Sidecar Blog

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Leadership (6)

Conceptual illustration showing two groups of professionals on separate cliffs—one in coral, one in teal—building a bridge between them with planks and a rope ladder. The teal group uses AI technology, symbolizing closing the education and technology divide.

7 min read

The AI Divide Isn't About Money (And Why That Makes It More Urgent)

Anthropic just released its third economic index report, and the findings are striking. The company analyzed millions of conversations across...

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A bright aerial view of a forest trail splitting into two sunlit paths. A few solo hikers walk calmly on the “Optional” path, while a friendly group in coral and teal gear walks together on the other path under warm, golden sunlight filtering through tall trees.

9 min read

The End of Optional: Why Leading Organizations Are Mandating AI Training

Citibank just made headlines by requiring all 175,000 of its employees globally to complete AI training within 60 days. Every single employee, from...

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Split rode to efficiency and innovation.

1 min read

From Gutenberg to Generative: What the Printing Press Can Teach Us About AI

I keep hearing the same question from association leaders: "Which AI tool should we use?"

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Retro 1960s-style illustration of a pit crew of men and women in business attire rapidly replacing “Manual Processes” with “AI Tools” on a sleek race car, under a stopwatch reading “6 Months,” while a rusty old car labeled “Traditional Tech Adoption” lags behind after “3 Years.”

4 min read

From Spectators to Participants: The Surprising Speed of Association AI Adoption

Looking back at the Sidecar Sync podcast journey from Episode 1 (October 2023) to Episode 100 (September 2025), what has surprised the Sidecar team...

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Sidecar Sync Episode 99 featuring Amith Nagarajan and Mallory Mejias

37 min read

100 Episodes Later: A Look Back at What We’ve Learned—and What’s Coming | [Sidecar Sync Episode 100]

Summary: In this special 100th episode of Sidecar Sync, co-hosts Amith Nagarajan and Mallory Mejias take a celebratory stroll down memory lane,...

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Conference center floor plan with labeled halls and session rooms dissolves into glowing streams of light and vibrant data nodes, forming a cosmic web of connections.

7 min read

Running 10,000 Experiments While You Sleep: AI's Next Evolution

What do 14 million labeled images of cats, dogs, and hot air balloons have to do with your next strategic planning session? What does a computer...

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Illustration of a man on a cliff shouting into the wind, colorful speech bubbles with AI symbols swirling away into a stormy sky.

4 min read

The Lonely Work of Innovation: Why Being Right Too Early Still Beats Being Late

I recently interviewed Thomas Altman on the Sidecar Sync podcast, and his story perfectly illustrates the innovation journey many of you are already...

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A surgeon’s gloved hands reach for a surgical instrument on a sterile tray, with faint blue AR grid overlays suggesting a VR training simulation in a bright operating room.

5 min read

World Models: The Next Frontier of AI for Associations

Three years ago, if you'd told association leaders that AI would be writing their member communications, answering complex certification questions,...

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Pointillist aerial view of a digital maze in muted charcoal and sage, with small professional figures navigating toward a glowing peach and gold exit.

5 min read

Your Members Need an AI Authority. It Should Be You.

You get it. You're reading about AI, experimenting with tools, maybe even using GPT-5 already. But when you bring up AI education at the board...

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