Caddy

Caddy is one of the more interesting takes on an AI assistant because it eliminates app fatigue entirely—you just text it like a friend. No new interface to learn, no web dashboard to check. For iPhone users who already manage life through iMessage, the friction reduction is real. The proactive features (calendar scanning, auto-RSVP, project brief creation) go beyond simple Q&A bots. We'd reach for this when we want to offload calendar management and group chat coordination without opening a separate tool. But where it bites: iOS-only means anyone outside Apple's ecosystem is locked out. The beta status also means occasional unreliability—Caddy can misinterpret ambiguous requests or miss context. Compared to alternatives like ChatGPT's voice mode or standalone productivity bots, Caddy trades feature breadth for convenience. Its personalization is impressive—each instance learns your 'vibe'—but that also means a cold start before it gets useful. In practice, Caddy excels for busy professionals who already live in Messages and want an always-available executive assistant. It's less suited for power users who need deep integrations with tools like Notion or Asana. The free tier is generous, so there's little risk in trying it.