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AI or Extinction? Chris Daigle’s Blueprint for Staying Ahead

 

Guest: Chris Diagle
WHY.os: Right Way – Simplify – Make Sense

Chris Daigle is a seasoned entrepreneur and the CEO of ChiefAIOfficer.com, where he teaches business leaders how to use AI in smart, simple ways. With decades of experience in fields like SaaS, real estate, and internet marketing, Chris has developed strategies for success that anyone can follow, especially in today’s fast-changing tech landscape. His insights on the power of AI for business are clear and actionable, making him a must-listen for professionals at any level. Tune in to learn:

  • How to make AI work for your business, even if you’re not a tech expert
  • Why knowing your purpose matters, and how to use it to keep going through challenges
  • The best ways to stay ahead in any industry by building relationships that last

Listen to the full episode for Chris’s top tips and real-life stories on succeeding with AI and business.

Connect with Chris!

LinkedIn
ChiefAIOfficer.com

Watch the episode here


 

 

  • 00:18 – The Importance of Knowing Your Why
  • 02:44 – Early Entrepreneurial Beginnings
  • 06:52 – Lessons from the Military
  • 11:48 – The Transition to Tech and Consulting
  • 17:53 – Entering the Real Estate Market
  • 25:18 – Shift into AI and Digital Marketing
  • 36:34 – The Role of Chief AI Officer
  • 42:30 – Understanding Generative AI
  • 46:24 – AI as a Business Advantage
  • 55:50 – Best Advice for Success

 

The Big “Why” in AI and Business Success: Insights from Chris Daigle on the Beyond Your WHY Podcast

In the latest episode of the Beyond Your WHY podcast, Dr. Gary Sanchez sits down with Chris Daigle, a veteran entrepreneur and AI expert, to dig deep into how today’s professionals can use AI not just to keep up, but to thrive. Chris, CEO of ChiefAIOfficer.com, has led a career through fields as varied as real estate, SaaS, and digital marketing, always guided by an instinct to find better ways of doing things. Today, he’s taking that same energy and applying it to the world of AI, where he believes the future belongs to those who know how to make this technology work for them.

If you’re wondering how AI can impact your work—or whether you’re prepared for the changes ahead—Chris’s insights might just answer those questions. With years of experience building strategies in fast-paced industries, he knows what it takes to stay relevant, especially in tech. In this post, we’ll break down the main takeaways from his conversation with Dr. Sanchez, so even if you don’t catch the full episode, you can take away valuable lessons on career growth, resilience, and what it really takes to succeed with AI.

From Selling Candy to Six Figures: The Entrepreneurial Spirit

Chris Daigle didn’t set out with a formal business plan; he started as a kid selling candy at a markup from his school locker. What he discovered, even back then, was that recognizing a need and finding a way to meet it could lead to real results. His journey from “arbitraging candy” to founding tech companies showed him that traditional paths aren’t the only ways to succeed—and that sometimes the boldest moves pay off the most.

His message? It doesn’t take a fancy setup to get started. In his words, “The best opportunities come when you identify a need and fill it with passion.” By the time he launched his first software company in 2002, he’d already mastered the art of finding his market. For Chris, the key to success isn’t a magic formula; it’s staying attuned to what people need and staying resilient enough to deliver it.

Why AI is Not Just for the Tech Gurus

While many people think of AI as an intimidating, highly technical tool, Chris breaks it down differently. AI isn’t about the complex coding for most of us; it’s about how it can be applied in practical ways. He explains that AI can make everyday tasks more efficient, which means more time for important work. “AI isn’t just a tool; it’s a thought partner that unlocks new ways to do business,” he says, emphasizing that AI can improve productivity, accuracy, and speed when used correctly.

The best part? Chris says you don’t need a technical background to benefit. In fact, he’s built a certification program to help non-technical professionals harness the power of AI without needing to learn code. For Chris, this kind of “thinking in AI” is the future, especially for people who want to be seen as indispensable in their fields. It’s about knowing how AI can support you in doing your job better, faster, and smarter.

Relationships First, Tools Second

In a world obsessed with efficiency and automation, Chris reminds us that relationships are still at the core of business success. He shares how his early relationships in internet marketing helped him gain access to valuable opportunities at companies like Agora. According to Chris, his network isn’t just a list of names; it’s a community of people he’s built trust with over decades, which has been instrumental in every major career move.

The takeaway? Don’t overlook the power of real connections. “Investing in relationships pays dividends years down the line,” Chris notes, pointing out that while AI and tools can help you work smarter, they can’t replace the loyalty and support built through genuine relationships. As technology advances, human connections will become even more valuable—and Chris’s success proves that blending AI with authentic networking is a recipe for lasting success.

Chris Daigle’s journey, from an enterprising kid to a leading AI strategist, shows that while technology is essential, it’s just one part of the puzzle. Success also depends on having a clear purpose, strong relationships, and the willingness to learn new skills—even ones that seem outside your comfort zone. In this episode, he breaks down what makes AI so powerful in business, why anyone can start using it today, and how the right connections can open doors no tool ever could.

About Chris Diagle

In 2024 and beyond, it’s AI enablement … or extinction. I make sure you end up on the winning side by helping your business gain the AI advantage. Our frameworks for teaching you how to start using AI at work make sure you create more time, create more revenue, and create more enjoyment from your business or role.

 

An early pioneer in SaaS, I launched my first software company in 2002 and since then have gone on to found several successful businesses where I was able to develop the entrepreneurial and leadership skills that have led us to where we are now, the cutting edge of AI empowerment for Mid-Market & SMBs, and from the C-suite to the solopreneur.