Christopher S. Penn
Christopher S. Penn shares practical AI and marketing lessons through Almost Timely, YouTube and Marketing Over Coffee, alongside his work as co-founder and chief data scientist at Trust Insights.
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Latest
Christopher’s happenings, collected from public sources, plus his backstory and Starbook, where fans write.
Known for
Book
Newsletter and YouTube
Trust Insights AcademyOverview
- Work
- AI educator, data scientist, author and keynote speaker
- Early community milestone
- Co-founded PodCamp with Chris Brogan in 2006
- Podcast
- Co-host of Marketing Over Coffee with John J. Wall
- Company
- Co-founder and chief data scientist at Trust Insights
- AI beginnings
- Started working with AI and machine learning in 2013
Mini bio
How it started.
Before the AI tutorials, Christopher was producing the Financial Aid Podcast while working in student lending. A 2008 interview describes how the show brought financial-aid information to listeners and introduced them to the Student Loan Network.
Building a community.
In 2006, he and Chris Brogan helped turn conversations among New England podcasters into PodCamp. Inspired by BarCamp’s participant-led format, they created a gathering for people making blogs, podcasts and online video. The first PodCamp took place in Boston on September 9 and 10, 2006.
Keeping the conversation going.
By 2007, Christopher was making Marketing Over Coffee with John Wall. The weekly show remains a place to hear them talk through new and established marketing ideas. His own publishing now includes Almost Timely, with written, video and audio editions.
From analytics to AI.
Christopher dates his AI and machine-learning work to 2013. He later co-founded Trust Insights with Katie Robbert. The company was incorporated in December 2017 and publicly launched on March 19, 2018. He serves as its chief data scientist and teaches through talks, demonstrations and courses.
Ideas that last.
In June 2025, he released Almost Timeless, a book built around 48 foundational principles of generative AI. His announcement explains that the project grew from a question he kept hearing in workshops and boardrooms: how to keep up with AI.
Creditschronological, newest first
Books and teaching
- 2026AI for WritersInstructor
- 2025Almost Timeless: 48 Foundation Principles of Generative AIAuthor
Podcasts and video
- 2026In-Ear Insights: Live from MAICON 2026Co-host with Katie Robbert
- 2025Mind Readings: Never Think Alone, AI as a Thought Partner, Part 5Presenter
- 2007–presentMarketing Over CoffeeCo-host with John J. Wall
Community
- 2006PodCampCo-founder with Chris Brogan
Awards
Quotes
When I make a claim, I show you the code. When I present findings, I share the methodology.Christopher S. Penn, About Christopher S. Penn
On his approach to showing the work behind his advice. Source: https://www.christopherspenn.com/about/
Trivia
- He has trained in ninjutsu at the Boston Martial Arts Center; in a 2007 autobiographical post, he described himself as a 14-year practitioner.
- He played music on the Financial Aid Podcast because he loved sharing it, even on a show about student funding.
- The standard edition of Almost Timeless included an audiobook read by Google’s AI; the deluxe edition also included his original rough audio recordings from his car.
Find Christopher
Follow his videos, read Almost Timely and keep up with his latest AI experiments.
Are you Christopher S. Penn?
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