Insights

AI leadership for the C-suite

Perspectives from the team building Co-CxO on AI strategy, executive decision-making, and what's actually working for CEOs.

Perspectives from the team building Co-CxO on AI strategy, executive decision-making, and what's actually working for CEOs.

The Wild West Inside Your Company 

The EU just gave companies an extra sixteen months to comply with its AI accountability law. If your reaction to that sentence is relief, keep reading.  Article 86 of the EU Artificial Intelligence...

Five Things Co-CxO Actually Delivers 

By Wade Wyant, Founder, REDEGADES.AI  When leaders ask me what Co-CxO actually does for a business, I don’t lead with technology. I lead with the five things every CEO is measured...

AI Didn’t Fail Ford. Ford Failed Their AI. 

The automaker just gave every business leader in America the most expensive lesson in AI strategy. Here is what you need to learn from it.  Ford had a problem. Quality was...

Stop Protecting Your Data from the Wrong Enemy 

Your AI paranoia is costing you more than a data breach ever would.  There is a conversation happening in boardrooms across the country, and it is costing businesses millions of dollars in lost...

Your Leadership Team Is Using AI. That’s the Problem.  

When every leader runs their own AI on their own data, the company doesn’t get smarter. It gets more divided. Here’s what’s quietly happening in your...

Bias: Build a Machine That Thinks Like You

Bias: Build a Machine That Thinks Like You  Generic AI doesn’t know your leadership bias, but REDEGADES.AI’s bespoke and private AI is trained on your judgment, priorities, and strategy. ...

You Just Bought a One-Way Ticket. Now What?  

AI has unlocked a gold rush of software development inside your business. Before you celebrate, answer four questions.  THE DAM JUST BROKE  For twenty years, your company did the smart...

The Lens That’s Costing You the AI Race

Most companies are not failing at AI because AI is hard. They are failing because they are looking at it through a lens that is twenty years old. And that lens was built from decisions that were, at...

Why Does Custom AI Give You a Strategic Advantage?

Why Does Custom AI Give You a Strategic Advantage?  There is a dangerous illusion happening in business right now. Executives believe they are gaining a competitive advantage simply because they...

AI as a Co-CxO: More Than Just an Answering Machine

AI as a Co-CxO: More Than Just an Answering Machine  How can you get a better ROI on AI? How can you use AI more effectively than your competition? Most executives are already using AI in some...

From 2D to 3D: Custom AI for All, Not Just One-on-One  AI Usage 

Most leaders today are still living in a two-dimensional AI world. Leaders work with AI in a flat, transactional space, a simple exchange between a person and a tool. You ask a question; it gives an...

The AI Paradox: Why We Avoid What Matters Most

There is a pattern playing out in boardrooms that no one is talking about. It is not technical or financial. It’s psychological and it may be the single biggest reason AI is underperforming at the...

Which Way Will AI Steer Your Business?

Contributor: Wade Wyant The morning I first realized an AI should challenge me (not assist and obey), I was sitting in my office staring at a polite, but useless answer ChatGPT had just given me. It...

Why AI Should Think Like You

Why AI Should Think Like You  Most companies are building AI systems that are incredibly intelligent, but they remain strangely disconnected from how their leaders actually think. Executives...

Independence: The Most Overlooked AI Advantage

Artificial intelligence has reached a strange moment in the executive world. Nearly every C-level executive is using it, and the majority of boards are discussing it. Even more, almost every company...

Generic AI Has Information. Custom AI Knows Your Company.

Most leaders today are experimenting with AI. They use it to summarize information, draft emails, or brainstorm ideas. And while these uses are helpful, they only scratch the surface of what AI can...

Contributing Authors for REDEGADES.AI

Wade Wyant
Founder

Jason Baker
Co-Founder | CTO

Chuck Hegerty
Chief Revenue Officer

Brian Beute
VP of Data Operations

Real Talk with REDEGADES.AI

Real Talk with REDEGADES.AI is a thought leadership video series from Wade Wyant and Jason Baker, Founder and Co-Founder of REDEGADES.AI. Each episode is a short, straight-talking conversation delivering real insights on AI, executive leadership, and what it truly takes to build an intelligent organization. No fluff, no theory — just honest, bite-sized discussions on how CEOs and leadership teams can harness AI as a strategic partner to make better decisions, scale faster, and stay ahead of the competition.