The archive · Developer & Business Tools · Product decision · 2026
Chert bets businesses will pay for an iMessage API — blue bubbles, tapbacks and all
YC P26 pair builds an API for iMessage — support, text-back, cart recovery — with SMS fallback; Launch HN drew 200 comments.
Chert
What the business is
Chert is an API and workflow layer for sending, receiving, routing and observing real iMessage conversations: REST API and webhooks for every inbound and outbound event, phone-line health checks, SMS/RCS fallback when a recipient is not on iMessage, automated line provisioning from a few test lines to hundreds, usage-based pricing, and native sync into CRMs (Salesforce, HubSpot, Attio), Slack, calendars (Calendly, Cal.com) and voice-agent tools like Vapi. It also runs concierge onboarding, starting each customer with a 20-minute kickoff call.
Starting capital：No round disclosed by the company; the EveryDev directory lists $500K raised from YC (P26), Z Fellows and Betafund.
How it started
Gary and Ian started by building products on top of iMessage because the blue-bubble interface, typing indicators and reactions made agentic conversations feel more human than SMS/RCS: a one-shot iMessage agent builder that reached 2,000 users in a week, and an automated outbound sequencer sending thousands of messages per day. Talking to companies, they found the highest-volume use cases were not B2C agents or sales blasts but customer service, missed-call text-back, cart abandonment and inbound lead capture in home services, DTC and property management.
What happened
They built Chert as an infrastructure layer rather than an app: real iMessage delivery through an API, webhooks, delivery receipts, SMS/RCS fallback, CRM and Slack integrations, and automated line provisioning. The team deliberately kept onboarding human — 'we're not completely self-serve right now' — so every customer's use case is reviewed before access, a direct response to the thread's central objection that this is a spam machine waiting for an Apple ban.
How it ended up
Still live and onboarding customers; the durable risk remains Apple platform policy — the Beeper precedent came up repeatedly in the thread — and Chert's answer is anti-abuse controls plus a focus on inbound and warm-opt-in conversations.
Background
Chert is an API for businesses to send, receive and automate real iMessage conversations — a 'Twilio for iMessage' — founded by Gary and Ian in YC's Spring 2026 batch. It exposes REST endpoints and webhooks for every message event, delivers true blue-bubble threads with read receipts, tapbacks and typing indicators, and falls back to SMS or RCS when a recipient is not on iMessage.
The founders found the highest-volume use cases in business conversations, not B2C agents: customer service, missed-call text-back, cart abandonment and inbound lead capture across home services, DTC brands, property management and sports programs, at the scale of hundreds of lines. Chert sells reliability — line health checks, automated provisioning, usage-based pricing — plus integrations into Salesforce, HubSpot, Attio, Slack, calendars and voice agents.
Traction evidence: the Launch HN (2026-05-25) sat on the front page with 200 comments and 62 points, the YC page confirms active B2C, CX and sales customers, and the EveryDev directory lists $500K raised from YC, Z Fellows and Betafund. The thread's dominant theme was platform risk: Apple's terms bar commercial iMessage traffic, and Beeper was blocked for the same reason.
Chert's counter is anti-abuse design — identity rotation, gradual warming, per-identity volume caps, SMS fallback — plus concierge onboarding that vets every customer's use case before access, betting that inbound and warm-opt-in conversations can avoid the spam flag that would end the business.
What has to be true
- iMessage is the most trusted messaging surface in the US, and businesses have no legitimate way to reach it — an API with fallback unlocks a channel nobody else owns.
- Blue-bubble conversations get read and answered at rates SMS and email can't match, making each message valuable enough to charge for.
- Anti-abuse controls and human onboarding directly answer the 'this is a spam machine' objection that dominates market skepticism.
- Twilio never built iMessage support, leaving an infrastructure gap Chert can fill before Apple ships a better business channel.
What can be applied
Building on a platform you don't control is a financing decision: the upside is a channel no competitor can copy; the price is living one policy change away from Apple's ban hammer.
Aftermath
As of September 2026 Chert is an active YC P26 company (two-person team, New York City, primary partner David Lieb) still onboarding customers via kickoff calls, with a Product Hunt launch behind it and integrations to Salesforce, HubSpot, Attio, Slack, Close, GoHighLevel, Vapi and calendar tools. The existential question is unchanged: Apple can restrict commercial iMessage traffic at any time, and the HN thread plus analyses like ic.work's treat that as the real risk. Chert's answer is volume caps, identity warming and a focus on inbound, warm-opt-in conversations rather than cold blasts.
Sources
- Launch HN: Chert (YC P26) – Twilio for iMessage
- Chert: iMessage infrastructure for business
- Chert - iMessage API for Developers
- Chert把iMessage做成API：蓝气泡会是企业触达新通道，还是平台风险？
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