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Not Brothers Podcast Not Brothers
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Not Brothers is a long-form show, which means the catalog gets better when it has paths through it. These are the easiest ways to understand the show fast.

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Ep 10May 13, 2026

Does AI Make Us Dumber?

Mark and Ryan pick up the AI-in-education thread and push it further: if AI can write the paper, build the tool, summarize the research, and automate the busy work, what exactly are humans supposed to learn, practice, and protect?

Ep 9Apr 29, 2026

AI in Critical Thinking and the Weirdness it Creates

When a school's strict no-AI policy expels two seniors weeks before graduation, Mark and Ryan dig into the real question: what are we actually testing — and where's the line between AI as a calculator and AI as plagiarism?

Ep 8Apr 15, 2026

Are You Working ON or IN Your Business?

In this episode of the Not Brothers Podcast, Mark and Ryan dig into one of the most important questions for entrepreneurs: are you working in your business, or on it? Using Oodle’s long-running offsite rhythm as the backdrop, they break down how stepping away from daily execution creates space for alignment, strategic thinking, and better decision-making.…

Ep 4Feb 19, 2026

Rants About Wasting Time in Meetings

Ryan and Mark rant productively about meetings: remote work, async vs synchronous collaboration, open offices, unstructured thinking time, calendar theater, Level 10-style structure, and why being busy is not the same thing as doing useful work.

Ep 2Feb 6, 2026

Build vs. Buy: Navigating Software Buying Decisions

Ryan and Mark unpack the build-vs-buy software decision: when custom tools make sense, where off-the-shelf platforms win, how internal politics and maintenance costs creep in, and why the real answer depends on appetite, resources, and organizational reality.

Ep 3Feb 6, 2026

AI Fireside Chat (sans fire)

Ryan and Mark talk through the fast-moving AI landscape: agentic models, tools, skills, business use cases, security risks, human oversight, model choice, experimentation, and what teams should understand before they shove AI into everything.

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