Launch HN: Chert (YC P26) – Twilio for iMessage

Launch HN: Chert (YC P26) – Twilio for iMessage(trychert.com)

19 points by garygao 2 hours ago | 58 comments

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 Slack. Finally, we let businesses reliably scale from a few test lines to hundreds of lines with automated line provisioning and a usage-based pricing structure.

We’re working with companies doing conversational messaging in DTC, sports programs, property management, and home services at the scale of hundreds of lines.

We’d love to hear your thoughts on this and other similar verticals where iMessage could be useful. All comments welcome!

dubcanada 1 hour ago |

How is this any different then

https://blooio.com/ https://www.sendblue.com/ https://www.lindy.ai/ etc?

I will say I am the exact opposite of your market, I want absolutely nothing like this. In fact I'd prefer iMessage to allow ZERO programmatic interfacing.

garygao 1 hour ago | |

While Blooio and Sendblue are more focused on B2C agents and sales, we're more focused on 2-way conversational business use cases such as customer service that require scale and stability.

dave_xt 57 minutes ago | | |

Lol not true. Blooio also starts at $39 for shared and $98 for dedicated. Source: I'm the co-founder of blooio. https://blooio.com/

arrsingh 1 hour ago |

How does this work? Do you have an agreement with Apple to connect to their iMessage service? If you do then kudos thats a real differentiator.

However if you're hosting your own mac mini farm and running bluebubbles or other such things that are not approved by Apple what is your plan to handle the case where you're sending enough traffic through Apple's services that they disable / ban / block you?

If its the former then awesome but if its the latter then Im not sure I'd want to depend on your service knowing that apple could ban you at any time.

garygao 1 hour ago | |

Apple wouldn't ban us since we're not doing anything that would qualify as spam or abuse. Even if that hypothetical event does happen, we have SMS/RCS fallback systems in place so no conversations get stopped or lost

Banditoz 50 seconds ago | | |

> Apple wouldn't ban us...

To me this screams you haven't talked to Apple. Given how macabre they were towards Beeper Mini, I almost expect the same treatment for Chert.

Nonetheless, best of luck if you can pull it off.

wewtyflakes 1 hour ago | | |

Much of what you mention in your post seemed spammy; messaging regarding cart abandonment, etc. I aggressively label messages like that as spam, and I suspect others do too. I also suspect after blasting out messages like that, your accounts will get burned.

roddylindsay 12 minutes ago | | |

As someone who has been in the messaging industry for more than a decade, it sounds naive to think that the litmus test for whether Apple will ban you is whether your traffic qualifies as spam. There is a long history of people trying to get around A2P spam filters / fees / traffic limits / onboarding / KYB requirements by running business messaging on P2P pipes, like you are doing. Some of it has been successful (see Twilio in the early days) but the industry has gotten a lot more sophisticated around this stuff and is not going to be receptive to your approach, which to me resembles the SIM farms that are a scourge when it comes to consumer fraud and abuse.

Calvin02 1 hour ago |

This doesn’t feel like something Apple would approve of. Are you concerned about them shutting this down?

rvz 1 hour ago | |

That is the platform risk. Apple blocked Beeper.com for the same reason.

garygao 1 hour ago | | |

Apple doesn't inherently prohibit programmatic messaging. In fact, they actually developed Applescript for people to do that. What they are against is spam and abuse. Therefore, as long as we stay compliant and prevent spam, Apple is not necessarily against this.

frumplestlatz 1 hour ago | |

This is definitely going to get banned, and as a customer of Apple’s, I will be glad for it.

I don’t need more iMessage spam.

garygao 1 hour ago | | |

We're not encouraging spam with this. We're mainly focused on existing conversational use cases that's currently done over SMS/RCS. They can be more human and expressive when done over iMessage.

liamcardenas 52 minutes ago |

A few ideas for you guys: 1. Apple already supports iMessage for Business which is intended to cover the use cases you are targeting. But the set up process is ridiculous (for example: https://help.webexconnect.io/docs/wxcc-apple-messages-for-bu...). It would be amazing to have "Vercel/Resend for iMessage for Business" 2. If you go the send blue route, please support iMessage app payloads. Send blue doesn't support that

garygao 45 minutes ago | |

Thanks for the suggestion! Yes, the setup process is extremely long and requires a lot of documents from the side of the business haha. It's definitely one of our goals to create the Vercel for iMessage for Business. Also, for the iMessage app payloads, that's an awesome suggestion! We can work on building that.

satvikpendem 43 minutes ago |

Isn't this a direct violation of Apple's terms of service? You say you aren't spammy but at a certain point you will get banned. I'm not sure how YC funded this based on the platform risk alone but I guess these days they're throwing anything and everything at the wall.

garygao 36 minutes ago | |

We're helping to support conversational customer support agents that can help users better during off-hours and scheduling assistants that can interact with and understand user requests better than current models over SMS/RCS. This is definitely not just spam but instead the future of conversational 2-way messaging.

zerozerotwo 23 minutes ago |

how is it possible to build this whole thing and not know there is a very rich first party api that does the same thing and more in iMessage https://www.apple.com/ios/business-chat/

garygao 11 minutes ago | |

iMessage for business has a very long and restrictive registration process, gray bubbles instead of blue bubbles, and is inbound only. We're democratizing iMessage for businesses that have good intentions on helping their customers more but can't afford to go through the long approval process.

dgellow 52 minutes ago |

> the blue bubble interface, typing indicators, and reactions made agentic conversations feel more human than ones on SMS/RCS

Would you mind detailing your reasoning why agents should feel humans, when they very obviously aren’t? Why should we want AI to impersonate humans?

xena 1 hour ago |

What is your plan to prevent spam from bad actors?

How do you ban bad actors so they can't spam again?

Does a user have to initiate contact in order to have messages sent to them?

garygao 1 hour ago | |

1. Since we're not fully self-serve right now, we can choose to only partner with businesses with use cases that are opt-in and non-spam. 2. If we find that one of our customers is using this for spam, we'll reach out to them asap and determine next steps 3. Not necessarily. We support both inbound (user texts the phone line first) and opt-in outbound (we text the user first) use cases

dgellow 38 minutes ago | | |

And what would be the next steps? Would you block them from using your services, even if they are paying customers? Do you have agreements in place with your users to cover those situations? Is there a way for end users to report to you what they see as spam or unsolicited content? How do you monitor customers activity to determine if they are bad actors?

You should have answers for those points if you want to build trust with end users

tequila_shot 1 hour ago |

This is a very simple integration and the fallback is also pretty straightforward to implement technically. What’s the differentiator? Why would companies use your product?

garygao 1 hour ago | |

I'd say mainly scale and stability. While people can definitely do this on their own through Bluebubbles or custom Applescript, stability is difficult to maintain, especially at scale. For most businesses, iMessage is not the core product they want to think about and maintain. They just want a reliable API and support/team to talk to so that they can reliably integrate it as a part of their existing business structure.

the_arun 40 minutes ago |

Assuming we have more customers using WhatsApp over iMessage, How did you decide to use iMessage over WhatsApp messaging?

Yannaner 19 minutes ago | |

we started with iMessage because it is still the most dominant, trusted channel in the US.

littke 1 hour ago |

As much as I want to applaud your progress here, as a user I want transactional stuff to stay in my email inbox. My iMessage is already starting to become overwhelming from spam and apps — I want fewer messages not more.

garygao 1 hour ago | |

Yeah I agree. Our goal behind this is not to clutter up people's iMessage inbox with more transactional messages. It's to replace the SMS/RCS conversations that people are already having with customer service and scheduling agents with something more conversational and human.

PantaloonFlames 1 hour ago | | |

Why is iMessage "more conversational" than RCS? and "more human"??

I don't get the distinction you're making. I'm not an expert in mobile messaging so maybe I am missing something obvious.

And what about WhatsApp?

frumplestlatz 1 hour ago | | |

My existence couldn’t possibly be any more digital, and I can’t remember a single time I’ve had a SMS/RCS conversation with customer service or a scheduling agent. I don’t want to have one either. My message inbox is already full enough.

My iMessages are for conversations with people that I actually want to talk to. The notifications are high priority because it’s with people that I want to talk to.

I can’t imagine my annoyance if I were to receive an iMessage notification while I’m expecting an important message, only to find that it’s more spam.

My email inbox is already a wasteland because of this. The absolute last thing I need or want is for the same thing to happen to iMessage.

frumplestlatz 1 hour ago |

> iMessage is intended for communicating with family and friends, and is not for conducting commercial activities or disseminating unwanted messages. iMessage misuse may result in service limitations.

https://www.apple.com/legal/privacy/data/en/messages/

Seems pretty damn clear.

garygao 57 minutes ago | |

We are not "disseminating unwanted messages". A lot of what we're doing (e.g. customer support or missed call text back) would be things that users would already be doing conversationally over iMessage.

icedchai 38 minutes ago | | |

You can't guarantee one of your customers isn't going to do that dissemination though, right? No spammer is going to sign up saying "I'm a spammer that just got banned from <other service>! Can you guys help?"

nvme0n1p1 40 minutes ago | | |

Are you "conducting commercial activities"?

huhrymuhry20000 1 hour ago |

I like the idea of explaining things like "<brand name> for <brand name>"

garygao 1 hour ago | |

Thanks, it felt like the clearest way to describe it haha

smashah 1 hour ago |

It's good YC is funding you because it acts as a later of protection from legal threats by apple. Hopefully if/when Apple litigate this I hope you will fight and set precedent for commercialisation of adversarial interoperability (A digital human right).

I suggest you implement Baileys also to your service so it can also be done with WhatsApp so we can accelerate the inevitable litigation.

Yannaner 23 minutes ago | |

We are def thinking a lot about interoperability and what it should look like in practice... >:)