Chert (YC P26) – Twilio for iMessage

Hey HN! We’re Gary and Ian, and we’re building Chert (https://www.trychert.com/), an API for businesses to send, receive, and automate iMessage conversations at scale. Check out our demo: https://www.youtube.com/watch?v=SRdwvVxMMoI.We originally started by building products on top of iMessage because the blue bubble interface, typing indicators, and reactions made agentic conversations feel more human than ones on SMS/RCS. These included a one-shot iMessage agent builder that reached 2,000 users in one week and an automated iMessage outbound sequencer that sent thousands of outbound messages per day.The hard part is that iMessage does not have a native API like SMS/RCS. Sending and receiving iMessages requires a separate infrastructure that is difficult to set up and maintain, especially at scale.As we talked to more companies, we realized that the highest-volume use cases for iMessage were not B2C agents or even sales. They were things like customer service, missed-call text-back, cart abandonment, and inbound lead capture in verticals like home services, DTC brands, and property management that drive the highest volume.Furthermore, these companies often need additional support, such as custom infrastructure setup (e.g. contact card, area code, or local worker sessions), integration support with their existing SMS/RCS or voice agent systems, and a reliable way to scale their volume over time.We built Chert to be an infrastructure layer for businesses to handle iMessage conversations at scale. Businesses can use our API to send and receive iMessages programmatically, route replies to humans or agents, and integrate conversations into the systems they already use.To maintain stability across both outbound and inbound use cases, we built phone line health checks and SMS/RCS fallback systems. We also integrate with existing SMS/RCS systems, voice agents, CRMs such as Salesforce, HubSpot, and Attio, and tools like S

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FL score

78

out of 100

Verdict

BUILD

high confidence

Competition

No competitor data yet

Trend

No signal yet

Infrastructure API enabling businesses to leverage iMessage's superior UX for customer engagement at scale, filling the gap left by Apple's closed ecosystem.

The pain

Businesses want to use iMessage for customer communication (higher engagement, better UX than SMS) but lack technical infrastructure to send/receive at scale. Current solutions require complex custom setup or don't exist. SMS/RCS alternatives feel impersonal for high-touch use cases.

The gap

Apple provides no native iMessage API. Competitors either don't exist or require DIY infrastructure. Twilio dominates SMS but can't solve iMessage. High-volume use cases (customer service, cart abandonment, lead capture) are underserved.

Build angle

Horizontal infrastructure play: abstract away iMessage complexity (phone line management, fallback systems, scaling) and position as drop-in replacement for SMS APIs in existing workflows. Vertical expansion through integrations (Salesforce, HubSpot, voice agents).

Strengths

  • YC-backed with proven founder credibility
  • Solved hard technical problem (iMessage at scale without native API)
  • Validated demand through 2K users in 1 week on earlier product
  • Clear TAM: home services, DTC, property management (high-volume, SMS-dependent)
  • Smart positioning: infrastructure layer, not consumer app
  • Built-in moat: technical complexity + Apple's closed ecosystem
  • Existing integrations reduce switching costs
  • Fallback systems (SMS/RCS) reduce risk for customers

Risks

  • Apple could shut down iMessage API access at any time (regulatory/technical)
  • Relies on jailbroken/non-standard infrastructure (phone line health checks suggest fragility)
  • Regulatory uncertainty: Apple ToS violation risk, carrier relationships unclear
  • Scaling challenges: phone line provisioning, carrier relationships, geographic limitations
  • Competition from SMS incumbents (Twilio, Bandwidth) if they gain iMessage access
  • Customer acquisition: B2B sales cycle in fragmented verticals
  • Unit economics unclear: phone line costs at scale could be prohibitive
  • Network effects limited: no multi-sided marketplace dynamics

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