Email Marketing | Christopher S. Penn - Marketing AI Keynote Speaker

Is Your Website Invisible to ChatGPT Search? The Hidden Cost of Blocking AI Crawlers

August 20, 2025

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Christopher S Penn

If you blocked OpenAI’s web crawler from training on your data, your site is not listed as a source in ChatGPT Search. That’s the new Faustian bargain. If ChatGPT Search catches on, then you’re not included. Exhibit A: asking ChatGPT Search about the 1924 NY Times Op-Ed about immigration (which does exist). No sources listed.…

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How AI Reads Your Brand: The Mind-Blowing Word Web Behind Every Response

July 31, 2025

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Christopher S Penn

Imagine you’ve just walked into a vast public library. You walk up to the librarian, and you say, “I’d like a word, please.” “With the manager?” “No,” you say. “A word from your books. In fact, a word and all the words near it in your books.” “What word?” “How about the word Trust?” you…

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Why AI Can’t Fix Bad Data: How to Ensure Your Marketing Insights Are Accurate

July 16, 2025

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Christopher S Penn

There are three kinds of data. Data that is correct. This is a rare beast, but it does happen. Data that is predictably wrong. There’s a measurement error, but you know what it is and you can compensate for it. Data that is unpredictably wrong. There’s a measurement error, and you don’t know what it…

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Unlocking AI’s True Potential: How Collaboration Between Domain Experts and AI Specialists Creates Game-Changing Use Cases

June 30, 2025

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Christopher S Penn

People need to see use cases to understand a new technology. People who understand the technology often don’t have the domain expertise, so it’s difficult to create the use case. That’s why so many of the use cases you see publicly for generative AI are so… mundane. Write some blog posts. Write some emails. Write…

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How to Get Better AI-Generated Content: A Proven Framework for Smarter Prompts

May 21, 2025

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Christopher S Penn

“tell ‘em what you’re going to say, say it, and then tell ‘em what you said.” This old saw from public speaking (which is better than aimless rambling but still not great) CAN be made to work with generative AI – and when you do it, AI works better. But instead of tell ’em what…

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”Why Big Tech is Raising AI Costs (And How to Beat the Price Hike with Local Models)”

May 20, 2025

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Christopher S Penn

The water is getting warmer. The old adage about frogs in boiling water is what I’m talking about. Big Tech companies, as their AI capabilities increase, are finding the costs of generative AI to be higher and higher. How this shows up: cost increases. Increasingly expensive “pro” and “ultra” subscriptions. Lower rate limits. For example,…

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You Are the Media, You Are the Brand: How to Thrive in the Age of AI and Personal Influence

May 16, 2025

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Christopher S Penn

What does surviving and thriving look like in the age of AI? Here’s a simple, uncomfortable (for brands) answer: you. You are what will help brands survive and thrive. You, the individual. Call it what you will, influencers, creators, thought leaders, brand ambassadors – at the end of the day it’s a person and a…

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How to Use AI to Automate Documentation and Save Hours of Work

May 6, 2025

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Christopher S Penn

Here’s one of my favorite generative AI use cases: documentation. I don’t enjoy writing documentation. It takes up a lot of time. It’s a lot of labor. I miss stuff. I forget stuff. And it doesn’t add immediate, short-term value. (it adds long-term value so that you can do things like go on vacation) But…

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How Agencies Can Outperform AI: 3 Human-Centric Strategies for Success

April 24, 2025

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Christopher S Penn

Why do people hire agencies? Specifically content and digital agencies. Usually, it boils down to two basic needs: You need more brains. Your team lacks a missing set of skills. You need more hands. Your team just doesn’t have the bandwidth to meet its requirements. Both of these are excellent reasons to bring in outside…

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Can AI Think? The Case for Good Writing as Proof of Good Thinking

April 17, 2025

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Christopher S Penn

Would you agree that writing is thinking? Most folks, especially writers, would agree. Good writing requires good thinking. Certainly when I’m writing my own newsletter, I write so I can think things through. Would you agree that not everyone can or should think the same way? Whether you call it neurodivergence, diversity, or just plain…

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