Sidecar Blog

Illustration of a glass-blower shaping a new glass vessel, representing the creation of new value.

5 min read

Beyond Automation: Creating New Forms of Value with AI

“How many hours can we save?” It is the first question most leadership teams ask when they start exploring artificial intelligence. The math is tempting. If an algorithm can draft a newsletter in ten seconds or process event registrations...

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A glowing desk lamp illuminates blueprints and a compass at the head of an empty boardroom table.

5 min read

Why Your AI-Native Strategy Needs a Dedicated Leader

The conventional wisdom in association management dictates that new technology belongs in the IT department. When a new association management system...

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A drafting compass and digital caliper on a blueprint.

4 min read

The 99% reduction: How AI changes the economics of innovation

The conventional wisdom in association management dictates that launching a new digital initiative requires a massive budget, a long timeline, and a...

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Sidecar Sync Episode episode 139 cover featuring Jon Cheney and Mallory Mejias

49 min read

The $400 AI Startup with Jon Cheney | [Sidecar Sync Episode 139]

Summary: What if building a million-dollar business no longer required a team, funding rounds, or even technical expertise? In this episode of the...

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An illustration of an architect using a magnifying glass to inspect a complex blueprint on a drafting table.

5 min read

From Wizard to Patron: The New Reality of Commissioning AI Work

The way professionals interact with artificial intelligence is undergoing a quiet but fundamental transformation. For the past couple of years, the...

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An illustration of a modular workshop with interchangeable tools on a pegboard.

5 min read

The 'TV Metaphor' for Choosing Your AI Model Strategy

Associations are intimately familiar with the concept of vendor lock-in. For decades, technology planning has often meant choosing a single ecosystem...

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A brass magnifying glass focuses on a single out-of-place data point on a hand-drawn scatter plot.

5 min read

Stop Asking AI to Write. Start Asking It to Find Paradoxes.

For many association professionals, artificial intelligence has become the ultimate administrative assistant. We use it to draft newsletters,...

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Sidecar Sync Episode episode 138 cover featuring Amith Nagarajan and Mallory Mejias

42 min read

AI Solves an 80-Year Mystery, Microsoft Agents Take Over, & Anthropic’s Claude Mythos vs. Fable | [Sidecar Sync Episode 138]

Summary: In this episode of the Sidecar Sync, Amith and Mallory explore three major developments shaping the future of AI. First, they unpack how an...

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Illustration of a weaver working at a loom, representing the process of weaving individual threads into a cohesive organizational fabric.

6 min read

What Is 'Owned Intelligence' and Why It Matters to Associations

Associations have long thrived on a very specific, highly valuable asset: deep, historical understanding of their members and their industries. This...

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