I Started My First Email Newsletter at Fourteen—This is What I learned

I launched my first email newsletter when I was fourteen. An avid pro-wrestling fan, I would email subscribers about developments in the wrestling world. It was a modern-day equivalent of an entertainment blog. To my surprise, and my parents’ shock, the newsletter eventually grew to over 50,000 subscribers. As email continues to be a leading marketing channel,  returning $38 for every $1 spent, I have realized that many of the lessons I learned from my first email newsletter are just as relevant today.

Content is king

Week after week, subscribers waited for my newsletter. I was a decent writer but there are many decent writers. Anyone can write okay content. You need a hook. Something that distinguishes your email and holds the audience captive. They should want to read your email the following week. They should look forward to it. If all your email ever says is “mega sale” or “$5 off,” the audience eventually becomes immune to the offer. My panacea was a “Top 10 Pro-Wrestlers of the week” email with a paragraph justifying the ranking. I always released it Monday morning at 7 a.m. before school. It was a simple concept—most good ideas are—that left audiences (and even pro-wrestlers!) wanting more. I remember getting emails from pro-wrestlers asking me why they hadn’t made the list…some less colorful than others.

Today, when every company strives to be a thought leader with great content, the example is more relevant than ever. Give your audience something unique. I couldn’t possibly have beaten better-established sites with photos, videos, or news, but I did beat them with something nobody was doing—ranking wrestlers weekly across promotions. When in doubt, remember that everyone still loves a top 10 list.

Successful campaigns start with a clean email list

That may sound basic, but it’s amazing how many email lists contain the wrong people, or even inactive email addresses. I put the most work into maintaining my audience list. I spent hours removing unsubscribes (that was particularly painful in 1999 with rudimentary list management tools) and inactive email addresses.

The same concept applies to marketing emails. Email lists decay quickly. Make sure any email list you use has been cleansed of unsubscribes, which is required by CAN-SPAM laws. Using SMTP checks and MX lookups can also help keep your email list clean. Remember, whether your list is organic or purchased, email lists always decay.

If you’ve ever followed professional wrestling, you probably noticed there is always a lot going on—far more than an email newsletter can cover. As a teenager, I lacked formal training in design or copywriting. But I did know how to choose the right content, and that was enough to make the newsletter successful.

The creative can make or break your campaign

Getting your creative right begins with the sender name and subject line. Remember that your sender name does not have to be an email address. It can also be your name or company name, and either one can look more trustworthy than an email address. As for subject lines, I always remember two things: be descriptive and always A|B test. What works for one email often doesn’t work with another, and often for no apparent reason.

Email design and copywriting get a lot of attention, and for good reason. They are the only things your audience will actually see. However, it’s also easy to focus too heavily on design and copywriting while ignoring the content itself. Too many beautifully designed and written emails fail simply because the audience doesn’t engage with the content.

Analyze the results

The most valuable part of an email campaign begins after the campaign ends. That’s the great thing about email—even unsuccessful email campaigns can teach you something. Your email statistics are a potential gold mine. Look over the open rates, click-through-rates, and any other data you can get your hands on. Consider adding further tracking pixels to get an accurate number of website clicks and conversions to weed out spam bots. Over time, you will find trends that can help you improve future email campaigns.

I used to pen my random insightful thoughts on pro-wrestling. But there’s a reason I stuck to the ‘Top 10’ newsletters the longest—it worked. It was read the most. When one of my newsletters would perform poorly, I would pore over what went wrong. Sometimes it was the subject line, sometimes it was the content, and sometimes I simply sent it at the wrong time of day. So, I started sending them at the same time and same day each time after various experimentation. Here’s the key lesson—test a lot but when you find a winning formula, stick to it! Don’t experiment for the sake of experimentation.


Even all these years later, email continues to be one of my favorite marketing channels. Email was the first agency service we offered at Stirista, and its effectiveness still amazes me today. I can track the foundation of my email knowledge to the wrestling newsletter I started as a teenager. I owe more to Bret ‘the Hitman’ Hart than he will ever know. But it was more than my first exposure to email—I eventually sold the list, making it my first foray into the data world as well!


About the author

At fourteen, Ajay made his first foray into the entrepreneurial world, publishing one of the first wrestling newsletters on the web. Armed with rudimentary SEO skills and a sharp pen, the newsletter grew to over 50,000 subscribers by the time the publication was sold in 2002 when Ajay was a college freshman. Most importantly, Ajay realized the ease with which communication could be carried out via e-mail. A decade later, after an eclectic mix of degrees in Financial Economics, Creative...

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