What happened when Caddy moved its assistant to texting

Caddy, a personal AI assistant created by former Loom leaders Rajiv and Connor, shifted from an installable voice-first Mac application to a text-message-based product after finding that users—including its founders—used the desktop version infrequently. Testing the same backend across email, Slack, and iMessage showed substantially stronger adoption through iMessage, which the team attributes to lower installation friction, mobile availability, and the informal, relationship-oriented nature of native messaging. Comparable findings from Lindy and VentNow suggest that text-based channels can drive more traffic, messages per session, and daily activity than standalone apps. A persistent message thread also changes agent behavior by removing fixed sessions, enabling the assistant to initiate conversations, supporting ongoing context and memory, and allowing users to send voice notes while mobile. The post presents Linq, a messaging API for iMessage, RCS, SMS, and voice, as the infrastructure used to productize Caddy.

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