I co-founded a company that found itself with a similar set of criteria for what we wanted. For us, VC worked out well. We weren't the typical company they saw, but going in with a very clear set of things we wanted from a partner was very helpful. Ultimately, they were high value add when relevant but otherwise let us focus on growing the business.

My guess is it comes down to the right VC/Partner and finding mutually agreeable terms.

I think it probably is, it just takes more planning. Take email A/B testing - if email is a main driver of your usage activity, you could split your users or list into two groups and then send them different emails over a period of months. It'd be slightly more manual (you'd have to segment the list) and then leave one group off for a few months, but it would let you easily gather very significant data.

These are great points, and speak to why measuring the impact of email is really, really important. Until you're holding your emails accountable to performance (whether it's getting someone to come back or to buy), you're just throwing darts in the air and potentially annoying someone.

At Klaviyo (I'm one of the co-founders, so note bias), we've helped many web apps and ecommerce sites setup full email strategies - and we definitely find that some emails don't work. You've got to test different emails and strategies, see what works - and then ideally optimize and personalize what (or even whether) you are sending based on individuals' actions.

How do you measure how pissed off I am? From your side of the table a lack of positive action is indistinguishable from absolute apathy, passive interest without action, undelivered mail (most tracking widgets fail in webmail), etc.

I've observed that some less-savvy people don't know how to unsubscribe from emails, or fear doing so will "upset someone" and so grin and bear an otherwise annoying deluge of email they never react to.

Why should they measure how pissed off you are? Why is that data point interesting to them if it doesn't affect any of the metrics they're actually interested in, such as making more money and satisfying a higher percentage of users?

It doesn't feel great to be told you're unimportant, and no company owner will say that to their own customer, but really — you and I are not that important. I do not expect McDonald's to abolish all their meat products because they offend me as a vegetarian — the rest of their customers manifestly do not share that opinion, so it would be a dumb choice if they killed the Big Mac. Similarly, it is not in a company's best interests to terminate an objectively successful email campaign just because some random guy got pissed off but was unwilling to click Unsubscribe. Successful companies lose customers all the time for all kinds of reasons — they would never get anything done if they tried to personally appeal to every single person on earth.

Avoiding pissing people off is a basic ethical concern, which is at least as important as making money. Obviously it can't be totally avoided, but you try anyway. If you can't make more money without pissing a bunch of people off, you should consider changing your business.

This isn't about a bunch of people. Remember, we're talking about so few people that they don't even make a blip in any of your metrics. If you're getting angry replies or all your emails are deleted without being read or lots of people are unsubscribing, yeah, that's bad and you should think about what you've done wrong. But that's not the situation we're talking about here.

Again, McDonald's pisses off millions of vegetarians every single day. Would you say on that basis that they should go meatless? Should churches close to avoid pissing off militant atheists?

The point is not that you should be callous about offending people. Obviously it is better for all involved to make people happy, and that should always be your goal. But the point is that one or two guys saying "I'm so angry!" on an Internet forum does not mean you've failed. No matter what you do, even if it's pure charity work, you'll eventually find someone who gets upset about it. All you can do is apologize and offer to unsubscribe them — it's not rational to throw your business away on that basis.

Did you ever think that if you don't want their emails, you're not their target audience? And so they don't give a fuck how you feel?

Having now spent a lot of time sending and analyzing email campaigns/triggered emails (I'm one of the co-founders of Klaviyo), we keep seeing that email is one of the best ways to turn analysis into action - not least because it gives you a complete feedback loop.

For example, say an Ecommerce store realizes most people only make 1 purchase and don't come back. With email, you can target exactly those people, but you also can quickly see if it worked (because you know who you sent it to, you can see if they actually made a purchase).

Retention is definitely really important, but I think what's at root here is that email is an ideal way to interact with users in a more targeted and personal way outside of when they proactively visit your website. The same feedback loop idea should (and will) apply to push notifications, texts, in-app messaging, etc as time goes on.

I'm setting up Inky now and excited to try it.

On the note of smart views, any idea how representative my data is of the typical email user?

Separately, I'm curious to know how far smart views go with aggregation - i.e. if I get 10 facebook friend request emails, are they combined? Or is this an irrelevant question in the smart view paradigm?

We don't know if your inbox is representative; we don't actually see users' emails so we don't have stats on what kinds of mail people have.

The smart views continue to evolve; we've been iterating them to find the right model -- it turns out to be pretty subtle from a UX standpoint. That's another reason we're not formally launched yet.

This is a really interesting point - I think the question will really come down to how well campaigns / businesses can measure the impact of their marketing. If your messages/posts aren't driving donations or purchases (or hurt the long term usefulness of the person you're marketing to), then you won't run them.

The problem is that today most marketing is blind - completely unlinkedin from the impact it causes. I'm counting on technology / big data / analytics to change that.

This point about Google and Facebook is interesting, not least because Google has certainly had numerous people join the campaigns. My guess would actually be that the level of testing by the campaigns (just based on the small subset of data that PP has) is incredible and much, much better than either of the tech giants - regarding email.

As a benchmark, the most analytically savvy paper mailers / marketers of the last 20 years could arguably be Capital One. They did elaborate testing that involved not running TV ads in markets for years at a time, tons of different message styles, frequencies, etc - all because optimizing these results was worth so much to them.

In short, if getting email right means millions of dollars, then there's a premium on getting it right - just as there is for Google for nailing search testing.

I think this is a good point about how the campaigns do have virtually of the resources to put together a sophisticated emailing system...but it may not be a question of pure resources, but of logistics and ingenuity.

Here are two things that I think we can assume:

1) The campaigns have enough data to draw a good guess of who/what you are like, even without you giving anything more than your location, gender and age. This was true at least a decade ago when campaigns (and other third-parties) had access to databases such as subscriber data.

2) The campaigns have the resources to tie this data to individual identities, even if you haven't explicitly done it yourself when signing up for a newsletter. The matching won't be 100% accurate, but the campaigns can be reasonably sure that you are this particular Jane Doe at this address who is 28-32 years old, who subscribes to Rolling Stone and Harper's, and who drives a 2-door sedan.

Then what?

There has to be a middleman who can use this granular data to write a coherent message that leverages the insights from the data...using a model that makes many permutations across the most common combinations of characteristics.

This is similar to how Google can tailor search results for "what's a good movie" for a near infinite combination of user characteristics...but producing discrete databits (search results) is a different problem than producing a coherent fundraising letter.

And while money/resources/desire may not be an obstacle, the question is logistics and other practical concerns that divide the data from the content producers. There are many industries (such as the medical community) in which money and brains are no factor and yet have unsophisticated ways of dealing with information.

I'm working to get it back up, but it looks like our host will keep us down for 30 minutes or an hour. Good sign that we need to invest in better hosting.

It's a great call - I'll post a follow-up with that detail and try to find a couple other examples from people in other geographies and demographics. My take (from this exercise and looking at ProPublica's data) is that behavior varies significantly based on both WHO campaigns think you are and WHAT you've done lately (what you've read, which sites you've visited, have you donated or volunteered, etc).

This complexity is going to make analysis nearly impossible in the future as political (and marketing) messaging becomes incredibly personalized.

(I'm actually author and OP here is my also-HN reading brother who beat me to the punch)

It's good to see Mixpanel building out its people analytics offering, but more broadly good to see momentum in the trend towards measuring the impact of email and other communications on customer behavior. To this point in time, to many companies send emails in a spray and pray fashion - not knowing if they really impacted customer behavior on feature usage, purchases, etc.

We're working on the some similar problems at Klaviyo (customer lifecycle management / targeting customers and measuring the impact). One of the most interesting related things we've seen is that measuring the impact of emails goes along way towards eliminating debate about email frequency or whether to send campaigns - because you can always just send the campaign to a subset and actually know if it works.