Posts from email hacks

The + Email Hack

I found myself using this hack a few times this week and I thought I would share it. I think many/most of you probably know it, but it is so damn useful that it’s worth sharing it anyway.

If your email is [email protected] and you want to create a new email address that will get email at [email protected], you just put a + and add something. Let’s say you want an email address for a netflix account, you enter [email protected]. To netflix, this seems like a different email address but the mail still goes to [email protected].

This is particularly useful for creating multiple accounts with the same service. Many services don’t let you use the same email address for multiple accounts. So you just add the + and something you will remember and you get around that issue.

This is one of those little things that is super useful and once you know about it, you will find yourself using it quite a bit.

Update: The comments to this post on Twitter tell me that this hack is a gmail feature and is not necessarily available on other email services.

#email hacks

Feature Friday: Gmail Predictive Typing

I was typing emails on my new Pixelbook yesterday and as I started a new word, Gmail would finish the word and often suggest an entire phrase to come after the word. All I had to do is hit tab to accept the suggestion.

I’ve had a version of that on the Gmail app on my phone for a while. It looks like this:

But the type assistance functionality on my Pixelbook was much more useful. First it was in line and it suggested entire phrases, not just words.

I’m of two minds on this feature:

1/ It is super useful and once I get used to it, I should be able to construct messages much more rapidly.

2/ I am not sure I want Google reverting my communication style (and yours too) to the mean.

I suppose if Google was using just its understanding of my writing style and nobody else’s in its algorithms, then it is helping me be me. And I like that a lot more.

But if it helping me be you, well I’m not as excited about that.

#email hacks

Feature Friday: Gmail Reminders

I don’t know when Gmail started doing these for me but it was around the time I switched over to the new UI. Most likely this is one of the features of that new UI.

When I have not responded to an email that Gmail thinks is important, or when someone has not responded to an email from me that Gmail thinks is important, it resurfaces that email near the top of my inbox.

It looks like this:

The first email is a reply I sent to an email and the recipient has not responded in seven days. Gmail is suggesting that I follow up.

The second is a back and forth with my brother and I failed to reply to his latest. I just did. Thanks Gmail.

While this is a relatively small feature in the overall Gmail offering, I have found it quite useful in the month or two that I have had it.

Thanks Google.

#email hacks


I read this story about how hackers got into Colin Powell and John Podesta’s emails.

It is somewhat shocking to me that Google’s algorithms allowed fake emails from Google to get into a Gmail user’s inbox.

One of the many reasons I use Gmail over any other email service is its algorithms that keep spam and malicious emails out of my inbox. They have done a remarkably good job of that for me over the ten(ish) years I’ve been on Gmail.

This is not only a black eye for the Clinton campaign and Colin Powell. It’s a black eye for Google and Gmail.

I hope they take this as a challenge to improve their anti-phishing algorithms.

#email hacks

Collaborating On A List

Every business has this situation, some many times a day.

Over the weekend, our team at USV was discussing an event we are putting together and people we might invite. One of us started the thread and suggested a dozen or so names. Replies started going back and forth with new suggestions. Many great ideas came out quickly via email. Then we decided to put all the names into a google sheet, which was obviously the thing to do to memorialize the suggestions and comments.

But then the discussion stopped. No new names were generated. The discussion ended.

Google sheets does generate an email when a change is made to a sheet, but it is not conversational the way a group email thread or a Slack channel is.

I suggested that we write a script that allows us to have the conversation in Slack and new ideas are autopopulated to the Google sheet. We could also do that in email but Slack felt like the better option.

I’m curious if other folks out there have had this same experience and how they have solved it. You want to database the list in a tool like Google sheets, but doing that seems to shut down the conversation that flows in an experience like Slack or email. It seems like the two functions need to be merged in some way.

#email hacks#enterprise#management

The Context.IO App Challenge

I recently agreed to be a judge for the Context.IO App Challenge. It is a long-format online hackathon. Developers and entrepreneurs have until September 1 to build and submit consumer applications that use the Context.IO API, with a chance to win over $50k ($125k cash prizes in total).

Context.IO is a product of Return Path, where I’ve been on the board since 2000.

Context.IO is an API that allows you to easily build applications on top of the data from your user’s email accounts. It removes the complexity of working with email servers and the nuances across different email providers (Gmail, Yahoo, Outlook, etc.) to greatly reduce development time.

The email inbox is a huge opportunity for entrepreneurs because so much of what happens in today’s world (commerce transactions, communications, content sharing) flows through email and there are over a billion active email inboxes.

The judges are Brad Feld, David Cohen and Matt Blumberg. This is our judging criteria:

  • Quality of Idea: Is the idea creative, original and innovative?
  • Implementation of Idea: Was the idea well executed?
  • Potential Impact: Is the app providing sufficient value to it’s users?
  • Market Readiness: Is the app market ready? Is it available in a public, online store? Has it been localized for international markets?

Anyone interested in participating should register for the challenge on the Challengepost website and get started with Context.IO by signing up for an API key on their website.

#email hacks

Feature Friday: Undo Send in Gmail

Here’s a good reason to read the comments at AVC. You learn things.

On Monday I wrote a post about sending stuff to the wrong people and a number of folks in the comments explained that there is a Google labs feature called Undo Send that holds your “sent mail” for up to 30 seconds before it actually sends it.

I immediately added it to my gmail and feel safer now knowing I have it. I have not used it yet, but I am sure I will.

Here’s how to add it.

Go to gmail settings, then click on the Labs tab and find “Undo Send” and click enable:

undo send

Save that change.

Then in the general tab, you will see this:

Undo Send Two

You can set the cancellation period to anything between 5 seconds and 30 seconds. Save that change too.

I’m honestly not sure why this isn’t a standard feature in Gmail. It seems so useful.

#email hacks

Fun Friday: Things We Hate About Email

It’s been almost a month since we did a fun friday. I was talking with an old friend yesterday about how much we all hate email.

So I thought we could spend friday at AVC collectively hating on email.

Here are a few things I hate about email:

– There is no easy way for me to keep track of the emails I’ve sent where I really care about the response. These important responses get caught up in all of the other email and I often miss them.

– Calendar invites. I wrote an entire blog post hating on them. I particularly hate Calendar Invite Spam. But I dislike all calendar invites because the interaction should be in my calendar not in my inbox.

– Folders/Labels – I can’t be bothered to organize my email into folders/labels, and I never ever look at anything other than my primary inbox. Once an email goes into a folder/label, it is gone and the only way I will ever react to it is finding it with search.

– No Multitasking Support – I have to open up multiple tabs in gmail to do some tasks. It would be great if I could multitask in a single inbox view.

– Doing email on my phone. As much as I hate doing email on the web, it is worse on mobile. You have less screen real estate. Cutting and pasting is harder. Everything is harder.

So those are some, but not all, of my pet peeves about email. What are yours?

#email hacks#mobile#Web/Tech

Feature Friday: Open In Drive

One of my favorite features of Gmail is the ability to get a file (.xls, .doc, .ppt, .pdf, etc, etc) and have the option to open that file in Google Drive. It is that single feature that allowed me several years ago to remove all desktop software from my machines and use only cloud based software.

However, recently Google changed the way that feature works and I can’t figure out how to (or even it is possible) revert back to the old way.

Now, Google offers two choices, download or “save to drive”, as shown below


The irritating part of this new set of choices is that I don’t want to download the file and most of the time I don’t want to save it to drive either. But now, if you want to open in drive, you must first save to drive, and then open in drive.

You might say that’s not a big deal. Two clicks instead of one. But it is a bit more than that. First it seems to me that it takes longer to go through the new save/open flow than it used to take to just open. Second, I really don’t want to clutter up my Drive with all of these attachments that mostly I just want to read. If I do want to save them, I could always have done that in the old flow after opening the attachment.

I suppose this is all part of Google’s desire to have you save everything so you can search for it later. I appreciate that to some extent, but there is so much that I just want to view and delete, emails, attachments, and many other things. Google is making it harder to do that and I don’t really appreciate that.

If anyone knows if it is possible to go back to the old flow, I would love to hear how.

#email hacks

Gmail Meter

I tried out a new service this past week called Gmail Meter. It's a free analytics service that tells you stuff about how you use Gmail. It is brought to market by the folks at ShuttleCloud, which does archive and data migration for cloud services. It's a way for them to get to know folks who might become ShuttleCloud customers in the future.

I learned a few things. I get 6,470 legit emails a month from 1293 different senders. I send/reply to 2,676 emails to 777 people. So the send/receive ratio across my inbox is 41% which is higher than I thought. I feel a tad better. But there are also at least 516 people who sent me an email last month that did not hear back from me. That makes me feel a bit worse.

The single highest send/reply ratio in my world is the Gotham Gal who sent me 133 emails of which I replied to 100, for a 75% return rate. I've got work to to do there. Sorry Jo. My partners Albert, Andy, Brad, and John get between a 50% and 70% reply rate. Sorry USV folks. The one cohort that I send more mail to than I get replies from is my three kids. I get a worse response rate from them than all of you get from me. Not sure how I feel about that.

This chart will not surprise anyone here at AVC but it does show that the one time I reply to more email than I get is the 5am to 7am time frame.

Daily traffic

Here are a few more interesting charts:

More gmail meter charts
The first chart shows that I get to most of my email within 24 hours but there is certainly a meaningful percentage that takes longer.

The second chart shows that I send a ton of short emails. 80% of my email is less than 30 words. Whereas greater than 50% of the emails I get are longer than 100 words.

I've asked the Gmail Meter folks to add a chart showing reply ratio on emails less than 30 words versus emails greater than 100 words. When I get that chart I will publish it here because I think that is single best secret to getting a reply from me.

Anyway, I found this data valuable. Maybe you will to. You can try it out at Gmail Meter.

#email hacks