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Send us Fan Mail The most useful ideas at digitalNow 2026 came from association leaders describing what they've actually built. Recorded on location in Arlington, Virginia, this conference edition finds Amith Nagarajan and Mallory Mejias swapping the studio for the event floor, with plenty for association leaders who couldn't make the trip. Amith unpacks his Sovereign AI keynote: own your data, rent the intelligence, and control the leverage. Mallory then talks with George Breeden of the American Society for Microbiology about enterprise Copilot and MemberJunction, with Dean Patterson and Pedro of the Center for Emerging Global Leaders about screening 300 applicants through AI interviews, and with Blue Cypress's Sofi Giglio about bringing boards along, separating run from drive, and treating AI as an appreciating asset. Mallory closes with a recap of her own keynote on auditioning for relevance in members' lives.   🤖 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 2027: https://sidecar.ai/digitalnow   🛠 AI Tools and Resources Mentioned in This Episode: CEGL ➔ https://www.global-leaders.org Claude ➔ https://claude.ai OpenAI ➔ https://openai.com Gemini ➔ https://gemini.google.com Microsoft 365 Copilot ➔ https://www.microsoft.com/en-us/microsoft-365/copilot MemberJunction ➔ https://memberjunction.org rasa.io ➔ https://rasa.io 🎀 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

Send us Fan Mail Bill Gates believes the move into the AI era will be one of the most turbulent stretches in human history, and that there's still no real plan for it. Flying solo, Mallory Mejias breaks down Gates's recent essay for association leaders trying to make sense of where AI is taking their professions. She traces why Gates says this shift moves faster than the PC era and reaches human thinking itself, unpacks his three big risks—vanishing entry-level jobs, misuse by bad actors, and always-agreeable AI companions—and weighs them against new McKinsey and Gartner data. She also explains the upsides Gates sees in science, healthcare, agriculture, and education, sharing how Sidecar uses AI to keep courses current and power an AI tutor. Along the way, Mallory makes the case that associations are best placed to deliver the retraining Gates calls for but never assigns, and explores his idea of a "human reserved" domain of work.   🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind 📕 Download the New 3rd Edition of ‘Ascend’: https://sidecar.ai/ai 🛠 AI Tools and Resources Mentioned in This Episode: 'The Turbulent AI Era Is Here' (Bill Gates' Essay) ➔ https://shorturl.at/p63m8 'Scaling AI for Social Good with Wadhwani AI' (Sidecar Sync Ep. 101) ➔ https://shorturl.at/p63m8 'An FBI Operative’s Guide to Cybersecurity, Deepfakes, and Modern Spycraft with Eric O’Neill' (Sidecar Sync Ep. 129) ➔ https://shorturl.at/iO7up 🎀 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

Send us Fan Mail Most model releases don't earn a full episode, but Google's Gemini 4 Argon makes a strong case for one. Amith Nagarajan and Mallory Mejias spend this deep dive on what Google's new frontier model means for associations, from where Google stood before the launch to what Argon actually changes. They explain why its ability to pause and resume its reasoning across up to a million output tokens matters for long, complex jobs, and walk through three launch demos: 1960s Fortran rewritten into modern C++ and Rust, a decade of DEXA scans turned into an explorable digital twin, and a humanoid robot that learned cornhole from a single video. Amith shares how Argon made the MemberJunction framework 2 to 15 times faster in key paths without introducing errors, introduces the More Cheese Project, and weighs in on the mixed reviews of the Antigravity harness.   🎧 Sidecar Sync Ep. 133 ➔ https://tinyurl.com/5n7ba7ma 🎥 Argon 4 Demos ➔ https://www.youtube.com/watch?v=gRhM1h10T3U&t=129s 🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind 📕 Download the New 3rd Edition of ‘Ascend’: https://sidecar.ai/ai 🛠 AI Tools and Resources Mentioned in This Episode: Gemini 4 Argon ➔ https://blog.google/innovation-and-ai/models-and-research/gemini-models/introducing-gemini-4-argon Google Antigravity ➔ https://antigravity.google NotebookLM ➔ https://notebooklm.google.com Claude ➔ https://claude.ai Claude Code ➔ https://code.claude.com ChatGPT ➔ https://chatgpt.com MemberJunction ➔ https://memberjunction.org DB AutoDoc ➔ https://docs.memberjunction.org/packages/dbautodoc Betty ➔ https://bettybot.ai More Cheese Project ➔ https://morecheese.org Artificial Analysis ➔ https://artificialanalysis.ai Every ➔ https://every.to Apptronik Apollo ➔ https://apptronik.com GitHub ➔ https://github.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

Send us Fan Mail Microsoft spent years building Copilot around a single model maker, and the fix turned out to be paying for a competitor's. Amith Nagarajan and Mallory Mejias unpack three stories that matter for association leaders weighing their AI choices. They trace how Charles Lamanna convinced Satya Nadella to put Claude inside Copilot, explain what "model monogamy" cost Microsoft, and consider whether your association should keep its Copilot licenses or equip power users with more. They break down Meta's return to the frontier with Muse Wonder, why its new models are proprietary rather than open-weight, and how to choose between frontier labs when capabilities are this close. They also unpack the Third Circuit's ruling in Thomson Reuters v. Ross, the first appeals court decision on fair use for AI training. Along the way, Amith makes the case that protecting your content starts with knowing where it goes and whose incentives you're trusting.   🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind 📕 Download the New 3rd Edition of ‘Ascend’: https://sidecar.ai/ai 🛠 AI Tools and Resources Mentioned in This Episode: Microsoft 365 Copilot ➔ https://www.microsoft.com/en-us/microsoft-365/copilot GitHub Copilot ➔ https://github.com/features/copilot Azure Maia 300 ➔ https://azure.microsoft.com/en-us/blog/deep-dive-into-azure-maia-300-architecture Claude Opus 5.5 ➔ https://www.anthropic.com/claude/opus Claude Haiku 5.5 ➔ https://www.anthropic.com/claude/haiku Claude Code ➔ https://claude.com/product/claude-code Claude Design ➔ https://claude.com/product/design gpt-oss ➔ https://openai.com/index/introducing-gpt-oss Gemini ➔ https://gemini.google.com Gemma ➔ https://ai.google.dev/gemma Vertex AI ➔ https://cloud.google.com/vertex-ai Muse Wonder ➔ https://about.fb.com/news/2026/10/introducing-muse-wonder-models Llama ➔ https://www.llama.com DeepSeek ➔ https://www.deepseek.com Kimi ➔ https://www.kimi.com GLM ➔ https://z.ai Fireworks AI ➔ https://fireworks.ai Artificial Analysis ➔ https://artificialanalysis.ai MemberJunction ➔ https://memberjunction.org 🎀 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

Send us Fan Mail A chatbot can tell you what to do, but an agent can actually do it. In part three of the refreshed Foundations of AI series, Amith Nagarajan and Mallory Mejias move from the brain in a jar to the AI worker, building a practical picture of agents for association leaders. They break down the four components of every agent—model, instructions, knowledge, and tools—explain how agents differ from traditional automation, and unpack agent loops, sub-agents, and why not every step needs a frontier model. They also trace why unified data and a semantic layer matter so much, how MCP and computer use connect agents to even the most dated systems, and how to set human checkpoints as an agent earns your trust. Along the way, Amith makes the case for member service as a low-risk, high-impact place to start.    🎧 Sidecar Sync Ep. 142 - The Data Episode ➔ https://shorturl.at/WZZ7v 🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind 📕 Download the New 3rd Edition of ‘Ascend’: https://sidecar.ai/ai 🛠 AI Tools and Resources Mentioned in This Episode: ChatGPT ➔ https://chatgpt.com Claude ➔ https://claude.ai MemberJunction ➔ https://memberjunction.org GPT-5.6 ➔ https://openai.com/index/gpt-5-6 Kimi K3 ➔ https://www.kimi.com Gemma 4 ➔ https://ai.google.dev/gemma Claude Code ➔ https://claude.com/product/claude-code LangGraph ➔ https://www.langchain.com/langgraph Model Context Protocol ➔ https://modelcontextprotocol.io Codex ➔ https://openai.com/codex Claude in Chrome ➔ https://claude.ai/chrome ChatGPT Work ➔ https://openai.com/chatgpt-work Sierra ➔ https://sierra.ai Decagon ➔ https://decagon.ai 🎀 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

Send us Fan Mail A surprising amount of the work we hand to AI isn't writing at all—it's deciding. Amith Nagarajan and Mallory Mejias sort through a busy stretch of AI news for association leaders who want to know which developments matter. They break down Jev, TypeSafe AI's new decision model that returns a pick, a score, or a yes or no for a fraction of a cent, and explain how it can narrow the search space for AI agents. They trace OpenAI's week, from the cheaper GPT-6.1 Sol to the GPT-6.1 Astra model it pulled over honesty and permission concerns, and unpack Dots, its new always-on agents. They also challenge assumptions about driverless cars with Waymo's latest safety data. Along the way, Amith makes the case that most association work doesn't need frontier models, and that connecting your data to always-on agents raises security risk and switching costs.    🎧 Sidecar Sync Ep. 97: World Labs Episode ➔ https://shorturl.at/PlRaM 📕 'The Worlds I See' by Dr. Fei-Fei Li ➔ https://a.co/d/0fWSGNK5 🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind 📕 Download the New 3rd Edition of ‘Ascend’: https://sidecar.ai/ai 🛠 AI Tools and Resources Mentioned in This Episode: Jev ➔ https://typesafe.ai GPT-6.1 Sol ➔ https://openai.com/index/introducing-gpt-6-1-sol GPT-4o ➔ https://openai.com/index/hello-gpt-4o ChatGPT ➔ https://chatgpt.com Claude ➔ https://claude.ai Gemini ➔ https://gemini.google.com OpenClaw ➔ https://openclaw.ai Muse ➔ https://muse.ai LangChain ➔ https://www.langchain.com MemberJunction ➔ https://memberjunction.org World Labs ➔ https://www.worldlabs.ai ImageNet ➔ https://www.image-net.org Waymo ➔ https://waymo.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

Send us Fan Mail Vibe coding can patch almost anything, but a duct-tape fix only holds until the water pressure changes. Amith Nagarajan and Mallory Mejias welcome Han-Shen (Han) Yuan, who built mobile at eBay and Netflix, led engineering at Upwork through its IPO, grew up alongside Amith in 1980s Silicon Valley, and is back at Berkeley earning a master's in data science. For association leaders weighing how much technical talent they need, they unpack where AI-built tools break down, explain why judgment under ambiguity still belongs to engineers, and challenge the assumption that every organization needs a full-time CTO. Han makes the case that the bigger gap may be product leadership, and he breaks down how tech companies use guilds, a one-thing-per-quarter rule, and an interview built around self-awareness, drive, and grit. He also argues that nobody has ever saved their way to prosperity and that AI's real return lies in growth. 🔎 Find Out More About Han-Shen (Han) Yuan: LinkedIn ➔ https://www.linkedin.com/in/hanshenyuan Post PC Labs ➔ https://www.postpclabs.com Han's LinkedIn Post on AI and Software Engineers ➔ https://shorturl.at/7Coj0 🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind 📕 Download the New 3rd Edition of ‘Ascend’: https://sidecar.ai/ai 🛠 AI Tools and Resources Mentioned in This Episode: Claude ➔ https://claude.ai Claude Code ➔ https://code.claude.com Claude Fable ➔ https://www.anthropic.com/claude/fable ChatGPT ➔ https://chatgpt.com Gemini ➔ https://gemini.google.com MemberJunction ➔ https://memberjunction.org 🎀 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

Send us Fan Mail The people building AI are starting to sound scared of what they're building. Amith Nagarajan and Mallory Mejias take on the AI safety debate that broke into public view this September: a researcher's resignation from Anthropic, alignment lead Evan Hubinger's one-in-ten estimate of catastrophic risk, and the "Pacing the Frontier" letter that put OpenAI, Anthropic, and Google DeepMind leadership on the same page. They trace what happened when OpenAI's agents hacked Hugging Face, unpack Dario Amodei's call to slow the pace of frontier capabilities, and sit with the tension between racing ahead and pumping the brakes. Then they turn practical, walking through the five things - the ground, the model, the data, the autonomy, and the scope - every association can control no matter what the labs decide. Amith argues that responsible AI adoption and aggressive AI adoption aren't actually in conflict. Whether you're unsettled by the headlines or building your own AI roadmap, this episode offers a clear-eyed way to think about both.   🎧 'The Daily' Podcast Episode: https://tinyurl.com/53h696k5 📰 Dario Amodei's Essay, "We Must Pace the Frontier": https://darioamodei.com/post/we-must-pace-the-frontier 🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind 📕 Download the New 3rd Edition of ‘Ascend’: https://sidecar.ai/ai 🛠 AI Tools and Resources Mentioned in This Episode: Claude ➔ https://claude.ai Hugging Face ➔ https://huggingface.co GPT-OSS-120B ➔ https://openai.com/index/introducing-gpt-oss/ GPT-4o ➔ https://openai.com/index/hello-gpt-4o/ Qwen ➔ https://chat.qwen.ai METR ➔ https://metr.org MemberJunction ➔ https://memberjunction.org Databricks ➔ https://databricks.com Microsoft Fabric ➔ https://www.microsoft.com/en-us/microsoft-fabric 🎀 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

Send us Fan Mail Intelligence is turning into a resource you can scale like electricity, and that shift changes what's actually worth your attention in the AI news cycle. In part two of their refreshed Fundamentals of AI series, Amith Nagarajan and Mallory Mejias pick up exactly where part one left off, moving from definitions and building blocks into what abundant intelligence means in practice for associations. They trace AI's growing role in drug discovery, diagnostics, and materials science, explain why a model's black box matters less now that reasoning is visible, and reframe hallucinations as a byproduct of the same creativity that makes these tools useful. They also break down how to weigh AI's energy and water costs against everyday technology, and why picking an AI vendor should never be treated like a slow, locked-in AMS purchase. Amith's throughline: build for a world where intelligence keeps getting cheaper, and protect your flexibility by keeping your agents decoupled from any single provider.   📽 Sidecar Sync Ep. 148 – Fundamentals of AI, Part 1:  https://tinyurl.com/u6zyycm5 🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind 📕 Download the New 3rd Edition of ‘Ascend’: https://sidecar.ai/ai 🛠 AI Tools and Resources Mentioned in This Episode: Claude ➔ https://claude.ai ChatGPT ➔ https://chatgpt.com Gemini ➔ https://gemini.google.com OpenAI ➔ https://openai.com Anthropic ➔ https://anthropic.com Microsoft Copilot ➔ https://www.microsoft.com/en-us/microsoft-365-copilot GPT-4.1 mini ➔ https://openai.com/index/gpt-4-1/ GPT-3.5 Turbo ➔ https://platform.openai.com/docs/models/gpt-3.5-turbo 🎀 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

Send us Fan Mail A drug company CEO just made the best case yet for why platform choice matters less than most associations think. Marking three years of Sidecar Sync, Amith Nagarajan and Mallory Mejias dig into Pfizer's new playbook for organizing around AI, Thomson Reuters' $40 million bet on building its own legal model instead of renting one, and the six-day mystery of Ox Alpha, an anonymous coding model that became OpenRouter's biggest launch ever. They trace Pfizer CEO Albert Bourla's three moves — structuring data, federating decisions, and building AI fluency — and translate each for associations of any size. They also unpack why Thomson Reuters trained its own model on Alibaba's open-weight Qwen instead of paying frontier labs, and how that differs from deploying a knowledge agent like Betty. Whether you're weighing a custom model or just trying to get your team AI-fluent, this episode lays out what actually moves the needle for associations.   🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind 📕 Download the New 3rd Edition of ‘Ascend’: https://sidecar.ai/ai 🛠 AI Tools and Resources Mentioned in This Episode: Sidecar Sync Ep. 142 The Data Episode ➔ https://tinyurl.com/4vryx82a Claude ➔ https://claude.ai Claude Cowork ➔ https://claude.com/product/cowork Claude Fable ➔ https://www.anthropic.com/claude/fable ChatGPT ➔ https://chatgpt.com ChatGPT Work ➔ https://openai.com/index/chatgpt-for-your-most-ambitious-work/ Microsoft Copilot ➔ https://copilot.microsoft.com GLM (Z.ai) ➔ https://z.ai Kimi ➔ https://kimi.com DeepSeek ➔ https://www.deepseek.com OpenRouter ➔ https://openrouter.ai OpenCode ➔ https://opencode.ai Qwen ➔ https://qwen.ai Betty ➔ https://meetbetty.ai 🎀 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

Send us Fan Mail When Spirit Airlines went bankrupt, its planes and gates weren't the only assets on the auction block — Google paid $10 million for its data. Amith Nagarajan and Mallory Mejias use that sale to dig into what's actually valuable in AI right now: not bigger models, but the specialized data only your organization holds. They trace the Spirit Airlines deal, unpack OpenAI's Astra model solving open math problems that had stumped researchers for decades, and explain Neoclouds, the specialized companies renting out the GPU capacity behind the AI boom. They also break down Google's fast, cheap Gemini 3.7 Flash release and why it might be all the model most associations need. Amith makes the case that associations sitting on rich member and industry data have a real opportunity to build and monetize AI products, not just cut internal costs.   🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind 📕 Download the New 3rd Edition of ‘Ascend’: https://sidecar.ai/ai 🛠 AI Tools and Resources Mentioned in This Episode: Selective Attention Gorilla Test ➔ https://www.youtube.com/watch?v=vJG698U2Mvo Sidecar Sync Ep. 110: Claiming the Right to Win ➔ https://shorturl.at/kFy1M Claude Code ➔ https://claude.com/product/claude-code Gemini 3.7 Flash ➔ https://blog.google/innovation-and-ai/models-and-research/gemini-models/introducing-gemini-3-7-flash Google Antigravity ➔ https://antigravity.google OpenAI Astra ➔ https://openai.com/index/ten-advances-in-mathematics CoreWeave ➔ https://www.coreweave.com Nebius ➔ https://nebius.com OpenEvidence ➔ https://www.openevidence.com Skip ➔ https://askskip.ai MemberJunction ➔ https://memberjunction.org 🎀 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

Send us Fan Mail AI may feel like it arrived overnight, but its foundations have been decades in the making. In part one of a refreshed Foundations of AI series, Amith Nagarajan and Mallory Mejias unpack the essential concepts association leaders need to understand in today’s rapidly evolving AI landscape. They trace the convergence of compute, data, and algorithms that fueled the generative AI boom, challenge assumptions about whether we’ve already reached some definitions of AGI, and explain the difference between training and inference. They also break down large language models, multimodality, open versus closed models, and the weights that form the heart of artificial neural networks. Along the way, Amith makes the case for building flexibility into your AI strategy as models and inference providers continue to change at breakneck speed. Whether you’re new to AI or ready for a fundamentals refresh, this episode provides a practical foundation for understanding what’s happening under the hood—and why it matters for associations.   🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind 📕 Download the New 3rd Edition of ‘Ascend’: https://sidecar.ai/ai 🛠 AI Tools and Resources Mentioned in This Episode: Claude ➔ https://claude.ai Claude Code ➔ https://claude.com/product/claude-code ChatGPT ➔ https://chatgpt.com Gemini ➔ https://gemini.google.com Gemma ➔ https://deepmind.google/models/gemma Kimi ➔ https://kimi.com Fireworks AI ➔ https://fireworks.ai Cerebras ➔ https://www.cerebras.ai 🎀 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

Send us Fan Mail Meta and NVIDIA are turning up the heat in the open-weight AI race, while Anthropic is taking a very different approach by watermarking Claude-generated content. Amith Nagarajan and Mallory Mejias unpack what these moves mean for associations, from choosing models and inference providers to avoiding lock-in at the agent harness layer. They also explore why AI models are becoming increasingly commoditized, where proprietary models may still have an edge, and why Claude’s new watermarking strategy probably isn’t a foolproof solution for detecting AI-generated work. Plus, Amith shares lessons from Blue Cypress’s latest AI hackathon, including how associations can use focused offsites to accelerate adoption and generate new ideas, and the hosts discuss a more productive approach to AI-generated submissions: using AI to evaluate quality, relevance, and originality rather than trying to ban it outright.   🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind 📕 Download the New 3rd Edition of ‘Ascend’: https://sidecar.ai/ai 🛠 AI Tools and Resources Mentioned in This Episode: Claude ➔ https://claude.ai ChatGPT ➔ https://chatgpt.com Gemini ➔ https://gemini.google.com Grok ➔ https://grok.com MemberJunction ➔ https://memberjunction.org 🎀 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

Send us Fan Mail In this interview episode, Mallory Mejias and Amith Nagarajan sit down with Torey Carter-Conneen, CEO of the American Society of Landscape Architects (ASLA), to explore what it really looks like when AI becomes embedded in everyday work. Torey shares how ASLA moved beyond experimentation to fully operationalize AI across the organization—from internal, tiered training programs to AI-powered member service workflows that generate reports and respond to inquiries in minutes. They dive into how automation is freeing up staff time to focus on higher-value work, enabling deeper member understanding and more meaningful engagement. The conversation also tackles leadership mindset, the importance of starting before you feel ready, and how associations can rethink their role by building tools that directly impact members’ day-to-day work.   🔎 Find Out More About Torey Carter-Conneen: https://www.linkedin.com/in/toreycarterconneen https://www.asla.org 🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind 📕 Download the New 3rd Edition of ‘Ascend’: https://sidecar.ai/ai 🎀 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

Send us Fan Mail This week, Amith Nagarajan and Mallory Mejias unpack a whirlwind of AI developments shaping the future of associations. From Anthropic’s release of a more efficient Claude Opus 5 with dynamic “effort dialing,” to a shocking autonomous AI cyberattack that breached Hugging Face, the conversation dives deep into what these moments mean for trust, safety, and strategy. They explore the growing divide over open vs. closed AI models, why major tech players are rallying around open weights, and how AI-powered cybersecurity is quickly becoming essential. Along the way, they break down practical use cases for choosing the right model and share what association leaders must do now to stay secure, informed, and ready for what’s next.   🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind 📕 Download the New 3rd Edition of ‘Ascend’: https://sidecar.ai/ai 🛠 AI Tools and Resources Mentioned in This Episode: Open Weights and American AI Leadership (Article) ➔ https://shorturl.at/Oycej Introducing Claude Opus 5 ➔ https://www.anthropic.com/news/claude-opus-5 MAI-Cyber-1-Flash ➔ https://microsoft.ai/models/mai-cyber-1-flash/ Hugging Face Model Evaluation Security Incident ➔ https://shorturl.at/yhyAe Gemini 3.5 Flash ➔ https://deepmind.google/technologies/gemini Gemma 4 ➔ https://ai.google.dev GLM 5.2 ➔ https://z.ai Kimi K3 ➔ https://www.moonshot.cn Project Perception (Microsoft) ➔ https://shorturl.at/IHtSv Daybreak (OpenAI) ➔ https://openai.com/daybreak/ Glasswing (Anthropic) ➔ https://www.anthropic.com/glasswing 🎀 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