Sidecar Sync

Send us Fan Mail Frontier models are now strong enough that the harder question is what to point them at. Back from Digital Now 2026, Amith Nagarajan and Mallory Mejias work through a crowded week of releases for association leaders trying to keep pace. They break down Gemini 4 Carbon and its million-token output, unpack Ethan Mollick's argument that Claude Fable 5.2 nearly clears his own bar...

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 you...

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 reach...

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 t...

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 Micro...

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...

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...

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 lead...

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, An...

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 pract...

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 a...

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&apo...

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 bo...

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 i...

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...

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 th...

Send us Fan Mail In this episode, Amith Nagarajan and Mallory Mejias unpack a rapidly shifting AI landscape where powerful, low-cost open-weight models from Chinese labs are challenging the dominance of major U.S. players. They explore Moonshot AI’s Kimi K3 and Alibaba’s latest model announcements, breaking down what “open” AI really means and why it’s driving costs down while increasing competiti...

Send us Fan Mail In this interview episode, Mallory Mejias and Amith Nagarajan sit down with Vicki Deal-Williams, CEO of the American Speech-Language-Hearing Association (ASHA), to explore how a century-old organization is thoughtfully embracing AI. Vicki shares how ASHA’s AI Innovation Day sparked a cultural shift across staff—from skeptics to the “suspenders group” eager to experiment—while rein...

Send us Fan Mail It’s been 130 episodes since Sidecar Sync last did a true deep dive on data—and a lot has changed. In this refreshed 2026 perspective, Amith Nagarajan and Mallory Mejias unpack what “association data” really means today, from structured CRM records to the massive untapped world of unstructured data like emails, community posts, and content libraries. They explore how AI—especially...

Send us Fan Mail This week on Sidecar Sync, Amith Nagarajan and Mallory Mejias break down a whirlwind week in AI, from Anthropic’s rapid-fire Claude releases to OpenAI’s tightly controlled GPT 5.6 rollout. They unpack the surprising performance of mid-tier models like Sonnet 5, the implications of government intervention in frontier AI, and what it means when access to the most powerful tools is s...

Send us Fan Mail In this episode of Sidecar Sync, Amith Nagarajan and Mallory Mejias explore one of the most provocative ideas in AI yet: companies owned and operated entirely by artificial intelligence. Sparked by a proposal out of Argentina, they unpack what “non-human corporations” could mean for accountability, governance, and the future of work. From there, they break down Agentic Resource Di...

Send us Fan Mail 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 $...

Send us Fan Mail 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...

Send us Fan Mail 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 navigating AI a...

Send us Fan Mail 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 “re...