2018 episode: the haunted-house business, escape rooms, and El Toro adtech — with bourbon.
2018-11-02
Speaking
Haunt Preview 2013: Asylum Haunted Scream Park
A 2013 interview on the Return of the Living Podcast about the Asylum Haunted Scream Park.
2013-09-06
Life
Monsters Wanted: The Documentary About the Year We Built the Asylum
The 2013 documentary about quitting our jobs and building the Asylum Haunted Scream Park in Louisville. Trailer, press, and where to watch.
2013-07-27
Life