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Posted by skeptrune 7/1/2025

Why email startups fail(forwardemail.net)
141 points | 133 comments
sethammons 7/1/2025|
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.
zaik 7/1/2025||
> email marketing companies

This means spammers, right?

colechristensen 7/1/2025|||
No, in order for their traffic to not get blackholed, places like sendgrid have to follow the rules and make their customers follow the rules. The marketing emails they send will be somewhere between things people actually want to see and mildly annoying. There are plenty of things I subscribe to which are marketing emails I want to see.
friendzis 7/1/2025|||
> places like sendgrid have to follow the rules and make their customers follow the rules

i.e. juggle between allowing allowing some paid spam and not being outright blocked by google/microsoft. That's the service they provide: VC-backed connections to get traffic unblackholed on behalf of their spammer customers.

amy214 7/2/2025||
exactly, then a leader says:

>There are plenty of things I subscribe to which are marketing emails I want to see.

Therefore: that's how I feel about my e-mail, meaning let's send a billion messages a day, surely a billion people also feel same as me about it.

friendzis 7/3/2025||
It's a classic example of anecdotal framing. Email traffic is blackholed by default and these mass-emailing services are needed precisely because majority of email traffic is marketing and majority of that subtraffic is spam.
BiteCode_dev 7/1/2025|||
"mildly annoying"

That's another name for spam.

fc417fc802 7/1/2025|||
Perhaps historically, but these days I think spam refers to senders that don't play by the rules. Unsolicited (ie didn't obtain the recipient's address in a legitimate manner), no unsubscribe link (or not honored), technical measures intended to circumvent various filters, etc.
selcuka 7/1/2025|||
I agree. These days I don't report email as spam if it has a (working) unsubscribe link.
dietr1ch 7/8/2025|||
Working unsubscribe link is hard to effectively see. I'd be getting no spam emails by now if they worked.

You'll get a link to unsubscribe (to just that campaign), or unsubscribe, but somehow get your email back into the victims table.

BiteCode_dev 7/1/2025|||
Oh, so a day is not rainy if your coat dries after it?
selcuka 7/2/2025||
No, rain is still rain. I just stopped complaining about it as it rains 24/7.
amy214 7/2/2025||
The ugly and awkward thing about the unsubscribe link is I never subscribed in the first place. Someone else did on my behalf. To even ask to be unsubscribed, I feel, is taking some ownership of the subscription and playing into a crooked system. It's like being sent an invoice for something I never ordered and needing to cancel the invoice. And even if you say, "buzz off", who is to say someone won't decide to "resubscribe" you next day, given it's outside your control.

Me personally I won't give a pass to business with an unsubscribe link, I have extreme disgust that we're in some make-believe pretend world that I asked for this in the first place

SaucyWrong 7/2/2025||
I’m with you. I learned about the concept of “implicit opt-in / consent” while I was building an email marketing feature on a platform and I found the concept disgusting, but was told that because it’s technically legal, our customers considered it table stakes.
s1mplicissimus 7/1/2025|||
You may define it that way, but the original property of spam seems to apply nevertheless: They are low quality and noone really likes them.

The fact that you have to frame it your way speaks mostly to the fact that apparently your income depends on spam being seen as acceptable and not a scourge to humanity. But that's just my perspective...

fc417fc802 7/2/2025||
That's a rather baseless assumption about my income. Does it really seem so unlikely to you that a reasonable person might not use the exact same criteria as yourself? Why are you so confident in the generalization of your own perspective to the population at large?

Define "low quality" and "not liked". Each person will classify a given message differently. At least in the general case it's hardly realistic to expect a sender to classify a message from the perspective of a specific recipient prior to sending it.

On the other hand, it is reasonable to expect addresses to be acquired via legitimate means (ie collected only with the consent of the recipient) and to cease attempts at contact when requested. That's essentially the boundary between reasonable conduct and harassment.

s1mplicissimus 7/13/2025||
I did not assume, I drew a conclusion from working on email marketing software and experiencing first hand the worldview that seems necessary to stay in this line of work while avoiding cognitive dissonance.

> At least in the general case it's hardly realistic to expect a sender to classify a message from the perspective of a specific recipient prior to sending it

I guess from the perspective of someone doing mass mailings that is true. A pointer to what I assume is your bias on the topic. But from the perspective of the recipient, who actually has to invest the cognitive effort of reading that message, I think it's only natural to expect a certain amount of average value out of that effort. And lets be honest, that mass mailing doesn't usually deliver that. It's just another trigger designed to manipulate people into buying shit they didn't even really want.

Let's rather have the default newsletter checkbox to be "off" and legal repercussions for repeated offenders, then I'll be on board for the term "reasonable conduct" too.

thorncorona 7/1/2025|||
marketing emails are mildly annoying until you want to buy something and they become useful for the 20% coupon
distances 7/1/2025|||
If I want certain marketing emails for these purposes, I create a rule to mark it read on arrival and moved directly to a certain folder where I can find it when needed. It will still never see my inbox.
whatevaa 7/1/2025||
Most people don't know what a rule is.
iancmceachern 7/1/2025||||
Or the band you love is in town
BiteCode_dev 7/1/2025|||
Sure, would you be kind enough to publish your personal phone number on this public thread?

I'm sure you'll get mostly useful feedback.

iancmceachern 7/1/2025||
I own and operate a public facing company with my name on it. This is already the case. Par for the course.
Viliam1234 7/1/2025|||
Or there is a discount for Viagra
BiteCode_dev 7/1/2025||||
That's what opt-in is for.

But it almost never is, isn't it?

BobaFloutist 7/1/2025|||
What if the product just cost 20% less in the first place?
satvikpendem 7/2/2025||
Then your company crashes in sales.

https://www.forbes.com/sites/panosmourdoukoutas/2017/02/24/a...

NoGravitas 7/1/2025||||
More likely bacn than spam. Stuff that you agreed to receive, but don't especially want. Even though people don't really want bacn, it's the compromise that society has generally accepted in terms of drawing a line against spam while still catering to allegedly legitimate marketing.
xandrius 7/1/2025||
Looking for a job, I see :P
albertgoeswoof 7/1/2025||
> 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!

zombot 7/1/2025||
> Turns out YC and others are funding wrappers on aws ses left right and center!

A groundbreaking innovation that will totally disrupt everything including pizza delivery!

DrillShopper 7/1/2025||
> Turns out YC and others are funding wrappers on aws ses left right and center!

Given what a giant pain in the ass (for good reason, fuck spam) it is to get into the Gmail inbox I can understand why the spammers do it.

tracker1 7/1/2025|||
Dunno... I'm running a mailu box, without delivery issues to Gmail... now Outlook.com hosted mail (not o365) is another story.

I have forward/backward dns configured as well as dkim, spf, etc. With TLS endpoints configured for secure transmission. It's worked pretty well in general. That said, I'm not using it that much, and there's no spam coming from my server (dedicated box on OVH), I dedicated a VM/IP to the mail server.

krageon 7/2/2025|||
This just isn't true. For some reason everyone keeps repeating it anyway, I suspect because they haven't tried it and someone told them confidently it wasn't practical.
laborcontract 7/1/2025||
My first thought was wow - 20% of email startups succeed? That’s actually pretty good.
dvt 7/1/2025||
> 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

ghusto 7/1/2025||
> No (real) customer has ever, or will ever, care about this. Discord and Slack are pretty much case-in-points

Worked at two companies full of "real" users who cared enough to look elsewhere.

Yes I know it's easy to find exceptions to every argument, but it's worth pointing out that it's such a bad experience that even some "normal" people care.

egglemonsoup 7/1/2025|||
I am a real Discord customer who is actively looking for an alternative due to how terrible the performance is on my M1 MacBook and on my gaming PC. I'm just one person—I'm not claiming to represent the 'average' customer. But I am part of the average.
CaveTech 7/1/2025||
The other part of the average is the 200m+ monthly active users who can't seem to find the uninstall button.
nottorp 7/1/2025||
It really depends.

If all you do is run games and discord on your home PC memory consumption won't matter.

If you have multiple uses or work from home ... Discord expanding to 4 G to display the meme channel with all those cat photos will be annoying to say the least.

Case in point, I stopped running Discord on my laptop. Still run it on a desktop to keep in touch with some people, but it's not my default goto for any communication.

Also, just because most users don't know better, it doesn't mean that Electron apps aren't basically disrespecting the user's resources and passing needless costs to them. Especially if you have hundreds of million users the extra cost they pay dwarfs whatever you the app developer would have paid for a working native application.

CaveTech 7/1/2025||
The whole thesis OP is making is that this isn’t really true, evidenced by real world behaviours. Electron apps have some of the highest market share, even the worlds most popular ide is an electron app.

The amount of people who won’t adopt based on pricipal is exceedingly small.

moooo99 7/1/2025|||
> No (real) customer has ever, or will ever, care about this. Discord and Slack are pretty much case-in-points:

This is just flat out false. Even my girlfriend - the least tech interest person I know - complained to me how its possible that a damn chat app (teams) is bad enough to make her entire computer feel slow.

So yeah, average users maybe don‘t hate Electron or React, bad many people hat the bad user experiences these solutions often entail.

bodge5000 7/1/2025|||
There's a slight difference, real customers care if the software feels slow, not if its using Electron or React. You might argue that they're one in the same, and I wouldn't disagree, but they don't know that (or arguably care about that), and so don't know what to look for and what to avoid. By the time they realise the software they're using is slow, they're often too embedded in it to quit for that reason alone.

The real question is; has your girlfriend stopped using teams since finding out how slow it is?

ghusto 7/1/2025|||
The argument was the slowness, not the name of the technology. He only mentioned named it because _we_ all know the relationship.

> The real question is; has your girlfriend stopped using teams since finding out how slow it is?

Don't know about his girlfriend, but two companies I was at did (one stopped with MS Teams, one with Slack).

bodge5000 7/2/2025||
> The argument was the slowness, not the name of the technology

I disagree. The crux of his argument was slowness, sure, but that's not why these applications fail because as I said, unless you know what to look for (Electron and React being the two main offenders), by the time you've found out that the application is slow, you're "locked in". Leaving these kinds of software after you've got setup with them is a lot more effort than starting with them. Email arguably more than any other, but messaging apps like Teams and Discord also suffer from this network effect.

moooo99 7/1/2025|||
> The real question is; has your girlfriend stopped using teams since finding out how slow it is?

That is the neat part. Teams, Slack and some other applications within that realm aren't actually something that we're choosing to use. It usually is something that is imposed onto us by the organization you're working for. With discord the effect is different, but the consequence is the same. Network effects basically force you to be on Discord.

At least in my department, Microsoft Teams is universally hated by everyone (that's only n=60). But we don't really have a choice in using it and we never had a say in the matter when the software was bought. With teams especially, it's basically an open secret that Teams is frequently only bought because its basically packaged in with an Microsoft 363 subscription.

And because of how software like this is imposed, I don't think the size of the user base serves as a good proxy to judge how well liked a piece of software is, at least in the enterprise space. For B2C apps, the effect may be less strong to non existent, but I would argue that the network effects of some apps can act as a similarly strong force.

bodge5000 7/2/2025|||
That's very true, I suppose my point was less that these kinds of software are well liked, but more so that the effort of leaving them outweighs the gains in the performance alone for a lot of users. But you're right, the argument doesn't really hold up for Teams because you rarely have a choice in the matter. Discord there is some choice, you can organise your friends and groups to leave, but its a monumental effort.
FireBeyond 7/1/2025|||
> With teams especially, it's basically an open secret that Teams is frequently only bought because its basically packaged in with an Microsoft 363 subscription.

In our case, we see Salesforce as our biggest competitor, so we did not want our corporate history on Slack (I don't think that's particularly a high risk issue, but our leadership does, so... Teams it is.)

mamcx 7/1/2025|||
Yeah. "No (real) customer has ever, or will ever, care about this. ", in fact means "No (real) customer has ever, or will ever, knows how to care about this".

And because they don't know, the heat is in somebody else. Like the tech support, or windows, or internet, or the anti virus or whatever (because even some tech support, if even exist, don't know but surely have a theory about it).

Let me tell you an example: When the local network, cloud flare, printer, windows, their firewall, etc fails and by coincidence they are using our app. they call US.

And blame US.

A sizable portion of the support calls that are handled by any provider of tech for small companies is about other peoples software.

impossiblefork 7/2/2025||
Yes, but couldn't you to market it as 'four times faster than teams', 'no action will ever take longer than 5 ms' 'enables cross-referencing many e-mails without delay-- other software can take half a second to bring up an e-mail', etc?
wlonkly 7/2/2025|||
> 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?

And, even more on point, so is Postfix!

shwouchk 7/1/2025||
> bloated Electron apps that just about everyone on the planet has installed on their computers

i guess im the one guy left that has neither

edit:quote

ajjenkins 7/1/2025||
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”.
CaveTech 7/1/2025||
It is mentioned, there's an entire section named "The HEY Experiment".
tristan957 7/1/2025|||
By reinvent are you referring to UX? Fastmail is reinventing email through superior open protocols.
benhurmarcel 7/1/2025|||
JMAP is mentioned in the article (negatively)
BiteCode_dev 7/1/2025||||
UX is what made the difference between the first iPhone and a palm.
worthless-trash 7/1/2025||
We have regressed as a society.
ericrosedev 7/1/2025|||
Obligatory “as far as the customer is concerned, the interface is the product”
jiveturkey 7/1/2025||
> 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.

AnonC 7/1/2025||
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.
nottorp 7/1/2025||
Because the "AI" wasn't trained on enough mentions of those :)
hanche 7/1/2025||
> Runbox.com is a one person operation.

Small team yes, but one person? https://runbox.com/about/runbox-team/ indicates otherwise. (I am a happy customer.)

muratsu 7/1/2025||
Mailbox raising 6M, having a 100M exit and getting called out failure is crazy
runako 7/1/2025|
Rapportive listed at having raised $120k for a $15m exit also stands out.
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