Hi. My name is Don and this is my story. Well, to be more precise, this is the story of how I almost ruined my business.

As someone with the spirit of an entrepreneur, I’ve always dreamed of running my own business and becoming the master of my destiny. It was a good dream. But I stumbled along the way, as often happens with new companies.

Building My Business

I won’t bore you with the details of the business itself, I’ll just say that it’s a consumer-focused website that sells products and services. I had quit my previous job as the head of IT at a mid-sized startup to follow my dream. Everything I had was being poured into this new company.

I still remember the day it all came to fruition. It was hot outside, the type of heat that sticks with you and makes you appreciate a well air conditioned office. It was for this very reason that I had locked myself away in my office, hard at work creating my empire.

Nothing can match the feeling of building a business from scratch. Sure, it’s hard work. Being responsible for all parts of the business is no easy task. But it was all worth it. After months of long days and longer nights, it was done. Right there, on that hot summer day, I had deployed my website. Version one of my brand new web application was live. My business was now online, ready and waiting for the whole world to flood through its virtual door. Slowly, I felt myself swell with excitement. A smile stretched across my face. This was it; I had arrived.

The Beginning of the End

The problem started in the days following the launch. I had built it, yet no one would come. Turns out the best website in the world is nothing without customers. So there I sat, staring at the flat-line of traffic in my Google Analytics dashboard. If this were a heart monitor, it would be telling me that my site was dead.

So I did what any rational person would do, I went to Google and searched for ways to drive people to a  website. It turns out there are a lot of different ways, all having something to do with marketing.

“I’m no marketer, but how hard can it be?” I remember asking myself. In truth, I knew next to nothing about marketing. Then something caught my eye: email marketing.

“I’ve been using email for as long as I remember. I can do that.”

Down the rabbit hole I went. It turns out there are a number of free email services that will allow you to send an email blast to a large list of people. Perfect! A free solution to my marketing needs. “What could go wrong?”

Now I just needed a list of potential customer email addresses. As luck would have it, there are people online who sell such lists. The key word here being “sells.” But as the saying goes, you have to spend money to make money. So I pulled out my credit card and purchased a list of email addresses that matched my desired customer profile. After all, when sending marketing emails you have to know the addresses of the people you are emailing. I assumed that everyone must buy lists. How else would you get their addresses?

“This marketing thing is a breeze.”

It was all so easy. I may be out a few hundred bucks, but now my email marketing tool was loaded with thousands of potential customers just dying for my products. That feeling of excitement I felt on that first, hot day was starting to return. Now I just needed to craft the perfect email.

I started with the “From:” line. When receiving emails in my own inbox, I remember seeing “no:reply@” addresses. That makes sense. I wouldn’t want a thousand email replies flooding my own inbox, which I was certain would happen.

Next came the subject line. It needed to be enticing enough to grab their attention and inspire them to open the email. So I put “FREE” in all caps, followed by a promise to provide a special gift. Of course, it would be a gift with purchase, but they didn’t need to know that yet. I was convinced that I was turning into quite the crafty marketer. “Maybe I missed my calling,” I said aloud with a laugh.

The rest of the email was simple text, with an adequate spattering of marketing lingo: “Act now,” “Supplies limited,” “Once in a lifetime offer.” I felt like I was repeating every bad car dealer commercial I had ever seen. But it must work, why else would those ads still run across my TV day in and day out?

Send and done.

I wiped my hands with a foolhardy grin. The next day I was so excited that I snapped my laptop open as soon as my alarm clock went off.

Flat-line. My business was still dead.

What happened to all the people I just emailed? “I should send it again,” I told myself. So back into the email tool I went. Wait…I’m BANNED from sending emails? That didn’t make sense. I didn’t do anything wrong.

I was angry. So I did what any frustrated business owner would do, I sent a colorfully worded email to their customer support department. Their response came like the slamming of a jail cell door on my business. I was banned for “Spamming.”

Spamming. I couldn’t believe it. Me, of all people… a spammer?

I’m embarrassed to say that we argued back and forth for more time than I would like to admit. But in the end, they were right. I had spammed. Even worse, because of this mistake, my domain was now included on spam blacklists found hidden in the deepest corners of the Internet.

Learning From My Mistakes

By now you are probably asking the same question I did: “What did I do so wrong?”

Apparently, a lot. For starters, I bought a list which was far and above my most egregious crime. According to the law, you can only email people who “opt-in” to receiving marketing emails from your business. In fact, this practice is so bad that it could put me at legal and financial risk.

How did they know I had bought a list? Because of something called hard bounces. Those happen when the email addresses you use either do not exist or are invalid. When email companies see a large amount of bounces come from an email blast, that is a strong indication that this was a purchased list.

The next giveaway was my subject line. It turns out that I was not as clever as I had thought because spammers scream the same type of “FREE” and all caps messaging I used. Then there was the content of the message itself and even the “no:reply” I used in the “From” line. It all pointed to spam and, as I now understand it, justifiably led me to email jail.

The following months were even more difficult. If I managed to get a customer, any email I sent to them would end up in their spam folder. It was a struggle to maintain communication and keep them coming back.

So here I sit, locked in email jail and working diligently to get out. It may not be as bad as real jail, but for my business it might as well be. My website is on life-support now, with small blips of traffic showing a small sign of life. I’ve since learned all the correct practices for email marketing and realize that it’s not nearly as easy as I once thought. If any good may come from this, it’s that you can learn from my mistakes. Don’t end up my cell-mate. Trust me, there is nothing good about email jail.

Note: Although the following story did not happen to me personally, this is a cautionary tale about how a seemingly small email mistake can seriously unravel your business and marketing efforts. Want to learn more about email marketing and avoiding the mistakes Don made? Check out our Email Marketing Mistakes webcast.



Mike Pace
Mike Pace leads the Demand Generation team at SendGrid, which focuses on driving revenue and leads through paid media and website optimizations. With a passion for data and analytics, Mike builds strategic marketing plans that focus on in-depth attribution data and customer behavior to improve results across a range of marketing channels. Over the past few years he has focused on content marketing tactics that play a key role in the customer conversion funnel and work to compliment a wide range of paid media initiatives.