Caddy Put Your AI Assistant Where You Already Are: Your Texts
The Y Combinator Fall 2025 startup skipped the app store entirely. You message it like a friend, or leave a voice memo, and it files the ticket, sends the reply, and books the meeting - across the tools you already use.
The most crowded real estate on your phone is the app grid, and Caddy decided not to move in. Instead, the New York startup planted its personal AI in the one place you never close - your text messages. You send a note the way you would to a coworker: "reschedule my 2pm to Thursday," "file a bug about the login screen," "remind me to call the plumber." Caddy reads it, connects to the tools behind the scenes, and does it.
That decision - to be a contact in your phone instead of another icon - is the whole company in miniature. Caddy is part of Y Combinator's Fall 2025 batch, and it was built by two people who spent four years watching how work software actually gets used, and mostly ignored.
01 / What it isA coworker you text, not a tool you open
Caddy calls itself a personal AI for everyday work. The interface is a text thread. Behind that thread sits an assistant that connects to email, calendar, Slack, Linear and Notion, and can take real actions in them - creating tickets, sending messages, scheduling meetings, setting reminders, and surfacing the things that need your attention before you go looking.
There are two ways to use it. In action mode, you tell Caddy to do something and it does it: the ticket gets filed, the message gets sent, the meeting lands on the calendar. In dictation mode, Caddy becomes a voice-to-text layer for email, messaging and comments - you talk, it writes, in your own phrasing. The company describes itself as a voice interface for your computer, which is another way of saying you should be able to run your day without staring at ten open tabs.
"A few months ago I left Loom to start Caddy, a voice interface for computers."Connor Waslo, Co-founder & CEO
02 / The foundersTwo people from Loom's AI team
Caddy's co-founders, Connor Waslo and Rajiv Sancheti, met the problem before they built the product. Waslo led product for Loom's AI Suite and its monetization team. Sancheti led design for Loom's AI suite, and earlier worked at Airbnb and the Kleiner Perkins Fellows program. Between them they helped ship the AI features that millions of Loom users touched to record and share work.
The lesson they took wasn't about bigger models. It was about location. The most useful assistant, they concluded, is the one that meets you where you already are - and for most people, that isn't a dashboard. Waslo now runs the company as CEO from New York.
03 / The problemContext switching is the tax nobody budgets for
The modern knowledge worker's day is a series of small hops: from inbox to calendar to Slack to a ticket tracker to notes, and back. Each hop is trivial. Added up, they fracture attention and drain momentum. Caddy's premise is that most of these hops are unnecessary - you shouldn't have to open Linear to file a bug you can describe in one sentence, or open your calendar to move a meeting you could reschedule out loud.
By collapsing those hops into a single thread, Caddy is targeting the gap between intending to do something and actually doing it. Voice-to-text has existed for years. Caddy's bet is on voice-to-done - the part where what you said becomes something that happened.
04 / What makes it differentThe app you don't install
Most AI assistants ask you to come to them - a new window, a new tab, a new habit. Caddy inverts that. There is no app to download; you interact with it in a messaging thread you already check dozens of times a day. That single design choice is also a distribution strategy: the lowest-friction product is the one that requires no onboarding beyond saving a contact.
| Approach | Where it lives | What it does |
|---|---|---|
| Caddy | Your text thread + voice | Acts across your tools for you |
| General AI chatbots | A separate app or tab | Answers; you still execute |
| Scheduling assistants | Email plugins | Mostly calendar-focused |
| Built-in phone assistants | Your OS | Broad, shallow on work tools |
The other differentiator is memory. Caddy is built to learn your preferences, your communication style and your priorities over time, so that a reply it drafts sounds like you and a task it flags is one you'd actually care about. Over time, the company wants it to be proactive - noticing the meeting you forgot or the reply you owe, and nudging first.
"Caddy is your personal AI for everyday work. It lives in your texts."Company description, Y Combinator
05 / Business & marketFree to start, built for the voice-first crowd
Caddy offers a free tier to get people in the door - "get started for free," "message Caddy" - with paid subscriptions the natural path as the product matures from beta toward general availability. The early audience skews toward founders, operators and productivity power users: people with too many tools and not enough hours, who are comfortable running their day by voice.
On funding, the company reports a seed round in the low six figures and counts Pioneer Fund among its backers, alongside its place in Y Combinator's Fall 2025 cohort. It's early - a small team, a public beta, and a big, contested market. General-purpose assistants like ChatGPT, Claude and Gemini all want to be your everything box. Caddy's wager is narrower and sharper: be the thread that actually gets your work done, and be the one you never have to open.
The name fits the ambition. A caddy carries your bag, reads the course, and hands you the right club at the right moment. It doesn't play the round for you - it removes everything between you and the shot.