Sidecar Blog

Technology

Whimsical pop-art illustration of a smiling retro copy machine spitting out bright yellow certificates like confetti, papers flying and stacking in messy piles against a coral-and-teal geometric background with risograph texture.

5 min read

AI Can Now Forge Your Credentials (Here's What to Do About It)

A post has been circulating on LinkedIn that should make every association leader uncomfortable. It shows what's now possible with AI image...

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POV walking down a wedding aisle toward five formal figures standing side by side; each has an abstract AI-logo head (Google colors, Anthropic amber, OpenAI black-and-white, Mistral geometric, DeepSeek blue). Coral-and-teal florals line the aisle, giving a slightly surreal, editorial-illustration vibe.

5 min read

Why Your Association Can't Afford to Marry One AI Vendor

The AI leader from January isn't the AI leader now. And the leader now probably won't hold that spot six months from now.

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A stylized Japanese woodblock print of a stream winding through land, widening into bold indigo and teal ocean waves with cream highlights.

7 min read

Beyond the Individual: Designing AI for Generational Impact

When you measure success, you count heads. How many people attended the conference? How many members completed the certification? How many downloaded...

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Retro-futuristic illustration of a man in business casual sitting beside a friendly robot driving a bubble-dome car, with data overlays visible on the highway ahead.

6 min read

Riding Shotgun with AI: Why You Can't Set It and Forget It

Your association just launched an AI assistant to handle member questions. The vendor demo was impressive. The pilot went well. Leadership expects it...

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A frustrated man tries to hammer a nail with a Swiss Army knife, multiple tools extended, while a real hammer sits unused in the background.

5 min read

Start With Reality: Why Deployment-First Beats Technology-First

Your association just spent six months building a new member portal. The features are impressive. The interface is clean. Leadership loves the demo....

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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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Cartoon of a father and son posing in front of a pagoda-style temple in a busy Nepalese square.

6 min read

When a 16-Year-Old Teaches AI: The Conor and Finn Grennan Story

The organizations Conor Grennan has trained on generative AI are undeniably impressive: OpenAI, McKinsey, Google, JP Morgan, NASA. But perhaps more...

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