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Why email startups fail

(forwardemail.net)
140 points skeptrune | 2 comments | 01 Jul 25 00:41 UTC | HN request time: 0.562s | source
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JimDabell ◴[01 Jul 25 02:41 UTC] No.44430078[source]▶
This is a weird article. Email is a hodgepodge of terrible protocols that have progressively had more and more technical debt laid upon them for decades and decades. Vendor quirks are everywhere, and it’s incredibly unreliable. Its defining quality – it’s decentralisation – has been beaten out of it by IP reputation so everybody ends up sending through a handful of providers.

The article kinda acknowledges that it’s a shitheap that’s awful to implement, but somehow still champions the idea that it all works fine.

And what’s with the repeated jabs at the “terrible” exit rate that actually seems pretty good?

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jesterson ◴[01 Jul 25 05:53 UTC] No.44430987[source]▶
> Email is a hodgepodge of terrible protocols that have progressively had more and more technical debt laid upon them for decades and decades.

May I know what is so "terrible" about those protocols ans what "technical debt" are you talking about?

> Vendor quirks are everywhere, and it’s incredibly unreliable

That has nothing to do with actual email protocols. Generic email protocols are extremely reliable and resilient to any sorts of disruptions. I wish any of modern protocols exhibit similar simplicity and reliability.

But of course if vendor would like to add their quirks and you would like to buy that - that's your choice innit.

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Chyzwar ◴[01 Jul 25 15:46 UTC] No.44435101[source]▶
> May I know what is so "terrible" about those protocols ans what "technical debt" are you talking about?

POP is pretty archaic and lack support for multiple clients accessing the same account.

IMAP is complex, slow and lack modern email futures threading, contacts. Clients often implement it in inconsistent matter, given there are plenty of extensions.

SMTP is not a single protocol but collection of bolted on protocols (DMARC, DKIM, SPF). Lack delivery tracking, and it is very opaque when it comes to spam filtering.

All these protocols are build on top of raw TCP. It is harder to implement any things we take for granted in http like: encryption, compression, multiplexing and debugability are not there by default.

> That has nothing to do with actual email protocols. Generic email protocols are extremely reliable and resilient to any sorts of disruptions. I wish any of modern protocols exhibit similar simplicity and reliability.

People spend decades building infrastructure, but even then only hardcore graybeard will self-host email.

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1. jesterson ◴[03 Jul 25 04:40 UTC] No.44451685[source]▶
> POP is pretty archaic and lack support for multiple clients accessing the same account.

There are no issues with POP and multiple clients whatsoever.

> IMAP is complex, slow and lack modern email futures threading, contacts.

What's "complex" about IMAP? Extremely simple and reliable protocol. Contacts are not part of IMAP and handled by different protocols.

> SMTP is not a single protocol but collection of bolted on protocols (DMARC, DKIM, SPF).

I suggest you to educate yourself on DKIM, DMARC, SPF and SMTP before making those statements.

> Lack delivery tracking, and it is very opaque when it comes to spam filtering.

It DOES have delivery tracking. Spam filtering is not a protocol feature and it shouldn't be. I suggest you again to educate yourself.

> All these protocols are build on top of raw TCP. It is harder to implement any things we take for granted in http like: encryption, compression, multiplexing and debugability are not there by default.

Let me tell you one of most hidden secrets in the industry - EVERYTHING we have online is built on top of raw TCP. Ok, and UDP as well. Every bloody fancy JS framework or mobile app you can think about is written on top of that raw TCP. Crazy world huh?

> People spend decades building infrastructure, but even then only hardcore graybeard will self-host email

If you don't know how to build something doesn't mean it's left out to "hardcore graybeards". You got to admit you just don't know how and either learn or surrender to companies who know, offering the same for a buck. It's pretty simple.

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2. Chyzwar ◴[04 Jul 25 07:46 UTC] No.44462168[source]▶
> There are no issues with POP and multiple clients whatsoever.

POP3 in standard only have "Leave a copy on the server" but lack synchronisation mechanism.

> I suggest you to educate yourself on DKIM, DMARC, SPF and SMTP before making those statements.

You cannot use SMTP in real world without these protocols. Your messages would automatically land in spam folders of big providers. For example, if you want to send email to Gmail, you need SPF and DKIM [1]. Any half decent implementation of SMTP need to support all these protocols [2].

[1] https://support.google.com/a/answer/81126?hl=en

[2] https://github.com/stalwartlabs/stalwart

> It DOES have delivery tracking. Spam filtering is not a protocol feature and it shouldn't be. I suggest you again to educate yourself.

SMTP have extension for DSNs (Delivery Status Notifications) but crucially it does not provide information if/why email was classified as spam. This is a reason why many website registration form have “check spam folder”. SMTP deliverability is a hard problem both on protocol level and infrastructure on spam filtering[3].

[3] https://blog.paranoidpenguin.net/2020/02/self-hosting-email-...

> If you don't know how to build something doesn't mean it's left out to "hardcore graybeards". You got to admit you just don't know how and either learn or surrender to companies who know, offering the same for a buck. It's pretty simple.

I spend a significant amount of time investigating feasibility of building an email product and build some libraries for email protocols. It is not just my opinion but other HNs users including OP. Search HN for "self hosting email" for others people experience.