Christopher S. Penn – Marketing AI Keynote Speaker

Choose good or fast.

_Almost Timely News: 🗞️ What Are Open Weights Models?

Leave Claude set on Opus 5.5 Medium.

Will AI kill us all?

It’s two weeks to one of the biggest events of the year, the annual Marketing AI Conference, MAICON, put on by SmarterX.

Use AI at the peak of the previous best.

What’s going on with AEO/GEO/AI Visibility/etc.?

_Almost Timely News: 🗞️ The Road to MAICON 2026 (2026-10-11) :: View in Browser_ The Big Plug ✍️ Enroll in my new course, AI for Writers and learn how to make AI write better.

It wasn’t the workshop I thought I was doing.

Summary In today's episode, I walk through the latest developments in agentic AI assistants and break down the five levels of AI enablement along with the risks and opportunities they create.

How do we make better AI tools?

Lexical?

The nerd herd is talking about Jev (and similar models).

I am now more convinced than ever that AI visibility softare is bullshit.

_Almost Timely News: 🗞️ Highly Opinionated Method of Building AI Agent Skills (2026-10-04) :: View in Browser_ The Big Plug ✍️ Enroll in my newest course, Introduction to Deep Research With AI. 👍 This issue features a new paid download, the The Highly Opi…

A very long time ago, I was the Thought Police.

“It’s your always-on assistant”.

Summary In today's episode, I break down what's new in the fifth edition of the LinkedIn Algorithm Guide from Trust Insights and explain how LinkedIn's ranking system really works.

AI doesn’t naturally see across domains.

Summary In today's episode, I walk through how to sanitize historical sales data so your AI models don't inherit and amplify the biases hiding in your CRM.

A bunch of new engines (AI models) came out today.

Summary In today's episode, I tackle how to handle compensation and performance reviews for employees who use AI to finish work in a fraction of the time.

Remember to include scope in your AI prompts.

Summary In today's episode, I break down how to analyze massive multi-year business reports with AI without falling victim to context window limitations or hallucinations.

_Almost Timely News: 🗞️ How I Use AI As a Keynote Speaker & Facilitator (2026-09-27) :: View in Browser_ The Big Plug ✍️ Enroll in my newest course, Introduction to Deep Research With AI. 📺 Watch my 25-minute Intro to GEO talk at Spotlight Summit!

oMLX just added dual ANE support for Qwen3.x models!

Lots of folks are confused by model choosers in AI tools.

“No problem, here’s how you build it.” – Reginald Barclay to the Enterprise computer There’s a fantastic, short scene in Star Trek TNG’s episode “The Nth Degree” in which Lt.

This one’s for Wil Reynolds.

“Show the smallest effective edits.”

_Almost Timely News: 🗞️ What's Changed in Basic AI Prompting (2026-09-20) :: View in Browser_ The Big Plug ✍️ Enroll in my new course, AI for Writers and learn how to make AI write better. 📺 Watch my 25-minute Intro to GEO talk at Spotlight Summit!

What does “responsible AI” even mean?

Summary In today's episode, I examine what becomes the new premium differentiator for brands when AI drives the cost of content creation to near zero.

Everyone in AEO/GEO/AIO/GAIO/LLMO/EIEIO is losing their mind about Reddit AI citations dropping like a rock.

Summary In today's episode, I explain how to justify escalating AI API costs to your CFO when direct revenue ROI isn't apparent, using a blender analogy to reframe the question.

Summary In today's episode, I break down how AI is rapidly making the traditional agency billable hour model obsolete and what firms must do to survive.

It is difficult to overstate how big a deal Qwen3.8 27B is as an AI model.

Summary In today's episode, I break down the strategic case for balancing commercial AI providers like OpenAI against self-hosted open source LLMs, using a "plan big, act small" framework.

Paul Roetzer asked over on Xitter: “I desperately want to understand how open-source absolutists believe open versions of this type of agent ability is safe.

Summary In today's episode, I break down how to choose between building a cheap local AI inference box and setting up a low-cost orchestration computer that hands the heavy lifting to a cloud provider.

Another week, another Pareto distortion in AI.

_Almost Timely News: 🗞️ Creating A Keynote Speaker Second Brain (2026-09-13) :: View in Browser_ The Big Plug ✍️ Enroll in my new course, AI for Writers and learn how to make AI write better.

Five new AI models hit the field this week, and only one of them is probably worth your time.

Summary In today's episode, I tackle whether traditional A/B testing becomes obsolete in an era of AI-generated hyper-personalized landing pages.

Summary In today's episode, I break down why traditional podcast analytics miss the mark and how to measure the entire content ecosystem around your show.

In 48 days – 7 weeks – I and a bunch of other folks are making our annual pilgrimage to Cleveland for #MAICON26, the SmarterX Marketing AI Conference.

Summary In today's episode, I explain how to build a blended scoring rubric by combining different stakeholder definitions of quality so AI can balance competing objectives like marketing appeal, technical depth, and legal safety.

“Every website AI designs looks the same.”

Summary In today's episode, I walk through how to build a proactive AI agent that identifies wasted ad spend and redistributes budget without manual prompting.

Claude Haiku is the single biggest weakness in the Anthropic ecosystem now.