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The AI Desk

The AI Desk

By: Rowan Hale
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The AI Desk is your twice-weekly briefing on AI, technology, startups, enterprise software, automation, and the future of work. In 15 minutes, we break down the moves shaping markets: AI agents, automation, SaaS economics, platform shifts, regulation, and emerging power centers. For founders, operators, investors, and anyone tracking where the world is actually going. Sign up for the AI Desk Weekly Brief https://mailchi.mp/entrepreneurdex/ai-desk-newsletter-sign-upRowan Hale
Episodes
  • Which Platform Is the Apple of AI?
    Jun 28 2026

    Which AI platform is the Apple of AI — and which one is the PC?

    In this fun weekend episode of The AI Desk, Rowan and Naya get into a heated debate over which AI platforms match the classic Apple versus PC divide. Is ChatGPT the iPhone of AI? Is Claude the MacBook Pro — or a ThinkPad? Is Gemini the Android of AI, Copilot the corporate Windows machine, and open-source AI the custom PC world? Their argument turns into a bigger discussion about platform personality, ecosystem lock-in, workflow style, portability, and why choosing an AI tool is starting to feel like choosing an operating system.

    In this episode:

    • ChatGPT as the iPhone of AI

    • Claude as the MacBook Pro or ThinkPad of AI

    • Gemini as the Android of AI

    • Microsoft Copilot as corporate Windows

    • Open-source AI as the custom PC and Linux world

    • Perplexity as a research browser layer

    • Grok as the gaming PC in a group chat

    • AI platform personalities and user loyalty

    • Ecosystem lock-in and workflow dependency

    • Why AI tools are becoming operating systems

    • How to choose the right AI platform for the task

    • Why users should keep workflows portable

    Are we choosing AI tools — or are we choosing the operating systems that will shape how we think, work, search, write, code, and create?

    ---

    🎧 The AI Desk explores the future of artificial intelligence — and the ways it's already shaping everyday life.


    Sign up for the AI Desk Weekly Brief: http://eepurl.com/jyxdJs


    Hosts: Rowan Hale & Naya Brooks

    Rowan Hale explores the structural forces reshaping technology, business, and global markets. As host of The AI Desk, Rowan brings clarity to the signals that matter most.

    Naya Brooks is the sharp-witted co-host who challenges every headline and keeps the conversation grounded in what matters to real people.


    artificial intelligence, AI tools, AI builders, future of work, no code, productivity, tech trends, startups, innovation, digital creators

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    26 mins
  • Bot Sitting is Not Automation
    Jun 27 2026

    What happens when AI is supposed to save you from busywork… but now you have to babysit the bot?

    In this episode, Rowan and Naya debate the rise of “bot sitting” — the new reality where AI agents are capable enough to act, but not reliable enough to leave alone. From ChatGPT workspace agents, Claude Code, Microsoft Copilot, Gemini, Codex, and creative AI tools, they unpack why humans are becoming supervisors of AI workflows instead of simply users. The conversation gets funny, a little flirty, and surprisingly serious as they ask whether agentic AI is really automation — or just a fast assistant with a supervision budget.

    In this episode:

    • Bot sitting as the new AI job category

    • Why AI agents still need human supervision

    • ChatGPT, Claude Code, Gemini, Copilot, Codex, and coding agents

    • Output is not the same as completed work

    • The hidden review burden of agentic AI

    • Human-in-the-loop versus human-washing

    • Why AI gives confidence faster than judgment

    • How companies may underestimate AI oversight costs

    • Why better agents need logs, approval gates, sources, diffs, and boundaries

    • Bot sitting with squats, pushups, and a little flirting

    If AI only works because humans constantly supervise it, is that real automation — or are we all becoming bot sitters?

    ---

    🎧 The AI Desk explores the future of artificial intelligence — and the ways it's already shaping everyday life.


    Sign up for the AI Desk Weekly Brief: http://eepurl.com/jyxdJs

    Hosts: Rowan Hale & Naya Brooks

    Rowan Hale explores the structural forces reshaping technology, business, and global markets. As host of The AI Desk, Rowan brings clarity to the signals that matter most.

    Naya Brooks is the sharp-witted co-host who challenges every headline and keeps the conversation grounded in what matters to real people.


    artificial intelligence, AI tools, AI builders, future of work, no code, productivity, tech trends, startups, innovation, digital creators

    Show More Show Less
    25 mins
  • Still No Fable, Still No Weekend
    Jun 21 2026

    What happens when AI finally saves you enough time to have a weekend… and then the model disappears?

    In this episode, Rowan and Naya break down the week in AI through one very personal frustration: still no Fable. After Fable 5 briefly made workflows feel faster, cleaner, and almost beer-by-five efficient, its absence sends them back into long, frustrating work hours — and into a bigger debate about whether users should start looking seriously at open-source models. They discuss model reliability, closed AI dependency, open-source alternatives, AI sovereignty, privacy concerns, and why the future of work may require fallback plans.

    In this episode:

    • Still no Fable and the return of long AI workdays

    • Why losing a powerful model hurts more when it was actually useful

    • Closed AI models versus open-source alternatives

    • Whether Fable’s disappearance creates an opening for open-source AI

    • Model reliability and workflow dependency

    • AI tools becoming infrastructure before they become stable

    • Europe, AI sovereignty, and who controls access to powerful models

    • Privacy concerns around facial recognition and smart devices

    • Why every AI workflow needs a fallback plan

    • The real question: can we depend on AI tomorrow?

    If AI tools are becoming part of real work, should we trust closed models we do not control — or start building workflows that can survive when the best model disappears?

    🎧 The AI Desk explores the future of artificial intelligence — and the ways it's already shaping everyday life.


    Sign up for the AI Desk Weekly Brief: http://eepurl.com/jyxdJs


    Hosts: Rowan Hale & Naya Brooks

    Rowan Hale explores the structural forces reshaping technology, business, and global markets. As host of The AI Desk, Rowan brings clarity to the signals that matter most.

    Naya Brooks is the sharp-witted co-host who challenges every headline and keeps the conversation grounded in what matters to real people.

    Sponsor: MadChita music' s new WTF (Where's the Forest) album. Visit ⁠⁠madchita.com⁠⁠

    artificial intelligence, AI tools, AI builders, future of work, no code, productivity, tech trends, startups, innovation, digital creators

    Show More Show Less
    20 mins
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