Shows / Christopher S. Penn – Marketing AI Keynote Speaker
Episodes
- Christopher S. Penn – Marketing AI Keynote Speaker
DeepSeek v4 Flash vs. Claude Sonnet 5: Why Paying 17.8x More for AI Is a Mistake
This one hastily made slide explains pre-IPO jitters better than anything else when it comes to AI. DeepSeek released its v4 Flash model earlier this year, on…
- Christopher S. Penn – Marketing AI Keynote Speaker
Blatant Sales Pitch: AI for Writers Course
Let's examine this pile of AI slop, generated by ChatGPT: If you’re a writer, you’ve probably noticed something changing fast: AI isn’t replacing the need for…
- Christopher S. Penn – Marketing AI Keynote Speaker
How Fifth-Generation AI Masters Time Budgeting for Smarter Workflows
Fifth generation AI models understand time. I discovered this morning, working in Claude Code with Sonnet 5, that it can have an awareness of time and work to…
- Christopher S. Penn – Marketing AI Keynote Speaker
Almost Timely News: 🗞️ How To Expand and Improve Content with AI, Part 2 (2026-08-23)
_Almost Timely News: 🗞️ How To Expand and Improve Content with AI, Part 2 (2026-08-23) :: View in Browser_ The Big Plug Pre-registration for my new course, AI…
- Christopher S. Penn – Marketing AI Keynote Speaker
Prove It’s Human: Why the Not AI Certification Is Your New Marketing Advantage
Scott Stratten called it early this year: certifying that something is NOT AI is a marketing feature now. This morning, as I was making a terrible drawing on…
- Christopher S. Penn – Marketing AI Keynote Speaker
So What? How to Set Up Your Own Claude Marketplace
Summary In today's episode, I walk through how to set up your own Claude marketplace using GitHub as a central version control system for AI skills and…
- Christopher S. Penn – Marketing AI Keynote Speaker
You Ask, I Answer: Processing Sensitive Data With Local AI Pipelines?
Summary In today's episode, I walk through how to build a private local AI pipeline for processing years of sensitive personal messages on a consumer laptop…
- Christopher S. Penn – Marketing AI Keynote Speaker
Beyond the 94% Hype: What AI Can Actually Do at Work Today
What percentage of your tasks can AI do? If you believe companies like Anthropic (which has a vested interest in selling as much AI as possible), that number…
- Christopher S. Penn – Marketing AI Keynote Speaker
You Ask, I Answer: Why AI Visibility Reports Are Snake Oil?
Summary In today's episode, I break down why most AI brand visibility tools are unreliable and what you should actually measure instead. Here's what this means…
- Christopher S. Penn – Marketing AI Keynote Speaker
Avoid AI Copyright Infringement: Start With Public Domain for Safe, Legally Sound AI Generation
Give AI safe starting materials to avoid infringement. DISCLAIMER: I AM NOT A LAWYER. I CANNOT GIVE LEGAL ADVICE. CONSULT A QUALIFIED LAWYER IN YOUR…
- Christopher S. Penn – Marketing AI Keynote Speaker
Hero or Villain: How Positive Messaging Wins Audiences
Compare these two sets of messages. Positive: You belong You are welcome here You are one of us You are not to blame You are part of the solution You are one…
- Christopher S. Penn – Marketing AI Keynote Speaker
AI Automation Accelerates: How One Year of Breakthroughs Is Reshaping the Future of Work
What a difference a year makes. I was putting together slides for a private workshop I’m doing today, and for fun I decided to take a snapshot of…
- Christopher S. Penn – Marketing AI Keynote Speaker
Skip the Cloud AI Bills: How Chinese Open-Source Models Slash Enterprise LLM Costs
China strikes again. Two big model releases this week – Minimax H3 (Hailuo), king-size video generator, which can run on a machine that can support 500…
- Christopher S. Penn – Marketing AI Keynote Speaker
Don’t Put a V8 in Your Prius: How to Safely Choose AI Models for Autonomous Systems
Be careful what engine you put in your car. GPT-5.6 is unquestionably a very smart model, highly capable, up there as an Opus-class model along with Opus 4.8…
- Christopher S. Penn – Marketing AI Keynote Speaker
The AI Hiring Crisis: Why Human Referrals Are Your Only Way In
Late Friday afternoon thoughts. AI has made recruiting nearly impossible. From a hiring manager’s perspective, every candidate looks identical now, all…
- Christopher S. Penn – Marketing AI Keynote Speaker
Almost Timely News: 🗞️ How to Build a Cheap AI Setup (2026-08-09)
_Almost Timely News: 🗞️ How to Build a Cheap AI Setup (2026-08-09) :: View in Browser_ The Big Plug 👉 New merch! The Trust Insights Deep Research Suite Content…
- Christopher S. Penn – Marketing AI Keynote Speaker
The Real ROI of AI in Education: Turning Mediocre Students Into Top Performers
Results oriented. Outcome driven. Proven track record. Do these phrases sound familiar? They should. They top the LinkedIn bios and CVs of millions of people…
- Christopher S. Penn – Marketing AI Keynote Speaker
So What? Theoretical AI Usage
Summary In today's episode, I walk through Trust Insights' new paper on theoretical AI usage and what jobs AI could actually do. Here's what this means for…
- Christopher S. Penn – Marketing AI Keynote Speaker
You Ask, I Answer: Optimizing for Agentic Mode?
Summary In today's episode, I break down how companies should navigate the gap between optimizing for AI-generated summaries and optimizing for AI agents that…
- Christopher S. Penn – Marketing AI Keynote Speaker
Stop AI Slop: 21 Generative AI Use Cases for Marketers
Are you tired of AI generating slop? I’m certainly tired of getting it, and content creation is arguably one of the least interesting use cases of AI…
- Christopher S. Penn – Marketing AI Keynote Speaker
You Ask, I Answer: Pivot or Stick It Out?
Summary In today's episode, I walk through how to decide whether to rebuild or pivot when your main marketing channel collapses. Here's what this means for…
- Christopher S. Penn – Marketing AI Keynote Speaker
AI Generated a Novel in 51 Minutes. Here’s Why Human Connection Still Wins in Influencer Marketing
Last night I used Minimax M3 to generate a steaming pile of AI slop in 51 minutes, a 50,000 word 1920s romance novel set in Venice. (and it’s terrible) I…
- Christopher S. Penn – Marketing AI Keynote Speaker
How to Generate Unique AI Music Using Public Domain Archives for Less Generic, Defensible Tracks
How do you generate less generic music with AI? You start by using existing music. AI, by definition, will create mathematical averages of the tasks you give…
- Christopher S. Penn – Marketing AI Keynote Speaker
You Ask, I Answer: Setting Test Timeline Expectations?
Summary In today's episode, I answer a question about how to set realistic client expectations for marketing A/B testing timelines using data-driven…
- Christopher S. Penn – Marketing AI Keynote Speaker
Don’t Trust Generative AI Until You Run the BBQ Bias Benchmark
Let’s talk about BBQ. Not the food, the Bias Benchmark of QA, a test of AI’s ability to navigate known human biases. BBQ dates back to 2021, when…
- Christopher S. Penn – Marketing AI Keynote Speaker
Almost Timely News: 🗞️ Can AI Be An Investment Expert? (2026-08-02)
_Almost Timely News: 🗞️ Can AI Be An Investment Expert? (2026-08-02) :: View in Browser_ The Big Plug 👉 New merch! The Trust Insights Deep Research Suite…
- Christopher S. Penn – Marketing AI Keynote Speaker
You Get What You Pay For: Why Supporting Human Authors Beats AI Slop
Two enduring maxims: Fast. Cheap. Good. Choose any two. You get what you pay for. Earlier today, my friend alerted me about a discussion on X, visible in the…
- Christopher S. Penn – Marketing AI Keynote Speaker
So What? How AI Detectors Work
Summary In today's episode, I walk through how AI detectors actually work under the hood and why their results are far less trustworthy than most people…
- Christopher S. Penn – Marketing AI Keynote Speaker
Hands-On AI Workshops for Marketers: Why You Need to Attend MAICON 2026
Back in 2019, Paul Roetzer asked me to speak at a brand new event, the Marketing AI Conference, MAICON hosted by the Marketing AI Institute. This was 3 years…
- Christopher S. Penn – Marketing AI Keynote Speaker
You Ask, I Answer: Handling AI Context Drift?
Summary In today's episode, I tackle Cooper's question about handling context drift and hysteresis in long-running persistent agent sessions, explaining why…
- Christopher S. Penn – Marketing AI Keynote Speaker
Stop the SaaS Trap: How to Use FOSS and AI to Build Custom Software You Actually Own
A reminder that there is a 3rd way between “vendor lock-in” and “YOLO vibe code an alternative”. That way is called FOSS: Free, Open…
- Christopher S. Penn – Marketing AI Keynote Speaker
You Ask, I Answer: Multi Agent AI Orchestration Costs?
Summary In today's episode, I break down why complex multi-agent orchestrations are wildly expensive and share practical model selection strategies to slash…
- Christopher S. Penn – Marketing AI Keynote Speaker
The Truth About AI Bias: Why It Can Never Be Completely Removed
There is no such thing as removing bias from generative AI completely. None. Zero. Anyone making that claim is lying, period, end of story. Here’s why. A…
- Christopher S. Penn – Marketing AI Keynote Speaker
You Ask, I Answer: Falsifying CRM Data?
Summary In today's episode, I tackle the question of whether falsifying CRM data using AI is a performance problem or a technology problem and explain why…
- Christopher S. Penn – Marketing AI Keynote Speaker
The Machines Are Taking Over: Why Your Digital Marketing Strategy Must Pivot to AI Bot Traffic
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…
- Christopher S. Penn – Marketing AI Keynote Speaker
How to Use Cloudflare’s New AI Bot Controls to Protect Your Content and Brand
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…
- Christopher S. Penn – Marketing AI Keynote Speaker
Stop Flying Blind: Why You Must Test Token Usage Before Scaling Enterprise AI
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…
- Christopher S. Penn – Marketing AI Keynote Speaker
Caught Red-Handed: How Hidden HTML Tags Are Exposing Secret AI Use in Fan Fiction
Disclose your use of AI. Ruby King and I were chatting about surreptitious use of AI earlier today and one of the hottest topics right now is use of AI in fan…
- Christopher S. Penn – Marketing AI Keynote Speaker
Almost Timely News: 🗞️ How to Connect an AI Agent to a Data Source (2026-07-19)
_Almost Timely News: 🗞️ How to Connect an AI Agent to a Data Source (2026-07-19) :: View in Browser_ The Big Plug 👉 New book! 21 Use Cases of Generative AI For…
- Christopher S. Penn – Marketing AI Keynote Speaker
Stop Overpaying for Chatbots: How to Tell if an AI is Actually an Agent
PSA: Agents do stuff for you. In all the buzz about AI agents, very few people are using the term for what it means. Agents in computing are not new…
- Christopher S. Penn – Marketing AI Keynote Speaker
So What? How to Analyze AI Visibility vs Human Search
Summary In today's episode, I walk through how to compare AI bot visibility against human search traffic using Bing Webmaster Tools and a coding-driven…
- Christopher S. Penn – Marketing AI Keynote Speaker
You Ask, I Answer: Autonomous Expense Recovery Via AI?
Summary In today's episode, I answer Zachary's question about when autonomous AI expense recovery hits a no-brainer price point for enterprise budgets. Here's…
- Christopher S. Penn – Marketing AI Keynote Speaker
Stop Paying for the Same Prompt: How to Use AI to Build Permanent, Zero-Cost Solutions
The best use of AI is to create tools so you don’t have to use AI. Unquestionably, generative AI is powerful. It lets you accomplish things outside your…
- Christopher S. Penn – Marketing AI Keynote Speaker
You Ask, I Answer: Replacing Fine Tuned Models With RAG?
Summary In today's episode, I explore why retrieval augmented generation and hybrid databases render fine-tuning obsolete for most enterprise AI applications…