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This could be solved an even more fundamental way: Don't run your own mailer as a startup. There are lots of companies that will be responsible for email delive

This could be solved an even more fundamental way: Don't run your own mailer as a startup. There are lots of companies that will be responsible for email deliverability on your behalf, via an API. If it took them 3 months to notice no mail was being sent at all, imagine how long it's going to take them to figure out that their IP is blacklisted in Spamhaus or any number of other deliverability issues?

spacefight 12y ago
Not everyone wants to outsource transactional mail handling to a third party.
- zrail 12y ago
  If someone wants to do that then they've never tried to handle even a moderate volume of transactional mail themselves. Or they're starting a transactional mail service provider. Either way, my hat's off to them. It's a giant pain in the ass that can be resolved for less than $20 per month.
  - w0rd-driven 12y ago
    I completely agree. I think unless your startup or core competency is something like that, why shard your core product's development/IT/whatever work to support an in-house product that's bound to have bugs(tm) right out of the gate? There very much should be a cost/risk analysis but there's an awful lot of NiH that honestly should be avoided if you can genuinely help it. You're still more than welcome to roll your own everything but you're just delaying your core competency to maintain something you could offload to someone that specializes in X, Y, or Z. I would also suggest if you do go that route, have accurate metrics on everything. How much time are you spending maintaining what essentially is a separate product? How much is it taking from your MVP or is it part of it? If you can translate that to cost then you can judge how much offloading that service would be to someone that specializes in it.
    - clickbyclick 12y ago
      That's the straight dope. #truth Having worked on the IT and Biz side of tech companies (happily SaaS closing that gap daily) I can tell you the logic patterns are diametrically opposed. IT = born problem solvers, nothing is too big, small or complicated BIZ = friction solvers, nothing can be too efficient The struggle isn't that 'you' could do it (better, faster or even cheaper) in your mind... but that if isn't a core competency moving your business forward, write a check and let someone else handle the core. Break free from the burden of 'undifferentiated heavy lifting' and improve your core product. We sell a SaaS solution and in turn I write ~20 checks to other SaaS providers a month to keep me focused on improving our customer's experience.
- rtpg 12y ago
  Just because you don't want to doesn't mean you shouldn't. The major advantage to outsourcing it is that the people you're handing the job over to actually know what they're doing and are experts at it. Plus they can spend 24 hours a day checking this stuff instead of you. The arguments for being in-house on absolutely anything but your core competency when you're an early-stage startup are really hard to justify.
  - Cyranix 12y ago
    Especially with the number of services that offer zero-cost plans at low usage levels! You can rarely even make a fiscal argument for keeping this kind of stuff in-house, much less a skills argument.
- mason55 12y ago
  This is the whole idea behind economic specialization & division of labor[1]. And even if you were to be better at sending email than Mailchimp it's likely that you're even more better at your core competency which means that you should farm out your email sending and focus on your specialization. [1]http://en.wikipedia.org/wiki/Division_of_labour http://en.wikipedia.org/wiki/Division_of_labour
  - joshuacc 12y ago
    I think the specific term you are looking for is comparative advantage: http://en.wikipedia.org/wiki/Comparative_advantage http://en.wikipedia.org/wiki/Comparative_advantage
    - mason55 12y ago
      Yup - that is indeed what I meant to put. That's what I get for posting while on the phone.
- mbesto 12y ago
  But clearly if an error in it is going to cause 40% of your business to drop off "overnight", you might want to outsource it to someone who can actually maintain it properly.
tankenmate 12y ago
I'd modify that by saying; if you really know how to run a mail server go for it, but if you don't then leave it to someone who does know. Same goes for just about every other service your start up relies on; accounting, legal, etc. Cost benefit analysis (even a brief one) will always help, even if you get the answer wrong. It's just a part of planning; your plans don't always work, but if you don't plan then you'll never know if you succeeded or not (or why) until it's too late.
- netcan 12y ago
  To ad a couple more cents to the pile: email is serious business, get serious about it. That doesn't mean spend a lot of time. Use services. But, be serious about it. Figure out if you're sending the right mail at the right time. Cut out unnecessary emails and unnecessary junk in the emails. Make sure they get delivered and read. Any service from a dating site to an app for accountants a wholesaler of underpants needs emails and how well you use them is important. You can be minimalist. Analytical. Formal, casual.. There are as many approaches to this as there are to anything else. Just don't take it lightly. Get good at email. Just because it's simple doesn't mean it's not important.
michaelbuckbee 12y ago
Excellent advice, the only thing I'd add is that it's like this for everything that isn't core to your service when you are getting started.
- eli 12y ago
  Maybe true, but a mail server in particular is one of those things that's a lot harder to set up and maintain than it looks.
protonfish 12y ago
If you want to send bulk email blasts from a large list then definitely use a 3rd party, but it seems their emails were triggered programmatically from many different parts of their application. The email providers I have used don't make this easy so it is usually better to run the server yourself. You don't need much knowledge or experience to run an email server (if you are competent at general IT tasks already) but you need one thing: to actually check once in a while to see if your sever is sending email. Which is the real problem here. Team members knew mail wasn't being delivered in the forums and they chose to ignore it. They must have never done any follow-up (personal email, phone call, survey) on new customers even when they were doing their big marketing "ramp-up." They must not have even checked with a test walk-through of the new user process. Leadership was just too far removed from the customer experience, whether they used a 3rd party email service or not.
- EGreg 12y ago
  I'm not sure I understand. Why couldn't they use a 3rd party hosted smtp server to send mail programmatically?
- dropbear 12y ago
  I've used SendGrid for transactional emails and it works like a charm.
- Encosia 12y ago
  I recently migrated a couple of my sites away from directly sending transactional email, to using MailChimp's Mandrill service. A few months later, I only wish I had done that sooner.
- sjs382 12y ago
  >> The email providers I have used don't make this easy so it is usually better to run the server yourself. Mandrill, Mailgun, Sendgrid all make this easy.
  - protonfish 12y ago
    It has been a few years since I have been saddled with email responsibilities so it's not surprising I am a little behind the times. But it still doesn't mean you shouldn't be checking that customers are receiving your emails.
NDizzle 12y ago
I don't entirely agree with this. I don't use my own mailer currently. I DO, however, use postfix to queue and relay email to rackspace, who actually sends my email. I don't think the API method is appropriate because then you need to run some other queue system so your app has an instant response time for the user. Their action would create a queue entry (with whatever data) that will eventually be fired off as an API call to whoever you're using to send email via an API. Or, you just set up an SMTP relay and use sendmail/postfix/whatever locally to handle that part of it. I often see these startups using the API calls as part of the customer facing flow (website or otherwise) and the increased latency waiting on that API call to return really, really sucks.
- alexk 12y ago
  Just wondering: would it work if your app provider supported email submission via Job queue (e.g. Amazon SQS/Iron MQ) ?
  - NDizzle 12y ago
    Yes, it would. In that case you are also punting on the job queue responsibilities and using a third party for both email and queueing jobs. That's not necessarily a good thing or a bad thing - it's just a thing. You'll want to queue those API calls so your queue mechanism returns to the user very quickly, and then the emails can fire out .5-5 second later.
- velocitypsycho 12y ago
  Every email service I've seen offers an API and SMTP. For many applications, SMTP will work just fine.
kenrikm 12y ago
Focus on your core competency, as someone who has run production mail servers in the past I know it's not something you really want to do (My advice: don't) there is always some fire to put out or blacklist you were put on that needs to be cleaned up. Mailgun offers 10,000 emails per month free and is dead simple to use.

spacefight 12y ago

Not everyone wants to outsource transactional mail handling to a third party.

zrail 12y ago
If someone wants to do that then they've never tried to handle even a moderate volume of transactional mail themselves. Or they're starting a transactional mail service provider. Either way, my hat's off to them. It's a giant pain in the ass that can be resolved for less than $20 per month.
- w0rd-driven 12y ago
  I completely agree. I think unless your startup or core competency is something like that, why shard your core product's development/IT/whatever work to support an in-house product that's bound to have bugs(tm) right out of the gate? There very much should be a cost/risk analysis but there's an awful lot of NiH that honestly should be avoided if you can genuinely help it. You're still more than welcome to roll your own everything but you're just delaying your core competency to maintain something you could offload to someone that specializes in X, Y, or Z. I would also suggest if you do go that route, have accurate metrics on everything. How much time are you spending maintaining what essentially is a separate product? How much is it taking from your MVP or is it part of it? If you can translate that to cost then you can judge how much offloading that service would be to someone that specializes in it.
  - clickbyclick 12y ago
    That's the straight dope. #truth Having worked on the IT and Biz side of tech companies (happily SaaS closing that gap daily) I can tell you the logic patterns are diametrically opposed. IT = born problem solvers, nothing is too big, small or complicated BIZ = friction solvers, nothing can be too efficient The struggle isn't that 'you' could do it (better, faster or even cheaper) in your mind... but that if isn't a core competency moving your business forward, write a check and let someone else handle the core. Break free from the burden of 'undifferentiated heavy lifting' and improve your core product. We sell a SaaS solution and in turn I write ~20 checks to other SaaS providers a month to keep me focused on improving our customer's experience.
rtpg 12y ago
Just because you don't want to doesn't mean you shouldn't. The major advantage to outsourcing it is that the people you're handing the job over to actually know what they're doing and are experts at it. Plus they can spend 24 hours a day checking this stuff instead of you. The arguments for being in-house on absolutely anything but your core competency when you're an early-stage startup are really hard to justify.
- Cyranix 12y ago
  Especially with the number of services that offer zero-cost plans at low usage levels! You can rarely even make a fiscal argument for keeping this kind of stuff in-house, much less a skills argument.
mason55 12y ago
This is the whole idea behind economic specialization & division of labor[1]. And even if you were to be better at sending email than Mailchimp it's likely that you're even more better at your core competency which means that you should farm out your email sending and focus on your specialization. [1]http://en.wikipedia.org/wiki/Division_of_labour http://en.wikipedia.org/wiki/Division_of_labour
- joshuacc 12y ago
  I think the specific term you are looking for is comparative advantage: http://en.wikipedia.org/wiki/Comparative_advantage http://en.wikipedia.org/wiki/Comparative_advantage
  - mason55 12y ago
    Yup - that is indeed what I meant to put. That's what I get for posting while on the phone.
mbesto 12y ago
But clearly if an error in it is going to cause 40% of your business to drop off "overnight", you might want to outsource it to someone who can actually maintain it properly.

tankenmate 12y ago

I'd modify that by saying; if you really know how to run a mail server go for it, but if you don't then leave it to someone who does know. Same goes for just about every other service your start up relies on; accounting, legal, etc. Cost benefit analysis (even a brief one) will always help, even if you get the answer wrong. It's just a part of planning; your plans don't always work, but if you don't plan then you'll never know if you succeeded or not (or why) until it's too late.

netcan 12y ago
To ad a couple more cents to the pile: email is serious business, get serious about it. That doesn't mean spend a lot of time. Use services. But, be serious about it. Figure out if you're sending the right mail at the right time. Cut out unnecessary emails and unnecessary junk in the emails. Make sure they get delivered and read. Any service from a dating site to an app for accountants a wholesaler of underpants needs emails and how well you use them is important. You can be minimalist. Analytical. Formal, casual.. There are as many approaches to this as there are to anything else. Just don't take it lightly. Get good at email. Just because it's simple doesn't mean it's not important.

michaelbuckbee 12y ago

Excellent advice, the only thing I'd add is that it's like this for everything that isn't core to your service when you are getting started.

eli 12y ago
Maybe true, but a mail server in particular is one of those things that's a lot harder to set up and maintain than it looks.

protonfish 12y ago

If you want to send bulk email blasts from a large list then definitely use a 3rd party, but it seems their emails were triggered programmatically from many different parts of their application. The email providers I have used don't make this easy so it is usually better to run the server yourself. You don't need much knowledge or experience to run an email server (if you are competent at general IT tasks already) but you need one thing: to actually check once in a while to see if your sever is sending email. Which is the real problem here. Team members knew mail wasn't being delivered in the forums and they chose to ignore it. They must have never done any follow-up (personal email, phone call, survey) on new customers even when they were doing their big marketing "ramp-up." They must not have even checked with a test walk-through of the new user process. Leadership was just too far removed from the customer experience, whether they used a 3rd party email service or not.

EGreg 12y ago
I'm not sure I understand. Why couldn't they use a 3rd party hosted smtp server to send mail programmatically?
dropbear 12y ago
I've used SendGrid for transactional emails and it works like a charm.
Encosia 12y ago
I recently migrated a couple of my sites away from directly sending transactional email, to using MailChimp's Mandrill service. A few months later, I only wish I had done that sooner.
sjs382 12y ago
>> The email providers I have used don't make this easy so it is usually better to run the server yourself. Mandrill, Mailgun, Sendgrid all make this easy.
- protonfish 12y ago
  It has been a few years since I have been saddled with email responsibilities so it's not surprising I am a little behind the times. But it still doesn't mean you shouldn't be checking that customers are receiving your emails.

NDizzle 12y ago

I don't entirely agree with this. I don't use my own mailer currently. I DO, however, use postfix to queue and relay email to rackspace, who actually sends my email. I don't think the API method is appropriate because then you need to run some other queue system so your app has an instant response time for the user. Their action would create a queue entry (with whatever data) that will eventually be fired off as an API call to whoever you're using to send email via an API. Or, you just set up an SMTP relay and use sendmail/postfix/whatever locally to handle that part of it. I often see these startups using the API calls as part of the customer facing flow (website or otherwise) and the increased latency waiting on that API call to return really, really sucks.

alexk 12y ago
Just wondering: would it work if your app provider supported email submission via Job queue (e.g. Amazon SQS/Iron MQ) ?
- NDizzle 12y ago
  Yes, it would. In that case you are also punting on the job queue responsibilities and using a third party for both email and queueing jobs. That's not necessarily a good thing or a bad thing - it's just a thing. You'll want to queue those API calls so your queue mechanism returns to the user very quickly, and then the emails can fire out .5-5 second later.
velocitypsycho 12y ago
Every email service I've seen offers an API and SMTP. For many applications, SMTP will work just fine.

kenrikm 12y ago

Focus on your core competency, as someone who has run production mail servers in the past I know it's not something you really want to do (My advice: don't) there is always some fire to put out or blacklist you were put on that needs to be cleaned up. Mailgun offers 10,000 emails per month free and is dead simple to use.