The ex-Apple team behind Anoria is betting that the next useful wearable will track the thing sleep scores and step counts only circle around: how you actually feel. The opportunity is intimate, useful and full of hard questions.
The Singapore startup learned that putting AI in your sightline is easy to demo and hard to live with. Halo is its third attempt - thinner, longer-lasting, more private, and open enough for developers to make the glasses useful in ways the company has not imagined.
Caddy is a personal AI for everyday work that lives in your text messages and responds to voice. Built by the team that led product and design for Loom's AI suite, it connects to the tools people already use - email, calendar, Slack, Linear, Notion - and gets work done without forcing anyone to open yet another app. You text or talk; Caddy handles the tickets, reminders, scheduling and follow-ups. The company is part of Y Combinator's Fall 2025 batch and is based in New York City.
Datost is a Y Combinator (Spring 2026 / P26) startup founded by Maceo Cardinale Kwik and Jason Wang. It launched as 'the proactive AI data analyst' - a Slack-native agent with a semantic layer that scored 75.2% on the BIRD-Interact text-to-SQL benchmark versus 33% for a frontier model alone - and has since become an applied research lab building ED1TH, a 25-gram pair of AI AR smart glasses with no cameras, an in-lens display, and a companion smart ring. Backed by Y Combinator and OpenAI.
jo is a voice-first personal AI agent for macOS that runs on your Mac and a private, per-user cloud machine. Rather than waiting to be asked, it proactively summarizes what is on your screen, drafts emails, manages your calendar, clips relevant content, and keeps up with the loose ends of work and life. Built natively in Swift for Apple Silicon and backed by Y Combinator (W24), jo reaches users across Mac, web, iMessage, Telegram, and WhatsApp while keeping personal data local and out of model training.
Town is a San Francisco AI startup building a personal AI assistant - your 'Townie' - that plugs into the tools you already use (email, calendar, Slack, docs, WhatsApp, desktop and web), learns how you work, and proactively does the work for you. Founded in late 2024 by former Plaid CTO Jean-Denis Greze and ex-Google applied-AI director Tony Vincent, Town launched in 2025 as an AI-driven tax-and-compliance service for small businesses, then widened into a general-purpose assistant. It exited beta in June 2026 alongside a $55M Series A led by Andreessen Horowitz.
Personal AI (legally Human AI Labs, Inc.) builds an identity-based memory layer and Personal Language Models (PLMs) - compact, individually trained AI models that capture a person's or organization's knowledge, voice, and decision-making. Instead of a single generic chatbot, the platform lets people and enterprises create AI personas trained on their own data, keeping ownership and privacy with the user. Founded in 2020 and based in San Francisco, the company positions its smaller, memory-grounded models as a more accurate, lower-cost, privacy-first alternative to centralized cloud LLMs for sales, healthcare, legal, HR and knowledge work.

Suman Kanuganti is the Co-Founder and CEO of Personal AI, a San Francisco-based platform building memory-first AI for enterprise workforce transformation. A two-time venture-backed immigrant founder, he previously built Aira - an AI-powered accessibility company serving the blind and low-vision community that was recognized by TIME Magazine and Fast Company - before turning his attention to giving everyone a permanent, personalized AI trained on their own knowledge. He holds 10 patents in emerging technologies and has raised $16M for Personal AI, with customers including Microsoft, NVIDIA, Verizon, AT&T, and T-Mobile.