Derek Weber

10 Life Lessons from Hiking 100km of El Camino

Meaning / 6 minutes of reading

“There’s a trail that goes up the coast where you walk from one small town to the next. Wanna do it?” Such a potentially cool and interesting experience…it was a quick and easy yes for me. My roommate all through college and best man in my wedding has worked internationally for the last 15 years and I’ve visited him at every stop of his journey from Seoul to Beijing, Copenhagen to Singapore. In early 2020, …

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AI Failure to Launch: The 5 Real Reasons Leaders Stay Stuck (And It’s Not What You Think)

AI, Leadership / 8 minutes of reading

The conversation started like so many others I’ve had with successful business leaders over the past six months. “I know we need to be doing something with AI,” he said, leaning back in his chair. “I read the articles. I’ve watched the demos. I even signed up for a ChatGPT account months ago.” He paused, and I could see the frustration building. “But honestly? I’ve used it maybe three times.  And when I do, I …

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From 0 to 1: How to Find Your First Win With AI

AI, Leadership / 7 minutes of reading

The Resistance No One Really Talks About Earlier this week I walked out of yet another conversation about AI feeling…flat and frustrated. I had just shared some of the most exciting ways I’ve been using AI as Partner, how it’s helped me think bigger, move faster, create at a higher level. The people I was with nodded, even said things like “That’s amazing!” and “I need to do more of that.” But then? Nothing. No …

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The Hidden Walls Between You and AI Mastery (And How to Break Through Them)

AI, Leadership / 6 minutes of reading

Leading with AI isn’t about mastering the tools — it’s about mastering yourself through every wall you face. The Fog Before the Climb I didn’t start my AI journey from a place of excitement. I started from a place of resistance. Fear. Doubt. Overwhelm. The quiet, reasonable voice whispering “You don’t have time to figure this out right now.” These emotions wrapped around me like a heavy fog, clouding my judgment and anchoring my feet …

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Build the Business You’ve Always Envisioned — A Personal Invitation

AI / 3 minutes of reading

I’m guessing you’re like me that you’ve got a pretty clear picture of the kind of business you want to build: one that runs smoothly, supports your team, creates real impact, and gives you more time (and profit) to focus on what matters most. The hard part? Finding the time and headspace for the building blocks you know will actually get you there. That’s exactly why I’m launching the Lead With AI membership. Not to …

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Leverage AI to Lead Smarter—3 Sessions to Transform Your Strategy

AI / 2 minutes of reading

Stop Wondering Where to Start Are you hesitant to dive into AI because you’re unsure where to begin? Many leaders feel the same—they’ve dabbled or held back, unsure if AI is relevant to their industry or worth the time investment. Here’s the truth: AI isn’t just for tech experts or specific industries. It’s for leaders like you, ready to work smarter, think bigger, and better align your team with the future. But making this leap …

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How I Used AI to Create a More Compelling Strategic Vision in 7 Steps

AI, Leadership / 9 minutes of reading

“Does this really even matter or am I just wasting my time?” Strategic planning, even in somewhat stable times, often felt like a mix of hopes, dreams, wishes, tea leaves, and spreadsheets. Now, with so many more things changing more quickly than ever, I found myself spinning and flailing, the sound of the ticking clock counting down to our EOS 2-Day Annual Planning drowning out any useful trains of thought. Intellectually, I know strategic planning …

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The Hardest Part of AI Isn’t the Tech—It’s Getting Started

AI, Leadership / 6 minutes of reading

5 Industries About to Be Turned Upside Down There was an audible gasp across the room of 70+ entrepreneurs, not the easiest cohort to knock off-center. John Sinai, a futurist who worked with NASA to help develop plans for a self-sustaining lunar city and an AI expert at both Duke and Singularity University, had just shared his prediction of the next five industries that will be disrupted down to a marginal cost of zero. When …

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The Hidden Trap of Resilience: When Pushing Forward Holds You Back

Leadership, Meaning / 4 minutes of reading

The Battle Unknown As the amount of change and volatility continues to accelerate, being a leader today requires more resiliency and adaptability than ever before. My resiliency, certainly like yours, was built one piece of hard-earned armor at a time until I became fully plated, fully confident I could power through to the other side of any situation. Which worked well, until it didn’t. Until the armor that protected me started to hurt me. The …

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Finding Opportunity in Uncertain Times

Leadership / 5 minutes of reading

The King’s Challenge In an ancient kingdom, a skilled jeweler with modest roots longed to elevate his standing and become the royal jeweler. When the king announced a search for a new master craftsman, the jeweler seized the opportunity. Summoned to the palace, he with hundreds of others, faced the king. “Craft me a piece of jewelry that can make a happy person sad and a sad person happy,” the king challenged. “Do this, and …

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