Sidecar Blog

Leadership (5)

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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Low-poly geometric illustration of two hands shaking, left in dark gray tones, right in teal and purple, with warm gold highlights where they meet, on a light background.

5 min read

The Association That Bought the Future: AAPC's Bold AI Move

In November 2023, the American Academy of Professional Coders (AAPC) made a move that surprised many in the association world: they acquired Semantic...

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A copper watering can labeled

5 min read

The 3% Problem: The Hidden Cost of Underinvesting in Technology

Nine out of ten nonprofit leaders say technology is vital to their success. Yet most spend less than 3% of their budgets on it.

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