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  • Almost Timely News: 🗞️ How to Demonstrate Your AI Chops in Job Hunting (2026-07-26)

    July 26, 2026

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    Christopher S Penn

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    AI, Almost Timely, Artificial Intelligence, Generative AI, Newsletter

    _Almost Timely News: 🗞️ How to Demonstrate Your AI Chops in Job Hunting (2026-07-26) :: View in Browser_ The Big Plug 👉 New book! 21 Use Cases of Generative AI For Marketers Content Authenticity Statement 90% of this week’s newsletter was made by me, the human. You’ll see multiple outputs from Claude Opus 5 including…

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  • Why AI Editing Is Making Your Writing Boring and How to Fix It

    July 24, 2026

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    Christopher S Penn

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    AI, Artificial Intelligence, Data, Generative AI, Law, LinkedOut, Public Relations

    A reminder that editing with AI makes works read more like AI. When GenAI works on text, it works in probabilities. That’s literally how it works at its heart, figuring out the most probable next item in a sequence based on the data in the sequence. It’s why it’s so good at things like predicting…

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  • So What? How to Build New Microsoft Copilot Capabilities

    July 24, 2026

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    AI, Almost Timely, Code, Generative AI, Marketing Technology, Videos

    Summary In today's episode, I walk through practical techniques for extending Microsoft Copilot's capabilities beyond its out-of-the-box limitations using skills, agents, and its built-in Python environment. Here's what this means for you. You can transform a tool often dismissed as inferior into a capable enterprise AI system that handles deterministic tasks like word counting, regression…

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  • You Ask, I Answer: AI For Churn Analysis?

    July 24, 2026

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    Christopher S Penn

    ·

    AI, analytics, Data Science, Generative AI, Marketing, Videos

    Summary In today's episode, I walk through how to use AI coding tools to run cohort churn analysis on your AI-generated leads. Here's what this means for you. You'll be able to determine whether specific lead sources are actually worth your marketing investment. You'll also learn these concepts: how to set up a coding environment…

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  • The Machines Are Taking Over: Why Your Digital Marketing Strategy Must Pivot to AI Bot Traffic

    July 23, 2026

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    Christopher S Penn

    ·

    AI, Almost Timely, Artificial Intelligence, Data, Email Marketing, Generative AI, Google, Law, LinkedOut, Marketing, Newsletter, Podcasting, Public Relations, Social media, Video, YouTube

    Today on the Trust Insights livestream, I showed how I wired AI bot traffic data into a separate Google Analytics 4 account. What this showed, which was fairly stunning, was a tale of 2 websites. On the left, a regular GA4 account which blocks bots so that you get a sense of the humans on…

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  • You Ask, I Answer: Structuring Data For AI?

    July 23, 2026

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    AI, Data, Generative AI, Marketing Technology, SEO, Videos

    Summary In today's episode, I walk through how to structure data for machines using JSON, schema, and lighter alternatives to improve AI search visibility. Here's what this means for you. You discover that GEO requires passing three sequential gates and that lighter weight formats like markdown and YAML may serve your AI visibility far better…

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  • How to Use Cloudflare’s New AI Bot Controls to Protect Your Content and Brand

    July 22, 2026

    ·

    Christopher S Penn

    ·

    AI, Artificial Intelligence, Brand, Data, Generative AI, Law, Leadership, LinkedOut, Marketing, Strategy

    Choose which bots to block carefully. Cloudflare, a couple days ago, made significant changes to how they identify AI bots. You can now block specific classes and types of AI bots, and they’re in three categories: AI Crawler: this vacuums up your content to feed model training data AI Search: this bot searches for stuff…

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  • You Ask, I Answer: Consuming High Velocity AI Content?

    July 22, 2026

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    AI, Content, Newsletter, Podcasting, Videos, YouTube

    Summary In today's episode, I answer a listener's question about how to keep up with the massive volume of content I create and explain the strategy behind that output. Here's what this means for you. You learn that you don't have to consume everything, because there are smart ways to filter, summarize, and access exactly…

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  • Stop Flying Blind: Why You Must Test Token Usage Before Scaling Enterprise AI

    July 21, 2026

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    Christopher S Penn

    ·

    AI, Artificial Intelligence, Business, Generative AI, LinkedOut, Public Relations, Review, Technology

    One of the best things you can do in enterprise AI is set up testbeds to count tokens. Here’s why. Claude’s enterprise pricing is this: Opus 4.8: $5/million tokens in, $25/million tokens out Sonnet 4.6: $3/million tokens in, $15/million tokens out Microsoft’s pricing is based on Copilot Credits; 1 credit is one penny, and they…

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  • You Ask, I Answer: How To Drive Enterprise AI Adoption?

    July 21, 2026

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    AI, Artificial Intelligence, Business, Management, Strategy, Videos

    Summary In today's episode, I tackle Tim's question about whether to mandate AI adoption across non-technical departments or let it grow organically, and I make the case for reframing AI as a way to save jobs and cut software costs instead of headcount. Here's what this means for you. You gain a sharper lens for…

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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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