Jeremy Caplan, of Wondertools, one of my favorite newsletters, took the time for a conversation about tools, teaching, and navigating AI. It was a lot of fun, and if you’re not following him, definitely check out his work!
It was my first Substack Live so pardon the poor camera angles. But I really appreciated Jeremy’s work as a whole as he does the really hard work of going out and playing with a lot of interesting and possible tools to give us a good sense of what’s great, what’s ok, and what’s its real value. He was one of the earliest folks highlight Notebook LLM and he’s been great for me to figure out what else might be worth looking at as it relates to the tools that I use to keep myself organized (mostly) and what might be interesting tools to think about from the education and learning space.
You can watch the (unedited) video above, or you can go over to Jeremy’s post, where he edited the conversation into the highlights.
Anyways, it was my first time with it, but I can see the appeal in jumping in, chatting and seeing folks join us live while we navigate the conversation and questions.
Bonus question for folks: Who can identify the person in the frame behind me? First person to comment with the accurate answer (and how you figured it out), may just get a prize!
The Update Space
Upcoming Sightings & Shenanigans
EDUCAUSE Online Program: Teaching with AI. Virtual. Facilitating sessions: ongoing
Recent Recordings, Resources, & Writings:
Margin of Thought with Priten: Season 1, Episode 5: How Can We Center Pedagogy During the AI Tech Wave? (February 2026)
Online Learning in the Second Half with John Nash and Jason Johnston: EP 39 - The Higher Ed AI Solution: Good Pedagogy (January 2026)
The Peer Review Podcast with Sarah Bunin Benor and Mira Sucharov: Authentic Assessment: Co-Creating AI Policies with Students (December 2025)
David Bachman interviewed me on his Substack, Entropy Bonus (November 2025)
The AI Diatribe Podcast with Jason Low (November): Episode 17: Can Universities Keep Pace With AI?
The Opposite of Cheating Podcast with Dr. Tricia Bertram Gallant (October 2025): Season 2, Episode 31.
The Learning Stack Podcast with Thomas Thompson (August 2025). “(i)nnovations, AI, Pirates, and Access”.
Intentional Teaching Podcast with Derek Bruff (August 2025). Episode 73: Study Hall with Lance Eaton, Michelle D. Miller, and David Nelson.
Dissertation: Elbow Patches To Eye Patches: A Phenomenographic Study Of Scholarly Practices, Research Literature Access, And Academic Piracy
AI Syllabi Policy Repository: 200+ policies (always looking for more- submit your AI syllabus policy here)
Finally, if you are doing interesting things with AI in the teaching and learning space, particularly for higher education, consider being interviewed for this Substack or even contributing. Complete this form, and I’ll get back to you soon!
We periodically host small-group workshops and leadership sessions for higher ed teams. You can learn more about our current offerings here.
AI+Edu=Simplified by Lance Eaton is licensed under Attribution-ShareAlike 4.0 International
