My Trust Issues with Small Businesses and Custom Domains

I got a referral the other day to a physical therapist that is good with backs. A literal paper business card. This email was something like this:

Now I’m an indie-web kinda guy for the most part. I’m all about people owning their own websites and taking control over their little slice of the web. And yet. My trust level with random small businesses managing their own email on their own domain is super low. I get this little twang of distrust when I have to type in an email address like this.


Their email was busted.

It could have been anything. They could have let their domain name lapse. The DNS (MX) records could have gotten screwed up somehow. They could have been trying to move to GSuite, for example, and gotten those records wrong. They could be moving hosts and something got funky. Who knows.

That stuff is complicated for me, and I’ve been working on the web for decades.

That’s why even though I like the idea of doing as much as you can yourself on the web, I think using a managed email service is a smart move for most. Even if you do “do it yourself”, you’re leaning on so much rented technology anyway, it’s not that different.

If I see an email like: – all my doubt is gone on if they are actually going to get that message or not. Heck, I even prefer just seeing an email like that on the website itself (rather than a contact form), because the contact form is just one more bit of technology that can go wrong.

I get the desire to have email on your own domain as well. “It looks more professional” I was just told the other week by someone I was helping out with a website. But there are other pokes too. Like if that small business uses MailChimp, MailChimp will literally tell you that your “from:” email address should be your own domain, not something like Gmail.

The middle-ground for me is using my own domain, but using Gmail on top of it. So I still have to deal with MX records, but once it’s set up correctly, I just never change it. It works for every company I run and every project I have that has a custom domain and email.

Email is not dead.

Interesting little landing page from Jordie van Rijn with lots of statistics and links to articles about email. All evidence points to:

  • Tons of people use email (more than any other communication tool)
  • Email isn’t dying, it’s growing.
  • People prefer it, particularly in business in business and marketing.

So many links in there to read. Like The Triumph of Email from Adrienne LaFrance in 2016:

Over the course of about half a century, email went from being obscure and specialized, to mega-popular and beloved, to derided and barely tolerated. With email’s reputation now cratering, service providers offer tools to help you hit “inbox zero,” while startups promise to kill email altogether. It’s even become fashionable in tech circles to brag about how little a person uses email anymore.

I think now in 2021 that last sentence isn’t as true as it was in 2016. I don’t doubt that most people don’t like email, but as nobody is even close to unseating it, it may be settling in that we might as well get good at it.

The Expectations of `cc`

When you “cc” someone on an email, what are the expectations?

The least you can do, is nothing. You just add additional recipients to the email, and expect them to understand what you meant by adding them to the thread. Depending on the group dynamics, different things can happen. If I’m your boss and I do that, you might be a little confused or annoyed, but the expectation might be that you read the thread and try to understand how you fit in. If a random stranger cc’s me on an email, I might be so unmotivated and unincentivized to guess what you are doing that I just archive it.

It’s more common to see a short inclusive statement. “Adding Bob and Julie to this thread!” a party-planning email thread might include when some other form of communication has confirmed that indeed, Bob and Julie can attend the party. That might not add any clarity, but at least it’s acknowledged.

If you’re going for complete clarity you might either:

  1. Include text in the email that acknowledges any new people cc’d, why, and what your expectations for them are.
  2. If that is awkward or distracting, cc them, but use another communication channel to do those same things. (“Julie, I cc’d you on the email thread about the party. Nothing for you to do there, I just wanted you to have the list of addresses in there in case you need them for the labels.)

I’d shoot for clarity no matter what, but I admit it’s a weak point for me to assume people know what I mean when I cc them (or forward things for that matter).

And another thing! Is there any implied difference for when you actually use the cc function of email, or when you just include them as a new recipient in the to field? My gut says people don’t even notice generally, an email in the inbox is an email in the inbox.

Unfortunate Warning

I visited my mom this week. We got her a new computer. MacBook Air. One of the new M1’s. Very neat. She loves it so far. As she was setting it up, she went for a new email address. The first thing she did with it was email me at my address. And behold:

That’s a little unfortunate isn’t it? My own mother looks like spam to Google. I get loads of email every day from people I don’t know and very rarely see a message like this. But my own mother emails me and somehow that looks suspicious?

Just Use Email

You can imagine I’d be all about a website named Just Use Email! There isn’t much on it yet, but I really like the first two posts:

The About Page is my favorite though:

You don’t have to be a Luddite to live in the modern world. You don’t have to go completely analog to get away from annoying apps or buzzing notifications. There is a highly reliable method that awaits you, one you may have never truly mastered, but one that has been there all along.

You can actually be more effective, informed and productive. You can actually contact friends, family, and clients in a deeper connected way, and with less stress.

How? By just using email.

Attachment Size Limits

I don’t know all the technical details of attachment size limits on emails. I assume it’s complicated. Any given email server might put hard-caps on what it accepts within the email itself. For example, in 2009, Gmail increase the limit it could send to 25 MB and mentioned at the time:

you may not be able to send larger attachments to contacts who use other email services with smaller attachment limits

Twelve years later, that limit is still 25 MB for in-email attachments, so it seems like the email ecosystem hasn’t scaled that up much.

What has changed is the work-arounds. As much anyone might have feelings about whether email is the appropriate mechanism for file sharing, files are a part of modern communication and because email still excels at modern communication, files come along for the ride.

So, companies that offer email as part of how their services, have made sending attachments, especially of large size, much easier.

Apple has Mail Drop, which supports up to 5 GB attachments. You don’t have to think about it, it just works by tossing your file into your iCloud (until you go over the 1B limit, god bless you), and the file “expires” in 30 days.

Gmail has a thing where large files are also auto-cloud-uploaded to Google Drive, and then explicitly shared with the recipients of the email.

I’ll pretty commonly use some cloud uploader tool to get around actually attaching big files to email as well, like I might chuck a .zip file on Droplr or something, which not only makes the email smaller, but I can control if it gets deleted, and has a better chance of making it through a spam/content blocker.

I love these kind of things. They take a gnarly friction point and smooth it over. That’s what tech is supposed to do.

Emails About Not Getting Emails Are the Worst Emails

Sarah Miller, in a story, ostensibly, about not getting emails:

The help guy said he would send me an email. And then he sent an email, to my email, the only email I ever use, the email that never doesn’t get emails, ever. I have no reason to disbelieve this. And I didn’t get it. He sent another one, I didn’t get it. He said I would have to call the university and talk to them about why I couldn’t get emails from the enrollment/grade/whateverthefuck portal. As soon as our chat ended, I got two emails from the help desk of the enrollment/grade/whateverthefuck portal I couldn’t get emails from, one saying, sorry you can’t get emails, we did everything we could, and the other a transcript of the conversation about how I couldn’t get emails. Just in case you’re not grasping this: I got two emails from the place I couldn’t get one email from about not getting that email.

There is no resolution in Sarah’s story, really. I was yelling check your spam folder, but also got the sense that Sarah isn’t stupid and that probably wasn’t it. Mostly it made me think… if you just can’t get an email from any particular sender, what kind of extreme roadblock that is. You can’t buy the thing. You can’t go on your trip. You can’t take the damn class.

Choosing a business model for Simplify

Simplify is a browser plugin by the one-man-team Michael Leggett that cleans up the UI of Gmail.

I like it OK. I’ve tried it a few times and it tends not to stick though, probably because I have some muscle memory for some feature that’s not hidden or something and generally I’m not distracted by the default UI enough to care.

But it has lots of fans, the blog, On Simplify, gets dozens or hundreds of comments on each post. Lately, particularly on a post about finding a business model for Simplify in Choosing a business model for Simplify. Michael is going charge money for it because none of the other options feel right to him.

Monthly pricing (a few bucks) sounds good to me, especially because the pricing he puts out feels fair. I imagine it’s a decent amount of work keeping up with a third-party and making sure your vision of the UI maintains. But it’s also not, like, accounting software vital to running your business or something.

When you’re public about changing your pricing, everyone is going to have an opinion. It looks like Michael is going a good job listening. My advice? Don’t listen too hard Michael. If you try to please everyone you’ll end up pleasing nobody, especially yourself.