👋 HEY.com vs Fastmail. A review.

I’ve been a fanboy of DHH and Jason of Basecamp since around 2006 when I first read Getting Real and started writing code in Rails. We used Basecamp (and for a brief time, Highrise) as our primary communication tool for the first few years of FreeAgent and it was a big influence from a product point of view. For the past 8 years though, I’ve not really used Basecamp products but I have remained a follower of the company and founders, reading their books and enjoying their Twitter rants. I’m still an ardent Rails fan as well 👨‍💻

When I heard about HEY, I was immediately interested. Not because I’ve lost control of my inbox (I’m an order-freak and avid filterer so my inbox is generally a tranquil place), but because the HEY statement about why “Email’s a treasure” rang so true to me and because a brand-new, Rails-based, Basecamp product is always going to be pretty exciting to try.

I got my invite early and I’ve been kicking the tyres for a while, so I’ve written up a few thoughts to get them out there and to hear about what other people think.

How I ended up being a Fastmail customer

I’ve been using email for 28 years. I got my first email account back in 1992 when I started university and I rarely received any email from what I can remember. I probably got the odd message from tutors, but during uni my online communication was largely centred on IRC. Remember that?

On leaving university I didn’t use email for a while. I got my first job via a Usenet forum so I must have used email for that, but it wasn’t until the arrival of Hotmail a year or two later that I had my first ‘permanent’ email address and could access it anywhere (still a limited choice in 1996!). I got my first work email with my second job and then I moved on from Hotmail to Yahoo and stuck that out until 2003 when Gmail launched (and after Yahoo inexplicably deleted all my email by accident).

I stayed happily with Google until 2015 when I moved over to Fastmail so I could use my own domain and pay for a proper email product and not be the product myself. I still use Gmail (via G Suite) for work though.

Hey, HEY

With the arrival of HEY, I loved the privacy-first focus (no more ‘spy trackers’) and the new workflows (Set Aside, Focus and Reply etc) sounded great. Jason’s demo was compelling. I’m fascinated by what they’ve achieved with modern Rails and Javascript, the simplicity of the front-end code and speed of it all really is a triumph.

However once I got invited, the reality of using it has been something of a mixed bag of utter delight with some frustrations. Let’s dig into it.

🧁 Utter Delight

Focus and Reply

This is a headline feature and it’s really very good. Flag your emails ‘Reply Later’ as you’re reading your new mails and stack them up for dealing with later. When you’re ready, Focus and Reply lets you hammer through them all at once from a single screen. It’s a brilliant workflow.

Focus and Reply screenshot

Spy Tracking

I think the Spy Tracker support is brilliant and should become the standard in all email apps. Perhaps it will. I actually emailed Fastmail about this and their reply was pretty interesting:

We’ve blocked remote images from loading by default for years: https://www.fastmail.com/help/receive/remotecontent.html.

And if you do enable remote loading of images for your known contacts, or just enable it for a single message, then our servers proxy the images, so all the sender can know is details about our hosts and nothing about you.

So, actually, Fastmail are pretty much doing the same thing other than alerting you to the fact that emails are using SendGrid or whatever?


Clips screenshot

Clips is a brilliant feature that I never knew I needed. Highlight some text and save it in your list of clips. I can see this feature being expanded in the future, such as filtering and being able to set expiry dates.

😣 Frustrations

Custom Domains

Perhaps the most common complaint I’ve seen on Twitter is the lack of custom domain support. I run email off my own domain so this is of course something of a blocker to my own full-time adoption. I did try forwarding my email into HEY for a while so I could use the app in anger, but I’m not yet ready to make my @hey.com address my default so I’ve paused this for now. Custom domains are coming in 2020 and I’m excited to see what they offer from day one. I hope they nail it.

🔕 Notifications

Despite being something of an inbox zero fiend, I have no problem with the Previously Seen list in my Imbox. I really like the idea of Paper Trail and The Feed, and autofiling email in there is great but I have a real gripe with notifications. I definitely don’t want to be notified via push on my phone when a new item hits either of these areas, but when I log into HEY I definitely do want to be notified, visually, that there’s something new to view in these areas. As it stands, I have to compulsively check each one irrespective of whether there’s something new. HEY’s philosophy is that I should ignore them entirely until I feel like reading my Feed, but in reality this is never going to work for me. I’d like to have HEY alert me to the fact that there’s something there, and if I feel like reading the feed at that time I will, otherwise I’ll come back later. If I don’t know, I feel compelled to check which is just a waste of time.

Now forgive me for my sins, but I actually want to receive notifications for emails that hit my Imbox by default, not the other way round. With HEY there is no way to do this – no notifications at all. You have to manually edit each contact and enable notifications for them specifically. I’d much rather HEY let me choose which is my preferred default, irrespective of the philosophy. Let me default to on.


Please just call it Inbox! I can never unsee a typo here, I’m sorry. I understand but it just doesn’t work for me.

Quoted text rendering

This is a total design challenge and HEY is no worse than Gmail in this regard, but I have to say Fastmail do a far better job of it. HEY rendering feels like a backwards step after using Fastmail and its multi-coloured threading. Hopefully it will improve over time.

Fastmail’s quoted text rendering
Fastmail’s tasty quote rendering


The export to MBOX feature is great – it’s my data and it means I’m not locked in. I know that if I decide to leave HEY, I can easily export all my mail and push it back into Fastmail. However, I like to label a bunch of my emails and currently this metadata will be lost when exporting from HEY. I suggested to DHH that they use IMAP folders in the export to maintain label information and he said it was a good idea, so perhaps it will see the light of day soon 🤞

😴 Snooze

Set Aside is great, I like it a lot. But sometimes there are emails that I want to set aside for a longer period and the Snooze feature in Gmail and Fastmail is super-handy for this. When you set something aside in HEY, the email is there in the stack, staring at you in the face every time you visit. This isn’t desirable for ‘set aside for ages’ emails, so a Snooze function (either as part of Set Aside, or just in general) would be great.

Can I just replicate the HEY workflow?

Undoubtedly the killer feature of HEY is the built-in workflow. Some people have suggested that this is a feature that could be replicated in standard email, so I had a crack at this with my Fastmail account. While not being a match for HEY, it actually worked surprisingly well!

I first created labels for Reply Later, Set Aside, The Feed and Paper Trail:

Using Fastmail labels to replicate the HEY workflow
Using Fastmail labels to replicate the HEY workflow

Moving mail into Reply Later or Set Aside is really easy in Fastmail because of their keyboard shortcuts: view the mail, click ‘m’ to bring up the ‘Move’ menu and then start typing ‘Repl..’ to label it as Reply Later. Admittedly not as slick as HEY but it’s blazingly fast (as are most things in Fastmail) when you’re used to it.

I then set up rules to move things into The Feed and Paper Trail. Again, not as simple as with HEY but the rules in Fastmail are very powerful so you do have a bit more flexibility here:

Using Fastmail's powerful rules to replicate The Feed
Using Fastmail's powerful rules to replicate The Feed

The Screener

I might be in the minority but I find The Screener more annoying than not. It turns out it’s extremely rare that I receive an email from someone that I want to screen out. I can do this in Fastmail using blocking, but my blocklist is virtually empty.

If I was using HEY for my work email, however, it would be a completely different story which does make me wonder whether HEY’s future success really lies in the business market.

In Conclusion

Using HEY is a really nice and unique email experience, but it’s early days and ‘power users’ like me will likely find it lacking in some areas.

I’ve already paid for my first year because I love the @hey.com email address, I really want to try HEY with custom domains when they launch, and I also want to see how it develops in the coming year. I’m also happy to pay Basecamp to keep developing this product as it feels important right now. The world needs more players in the email provider space, especially high-quality, privacy-focused products. Until HEY arrived, Fastmail was the only major player other than the obvious ‘free’ options of Gmail, Microsoft and Yahoo.

Can HEY fully replace Fastmail for me though? Will I be renewing in 12 month’s time?

Once custom domains land, I think it could replace Fastmail for me. That said, I’ll likely still end up paying for Fastmail irrespective of how HEY develops simply because of their excellent multi-domain support. So I’ll probably end up paying for both! 😅

With Fastmail I can create forwarders on my family domain for the kids (I really hope HEY’s custom domain feature will support this, but I’m not confident they will). I can also support fully-featured email on all the domains I own (such as the one for this blog!) without incurring any additional cost or hassle dealing with other email providers. Much as I’d like to see HEY offer feature parity here, I think it’s unlikely they will, at least not for a while. Fastmail have been developing their service for over 20 years and it’s a highly tuned machine, so it will take a while for HEY to fully catch up, assuming they even want to.

Have you considered using HEY and replacing Fastmail? I’d love to hear what you think. My blog doesn’t have comments so feel free to drop me a line at olly@hey.com, send me a tweet or discuss on Hacker News 👋 😀