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  • You Ask, I Answer: Managing LLM Context Window Decay?

    June 29, 2026

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    AI, analytics, Artificial Intelligence, Generative AI, Videos

    Summary In today's episode, I tackle Cecil's question about the best strategies for managing LLM context window decay and token limits during long-running analytical sessions. Here's what this means for you. You'll discover that offloading work to deterministic tools and persistent notes lets you squeeze dramatically more value out of any LLM you use. You'll…

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  • Almost Timely News: 🗞️ How To Improve Advertising with AI (2026-06-28)

    June 28, 2026

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    Christopher S Penn

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    Advertising, AI, Almost Timely, Artificial Intelligence, Generative AI

    _Almost Timely News: 🗞️ How To Improve Advertising with AI (2026-06-28) :: View in Browser_ The Big Plug 👉 My new course, GEO 201 on competitive GEO measurement, is now for sale. Content Authenticity Statement 100% of this week’s newsletter was made by me, the human. In the video version, you’ll see Claude outputs. Learn…

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  • Warning: Why You Must Delete Your Cursor Data Before the SpaceX/xAI Acquisition

    June 26, 2026

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    Christopher S Penn

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    AI, Artificial Intelligence, Business, Data, Generative AI, Law, LinkedOut, Privacy, Public Relations, Technology

    SpaceX/xAI has acquired Cursor. What does that mean for your data privacy? If you are NOT an enterprise customer, and you are using private data with Cursor, now is the time to find a competing product and request deletion of your data, before the deal fully closes. DISCLAIMER: I AM NOT A LAWYER. I cannot…

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  • So What? Top 5 Use Cases of Job Descriptions

    June 26, 2026

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    AI, Business, Jobs, Research, Strategy, Videos

    Summary In today's episode, I walk through the top five strategic use cases of job descriptions beyond just listing job duties, using McKinsey as a real-world example. Here's what this means for you. You'll discover how a single batch of postings can reveal a company's tech stack, strategic direction, and even your own job's vulnerability…

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  • Is the AI Investment Bubble About to Burst? The Hidden Math and Global Shifts Threatening the Hype

    June 25, 2026

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    Christopher S Penn

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    AI, Artificial Intelligence, Books, Data, Generative AI, Google, Influence, LinkedOut, Public Relations, Technology

    Is the AI bubble going to burst? Depends on what you mean. Is the absurd hype, the crazy valuations, and the insane speculation around AI going to burst? Without a doubt, yes. The trillions of dollars flowing into things like data centers and software companies are one math paper away from complete obsolescence, something I’ve…

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  • You Ask, I Answer: Preventing A Dead Enterprise AI Workplace?

    June 25, 2026

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    Artificial Intelligence, Business, Enterprise, Generative AI, Strategy, Videos

    Summary In today's episode, I explore whether offloading cognitive tasks to AI in the enterprise is creating dead workplaces and what you can do to avoid that trap. Here's what this means for you. You can defend your executive function by handing templated work to machines and doubling down on non-templated, judgment-heavy tasks. You'll also…

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  • Why Local AI Is the Reality Check We Need to Stop Anthropomorphizing Machines

    June 24, 2026

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    Christopher S Penn

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    AI, Artificial Intelligence, Data, Generative AI, Google, LinkedOut, Public Relations, Social media, Technology, Video, YouTube

    The greatest gift local AI gives us is bursting the illusion. If you’ve ever spent any time on YouTube or other places watching videos about how magic tricks work, you’ve inevitably felt some level of disappointment once you know how the trick works. You see the double lift on the card or know the numerical…

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  • You Ask, I Answer: Enterprise AI And Institutional Knowledge Loss?

    June 24, 2026

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    Artificial Intelligence, Bias, Business, Generative AI, Management, Videos

    Summary In today's episode, I answer whether replacing mid-career staff with AI risks losing institutional knowledge and explain why your corporate knowledge bases always miss the failure history that actually lives in your employees' heads. Here's what this means for you. You discover that AI systems inherit hidden survivor bias when you train them on…

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  • Why Better AI Tools Aren’t Giving You Better Results: The Power of High-Quality Data

    June 23, 2026

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    Christopher S Penn

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    AI, Artificial Intelligence, Data, Generative AI, LinkedOut, Marketing automation, Productivity, Public Relations, Technology

    The appliances keep getting better. So why isn’t our food? This is the situation a lot of folks are experiencing right now with AI. OpenAI released a new version of Codex today that tries to be Claude Cowork. OpenCode has a slick new UI. Claude Code has new dynamic workflows, in the style of Paperclip…

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  • You Ask, I Answer: Protecting Intellectual Property From Enterprise AI?

    June 23, 2026

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    Artificial Intelligence, Enterprise, Governance, Privacy, Security, Videos

    Summary In today's episode, I explain why enterprises need both contractual agreements and technical safeguards to protect intellectual property from AI model training. Here's what this means for you. You gain a layered defense strategy that closes off the most obvious vulnerabilities before they turn into data leaks. You'll also learn these concepts: how the…

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Christopher S. Penn – Marketing AI Keynote Speaker

Practical, engineering-grade AI strategy for enterprise audiences. No hype, just results.

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