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”.

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.

>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.

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.

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

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?

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

compared to other businesses this number seems OK :-)

> 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.

> The Acquisition-to-Shutdown Pipeline

For the founders and their investors, that’s nut a bug it’s a feature

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

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.

I fell in love wirh Zenbe back in 2009 and i’m still angry at Facebook for acquishutting them down in 2010

> 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

Pretty sure this is AI written, hence the inconsistencies mentioned in this comment section.

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.

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

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?