Basecamp’s Hey Email Service with Apple Mail (for free?)

Can’t Apple’s email do almost all of Basecamp’s new Hey email’s top 20 features?

The reason Hey’s email service caught my attention is that Basecamp specifically calls out Apple (among the other big email providers). I was a bit surprised when I read Hey’s Top 20 features.

The Hey Email service was started by long-time internet developers Jason Fried, a co-founder of project planning software Basecamp. He and his business partner, David Heinemeier Hansson (frequently referred to as DHH) have been in the news lately for some rather loud missteps about how they handled some workplace controversies. That’s not the point of this article; running a business is hard. The reason they get noticed is because they’ve written loudly themselves for many years on the “proper” way to do business, remote work, and other initiatives. They have contributed some good things to the conversation and, for such a small company, have a rather broad reach.

However, when I saw that they started a new company called “Hey” and that their main premise, much like Slack’s, is that “Email is broken” and that, of course, they were the latest ones to claim they had a fix for it (for your hard-earned dollars, of course), I started following their new service closely.

To be fair, a few features are unique to Hey. But are they worth $100/year?

The only way I can support Hey’s concept is for those who don’t understand email and never will. (This article is for them if they want to be in more control their email, and not spend $1,000 over the next 10 years.

To be fair, to follow the tips in this article, you’ll need a Mac or iPhone and those aren’t free, whereas (arguably) you could run Hey’s Email service on a cheap laptop or older smartphone. I might later write another version of this article to cover doing these same tips with Mozilla’s Thunderbird. But for now, let’s stick with Apple Mail which comes free with any version of MacOS.

Other reviews of Hey

For those who use Fastmail, you might find Nuno Donato’s guide to recreating Hey’s features to be of interest. Olly Headey has been using Hey for a year (despite being a 7-year Fastmail customer) and in his one-year review of Hey, he almost cancelled but decided to keep it to see how it continues to develop. His laundry list of complaints are worth a read though. Famed blogger M.G. Siegler decided to keep using Hey after a trial evaluation. Per Axbom has a solid breakdown of Hey’s market noise in his post titled Hey, your email matters more than hype.

My problem with Hey’s advertising

There is an underlying conspiracy theme in the way the Basecamp camp (?) has marketed Hey. DHH wrote a rather screed-worthy post titled (in clickbait fashion) “On Apple’s monopoly power to destroy HEY”. This post was likely designed to get like-minded theorists to sign up for Hey. There’s something bizarre about claiming Apple wants to “destroy” a service that isn’t, well, really anything yet. He seems to think that if it weren’t for Apple, the then-new Hey email service would have been the next Angry Birds. Maybe I just don’t like whiners, so that post was somewhat my motivation to use Apple Mail, a long-standing well-designed email client, as a comparison point against Hey’s so-called ‘features’.

Hey’s feature tour says “you’ll never go back” even though Brian Li apparently did go back – and only after two weeks. Raul Chowdhury initially blogged he would never go back after only using it two weeks, but a year later, he listed a massive series of gaffes as to why he was leaving Hey for… Google Workspace, chief among them being the inflexibility of Hey’s designers to not address, not surprising to me, some fairly standard ways of dealing with email.

This always happens when someone tries to make an “email killer” app: they create what works for them and then try to charge everyone money for it. Trust me: it’s better to learn how to just use email and then create your own workflows and rules to make it work for you.

Hey says that its email service “replaces workarounds, messy hacks, and daily frustrations, with built-in workflows, effortless organization, and clever features that levels-up email in meaningful ways”.

I sort of like how they use deep marketing speak to trash common long-standing uses of email. Phrases like “workarounds” and “hacks” are tossed in to scare people into buying. Hey calls their features “clever”, but I’d say their marketing is far more clever than most of their features.

What they call a “workaround”, I would call a “workflow”. What Hey calls a “hack”, I’d call a system or a rule. What they call a “daily frustration”, I would point out is any tool if you don’t spend 20 minutes learning it. Many SaaS (Software As A Service) companies use nonsensical (and quite frankly, fraudulent) language like “effortless”. They solve one “problem” so that you can now put your effort into learning their solution for the problem. My advice is to put your effort into learning the original technology and its available solutions first rather than be a slave to a private vendor. What’s next? A mouse and keyboard monthly cleaning service? Because you won’t learn to use a can of compressed air?

If I have to applaud Basecamp for anything, it’s that the mere creation of this product, along with other johnny-come-lately products like Superhuman, proves that email is the place to be. What other 50-year old technologies have companies putting hard work into creating new and supposedly innovative ways to use what is working just fine ‘as is’ (as I attempt to argue here in the pages of Just Use Email)? I am sure we will see further stabs at this by many companies because email is here to stay.

Hey’s Email Features on their Tour

1. Screen emails like you screen calls: Hey says that “The first time someone emails you, you get to decide if you want to hear from them again”. With Apple, you can “block” a sender and it will never get in your inbox again. (This also applies to phone numbers for calls, texts, iMessages, etc.). Granted, there is no special “screening” interface like Hey has, but for both services, you still have to get the email first to decide if you want to block it later. The whole point of an email address is to be able to give it out without fear. This initial feature of Hey does nothing more or less than any other normal email service.

2. Fix bad subjects without busting threads: Hey allows you to rename email subject lines and still keep conversation threading working. Hey wins here, but I see trouble for this feature, even though every rainy day or so I might wish for it. Hopefully with Hey one can still search for the original subject title after altered, because at in-office work environments, it’s a weekly event for someone to come and say, “pull up that email I sent you last month; it’s called ‘Friday Budget Mtg'”, and hopefully you didn’t rename it “Toxic Suffocation in Finance”. Once in a while someone does send subjectless emails, or sends a subject with about a dumb of a name as “Hey” itself, but it’s not a problem in need of a solution. Email searching has long been full-text and if the email discusses the Super Bowl party and who is bringing nachos, it’s not necessary to rename it “Nachos at Super Bowl party” unless, uh, you’re an engineer and you simply can’t stand to see “Hey…” in your email inbox. Let’s recall that email subject lines are an Email Superpower, so I’m loathe to hear about a service that tinkers with them. Plus, there’s absolutely nothing wrong with you replying and changing the subject (or adding one) in your reply. That’s the beauty of email: do what you want. Plus, even if your newly titled subject line won’t break your Hey conversation thread, will it not show in your recipient’s differently? I often will reply to an email in several chunks, renaming the subject line to cover the specific parts of my reply, the whole point of which is to keep that portion of the conversation noticeable by the recipient and answerable by them (asynchronously) and forwardable by them to others. Hey just offers this to allow you to rename the subject for your own internal idealogy, but not officially as part of the email protocol.

3. The IMBox – No, it’s not a typo: Hey claims “Your Imbox is where important, immediate emails go from people or services you care about.” Here we go again. We all have filtering capabilities. I always have emails from my immediate boss flagged and pinned (until dealt with). Set it up once and it works forever. Hey makes it sound like we don’t know how to filter, pin, or use other rules that most email services have. I don’t understand the attraction. Gmail came up with this smart-ish inbox concept years ago; it created more problems than it solved. Hey even tells you that they will decide for you. Watch out! Here we start again down the path of Big Brother dipping their fingers into our email inboxes to tell us what’s best for us. Hey says, “No random receipts, no ‘I rarely read these’ newsletters, and no special offers crowding out the stuff you really care about”. Those receipts aren’t random sometimes. We need them, and sometimes in the moment. Thank you, but how about letting us plebeians decide what email newsletters we will read? If there’s anything we’ve learned about Big Tech/Brother these past years, it’s to be very careful when they start telling us that they will filter information on our behalf to show us what we really care about. What’s worse than a busy inbox? Multiple busy inboxes based on invisible filters designed by someone else.

4. Find files without digging through threads: Here, Hey’s marketing department calls using a basic email search “digging through threads”. I don’t know what “digging through threads” means, but if I type “budget2020.xls” in my search bar, the file will appear. Granted, I’ll have to see the thread, but so far I haven’t died from that exposure. But who looks for files in emails anymore anyway? Maybe once a year? I can also just type “xls attachments” in Apple Mail’s global search and filter and sort from there if I don’t recall the exact file name. Option-Command-F is your friend.

5. Quiet by default, loud at your discretion: Basically, Hey puts notifications on quiet mode. That’s nice, but after spending 45 seconds, I did the same thing a few years ago. Only my “favorite” contacts notify my iPhone or Mac. Other than those, if you saw my Mail App icon, you might think I have no new email. But yet, I might have a dozen. Or even hundreds if you count other new emails going into folders or being “marked as read” by Rules. I don’t understand building a whole new service for this feature. It’s been available for many years (for free) to anyone who wants it.

6. Reply Later: I hear some services (Outlook?) have this and it sounds nice. Because only personal and important emails are in my Inbox (i.e. what Hey calls an IMBox), it’s really not a problem for me, even at work. I keep it lean and mean. I suppose if people are struggling to manage the emails they need to reply to, this could be a handy one-click solution, but even when I’ve been temporarily overwhelmed (usually at work), I have a folder under my inbox called “Reply Later”. It works… like magic! You drag the email into it, and that folder shows the number of total emails in it (read or not). Then, guess what? You still have to “reply later”. You can guess that this works out just as well as “Read Later” services… but hey, it makes me feel good in the moment that I “did something”, even though I actually did nothing. Hey goes on to say “What if you need to reply, but you don’t have time right now?”. It’s a typical marketing gimmick where they ask the question that causes people, in their hurried state, to say, “Yeah, what if! I’d be screwed! Thank goodness I can give them money to solve it!”. Except they haven’t solved it. It was solved ages ago by something called folders and flags. You could have been doing it ten years ago.

7. Just Set it Aside: Hey says “you can ‘Set Aside’ any email in a neat little pile for easy access whenever you need it. At hand, but out of your face”. So, basically, Archive with Global Search. Great. Let’s also see if we can invent a round container of air that rotates on the bottom of platforms. Then we could really revolutionize transportation! Hey claims that “Sometimes you get emails you need to reference later – travel info, handy links, numbers you need, etc”. Sometimes you get these emails? How about almost every day? Why do people always try to create a middleman between the inbox and your archived email? It’s either here or there. It’s a beautiful system. If you need an in-between location, you have folders and flags. Learn to use them.

8. Blocking Email Spies: Right. Good. Educate people about this. And then everyone go into your email services settings and turn off auto-loading of images. No need for a new email address or service for this. Some services allow you to do this for just people not in your contacts, which is really great. But point is, it’s available now and has been for years. As of today’s announcement in WWDC, an enhanced version of this is also coming to Apple Mail.

9. Separating and Merging Email Threads: Good idea, but now you’ve actually created more work. We don’t want to manage emails. When are they all going to understand that? This is an edge case. I have threads (conversations) turned off. (I know… gasp! A heretic to all that is Gmail and Holy). For most personal emails, the whole thread is in the last reply. For all others, I don’t want to see them. When you go into your archive and sort by sender/date, you can pretty much see the whole thread. I do this exactly once per year for some edge case reason where I needed to find it, else it’s global search.

10. Open Multiple Emails at Once: Why? Because we can? Hey references people also closing emails. I don’t know who is doing this, but I haven’t “closed” an email in 20+ years. I can’t see why I need to read/see multiple emails at once. Can anyone else? Maybe specific ones (to compare or refer to while writing a new one), but to just read multiple emails in sequence as they arrive in my inbox as Hey mentions? Why? But if I wanted to, I could do so in Apple Mail. It’s called “double-click”. (Shhh… don’t tell Hey about this secret high-tech trick). It opens up each email into it’s own window. I can even place them side-by-side, top-bottom, all over, use different virtual desktops! So powerful! Except, I never do it. But I could. But I won’t. But I could. But I won’t. Seriously, Hey says this about this ‘feature’: “Why do you have to open one, close one, open one, close one, open one, close one, and so on. It’s ridiculously inefficient. With HEY, you can open multiple emails at once and just scroll through them, just like you would a newsfeed. It’s a revolutionary way to read your emails. You’ll never go back to the old way”. When I read this, all I could wonder is what email interface Fried and Hannson were using when they invented Hey. Open and close? Open and close? Most email clients let you use up/down arrows (or Vim hotkeys) to scroll through your emails with a preview pane to the right or below the mail list. I think I can recall exactly one email client from the 90s where I had to do this “open and close” manipulation to which Hey refers.

11. Focus and Reply: Here, Hey starts to get really wonky. This idea of Hey’s is that you are unable to reply to emails because new ones keep coming in and distracting you. This only ever happened to me with Gmail email many years ago as the Javascript notifications get annoying and everything is buried in “conversations”. Desktop-class email that has proper rules and notifications set has never been a problem. But if I had a “Reply Later” folder (see #6 above), I could easily handle this. You can also Option-Click your Mac’s Notification triple line thingie in the upper-right corner and turn off all notifications temporarily so you can Get Work Done. After all, it’s not just email notifications that can be disruptive to quality work.

12. Bundle dominating senders into one line: Step 1, get rid of such people but if not possible (e.g. your boss), then Step 2, create a rule to put them in their own folder, or better yet, make a smart folder for them and have their stuff auto-archived out of your regular Inbox (or whatever works well for you). Point is, there’s no reason to let any email sender “dominate” your inbox unless you can’t learn a few quick clicks to control your inbox. Hey offers nothing new here except the idea of smushing all their emails down to one line. Watch their demo for this feature. Makes no sense, and once again, it’s a feature that creates more constant management. Rules and filters were long ago invented for the purpose of “fix it and forget it”. I don’t understand how Hey is basically using rules and calling it something new.

13. Send Massive Files: Apple calls it Mail Drop. Been out for a few years. Works perfectly and auto-deletes access to the file after 30 days. Nice that Hey has this but in my opinion, this isn’t a novelty or anything new; it should be the standard now for any serious email service. Microsoft’s OneDrive, DropBox, and a dozen other services are available also. One downside to Hey’s large file attachments is that the link does not expire. Hey brags about it, but I think that’s a gaffe. Apple’s Mail Drop links expire after 30 days. That’s a good thing, in my opinion. If you want to publish to the internet, then do so, else you need to manage those prior uploads and that, again, is more work.

14. Clips: So basically you “clip” out pertinent info from emails and save it in their propriety Clips section. Again, more work. They even give the example of phone numbers. No, no, no. You copy/paste a phone number into your contacts app where you most definitely will look for it in the future. The last thing anyone wants is yet another online storage pile to rummage through. Put like items with like items. This is just bad design all the way to the bank. Their bank.

15. Speakeasy: This is the strangest of all. Hey wants you to give a stranger a special coded keyword email so that when that person emails you later, you don’t miss it and it goes straight to your IMBox, Hey’s idea of an inbox. I have never had this problem ever and I’ve given out my email thousands of times. When someone emails me, it arrives in my inbox. You see, this may come as a shock to some, but that is how email actually works. All these silly variations on email addresses (like Gmail’s + email addresses) defeat the whole purpose. You only need one email address, but yes, you do need rules and filters. The only reasons why someone’s initial email would not land in your inbox is because they have been abusing the email system and got on the wrong side of SPF, DKIM, or that you have signed up for Gmail, Hey, or another email service that tries to outsmart you and filter your email for you, or because you don’t use rules and filters well. Fix that and you don’t have to get Yet Another Email Service (Hey, or anyone else).

16. Add Notes to an Email: Hey calls these “sticky notes” or “Inbox Notes”. It’s an interesting idea, but if it ever caught on, I’d be surprised. Even Hey’s screencast demo of this isn’t convincing (the recipient just adds a note that says “I have to remember this” which could be done with Flags) so it seems like even Hey couldn’t come with a really good use case for this. But I’ll give Hey credit on this one since I don’t think anyone of the big players have this “feature”. I tend to keep notes elsewhere and, if necessary, would copy/paste relevant portions of an email with my notes, not the other way around. Hey says “They’re great for jotting down phone numbers, dates, addresses, links, and personal, private thoughts you’ll need next time you reference that email.” Maybe some will really like this and find that email becomes more productive and useful for them, but I have my sincere doubts at the moment. Email ≠ CRM. Don’t conflate the two.

17. Add Private Notes to Self: This is an extension of #16. Attach files, notes about a lunch meeting, etc., to the email “thread” itself. Again, not for me. Maybe some will find this helpful (if they don’t keep separate notes elsewhere), but I have my doubts. There seems to be a marketing effort to convince us that email archives are The Source of Truth. Outside of certain legal requirements or workplace policies, I actually delete nearly all my archived email every year or two. And no, I’m not paranoid. I just will never go back and read it, so why keep it? For my kids? They sure as heck don’t want to read it and I don’t want them to waste their lives on something so useless. Go read “The Old Man and the Sea” instead. But that’s just my narrow view on notes versus archived email. It’s a topic for another time. Here, Hey wins technically because they added a “feature”, but I don’t think it will be useful to many people. Again, email ≠ CRM. Don’t conflate the two. Keep your notes as notes, not stuck with an email chain.

18. Put Receipts in The Paper Trail: What do you first think of when you read this? “Receipts, confirmations, and transactional emails getting in your way? With HEY, you can send those types of emails to The Paper Trail where they’ll be out of your way, but easy to find when you need them.” Did you think of a folder? I am actually surprised that same geniuses that invented Basecamp and Ruby on Rails created this Hey service. They actually named this “folder”, “The Paper Trail”. Was I wrong to call mine “receipts” and have a rule created for it? Apparently so. Home Depot and Square receipts automatically go into it (along with quite a few others) and I occasionally drag a random one into it. How on earth is this innovative and worth talking about? This could have been done in 1999 in Eudora if companies were emailing us receipts back then. I think Hey should actually lose points here for basically creating “AI”-based folders and telling us that they are restoring sanity to email. We have been able to do this from the Beginning. I wouldn’t be surprised if this was possible in Unix in 1970. The difference here is that Hey is the one that decides what goes into your Paper Trail folder, just as Gmail tries to decide what goes in their category called Purchases. Better for you to make up your own folders and rules to sort what goes into each.

19. New For You and Previously Seen: Am I missing something? “With HEY, new messages are always grouped together at the top, and previously seen emails are always at the bottom.” Isn’t that how all modern email services now work by default? This is another Hey embarrassment. In Apple Mail, it’s called “Sort by Unread”. I can’t imagine there’s an email service out there without this “feature”. Thankfully, Hey buries this at #19 on their Top 20, but why even mention it? What’s next “Sort by Date”? “Sort by Sender”? The Innovations Keep A Coming!

20. Get Off Threads (Ignore): Apple Mail has “Mute Selected Conversation”. Same thing, as far as I can tell.

Bonus Round

Hey recently added:

21. Email the Web: What is it? You email your blog post to a special address and it is published automatically at a special website on hey.com. WordPress has had this (for free) for more than a decade. When Hey first introduced this, aside from the fact it has zero to do with running an email service, it was lauded as some kind of revolution. Maybe if you’re 17 and you just got on the internet a few years ago, this might seem novel. However, almost every major blogging and publishing platform has this feature built-in, along with a ton more to help with web publishing.

22. Custom Domains: Believe it or not, you were initially forced to use an @hey.com email address, but they did what all email services must do eventually. Now you can own your own domain, and Hey even tries to make it sound cool that you can add various group email address like sales@ or info@ that auto-send to a set group of people. Hey calls them extensions (no idea). Nothing that couldn’t be done before.

23. Add Cover Art to your Imbox: This is just dumb. Jason Fried spends a whopping four minutes explaining it in a video that you really don’t want to watch, unless you’re the type that adores logo redesigns or instagram filter explanations. Basically, Hey wants to give you a pretty image to hide your previously seen emails so you don’t actually have to see them below your new emails. After you waste time choosing an image, you get the extra fun of clicking the cover art to expose your previously seen emails and then clicking it again when you don’t want to see the previously seen emails. If you have severe Attention Deficit Disorder, this may be a helpful feature, but for the rest of us who just understand that most email clients have new email bolded and sorted at the top and older email in a normal font and sorted after the new incoming email, this is just dumb UI masking as innovation. There may be some benefit for those who need high privacy and tend to work on their email in public settings. You could just resize your email window, but who am I to judge if someone wants a pretty image of some confetti or graph paper instead?

24. Link accounts and see all your email in one place: When I see this, I wonder if Hey is just counting on its buyers to be completely ignorant of how email works. You can do this in nearly every email client out there: Gmail, Outlook, Yahoo, Thunderbird, Eudora, and of course email clients like Apple Mail (even if you don’t use iCloud). It’s not a feature, but the lack of it would definitely be noticeable.

So my question stands: can’t Apple Mail (and possibly others) do almost all of Basecamp’s Hey Email Service? Why would anyone sign up for it, much less pay for it, (short of just wanting to play with it or to get a new email address)?

It’s probably worth noting that Hey doesn’t have a public-facing support site, but just a support@ email address for anything outside their very short FAQ.