email-spamPeople often ask Greg Kraios, Founder of 250ok: Why is there spam? He knows that the answer is simply “because it’s profitable…If it didn’t make money, people wouldn’t do it.”

Kraios spoke at the August Smartups event about the ins and outs of email marketing. He told of his days at ExactTarget and how spam filtering has evolved since. Back then, emails were content filtered, with words like “free,” “viagra,” and exclamation marks creating the basis for screening. Spammers were quickly able to game the system and be one step ahead of it.

So, Internet Service Providers (ISPs) changed the game. It didn’t matter what the message is, but rather who the message is from. This created a structure based on reputation tied to an IP address. Now, companies (like Pfizer) that want to promote products (such as Viagra) legitimately finally can.

Once again, spammers figured out how to beat this system too. This brings us to how spam filters work today: reputation + engagement. ISPs look at engagement data from an IP address to find out how many people are opening an email, clicking a link, forwarding the message, replying to the sender. We all interact with emails from friends and family. But, this becomes a problem when it’s a marketing email.

How does a business get through the spam filters and get the user to open that email?


Young companies are anxious to broadcast their message to large audience. And email has become an important tool for startup marketers for doing just that. But, they often think the best way to do that is to buy a list. To that, Kraios asks “would you share your customer list with anybody ever? I’ll take it if you guys are.”

Not only does buying an email list not work, but often times the addresses provided are invalid by the time you get to them (which counts against your reputation) – or they could be filled with “spam traps.” A spam trap is when an ISP creates an address that has never been used by a human being. The only way to get that email on your list is if it’s scraped off the internet. When that happens, ISPs flag you as a spammer because they caught you capturing addresses without permission.

For startups, Kraios recommends finding a partner company that has a subscriber base that might benefit from your product or service. Some businesses may ask for a fee for this. Others will do it because they want to help other companies. The key here is to get that company to promote you in their newsletter, to push people to a landing page, and get the permission yourself to have them on your mailing list.

Google has become really good at determining spam emails. More times than not, people go into their spam folder, find an email from a friend or family member with a link inside and think, Google messed up. Once the email is back in the inbox, they click on the link and are redirected to a malware site. It looks harmless – like their bank. So, they enter all their personal information. And, they’re phished!

To counter this, email providers have started deleting spam emails before the user can view them.

Another tactic bigger companies use is sending emails with a “no reply” for the sender. Email is about communication, having a conversation. Using “no reply” alienates the target audience – “just tells me you don’t care about me.” Realizing that replies can help get your email delivered changes the entire playing field – especially for startups. You’re the most accessible business owner the user will come in contact with. Why not use that to your advantage and include your own email as the sender?

Set Clear Expectations

You’re already familiar with implicit email permission. You’re about to buy your items at a store when you’re asked for your email address. You give it willingly – not realizing that you’ve been added to their email list. Kraios stresses the importance of obtaining explicit permission for someone’s email. This not only serves to let the potential customer know that they’re signing up for a newsletter or promotion, but also creates an expectancy phenomenon in their minds. They will look for your email in their inbox. They won’t ignore it. They won’t delete it. They won’t mark it as spam.

Be clear about what your subscribers are going to get. Like Kraios, you may have been surprised when you think you’ve signed up for one company’s emails, and then you start getting promotions from other companies. You click the unsubscribe button and are sent to their preference center only to find out you’ve got five different content items checked.

In order to prevent the user from associating this nightmare with your startup, it’s best to outline exactly what they’ve signed up for and stick to it. You’ll see better engagement rates from potential customers and get rewarded from ISPs (by not getting marked as a spammer).

Kraios believes there’s no right or wrong when it comes to frequency. If you tell people they’re going to receive a weekly newsletter, you should send the a weekly newsletter. Your email readers want to consume things differently. As long as you set an expectation and deliver on it, you’ll be in good shape. He evens offers Doug Karr’s newsletter as an example. Kraios likes the monthly digest because while he wants to stay on top of what’s new in marketing, he’s too busy to read the weekly newsletter. He loves that Karr gives him the option to do that.

So, take your cue from these marketing giants and go beyond setting an expectation for the frequency of your emails: give your subscribers options for frequency.

Tips For Successful Email Marketing

Track sources

Startups that don’t track where they’ve acquired an email address from – even if it’s from a tradeshow prize bowl – cannot tell what their highest performing source is in order to reinvest energy and effort into that. They also can’t tell where negative experiences are coming from. When people mark an email as spam, did you know they came from that tradeshow? from your website? from a partner?

Tracking the different sources allows you more control over the messaging and provides you clear direction on which channels are working best.

Collect actionable data

Turn your email campaign from broad to actionable by asking a few telling questions at the point of acquiring an email. By adding a zip code field to the email signup form, Kraios and then-ExactTarget team gave one large lawn care service provider the advantage in targeting customers by serving relevant emails based on location and grass type.

Don’t obsess over the subject line

When he sees marketers still focusing on things like putting “free” in the subject line, Kraios wishes they’d spend their energy on what their target audience are actually looking for. People aren’t looking for the word “free.” They’re not counting how many exclamation points you’ve typed. Knowing what your goals are and delivering personal, relevant, targeted content trumps a formulaic subject line any day.

Test Deliverability

“It’s never too early to be concerned about delivery….if you’re not getting (the email) to the inbox, all that work you’ve done doesn’t mean anything.” Some companies will provide you with a sender score based on your IP address. According to Kraios, that number is meaningless if you cannot drill down to the deliverability issue itself. That’s why he recommends a tool like 250ok where a test email is sent to a pre-defined set of email addresses. Then, you can exactly track where the email winds up. Combined with data on opens, clicks, conversions, bounces, and unsubscribes, you can start to understand why people are unsubscribing. “The story’s in your own data if you know what to look for and what you’re trying to figure out.”

Following these tips will get your emails in your customers inboxes – and get them loving your emails!