The numbers tell a familiar story. Email open rates languish somewhere in the single digits. SMS messages fare better, but not by much. Then there's iMessage—the blue-bubble conversations where response rates sometimes hit 90 percent, according to various user studies. The catch? No business has figured out how to tap that channel at scale. At least not officially.
Gary Gao and Ian Fong think they have. The two founders, part of Y Combinator's Spring 2026 cohort, spent the better part of 2026 building what they call "API infrastructure for iMessage." Their startup, Chert, went live in early May with a straightforward proposition: what if businesses could send messages that land in those same blue threads consumers actually read?
It's the kind of pitch that sounds almost too good to be true, particularly given Apple's reputation for walled gardens. And perhaps it is—though the early numbers, limited as they are, suggest something interesting is happening.
"We're seeing 10× response rates over email, sustained across early customers running Chert in production," the company claimed in its launch announcement. That figure comes from a small set of pilot customers, the most detailed being Getcho, a retail fulfillment platform that migrated its entire notification system to iMessage via Chert. According to the case study, Getcho's team got up and running in about 15 minutes and now coordinates across shippers, carriers, and retail locations through group iMessage threads.
The appeal is obvious. The technical execution? That's where things get complicated.
Building on Borrowed Infrastructure
Chert doesn't use Apple's official business messaging platform—Messages for Business—which requires carrier partnerships and Apple approval. Instead, the startup has constructed what amounts to a peer-to-peer iMessage network, stitching together individual sending identities, rotating them to avoid Apple's abuse-prevention systems, and capping daily volume per account.
It's a high-wire act. Send too many messages from one identity, and Apple's filters kick in. Push too hard, and accounts get banned. The founders describe their approach as treating delivery like an "observed state machine," distributing sends across multiple devices and accounts while providing the webhooks and reliability guarantees that Apple's consumer platform was never designed to offer.
"We explicitly warn against unlimited blast vendors that risk account bans," Gao and Fong wrote in a Product Hunt Q&A thread from May. The implication: they're walking a fine line, and they know it.
The product itself surfaces all the iMessage features businesses would want—typing indicators, read receipts, tapbacks, attachments, group chats with named senders. If a recipient isn't on iMessage, Chert automatically falls back to SMS or RCS and reports which channel was used. Integrations span the usual suspects: Salesforce, HubSpot, Slack, Calendly. Pricing is per-message rather than per-recipient, though the company hasn't published a rate card yet.
The Shadow of Beeper
None of this happens in a vacuum. In December 2023, Apple shut down Beeper Mini, a service that reverse-engineered iMessage access for Android users. Apple's rationale centered on security and privacy, but the message was clear: unsanctioned access wouldn't be tolerated.
Chert's model appears different—built on compliance controls, TCPA and CAN-SPAM adherence, gradual identity warming—but the precedent lingers. The company's Terms of Service, dated April 27, 2026, require customers to follow "Apple iMessage terms," though what exactly those entail for a service Apple doesn't officially sanction remains murky.
The startup isn't alone in testing these waters. Sendblue, Blooio, Linq Blue, messages.dev, urelay, and Courio have all emerged in 2026 offering similar iMessage API products, many targeting the AI agent market where conversational channels matter more than blast emails. The space feels less like a single company making a risky bet and more like an ecosystem probing for where Apple's boundaries actually lie.
Interestingly, Apple itself just approved its first AI agent for the official Messages for Business platform—a product called Poke—on June 4, 2026. That suggests the company sees business messaging as a growth area, even if it's approaching it through tightly controlled channels.
Technical Pedigree Meets Market Timing
Gao and Fong bring complementary backgrounds to the challenge. Gao studied computer science and business at Penn, with research stints in ML architecture and neuromorphic chips. Fong, who studied math and economics at NYU, worked on fast-algorithm research at Courant and claims eight hackathon wins (a detail that feels almost quaint in the context of enterprise infrastructure, but speaks to a certain builder mindset).
They're backed by Y Combinator, Z Fellows, and Betafund, plus what appear to be individual angels from LinkedIn and Grafana, judging by logos on the site. It's a relatively light funding footprint for a company tackling deliverability problems that have stymied larger players.
The bet hinges on timing as much as technology. Business messaging has cycled through hype before—remember chatbots circa 2016?—but the current wave feels different. AI agents need conversational interfaces that people actually use. Email doesn't cut it. SMS is crowded and increasingly filtered. iMessage, for all its consumer orientation, might be the path of least resistance.
Assuming Apple doesn't close the door.
The Unanswered Question
What happens when iMessage threads fill with appointment reminders, shipping updates, and CRM follow-ups is anyone's guess. Does Apple tolerate the traffic because it flows through individual accounts rather than centralized APIs? Does the company eventually crack down, Beeper-style? Or does it quietly absorb the activity, watching to see if there's a business model worth formalizing?
Chert's founders are betting on the third option, building compliance infrastructure and conservative rate limits as insurance. "Better deliverability, paired with compliance," is how they frame it. The subtext: we're not cowboys blasting messages into the void; we're building infrastructure that respects Apple's guardrails, even the unwritten ones.
It's a narrative that might hold—or might collapse the first time a major customer gets throttled. For now, the startup occupies a peculiar space: delivering real iMessage threads at business scale, on a platform that was never meant to support them, waiting to see if the ground shifts underfoot.
One API call at a time.
