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Re:Twilio to Acquire Sendgrid by jm20 on Monday October 15, 2018 @05:55PM (#18224180)
Exactly, if you're at the point where you're sending 1 million emails a month you're either spamming people or you don't care about the difference between $100 and $900.
Re:Twilio to Acquire Sendgrid by Twilicorn on Monday October 15, 2018 @06:58PM (#18224751)
I have a counterexample for you. Start an Internet forum as a side project that lets users subscribe to threads for email notifications. Grow it to xx,xxx users making x,xxx posts per day.

Before you know it, you're sending 20k-50k notification emails every day, and over a million emails a month, without making any money or while barely staying afloat with $100-400/month in ad and donations revenue.

Almost none of the SaaS or IaaS solutions HN loves to praise are within this use case's price range but scrappy not-for-profit communities like this deserve to exist, too. You're basically limited to leasing a bare-metal server or two and making it do almost everything you need.

The difference between $100/mo and $900/mo is the difference between getting to stay online or shutting the forum down. Even the difference between $10/month and $100/month might be enough to close shop over.

Personally, in this scenario, I've found setting up my own mail server with a tool like Postal or Cuttlefish to be worth every minute and delivery rates to even be better (due to getting to manage my own IP address's reputation vs sharing a mail-sending IP with anyone else).

Re:Twilio to Acquire Sendgrid by ultrasaurus on Monday October 15, 2018 @07:23PM (#18224983)
SendGrid (and I assume the other similar services) charges a premium to pay for the work that your emails don't get blacklisted anywhere enroute -- that's worth 1/20th of a penny to most business emails (since it increases open rates), but it may not be worth it for every use case.
Re:Twilio to Acquire Sendgrid by resters on Monday October 15, 2018 @07:49PM (#18225164)
Isn't it the case these days that if you aren't sending spam and have a stable sending IP that the system will eventually learn that you are not a spammer and your emails will get delivered?

It can take months for an IP to earn a reputation as a non-spammer, but once it's earned I find it hard to believe that Sendgrid offers any additional ability to get emails delivered outside of the natural earning of reputation.

Re:Twilio to Acquire Sendgrid by Twilicorn on Monday October 15, 2018 @08:30PM (#18225398)
It doesn't even take months. Reputable hosting companies give you a "clean" IP that isn't on any blacklists; its reputation is yours to make or break from that point onward. Send clean mail from the get-go and the IP's reputation goes from "neutral" to "trusted" very quickly, in a week or two tops.

You end up on blacklists by sending out spam. Don't spam - meaning, don't send unsolicited emails. That's it. That's all. Done. There's no magical secret sauce to this like SES, SendGrid, Sparkpost, and friends want you to believe.

There are two things you have to do to not spam:

- Don't be the one sending spam. Don't send your users any email they don't ask for short of extenuating circumstances that truly or legally warrant it, like a security breach. Just don't. This also includes making it brain-dead simple to unsubscribe from anything they once signed up for.

- Don't let anyone else send spam through your server. Keep it locked down. Lots of criminals are constantly prowling the IPv4 address space for poorly secured mail servers to fire out a million crappy scam mails from before a blacklist notices.

The amount of work that blacklists create is grossly overblown. If you're doing email right, the only time you'll ever interact with one is when your mail server gets owned - in which case, you send the blacklists a quick note to explain what happened, that you fixed it, and they take you off of it within a day.

Sign up for mxtoolbox.com, secure your server, respect your users' inboxes, and you only have the box's uptime to worry about.

Re:Twilio to Acquire Sendgrid by disiplus on Tuesday October 16, 2018 @04:18AM (#18227620)
That's simpty not true. We never ever do send spam, and i mean not even newsletters for our customers. And i still had problems when delivering invoices (PDF attachments), And thats with paying mxtoolbox 25$ to monitor blacklists. The biggest problem was microsoft365 mail service. We then switched to external local mail provider (europe) that had better delivery but even then some of the invoices would simply get stuck in microsoft365 and i would get no reponse. We are now using mandrill, and it works ok. I did not want to host it outside of europe but i did not have any other option.
Re:Twilio to Acquire Sendgrid by Twilicorn on Tuesday October 16, 2018 @06:10AM (#18228093)
One anecdote against another. My suspicion is that you were in a "bad neighbourhood" - ie. using a hosting or email service that didn't keep their IP's squeaky clean. AWS/EC2 is a common host among the HN crowd but is one of the worse places to host a own mail server at for this reason - they'd also rather upsell you SES than fix the EC2 IP ranges' reputation.

Microsoft is the pickiest email provider to get good delivery rates to - they require a gradual volume ramp-up over 1-4 weeks on a fresh IP to see it as good, in my experience, and SNDS is something to keep a close eye on during that time - it clearly indicates your IP's reputation with them and how much mail they see from it. That number being higher than expected plus the sample emails they provide may indicate something going wrong - through this, I once discovered an obscure feature in a software package I used that allowed visitors to send emails to arbitrary addresses.

Mandrill has better delivery than the other email services I've tried but is cripplingly expensive for a hobby project that happens to have a nontrivial userbase.

Re:Twilio to Acquire Sendgrid by disiplus on Tuesday October 16, 2018 @08:07AM (#18228654)
> My suspicion is that you were in a "bad neighbourhood" - ie. using a hosting or email service that didn't keep their IP's squeaky clean.

No, not really, we are using one the most expensive offerings in Switzerland. Renting dedi servers for spamming would be not only extremely expensive, they would kick you right away if they noticed. As i said we did nothing wrong, used monitoring and our invoice emails would sometimes end in the spamlist for microsoft, after trying to get it right i gave up and hooked mandrill.

if you are runnig some random internet forum, some part of your notifications ending in spam is not a big deal, but for us, invoices ending in spam box is not something you can ignore.

Re:Twilio to Acquire Sendgrid by e12e on Tuesday October 16, 2018 @01:16PM (#18231168)
I remember I had to go through a couple of hoops with outlook.com and gmail(?) using some un-/under-documented web sites to get "approved" (sending a mail, getting a reply, typing reply in web form).

And in my experience the major services have unpredictable spam filter behavior.

I even saw Google being cute and assuming mail in Japanese was spam - because my profile is western.

So yeah. If your goal is 100% (not high 90s) deliverability - including the odd big attachement or foreign encoding mail - it's not trivial.

Thankfully I don't care that much if a recepient at Gmail or outlook don't get my mail;it's their fault. If it's a problem the recipient should move to a more reliable mail provider.

It's obviously not as easy for commercial/work mail...

Re:Twilio to Acquire Sendgrid by wolco on Monday October 15, 2018 @11:29PM (#18226186)
Reputable only matters when small. When large like aws you could be getting anyone's ip.
Re:Twilio to Acquire Sendgrid by Twilicorn on Tuesday October 16, 2018 @06:51AM (#18228224)
AWS has a vested interest in upselling you SES for email-sending needs. The quality of their EC2 IP ranges has little to do with their size; running a tighter ship with those IP's is merely bad for their business model.
Re:Twilio to Acquire Sendgrid by jsjohnst on Monday October 15, 2018 @08:13PM (#18225307)
Don’t respond to spam feedback loops from major mail providers and you’ll quickly get blacklisted no matter how much reputation you built up. This could happen at any point and doesn’t require that many people to mark as spam.

It’s worth paying someone if deliverability is important.

Re:Twilio to Acquire Sendgrid by Twilicorn on Tuesday October 16, 2018 @06:20AM (#18228124)
Deal with the spam feedback loops - they exist for a reason. You have to treat an FBL email as someone hitting the "unsubscribe" link (though it might also be an indication your unsubscribe link has to be more visible or your unsubscribe process less obtuse). Some off-the-shelf software can monitor your bounce and FBL messages and automatically process them as such.

Getting blacklisted is a temporary state and I maintain it's easy to recover from if your IP's and domains had a good history. I've experienced the IP's that email hosting services send my mail through being blacklisted and then waiting days for them to deal with it versus being able to contact blacklists on my own behalf to resolve things same-day.

I used to pay one of these services $xxx/month and experienced delivery rates around 60-70% that they couldn't do anything about other than offering me a dedicated IP for a lot more money. Moved to my own mail server with an OSS transactional email system and delivery rates shot up to 99%-ish while eliminating the email bill.

Re:Twilio to Acquire Sendgrid by jabart on Tuesday October 16, 2018 @09:33AM (#18229187)
What OSS projects did you use for this?
Re:Twilio to Acquire Sendgrid by Twilicorn on Tuesday October 16, 2018 @12:47PM (#18230884)
Postal is my favorite: https://postal.atech.media/
Re:Twilio to Acquire Sendgrid by e12e on Tuesday October 16, 2018 @01:30PM (#18231306)
I'm not sure I see how this is a problem (or viable market). No income, volunteer resources - your best bet would be run it yourself (affordable dedicated servers, lots of free volunteer hours) and/or do it for/with others (like neocities.org is doing for web hosting).

Seems to be fewer such services now than a decade ago, but maybe something like: https://www.freelists.org/

The idea behind SaaS is that it's wildly more expensive (higher margins) because it frees up all those hours to making profit. So make a hundred spend fifty, versus make twenty spend ten on hosting. Or something along those lines.

Re:Twilio to Acquire Sendgrid by jazoom on Monday October 15, 2018 @06:05PM (#18224267)
Or you run a popular free service or service that makes so little money this is important. Consider F5bot. It wouldn't take too many subscribers getting several emails per day to hit 1000000 per month.
Re:Twilio to Acquire Sendgrid by overcast on Monday October 15, 2018 @08:41PM (#18225456)
That's why you don't run a free service with actual value that people would pay for. F5Bot is just being taken advantage of in my opinion. They recently got front page of HN again, and their patreon page went from $41 a month to a whopping $50.
Re:Twilio to Acquire Sendgrid by jazoom on Monday October 15, 2018 @09:02PM (#18225551)
I can come up with examples all day of things people could create where they care about $900 leaving their pocket each month. Dismissing all these projects wholesale (as the parent comment did) is not helpful.
Re:Twilio to Acquire Sendgrid by manquer on Monday October 15, 2018 @11:12PM (#18226102)
If you are on shoe string , sending your own email is a better solution. It will take few weeks to establish your rep, as along you process the abuse reports , it is not a problem for transactional email.

The original question was for marketing email, if you are sending a million marketing emails a month and not making enough money then the conclusion that you are sending spam is not unreasonable

Re:Twilio to Acquire Sendgrid by jazoom on Monday October 15, 2018 @11:26PM (#18226167)
> If you are on shoe string , sending your own email is a better solution.

Or just use something like Elastic Email or SES.

> The original question was for marketing email, if you are sending a million marketing emails a month and not making enough money then the conclusion that you are sending spam is not unreasonable

That's fair enough.