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  "markdown": "Co-founder and CEO.\n\nConnor Waslo is co-founder and CEO of Caddy, a personal AI assistant that works over text messages, from Y Combinator's Fall 2025 batch. He previously led product for Loom's AI suite and its monetisation team.\n\n- LinkedIn: https://www.linkedin.com/in/connor-waslo/\n- X: https://x.com/ConnorWaslo\n\n## What Connor builds\n\n- [Caddy](https://www.anchorterminal.com/tools/caddy-app.md), graded F, 16.9/100, in Personal assistants. Caddy is a hosted personal AI assistant people text over iMessage or RCS. It watches connected mail, calendars and work apps, sends reminders and briefings, and drafts replies and calendar changes for the owner. Co-founder and CEO, researched 2026-10-28.\n\n## Works with\n\n- [Rajiv Sancheti](https://www.anchorterminal.com/people/rajiv-sancheti/), Co-founder and COO\n\n## Backed by\n\n- [Y Combinator](https://www.anchorterminal.com/investors/y-combinator/)\n\n## Questions\n\n### Who is Connor Waslo?\n\nConnor Waslo is co-founder and CEO of Caddy, a personal AI assistant that works over text messages, from Y Combinator's Fall 2025 batch. He previously led product for Loom's AI suite and its monetisation team.\n\n### What does Caddy Technologies Inc. make?\n\nAnchor Terminal lists Caddy from Caddy Technologies Inc.. Caddy is a hosted personal AI assistant people text over iMessage or RCS. It watches connected mail, calendars and work apps, sends reminders and briefings, and drafts replies and calendar changes for the owner.\n\n### Who has invested in Caddy Technologies Inc.?\n\nThe sources our research read name Y Combinator.\n\n### How are Connor's tools graded?\n\nCaddy is graded F, 16.9 out of 100, on Anchor Terminal's benchmark, which scores every listing against the same checklist.\n\n## Sources\n\n- https://www.ycombinator.com/companies/caddy\n- https://caddy.app/\n- https://caddy.app/about\n\nThese are the people building the tools we list, named for their public role in the company or project behind a listing, from public pages, with the date it was researched. They don't work for Anchor Terminal (our own team is on the about page, /about/#author). We show public roles, public profiles and what the listing pages show, nothing private. To correct something, send an about or a photo, or have a page removed, write to privacy@anchorterminal.com.\n",
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