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Ask HN: How are you hosting email for your startup employees?

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Re: Ask HN: How are you hosting email for your startup employees?

#21

Post by CharlesW »

solardev wrote: post #2

Definitely don't do this yourself if you're not familiar with how it works. If you don't set up all the SPF, DMARC, DKIM etc. perfectly, you're going to get terrible deliverability (your outgoing emails will get auto marked as spam). Just pay Google or Microsoft or Yahoo or whoever to do it for you. Reliable email is not something to skimp on. Edit: Also, IMHO: gsuite (or whatever they renamed it to) is a huge produc…

> It's also much more usable cross platforms than the nightmare that is MS Office. Outlook is terrrrrrrrible.

In what way? I’ve used both Google Workspace and Office 365 during my career. I don’t dislike Google Workspace, but Office 365 is notably more mature, capable, and complete. (I mostly use Macs, but the web apps work the same on any browser/OS.)

Re: Ask HN: How are you hosting email for your startup employees?

#22

Post by happymellon »

jcz_nz wrote: post #8
fencepost wrote: post #6

If you're going to be partially or fully on the Microsoft ecosystem (Office most obviously, especially if you're going to be doing document exchange), just go ahead and get M365 Business Premium - along with Office it gets you Azure AD for signins, Onedrive for per user storage, SharePoint for shared storage, email, etc. Premium adds email encryption, plus Intune as a somewhat replacement for domain Group Policy, Win…

AD is ok until you have to get some oddball issue fixed. It’s obtuse, with a mix is old and new (and really old) front ends, and a bajillion options that interact in non-obvious ways. Eventually your salvation will be found in a 17 minute video walkthrough recorded by some Brazilian hacker who happens to mention that you must configure X like so, or Y won’t work. This is setting up SSO btw. MS management tools are a…

There are so many odd limitations with Azure, such as the inexplicable inability to make a mailing list.

Re: Ask HN: How are you hosting email for your startup employees?

#23

Post by jfim »

solardev wrote: post #2

Definitely don't do this yourself if you're not familiar with how it works. If you don't set up all the SPF, DMARC, DKIM etc. perfectly, you're going to get terrible deliverability (your outgoing emails will get auto marked as spam). Just pay Google or Microsoft or Yahoo or whoever to do it for you. Reliable email is not something to skimp on. Edit: Also, IMHO: gsuite (or whatever they renamed it to) is a huge produc…

Outlook beats the pants out of Google calendar when it comes to reminding people of meetings.

As an IC, I used to miss meetings due to the Google calendar browser notification being so tiny and unintrusive. Contrast with the totally in your face Outlook meeting notification that can't be missed.

Re: Ask HN: How are you hosting email for your startup employees?

#24

Post by solardev »

CharlesW wrote: post #21
solardev wrote: post #2

Definitely don't do this yourself if you're not familiar with how it works. If you don't set up all the SPF, DMARC, DKIM etc. perfectly, you're going to get terrible deliverability (your outgoing emails will get auto marked as spam). Just pay Google or Microsoft or Yahoo or whoever to do it for you. Reliable email is not something to skimp on. Edit: Also, IMHO: gsuite (or whatever they renamed it to) is a huge produc…

> It's also much more usable cross platforms than the nightmare that is MS Office. Outlook is terrrrrrrrible. In what way? I’ve used both Google Workspace and Office 365 during my career. I don’t dislike Google Workspace, but Office 365 is notably more mature, capable, and complete. (I mostly use Macs, but the web apps work the same on any browser/OS.)

Really? Surely you're joking..? I've had the complete opposite experience, and in fact have never found a piece of productivity software as horrible as Office 365. Also on a Mac...

Email: Outlook UI and hotkeys are totally different from MacOS, Windows, and Web. Rules don't really work and are impossible to debug. Search is terrible. Threading is terrible (expands the subjects of each child message, but not their bodies... whyyyy).

Calendar: How the heck do you find an event you previously declined but changed your mind on? Why does Teams and Outlook both offer a calendar, with subtly different UIs and features, and the web interface is totally different yet again? It is incredibly slow (things take multiple seconds, like loading someone else's calendar, or clicking on an event it has to take time to load in the attendees...). The "suggested times" feature is hard to find and there's no visual guide (like a week view); also it again seems different between the apps.

Teams: Oh god. This... is what they came up with? It's sooooo slow on startup. It duplicates Outlook notifications. It is hard to find the meeting you're supposed to join when you first clicked on a join link, but then it asks you to login, etc. It's so much less feature-ful than Zoom, yet so much harder to use (and uglier) than Meet. Why do the chat rooms persist not only after a meeting but get resurrected later in the week, and why do they notify you for chats in a meeting that you're not even in. The share screen sidebar is atrociously hard to see to determine which window you're trying to share. Like... literally all the basics they got wrong, and this one software has the worst UX of anything I've seen.

Excel, Word, etc.: My god, the UI has gotten even worse, the forced OneDrive integration is terrible, etc...

I grew up using Microsoft stuff until Google started popularizing their online suite. In the years since, every employer except this most recent one has used Google and while it never struck me as particularly pretty, it was pretty easy to use for the most part. I was actually kinda curious to try the Microsoft stuff again, figured they had 20 years to catch up, it's gotta be better now, right? Nope. I've never hated a stack as much as this, even as a long-time Windows user... in fact it's going to be one of my questions for employers in the future, and a big red flag.

Sorry, I know I sound pretty agitated about this. Their software griefs me on a daily basis and is the single thing I hate the most about my job. It's just SO terrible. I guess YMMV, eh? I didn't realize there were actually people out there who preferred the Microsoft stuff... of the folks I've spoked to casually, all vastly preferred Google's implementations. But that's just anecdotal.

Re: Ask HN: How are you hosting email for your startup employees?

#25

Post by solardev »

jfim wrote: post #23
solardev wrote: post #2

Definitely don't do this yourself if you're not familiar with how it works. If you don't set up all the SPF, DMARC, DKIM etc. perfectly, you're going to get terrible deliverability (your outgoing emails will get auto marked as spam). Just pay Google or Microsoft or Yahoo or whoever to do it for you. Reliable email is not something to skimp on. Edit: Also, IMHO: gsuite (or whatever they renamed it to) is a huge produc…

Outlook beats the pants out of Google calendar when it comes to reminding people of meetings. As an IC, I used to miss meetings due to the Google calendar browser notification being so tiny and unintrusive. Contrast with the totally in your face Outlook meeting notification that can't be missed.

I never had a problem with this, between Slack integrations and connecting GCal to the desktop calendar app and using its notifications.

On the other hand, I seem to get 3-4 reminders about the same meetings -- even ones I'm already joining -- between Outlook and Teams.

Re: Ask HN: How are you hosting email for your startup employees?

#26

Post by metadat »

technion wrote: post #4

It's a long running meme on /r/webhosting. A person buys "email hosting " somehow, insists they don't need the spend of o365 or Google, loses time and money and ends up on one of those. For background, the number's coming down these days but not long back I managed a lot of Exchange clusters. I'm not afraid to manage mail, I just know it isn't worth it.

This is the sad state of reality today. You can self-host in theory but it's a big, nasty, error-prone burden in reality.

Re: Ask HN: How are you hosting email for your startup employees?

#27

Post by mekster »

solardev wrote: post #2

Definitely don't do this yourself if you're not familiar with how it works. If you don't set up all the SPF, DMARC, DKIM etc. perfectly, you're going to get terrible deliverability (your outgoing emails will get auto marked as spam). Just pay Google or Microsoft or Yahoo or whoever to do it for you. Reliable email is not something to skimp on. Edit: Also, IMHO: gsuite (or whatever they renamed it to) is a huge produc…

Using services like Postmark, the concern becomes smaller.

No one should send emails that should land in a human's inbox directly off a bare random IP.

At least, by running your own email instance, it gives you the ability to easily debug what the problem is with direct logs.

Re: Ask HN: How are you hosting email for your startup employees?

#28

Post by mekster »

jfim wrote: post #23
solardev wrote: post #2

Definitely don't do this yourself if you're not familiar with how it works. If you don't set up all the SPF, DMARC, DKIM etc. perfectly, you're going to get terrible deliverability (your outgoing emails will get auto marked as spam). Just pay Google or Microsoft or Yahoo or whoever to do it for you. Reliable email is not something to skimp on. Edit: Also, IMHO: gsuite (or whatever they renamed it to) is a huge produc…

Outlook beats the pants out of Google calendar when it comes to reminding people of meetings. As an IC, I used to miss meetings due to the Google calendar browser notification being so tiny and unintrusive. Contrast with the totally in your face Outlook meeting notification that can't be missed.

Google is always about backend. They suck on the frontend (except Maps) but somehow they never want to change that habit.

Re: Ask HN: How are you hosting email for your startup employees?

#29

Post by solardev »

mekster wrote: post #27
solardev wrote: post #2

Definitely don't do this yourself if you're not familiar with how it works. If you don't set up all the SPF, DMARC, DKIM etc. perfectly, you're going to get terrible deliverability (your outgoing emails will get auto marked as spam). Just pay Google or Microsoft or Yahoo or whoever to do it for you. Reliable email is not something to skimp on. Edit: Also, IMHO: gsuite (or whatever they renamed it to) is a huge produc…

Using services like Postmark, the concern becomes smaller. No one should send emails that should land in a human's inbox directly off a bare random IP. At least, by running your own email instance, it gives you the ability to easily debug what the problem is with direct logs.

I believe the OP is talking about emails for their employees, like personal inboxes. Postmark is more about transactional emails, no? And even that is offloading a lot of the deliverability concerns to a specialized vendor.

> At least, by running your own email instance, it gives you the ability to easily debug what the problem is with direct logs.

You really really should not need to be doing this yourself. I've had to fix a few of those and it's REALLY not worth anyone's time.

Getting email from Google is $6/mo, Microsoft $6/mo, Zoho $1/mo, Proton $4/mo, Fastmail $3/mo, etc.

Then it's just set it and forget. You don't have to track down quarantined messages, cross-examine a bunch of headers, check blacklists and whitelists, figure out how your SPF is propagating, blah blah blah... it's just not a wise thing to skimp on.

Do you really want your startup employees to be running into email problems while you're still trying to establish yourself as a business? At some huge corporate scale it might make sense to in-house this again (and even then it's questionable), but it's certainly not worth having a dedicated person (or generalist IT scapegoat) waste time setting this up and debugging it in a small or medium-sized business.

Re: Ask HN: How are you hosting email for your startup employees?

#30

Post by TheNewsIsHere »

CharlesW wrote: post #21
solardev wrote: post #2

Definitely don't do this yourself if you're not familiar with how it works. If you don't set up all the SPF, DMARC, DKIM etc. perfectly, you're going to get terrible deliverability (your outgoing emails will get auto marked as spam). Just pay Google or Microsoft or Yahoo or whoever to do it for you. Reliable email is not something to skimp on. Edit: Also, IMHO: gsuite (or whatever they renamed it to) is a huge produc…

> It's also much more usable cross platforms than the nightmare that is MS Office. Outlook is terrrrrrrrible. In what way? I’ve used both Google Workspace and Office 365 during my career. I don’t dislike Google Workspace, but Office 365 is notably more mature, capable, and complete. (I mostly use Macs, but the web apps work the same on any browser/OS.)

My experience matches yours. I loved Google Workspace at a small nonprofit. But if you’re running a business that has “hardcore admin needs” on the productivity services side, MS365 beats the pants off Google Workspace all day.

Tools like GAM used to make things easier and expose just how much UI Google never bothered to write, but at least as of this year I can’t find a feature in Google Workspace that isn’t in MS365, plus you have -all- of Azure right there.

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