Jonathan Brill on Get Down to Business with Scott “Shalom” Klein

Oct 22, 2025

Jonathan Brill spoke with Scott “Shalom” Klein on the Get Down to Business radio show about why most AI initiatives are failing. The problem isn’t the technology, it’s that leaders are trying to force cutting-edge tools into outdated, rigid organizational structures.

During the conversation, Jonathan explains an alternative approach: the “octopus organization,” inspired by how octopuses distribute intelligence across their tentacles rather than centralizing all decision-making in one brain. As AI makes every employee exponentially smarter, he argues, companies must stop micromanaging and start empowering teams to innovate independently.

Whether you’re leading a startup or transforming an established business, this conversation offers a provocative framework for thinking differently about AI implementation—focusing less on automation and more on organizational transformation.

Listen to the full conversation here:

The full episode is also available on Spotify.

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