Sidecar Sync
Welcome to Sidecar Sync: Your Weekly Dose of Innovation for Associations. Hosted by Amith Nagarajan and Mallory Mejias, this podcast is your definitive source for the latest news, insights, and trends in the association world with a special emphasis on Artificial Intelligence (AI) and its pivotal role in shaping the future. Each week, we delve into the most pressing topics, spotlighting the transformative role of emerging technologies and their profound impact on associations. With a commitment to cutting through the noise, Sidecar Sync offers listeners clear, informed discussions, expert perspectives, and a deep dive into the challenges and opportunities facing associations today. Whether you're an association professional, tech enthusiast, or just keen on staying updated, Sidecar Sync ensures you're always ahead of the curve. Join us for enlightening conversations and a fresh take on the ever-evolving world of associations.
Episodes
What if building a million-dollar business no longer required a team, funding rounds, or even technical expertise? In this episode of Sidecar Sync, Mallory Mejias sits down with AI strategist and GenAIPI CEO Jon Cheney to explore how artificial intelligence is radically changing the economics of innovation. Jon shares the story of launching a company in a single weekend for just $400—and scaling it to $1M in s...
In this episode of Sidecar Sync, Amith and Mallory explore three major developments shaping the future of AI. First, they unpack how an OpenAI model independently solved a decades-old mathematical problem—challenging long-held assumptions and proving AI can generate truly novel insights. Then, they break down Microsoft Build 2026 and the shift toward an “agent-first” world, where AI systems take on...
In this jam-packed “mini” episode, Amith Nagarajan and Mallory Mejias break down a whirlwind of recent AI model releases—from Anthropic, Alibaba, Microsoft, and beyond—and what they signal about the rapidly evolving AI landscape. Then, they dive into Microsoft’s 2026 Work Trend Index Report, unpacking the “agency equation” and what it really means for organizations navigatin...
In this episode of Sidecar Sync, Mallory Mejias welcomes Dr. Jessica Miles, founder of The Informed Frontier, former VP of Strategy and Investments at Holtzbrinck, and advisory board member for Johns Hopkins University Press, for a fascinating look at how AI is transforming publishing, research, and trusted content ecosystems. Jessica explains what happens when AI becomes a “reader” instead of just a wri...
In this episode of Sidecar Sync, Amith Nagarajan and Mallory Mejias unpack Google I/O 2026 and what it signals for the future of AI-powered work, search, and member engagement. They explore Google’s push toward proactive, agentic AI across Gemini, Workspace, Search, and new infrastructure like Antigravity and TPU chips, while digging into what these changes mean for associations trying to protect their content...
In this episode of Sidecar Sync, Amith Nagarajan and Mallory Mejias dig into two major shifts happening beneath the surface of AI: how enterprise software vendors are responding to the rise of AI agents, and why diffusion language models may be moving from research curiosity to real-world infrastructure faster than expected. They unpack Salesforce’s open, agent-friendly “Headless 360” strategy, SAP...
In this episode of Sidecar Sync, Amith Nagarajan and Mallory Mejias dig into the hidden world of “dark databases”—messy, undocumented systems quietly powering many associations—and explore DBAutoDoc, a new open-source tool from Amith and Thomas Altman that uses AI to map database structure, infer relationships, and generate documentation at scale. Amith & Mallory also unpack the state of ...
In this episode of Sidecar Sync, Amith Nagarajan and Mallory Mejias dive into Anthropic’s latest moves with Claude Opus 4.7 and the new Claude Design, a conversational visual creation tool that can generate decks, prototypes, one-pagers, landing pages, and even animations from simple prompts. Mallory shares her first hands-on experiment with Claude Design, while Amith breaks down why stronger visual intelligen...
What happens when you put a Siri co-creator and longtime AI pioneer together with a next-generation events strategist? Adam Cheyer—co-creator of Siri, founder of Viv Labs, and a builder behind several influential AI startups—and Noah Cheyer, founder of Silicon Valley Speakers and a close observer of how event planners and audiences are responding to AI, join Mallory Mejias for a father-son conversation o...
This week on Sidecar Sync, Amith Nagarajan and Mallory Mejias trace one of the biggest stories in AI: how cutting-edge intelligence keeps getting compressed into smaller, faster, cheaper models. From GPT-4-era pricing to today’s open models like Gemma 4, they unpack the forces driving this shift, including distillation, mixture-of-experts architectures, quantization, and Google Research’s new TurboQuant ...
In this interview edition of Sidecar Sync, Mallory sits down with Eric O’Neill—former FBI counterintelligence operative, attorney, cybersecurity expert, and founder of The Georgetown Group and NeXasure AI—whose career has spanned undercover FBI work, national security law, and advising organizations on how to defend themselves against modern cyber threats. Eric shares stories from the extraordinary...
This week on Sidecar Sync, Amith Nagarajan and Mallory Mejias unpack a whirlwind of Claude news, from Anthropic’s accidental “Mythos” leak and what it could signal about the next major leap in AI capability, to the increasingly practical reality of Claude using your computer to complete real tasks on your behalf. They also dig into Mistral’s new open-weight text-to-speech model, the growing c...
In this episode of Sidecar Sync, co-hosts Amith Nagarajan and Mallory Mejias dive into the explosive rise of OpenClaw—an open-source AI agent that’s taken the tech world by storm. From being dubbed “the next ChatGPT” at NVIDIA GTC to triggering widespread security concerns, OpenClaw represents both the promise and peril of the agent era. Amith breaks down what OpenClaw actually does, why its ...
In this episode of Sidecar Sync, Amith Nagarajan and Mallory Mejias pull back the curtain on one of Sidecar’s most ambitious experiments yet: Grace, a real-time AI audio agent designed to transform how organizations engage with users. From a beachside hackathon to a live deployment in under two months, they unpack the full journey—covering the business case, rapid development process, tech stack decision...
In this episode of Sidecar Sync, Amith Nagarajan and Mallory Mejias unpack three major developments shaping the AI landscape for associations and nonprofits. First, they explore the rapid evolution of AI models—including ultra-fast releases like Gemini 3.1 Flash-Lite and the growing capabilities of systems like GPT‑5.4 that can interact directly with legacy software. Next, they discuss how AI agents could disr...
In this special solo edition of Sidecar Sync, Mallory Mejias unpacks Anthropic’s 2026 State of AI Agents report and translates what it actually means for associations. Drawing from data across 500+ technical leaders, she explores how organizations are moving beyond basic chatbots to multi-stage AI agents that handle workflows end to end. From research and reporting to customer service and coding, the results a...
In this episode of the Sidecar Sync, Mallory and Amith dive deep into two seismic shifts rocking the AI landscape for associations: the rise of “agent tollgates” in SaaS platforms and the growing security concerns around Model Context Protocol (MCP). Sparked by comments from HubSpot’s CEO about monitoring and monetizing agent access to customer data, the conversation explores what happens when vend...
In this episode of Sidecar Sync, Amith Nagarajan and Mallory Mejias zoom out to explore the AI infrastructure quietly reshaping everything beneath the surface—from Microsoft’s new Maia 200 custom AI chip and the race to lower inference costs, to Google’s Project Genie and the rise of interactive world models that could transform everything from credentialing simulations to digital twins of annual c...
If you think the future of AI is being decided only in Silicon Valley or Beijing, this conversation will stretch your perspective. Amith Nagarajan and Mallory Mejias sit down with Benjamin “Benji” Rosman—Professor at the University of the Witwatersrand, Founder of the Machine Intelligence and Neural Discovery (MIND) Institute, and recently named to the Time 100 Most Influential People in AI for 202...
In this high-octane episode of Sidecar Sync, Amith and Mallory cover an ambitious trio of AI developments with massive implications for associations. They dive into Kimi K2.5, a Chinese open-source model built for multimodal agent swarms that rival GPT-5.2 at a fraction of the cost. Then, they explore Claude’s new domain-specific plugins for Cowork and what it means for associations when Big AI moves into vert...
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