Ep. #3: A New Strategy For Email

Jun 14, 2018

It's been a while since my last newsletter, but I wanted to share about a new tool that I've been using a lot recently.

I'll start by sharing that most of the people I know in the world of cybersecurity rightly focus on more deeply entrenched matters: server virtualization and containerization, software sandboxing, and training their staffs to avoid social engineering hacks. But there's one technology that we all continue to use that hasn't really evolved at all since the 1960's: EMAIL.

That's right, friends: the technology behind today's email is nearly identical to the tech behind email during the early days of ARPANET. But despite the availability of newer technology like texting, social media, Slack and video chatting, email is not only still going strong, it's actually thriving. Don't believe me? Businesses and individuals use email at an almost alarming rate. During the time I worked at Nike (2014-2016), most of the staff I knew LIVED in their email inboxes: it was, even more than Slack, the endless hole from which no light could escape. Ok, that's a bit dramatic, but you get my drift.

Email is still a powerful and preferred tool. As powerful as it is, however, email comes with one notable problem:

You Can't Have Just One

The demands of modern life and business require that we have multiple email addresses for different functions. I'm a tech writer, a teacher of improvisation, and a technology consultant: to better organize my life, I maintain different email addresses for each of those roles. Then, when people email me, I already know what topic we're going to discuss by virtue of the email address someone has used when reaching out to me. I've configured my email so that all emails regarding tech consulting go to one folder, while correspondence from my writing team at Medium goes into a second folder and so on.

In addition to my personal email needs, there are an endless number of secondary email needs:

  • I belong to various groups and organizations with web portals that require an email to sign up and log in.

  • I've subscribed to various newsletters and services which require an email to sign up.

  • I shop online, like every other good American. Every new store from which I purchase requires an email to register before buying.

In the early days, I'd give out my personal email address to any person, company or service that asked for it. In short order, I found my inbox had become overrun with spam and sales pitches from solicitors and advertisers. I quickly discovered that the email's ubiquity and popularity forced me to rethink how I used the technology:

I Needed A New Email Strategy

I needed a different approach to help prevent spam while increasing privacy and security. The solution, I guessed, was to create and use a bunch of non-personal email addresses. So I created different email addresses for banking, for shopping, and for the various web memberships I maintained. It didn't take long for me to have a collection of 20+ email addresses along with a need to manage all of their various logins and passwords. Blech. It was awful, time-consuming and very inconvenient.

I needed to rethink email entirely and employ both a new strategy and, if it even existed, a new tool. As a joint solution, this new strategy and tool needed to be cheap or free, simple and convenient to use, and easily scalable.

I recently found my solution: 33mail.

I discovered 33mail while doing research for a recent article for Medium on restricting personal data and was intrigued. The free service seemed to offer exactly what I was looking for in an email strategy solution: unlimited, free, customizable email addresses, a simple interface, and the ability to halt spam instantly. I had to take a deeper look. Now, I'm sure glad I did. It's saved me so much time that I decided to sign up for the company's premium service for $1/month. That tier provided me with: no advertisements in forwarded emails, use of my own customized domain, and a higher monthly data cap. More on all of that in a moment. But first, a basic video primer. Click the video screengrab below to launch...

How It Works

When you sign up for a free account, 33mail lets you pick a handle for your account. If your nickname is "InsaneClown" and that name is still available, 33mail gives you the email suffix of "@InsaneClown.33mail.com". Now, when you sign up for any online service, don't provide your personal email address. Instead, provide a custom 33mail.com email address that's built from the name of the service along with your new 33mail email suffix. For example:

  • if you're signing up for Netflix, use "Netflix@InsaneClown.33mail.com" as your email address.

  • if you're signing up for the AAA newsletter, use "AAA@InsaneClown.33mail.com".

  • if you're signing up for the home decor website Houzz, use "Houzz@InsaneClown.33mail.com".

After you've created each email alias, 33mail will auto-forward every email from each of your email aliases to a personal email account of your choice. I set up a dummy account to show you what typical auto-forwards looks like:

You'll note two things right away:

  1. 33mail places all auto-forward information at the top of each email so it's simple to find

  2. In the auto-forward box at the top of every 33mail email is a link to block all further emails from that alias. Click the link once and all emails to that address are blocked!

Using 33mail as a solution has eliminated hassle: I just continue to receive emails in my personal email inbox without ever needing to provide that info to anyone other than 33mail. Pretty sneaky, sis.

Even better, I can REPLY to any of my auto-forwarded 33mail messages as I would any other "normal" email. My reply gets routed through 33mail's servers, removing any header information (called MX records) relating to my actual email address. Note to self: just remember to remove any info from my emails (including the 33mail auto-unsubscribe links)!

So what, if any are the limitations? First, the good news: ALL tiers, including the free tier, allow you to create and use as MANY email aliases as you like. After that, there are a few on the free service: some limits on the amount of total data sent to you via all of your accounts, small advertisements included on each forwarded email, and no ability to use your own domain. That means free-tier users will need to use their Yahoo/Gmail/Outlook email domains instead. 

The free, basic tier is enough for most casual users, but I've enjoyed the service so much that I signed up for the $1/month paid tier.

No matter which tier you choose, stop giving out your personal email address to anyone and everyone, friends. Instead, sign up for and start using 33mail instead. Full transparency: signing up through me, also grants me some number of free months of their paid tier, a nice way for you to say thank you to me for the recommendation. 


If you liked what you read today, please: feel free to forward this email to friends and family. This email & post is a part of my free-to-all series. Only paying members have access to my deeper, paid newsletter and archives.