Gary and Ian launched Chert, an API that lets businesses send, receive, and automate iMessage conversations at scale. The problem they set out to solve is straightforward: iMessage has no native API like SMS or RCS, so companies building on Apple's messaging platform have been forced to maintain complex, custom infrastructure. Chert abstracts that away with a REST API and webhooks for every inbound and outbound event.

The founders originally tested the waters with a one-shot iMessage agent builder that hit 2,000 users in a week and an outbound sequencer pushing thousands of messages daily. But the real volume came from customer service, missed-call text-back, cart abandonment, and lead capture in verticals like home services, DTC brands, and property management. These use cases demand reliable line health checks, SMS/RCS fallback, and integration with tools like Salesforce, HubSpot, Attio, Slack, and Vapi.

Chert supports automated line provisioning from test lines to hundreds of lines with usage-based pricing. Companies reporting 10x reply rates over cold email have already signed on. The platform routes replies to human agents or AI systems while maintaining the blue-bubble UX customers trust.