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In this episode of Sidecar Sync, Amith Nagarajan and Mallory Mejias dig into the startling findings of a recent MIT study: 95% of enterprise AI initiatives are failing to deliver measurable impact. Why are so many organizations investing in AI only to watch their efforts fizzle? Mallory and Amith unpack 10 core reasons for these failures—ranging from building chat-first features instead of end-to-end workflows, to skipping the unglamorous data cleanup that powers real results. Drawing from Vishwas Lele’s insightful LinkedIn post and their own experiences in the association world, the duo shares practical guidance for leaders ready to move beyond flashy demos and into lasting value. Plus, they explore why your staff still prefer ChatGPT over that expensive new AMS add-on, and what associations can do to shift from AI experiments to real transformation.

🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind

📕 Download the New 3rd Edition of ‘Ascend’:
https://sidecar.ai/ai

📅 Join the pre-registration list for digitalNow 2026:
https://digitalnow.sidecar.ai/digitalnow2026

📧 Test out our customer service agent Izzy by emailing help@sidecar.ai

🛠 AI Tools and Resources Mentioned in This Episode:

ChatGPT ➔ https://chat.openai.com
Claude ➔ https://claude.ai
pWin.ai ➔ https://www.pwin.ai

🎀 Use code AIPOD50 for $50 off your Association AI Professional (AAiP) certification at https://sidecar.ai/aaip

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Amith Nagarajan is the Chairman of Blue Cypress, a family of purpose-driven companies and proud practitioners of Conscious Capitalism. The Blue Cypress companies focus on helping associations, non-profits, and other purpose-driven organizations achieve long-term success. Amith is also an active early-stage investor in B2B SaaS companies. He’s had the good fortune of nearly three decades of success as an entrepreneur and enjoys helping others in their journey.

https://linkedin.com/amithnagarajan

Mallory Mejias is passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space. Mallory co-hosts and produces the Sidecar Sync podcast, where she delves into the latest trends in AI and technology, translating them into actionable insights.

https://linkedin.com/mallorymejias

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In this annual predictions spectacular, Amith Nagarajan and Mallory Mejias kick off 2026 by looking back at how well their 2025 AI forecasts held up (spoiler: pretty darn well) and then boldly lay out what’s coming next for artificial intelligence, associations, and knowledge work. From real-world AI recruiting agents and voice-first interfaces to the rise of AI literacy as a job requirement, the shift from SEO to AEO, and the very real possibility of AI-native platforms disrupting traditional associations, this episode is packed with practical insight and big-picture thinking. Whether you’re an association leader or just trying to stay ahead of the curve, this conversation is both a wake-up call and a roadmap for making 2026 the year you move from experimenting with AI to truly leading with it.

🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind

📕 Download the New 3rd Edition of ‘Ascend’:
https://sidecar.ai/ai

📅 Join the pre-registration list for digitalNow 2026:
https://digitalnow.sidecar.ai/digitalnow2026

📧 Test out our customer service agent Izzy by emailing help@sidecar.ai

🛠 AI Tools and Resources Mentioned in This Episode

Gemini 3 Pro ➔ https://deepmind.google/technologies/gemini/
Claude Haiku 4.5 ➔ https://www.anthropic.com
ElevenLabs ➔ https://elevenlabs.io
ChatGPT ➔ https://chat.openai.com
Sora 2 ➔ https://openai.com/sora
Veo 3 ➔ https://deepmind.google/technologies/veo/
NotebookLM ➔ https://notebooklm.google
Gamma ➔ https://gamma.app

🎀 Use code AIPOD50 for $50 off your Association AI Professional (AAiP) certification at https://sidecar.ai/aaip

🚀 Help Us Grow Our Reach - Share With a Friend or Colleague!

👍 Like & Subscribe!
https://x.com/sidecarglobal
https://www.youtube.com/@SidecarSync
https://sidecar.ai/
https://www.linkedin.com/company/sidecar-global/

Amith Nagarajan is the Chairman of Blue Cypress, a family of purpose-driven companies and proud practitioners of Conscious Capitalism. The Blue Cypress companies focus on helping associations, non-profits, and other purpose-driven organizations achieve long-term success. Amith is also an active early-stage investor in B2B SaaS companies. He’s had the good fortune of nearly three decades of success as an entrepreneur and enjoys helping others in their journey.

https://linkedin.com/amithnagarajan

Mallory Mejias is passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space. Mallory co-hosts and produces the Sidecar Sync podcast, where she delves into the latest trends in AI and technology, translating them into actionable insights.

https://linkedin.com/mallorymejias

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In this special holiday edition of Sidecar Sync, Amith Nagarajan and Mallory Mejias unwrap two stories that feel wildly different—but point to the same big idea: technology breaks barriers we once assumed were permanent. First, they dive into the NFL’s quiet fascination with supersonic flight and how faster-than-sound travel could reshape sports, conferences, and global strategy. Then they shift gears to AI, unpacking a massive new study analyzing 100 trillion tokens of real-world usage to reveal how people actually use AI—from role-play and storytelling to agentic workflows and open-source models. Together, these stories challenge associations to rethink what’s “unsolvable,” adopt an abundance mindset, and ask the most important question of all: what’s your supersonic moment?

🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind

📕 Download the New 3rd Edition of ‘Ascend’:
https://sidecar.ai/ai

📅 Join the pre-registration list for digitalNow 2026:
https://digitalnow.sidecar.ai/digitalnow2026

🛠 AI Tools and Resources Mentioned in This Episode:

NFL & Supersonic Flight ➔ https://shorturl.at/hnedE
OpenRouter’s State of AI ➔ https://openrouter.ai/state-of-ai
OpenRouter ➔ https://openrouter.ai
DeepSeek ➔ https://www.deepseek.com
Qwen ➔ https://qwen.ai
Claude (Anthropic) ➔ https://www.anthropic.com

🎀 Use code AIPOD50 for $50 off your Association AI Professional (AAiP) certification at https://sidecar.ai/aaip

🚀 Help Us Grow Our Reach - Share With a Friend or Colleague!

👍 Like & Subscribe!
https://x.com/sidecarglobal
https://www.youtube.com/@SidecarSync
https://sidecar.ai/
https://www.linkedin.com/company/sidecar-global/

Amith Nagarajan is the Chairman of Blue Cypress, a family of purpose-driven companies and proud practitioners of Conscious Capitalism. The Blue Cypress companies focus on helping associations, non-profits, and other purpose-driven organizations achieve long-term success. Amith is also an active early-stage investor in B2B SaaS companies. He’s had the good fortune of nearly three decades of success as an entrepreneur and enjoys helping others in their journey.

https://linkedin.com/amithnagarajan

Mallory Mejias is passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space. Mallory co-hosts and produces the Sidecar Sync podcast, where she delves into the latest trends in AI and technology, translating them into actionable insights.

https://linkedin.com/mallorymejias