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Sending an email to your entire list is one of the scariest things that you can do as a marketer.

The moment you hit send, bad things may happen. Your email gets marked as spam. A valued customer unsubscribes. Or worst of all, total silence — no one opens, clicks, replies, or does anything.

That makes you want to send email even less frequently — maybe once a month — because that feels safe. It’s counterintuitive, but sending email only once a month is actually your problem. “Sending one monthly marketing blast increases the likelihood that your emails aren’t relevant to your users.”

Increasing your sending frequency (while avoiding annoying email blasts) also increases the chances for your emails to hit home with your subscribers.

SumoMe founder and famous email marketer Noah Kagan takes this philosophy to an extreme. He uses an email marketing technique called double opens, which can increase email opens by 30%+ with 1 minute of work. With this technique, he sends at least 70% more email than most email marketers, and that drives massive business results.

Here’s how he does it, and how you can increase any outcome — opens, clicks, signups, sales — by using Noah’s technique with your emails.

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The email that doesn’t make it to the inbox is like the proverbial tree that falls in the forest with nobody around to hear it – what’s the point?

One of the eternal quests of email marketers is to stay out of the spam folder. Still, deliverability, while at the heart of all email communication, is often one of those priorities that gets buried by our focus on measurements like list growth and open rates.

Times have also changed for how email clients and internet service providers decide what does and doesn’t get into the inbox. You may remember the First Age of Deliverability, the Wild West, no-rules era of email — or the Second Age, which centered around the “report as spam” button.

As email marketing expert Chad White describes, we are currently in the more nuanced, complex “Third Age of Email Deliverability,” where filtering decisions take into account both individual and collective engagement. That means the same message from a company following all the deliverability best practices can get stuck in the spam folder in one person’s email and waltz into the main inbox for another.

So how do you optimize deliverability and what do you do when you find your labored-over emails plunge into spam purgatory? I chatted with our email and support expert Diana Potter to find out.

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We’re taking a page from the great user onboarding teardowns of Samuel Hulick to walk through how Asana handles new user registration, onboarding, and email flow.

Along the way, you’ll learn how Asana:

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Here’s an interesting scenario. Let’s say you have the chance to win $200 if a coin toss lands on on heads, but if it came up tails, you’d lose $100. Would you take that bet?

Most people wouldn’t.

Nobel-winning psychologist Daniel Kahneman poses a similar question to both his students and other classes of folks alike:

I say: ‘I’m going to toss a coin, and if it’s tails, you lose $10. How much would you have to gain on winning in order for this gamble to be acceptable to you?’

People want more than $20 before it is acceptable. And now I’ve been doing the same thing with executives or very rich people, asking about tossing a coin and losing $10,000 if it’s tails. And they want $20,000 before they’ll take the gamble.”

Why does this happen? People hate losing more than they love winning — and it turns out this very human tendency can impact the success of your business.

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Upgrade emails are your bread and butter messages. They help convince and remind people to convert and upgrade from free to paid accounts and to higher plan tiers.

Before we dive into one of the most important types of emails for your business, a reminder: if you really want to grow conversions and upgrades, you have to lay the groundwork first. Invest in your product, onboarding, and support to bring value to people — all before you make your big asks. As Wistia says in one of its trial expiring/upgrade emails, you have to do some work up front:

“If we’ve done our jobs right, you’ve gotten a good feel for what Wistia can do for your video marketing.”

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