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I was engineer 12 at SendGrid and left after IPO and subsequent acquisition by Twilio. Being infrastructure and the backing many email marketing companies, we did really well. Kind of like selling shovels in the gold rush. We struggled more on the product front breaking into the much larger marketing space. Learned a lot there leading and scaling teams and scaling the email infrastructure to support over 8 billion daily sends.

7 months agoby sethammons

> Every single "email startup" is just building UI on top of existing infrastructure. They're not building actual email servers - they're building apps that connect to real email infrastructure.

This is something that shocked me when I built https://mailpace.com I just assumed that everyone doing email ran their own smtp servers. Turns out YC and others are funding wrappers on aws ses left right and center!

7 months agoby albertgoeswoof

My first thought was wow - 20% of email startups succeed? That’s actually pretty good.

7 months agoby laborcontract

> Electron Performance Crisis: Modern email clients built with Electron and React Native suffer from severe memory bloat and performance issues. These cross-platform frameworks, while convenient for developers, create resource-heavy applications that consume hundreds of megabytes to gigabytes of RAM for basic email functionality.

No (real) customer has ever, or will ever, care about this. Discord and Slack are pretty much case-in-points: bloated Electron apps that just about everyone on the planet has installed on their computers. I personally hate React, but technology decisions are irrelevant to the long-term success of startups. (As long as they don't grossly interfere with customer experience, the feature set, etc.)

> Final Warning: After analyzing hundreds of email startups, the evidence is overwhelming - 80%+ fail completely. Email isn't broken, and trying to "fix" it is a guaranteed path to failure.

First, I'd bet money that figure is actually wrong: the failure rate is likely way higher than 80%. And I'm honestly not sure how anyone could seriously think a 20% exit rate is bad in just about any vertical (but especially a "boring" one like email).

> Resources: Volunteer developers can't sustain enterprise-level software

What am I even reading here? Author does realize openssl[1], Linux[2], and many other "enterprise-level" pieces of software are entirely (or almost entirely) maintained by volunteer developers, right?

Anyway, the post had its opposite intended effect on me: it made me think about ways I could reinvent email.

[1] https://github.com/openssl/openssl

[2] https://github.com/torvalds/linux

7 months agoby dvt

I’m surprised Hey isn’t mentioned. That’s the only example I know of someone recently trying to reinvent email. Maybe it wasn’t included because it’s part of Basecamp and not its own company. But I think it’s important to discuss if your argument is that “no one has successfully reinvented email”.

7 months agoby ajjenkins

> Techstars alone has 28 email-related companies with only 5 exits - an exceedingly high failure rate (sometimes calculated to be 80%+).

This is actually better than overall failure rate. At 80% I would absolutely be investing in more email companies!

The entire analysis is skewed to satisfy their own messaging or perhaps internal motivation. Mentioning Cyrus IMAP and SpamAssassin is ... being stuck in a time warp.

Being self-funded, their position is not surprising. However they really need some perspective.

7 months agoby jiveturkey

If Fastmail is included in the startup category, why aren’t email companies like Posteo and Mailbox.org included? Runbox.com is a one person operation. They’ve all been around for decades and are still going strong. Posteo hasn’t even taken any VC investment (which could be one reason, as the article points out, for failure). Migadu has been around for quite sometime and doesn’t find a mention in this list.

7 months agoby AnonC

Mailbox raising 6M, having a 100M exit and getting called out failure is crazy

7 months agoby muratsu

Been There, Done That, Bought The T-Shirt.

Around 2008, tried to M&A regional email providers that served commercial and government enterprises throughout UK and Europe onto a more secure, standardized, and centralized infrastructure with lower employee count.

Totally obliterated by GMail and Hotmail because competing with (almost) free on something people really don't want to change once established is really, really hard even if you're gobbling up the supply-side.

Maybe it scales where there are compliance aspects like ProofPoint, but otherwise people don't want to change utility infrastructure without a big win or significant existing pain.

Times have changed but getting people to move on low cost commodity utilities with lots of options is almost like going into the restaurant industry.

7 months agoby burnt-resistor

It seems Forward Email has come to the exact same conclusion I did in a blog post awhile back: https://marcoapp.io/blog/marco-an-introduction

I agree that "reinventing" email, or building a business based on "AI features" are both terrible ideas.

We began building Marco not to do either of these things, but simply because _there wasn't_ any actual cross-platform IMAP client.

Apple Mail exists (but is terrible) if you only have Apple devices. Lots of other options like Superhuman and Shortwave exist, but only support Gmail+Outlook.

All we're doing is building the app that should have existed 10 years ago: a cross-platform, offline-first "Thunderbird". Except far more lightweight and modern. And yes, we've built it from the ground up. And no, it's not Electron.

https://marcoapp.io

7 months agoby isaachinman

What's left to conquer in email land?

Most of the large marketing ecommerce/enterprise market was captured via ExactTarget/Salesforce, Oracle/Responsys/Eloqua, IBM/SilverPop/Acoustic, Adobe/Neolane/Marketo by the mid 2010's.

SendGrid/Twilio was another a few years later, Amazon SES is ok, then you have some of the smaller market players (MailChimp, Constant Contact, etc).

Hard to scale/grow a startup in any real way when there are so many fairly well entrenched solutions across industries and company sizes.

7 months agoby chevman

> Email works perfectly

OMG. How can someone say this in the age of AI spam. Legitimate emails categorized a spam. Impossibility to run independent email servers because getting blocked by the big players. Forced subscriptions to mailing lists. Tracking through images....

7 months agoby meinersbur

We’ve worked on email infrastructure for multiple clients at Axon, and everything in this write-up checks out. Most startups just build wrappers around Postfix or SES and call it innovation. The hard problems, such as spam filtering, deliverability, and auth protocols, never get touched. That’s why 80% fail.

7 months agoby Leon_25

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?

7 months agoby JimDabell

> Quantum-Safe Email Security: Forward Email is the world's first and only email service to use quantum-resistant and individually encrypted SQLite mailboxes

lol thanks but no thanks

7 months agoby taki

If 1 in 5 takes off, is that really a bad success rate given that's widely considered the average startup success rate?

7 months agoby aussieguy1234

> Email Statistics: 347.3 billion emails sent daily without major issues, serving 4.37 billion email users worldwide as of 2023.

The average user receives 86 emails per day?! And I get a bit overwhelmed if I receive more than 3. Kinda puts things into perspective :-)

7 months agoby mslansn

I wouldn't say Sparrow failed -- it got bought because it was successful. Did it reach its full potential? Certainly not. But certainly Google determined that it potentially could or it wouldn't have spent $MM to kill it.

7 months agoby insane_dreamer

>But they ignore the fundamental reality: email works perfectly for what it was designed to do.

Yeah the fundamental thing is email does it's job, and if you want to change that job in any dramatic fashion ... it no longer does its core job.

7 months agoby duxup

Actually recent email innovation I enjoyed is Mimestream, the macOS native client for Gmail. Apple’s smart inbox is half baked but better than nothing. Cloudflare now also has a pretty good email forwarding service.

7 months agoby chazeon

Long article, but the fundamental premise is that IMAP, SMTP, and POP are all you need. And that email clients are good... This is just false IMHO. There is a reason why both Fastmail and Gmail implement their own protocols in addition to those.

But fundamentally the "folder" view of email does not work. A single message often needs to be in several different folders simultaneously. And when the thread is spread across many folders, there needs to be a way to see the whole thread.

The only way to accomplish this is with email tags or labels. These are implemented by nearly all successful email companies. Gmail, Fastmail, and Proton are examples. Labels are a fundamental feature in this day and age, and neither IMAP nor POP can handle them gracefully.

Gmail is so big that when Outlook, Apple Mail, and even Thunderbird connect to it, they do an OAuth exchange and then talk over a proprietary protocol.

JMAP may have poor adoption, but it's the only open protocol that understands labels well. The lack of adoption is mostly due to email providers not implementing it. There is not a lot of incentive for clients to implement it for the few providers. And providers would prefer you use their web clients anyway, as then they control access to your email.

7 months agoby georgyo

Is 80% even that high? I thought the idea behind VC was to fund companies where 90% are doomed to fail, 9% might do okay, in order to cash in big on the 1% that have stellar success.

Am I way off with my numbers there?

7 months agoby cedilla

My god this "article" is an inconsistent pile of AI slop. It actively contridicts itself and changes the thesis several times as it goes on and on and on.

7 months agoby fyrn_

Not sure why they attack Fastmail and JMAP all the time.

7 months agoby andrewshadura

> Gmail's threading: Enhanced email organization

Gmail's threading is an abomination.

"If you want to fork a thread, just change the subject!" This idea is so brain-dead and antithetical to deep mailing list conversations.

"Oops too many people replied, guess gmail'll fork the thread without changing the subject"