🚀 What Shipped (Projects & Tools)
Wrapped up September in Las Vegas on stage at InsureTech Connect (ITC Vegas 2026) alongside Robin Gordon (Chief Data Officer, Hippo) and Vishy Padmanabhan (Chief Transformation Officer, Sedgwick). We explored how enterprise insurance is deploying agentic architectures into production: moving past pilot purgatory, establishing rigorous evaluation harnesses, and re-architecting workflows around human oversight (“We all lost our jobs in 2026, but not our roles”). Also sat down in the official press room to discuss agentic AI economics and customer-first comparison models.
Tired of laggy, ad-encrusted smart home hubs that require continuous cloud tethering and monthly fees, I built and open-sourced Danboard—a 100% standalone, privacy-first smart display designed specifically for wall-mounted Amazon Fire TV screens. Built with React, Vite, Capacitor, and Open-Meteo. Features client-side Google/Apple Calendar recurrence (RRULE) parsing with zero server dependencies, real-time hourly precipitation curves, live Ring camera picture-in-picture feeds, and an auto-dimming night mode.
Beyond frontier models and domestic IoT, real-world software engineering often means fixing high-friction legacy systems. Documented an end-to-end modernization case study taking American Detail Cleaning from an unmaintained, sluggish platform to a high-speed, modern static and headless web platform. Shipped streamlined multi-tier booking flows, sub-second mobile page loads, and structured local SEO without recurring SaaS bloat.
ClassDojo is essential for parent-teacher communication, but modern classroom feeds quickly degrade into noisy streams of photo dumps and announcement spam. Dojo Zen runs an autonomous, local-first intelligence pass over daily feeds—isolating actionable parent requirements (field trip permissions, early dismissal days, supply requests) and extracting dates directly into calendar formats while suppressing celebratory emoji noise.
Built as a personalized interactive game for my daughter Izzy, merging classic board game mechanics with generative media pipelines: 64 unique candy-themed landmarks brought to life with Google DeepMind's Gemini and Veo video architectures, dynamic event cards, and responsive sound design built as an offline-first PWA.
Architecture Deep Dive • 3 min
Integrated a sub-10ms, entirely serverless client-side vector search index and Model Context Protocol (MCP) tool server into herrington.ai. Visitors and local AI assistants can semantically query all 50+ essays, architecture notes, and case studies directly in-browser without sending user queries to third-party embedding APIs.
Shipped a mobile-first progressive scheduling tool solving multi-caregiver logistics and Google Calendar recurrence isolation, alongside our open methodology for Critical User Journey (CUJ) Driven Development that bridges raw user friction into automated test suites and verified pull requests.
🧠 Perspectives & Featured Writings
My featured thought leadership piece in CIO on why enterprise AI requires standardized agent harnesses, deterministic state machines, and operational governance. As models become more capable, the competitive moat is no longer just the weights—it is the control harness that keeps autonomous agents bounded and reliable.
Within hours of Meta Muse’s release, The Zebra updated robots.txt to welcome AI agents. While some in the industry opt to shut the door, we believe in meeting consumers wherever they (or their agents) are—building safeguards and defining the future of agentic insurance shopping rather than blocking it.
An exploration of how synthetic generation and commoditized LLM outputs risk flattening stylistic nuance and intellectual depth—and why craftsmanship, domain specificity, and authentic voice matter more than ever.
A breakdown of the hardest engineering problem in enterprise AI adoption: why building the evaluation dataset and red-teaming harness before fine-tuning or purchasing models is the only way to avoid catastrophic production edge cases.
Reflections on building AI in the insurance sector: how statutory compliance, zero-hallucination tolerance, and actuaries enforce architectural elegance that unconstrained consumer AI often overlooks.
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📍 Upcoming Field Travel
Traveling over the next few weeks for executive AI working groups, summits, and meetings:
🤠 Austin, TX: Oct 5 – Oct 8
🤠 Austin, TX: Oct 27 – Oct 28
🗽 New York City, NY: Oct 29 – Oct 30
If you're in any of these cities and want to connect on production AI architectures or agent engineering, reach out directly via LinkedIn.
