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

Comments (Archived):

  1. tyronerubin

    From a post by Paul Graham in March 2012 Titles: Frighteningly Ambitious Startup Ideas…excerpt:Replace Email:Email was not designed to be used the way we use it now. Email is not a messaging protocol. It’s a todo list. Or rather, my inbox is a todo list, and email is the way things get onto it. But it is a disastrously bad todo list.I’m open to different types of solutions to this problem, but I suspect that tweaking the inbox is not enough, and that email has to be replaced with a new protocol. This new protocol should be a todo list protocol, not a messaging protocol, although there is a degenerate case where what someone wants you to do is: read the following text.As a todo list protocol, the new protocol should give more power to the recipient than email does. I want there to be more restrictions on what someone can put on my todo list. And when someone can put something on my todo list, I want them to tell me more about what they want from me. Do they want me to do something beyond just reading some text? How important is it? (There obviously has to be some mechanism to prevent people from saying everything is important.) When does it have to be done?This is one of those ideas that’s like an irresistible force meeting an immovable object. On one hand, entrenched protocols are impossible to replace. On the other, it seems unlikely that people in 100 years will still be living in the same email hell we do now. And if email is going to get replaced eventually, why not now?If you do it right, you may be able to avoid the usual chicken and egg problem new protocols face, because some of the most powerful people in the world will be among the first to switch to it. They’re all at the mercy of email too.Whatever you build, make it fast. GMail has become painfully slow.[2] If you made something no better than GMail, but fast, that alone would let you start to pull users away from GMail.GMail is slow because Google can’t afford to spend a lot on it. But people will pay for this. I’d have no problem paying $50 a month. Considering how much time I spend in email, it’s kind of scary to think how much I’d be justified in paying. At least $1000 a month. If I spend several hours a day reading and writing email, that would be a cheap way to make my life better.

    1. LE

      Paul Graham: GMail is slow because Google can’t afford to spend a lot on it. But people will pay for this. I’d have no problem paying $50 a month. Considering how much time I spend in email, it’s kind of scary to think how much I’d be justified in paying. At least $1000 a month. If I spend several hours a day reading and writing email, that would be a cheap way to make my life better.To which I say “so how much have you spent yourself to write a custom solution to whatever problem that you have with gmail?” $1000 per month would justify spending $50k at least for a custom solution. And the custom solution doesn’t have to be written by the type of person that ends up applying to YC either.Separately google can obviously afford to spend money on gmail they just don’t choose to do so or they don’t give a shit. They certainly waste all sorts of money on other things.On the other, it seems unlikely that people in 100 years will still be living in the same email hell we do now. And if email is going to get replaced eventually, why not now?It’s not really fair to look at a long horizon and say “people won’t be doing that in 100 years”. Because on that long horizon many things will change that will make some new way of doing things possible or an old way obsolete. It’s like saying 100 years ago “surely in 100 years people won’t need boats to get across the ocean” when technology and other factors don’t exist to make airplanes possible so “why not now”. Why? Because, among other things, you can’t do it now, that’s why.

  2. JimHirshfield

    What kind of email multi-tasking are you referring to?

    1. fredwilson

      Let’s say you got an email that requires you to do three separate things with it. This happens to me a lot. I want the ability to do all three without having to open a new tab

      1. Mohan R

        its almostl like instead of adding extra tabs, you want to split your main browser tab into 2 kind of like frames on a website back in the late 1990s.Also I suggest bommerang, great gmail plugin so you can track if an e-mail is responded to or, was really helpful when networking thru grad school

      2. LE

        I want the ability to do all three without having to open a new tabI’m sure that when you redid your kitchen you probably spent money and brought in a designer or architect to create the perfect experience without regard to cost. I think you need to do the same here to solve this problem. (to repeat myself and further brainwash you).Don’t be fooled into believing that because there is no social proof that people do this type of thing that it’s not a potential way to solve the problem.Of course (like the wordpress change) it’s going to take some effort upfront. But the benefits could be huge in terms of your efficiency. Right now you are operating in “death by a thousand needles” mode.

  3. awaldstein

    Email string of 5+ people, 3 continents, 4 timezones=migraine!I have at least one of these weekly.NOTE–>AVCer Andrew Kennedy has built a solution to address this on mobile with a really interesting take on cross network, private and public groups.It’s here–

    1. JimHirshfield

      fix your link plz by removing —

      1. awaldstein

        fixed.Check this out Jim–I can see this working for you within your team.

        1. JimHirshfield

          Looks cool. Reminiscent of Circles, yes?

          1. awaldstein

            More contextual. Built from the ground up for mobile. And more a series of potentially interconnecting groups than a horizontal platform.Gonna wake Andrew up and let him speak for himself.

          2. Andrew Kennedy

            Hey Jim — It’s a multi-threaded group messenger (multiple convos can occur without notification spam as you can follow / mute a thread) that has a professional feel (Profile pic required, Posts not bubbles, you can’t post photos) and allows (with the permission of the person that posts) for information to be reposted from group to group (like a sticky note) and responses to be swiped back to the original post. It has search, and all posts can be edited and deleted. Focus is on delivering a far more valuable product than email groups with an eye on affinity group connectivity.

          3. JimHirshfield

            So, is it intended to be in place of email? Or is this more of a collab tool, like a better basecamp for mobile?

          4. Andrew Kennedy

            It’s for sure an email group killer. Intended to be more of a networking tool (I think LinkedIn Groups are just the pits) and email is just a real pain to deal with. Have been using it for collab, but not for task management.

    2. William Mougayar

      thanks Arnold. I’m going to give it a spin.

  4. JimHirshfield

    BTW, email notifications for gCal to gMail can be turned off. Cakendar settings–> Calenders tab –> New events (uncheck the box under email column)

  5. jason wright

    i like the way my yahoo email has been slowly improving over the last year or so after a decade of neglect. Marissa Mayer has had an impact.

    1. JimHirshfield

      Details please

      1. jason wright

        it’s been a drip feed of little enhancements into the system over the last year or so. no single one has been transformative, but collectively they make for a superior experience. managing the inbox and archiving et.c. has become more convenient. you’d have to be a user before and after to appreciate it.

        1. JimHirshfield

          I’ll check it out if they haven’t given away my old email address.

    2. Matt A. Myers

      Probably just took the simple step of someone giving the green light or finding people within company that had ideas to improve the service, get them together, and then execute on that maybe with some oversight. Big companies can get stale.

      1. jason wright

        i’m sure you are right.

        1. Matt A. Myers

          The “it’s good enough” mentality isn’t helpful for anyone.

    3. William Mougayar

      Are you being sarcastic? Yahoo Mail is a joke.

  6. William Mougayar

    I think you could have replaced the title by: “Dear Google…”. Most of these are product related asks.I recently started using Acompli to check it out. It does have some improvements over Gmail, like a tighter Calendar integration (it’s a tab), and better search. (Android is coming)

    1. JamesHRH


  7. John Revay

    Agree w/ post – however I think email is still a killer app.Just shut it off for a few days.Some of my email traffic needs have shifted to txt.

    1. Donna Brewington White

      Yeah, I don’t want to replace it , but rather improve it.Although that is from the vantage point of not knowing anything better. 20 years from now I may look back and be shocked that I settled for so little.

    2. JimHirshfield

      I sent you a telegram 2 weeks ago. Did you get it yet?

      1. John Revay

        No Telegram received

    3. fredwilson

      the things you hate the most are the things you can’t live without

  8. Ruth BT

    I hate sorting emails into folders – I always feel like a rebel when the inbox gets too big and I just make a new one and rename/archive the old one. I agree with Fred, the only time I’m going to retrieve them is if I search and then it doesn’t matter where it lives.Having said all this I am rather envious of those who delete the bulk of all emails and keep their inboxes pristine. How many people actually do that?

    1. bsoist

      I clean out my email inbox almost every day, but I rarely get over 100 emails in one day.

    2. JimHirshfield

      I no longer strive for inbox zero. That’s some contrived state that I feel no pressure to conform with. My life is no different when I have 0 unread messages versus 230 unread messages. Just doesn’t matter.

    3. Jeremy Toeman

      i do this. one folder called “keep”, everything else to trash…

  9. JLM

    .Rich folks problems?It isn’t Kiev, I guess. How must it feel to be conducting business in a city under the threat of invasion? Wonder if they will be able to keep the Internet functioning?JLM.

    1. fredwilson


      1. JLM

        .I’m really starting to like you, Fred Wilson.And I’m starting to think you may be getting good at the venture capital stuff.Have you ever stopped to think the voice of the next great thing in the world will be heard first on Twitter and you helped them get born.Thanks for being a mensch from a mensch.JLM.

        1. fredwilson

          it’s nice to have a friendship that is distant in terms of geography but daily or near daily in terms of talkingand i doubt we would have ever known each other before this thing they call the internetit has made my life richer in material terms but also richer in other ways

          1. JLM

            .[Fred, this is a private conversation not to be shared with anyone else.Have you noticed how nice all the people on this blog are?It is truly the most civilized group of people with whom I interact.Smart, polite and refined. Very nice folks.A huge credit to whomever has brought them together.As Charlie, the Sage of Lancaster is wont to say: “This InterWeb stuff might really become something, no?”Shhh.]JLM.

          2. LE

            I think when I started commenting here Charlie had a dog licking his face. Or was that Swan?

          3. LE

            and i doubt we would have ever known each other before this thing they call the internetI know you love JLM very much but as someone who met their current wife using online dating (she was younger and lived in another nearby state) you can’t imagine what the net has done for love and happiness.

          4. fredwilson

            My brother met his wife that way too. It’s awesomeAnd I love you too Larry

          5. JLM

            .Haha, it’s respect. Respect is a funny thing. It builds over time. I respect everyone on this site. Everyone.JLM.

          6. Donna Brewington White

            This little exchange between you and @JLM:disqus has made my day! Okay, group hug! Must find a way to do this via internet.

    2. LE

      I tried posting this two times already but for some reason disqus won’t accept it.I will try again w/o the link and see what happens (then add the link by editing).”Rich folks problems?”This PBS show, which I started to watch, about poverty and people ending up in prison really touched me.…Imagine, if when growing up, your dad and your family and those who surrounded you were not the way it was for you. Or me. This has nothing to do with skin color either.You know I’m no bleeding liberal by any means or stretch at all. But it’s amazing how sucky the situation is in some of those communities.Oh my point. We spend so much time on what is happening in other countries when there are problems here that are ongoing and because they are not emergent (like an airplane crash or boat accident) aren’t given any thought or equivalent effort. Or we spend time on social issues in this country that quite frankly are really no where near as important in the triage.

  10. William Mougayar

    I’d like a better Search. Gmail mobile search just sucks.

    1. Donna Brewington White

      Search with multiple filters! That’s what I want.

      1. cmackge

        Agreed — sort by date and name, with & without attachments.

    2. Andrew Kennedy

      Gmail mobile search is terrible. It’s nice that email lasts forever (I guess), but I have a hard time getting access to it via search.

      1. JimHirshfield

        That hasn’t been my experience on Android cc @William Mougayar:disqus @donnawhite:disqus

        1. Donna Brewington White

          I’m on Android and after reading your comment just did a two word search in gmail that seemed to work. But not so much for my other email accounts. And not at all in Outlook on my laptop. But that’s for a different hater post.

          1. JimHirshfield

            Outlook? What’s that? πŸ˜‰

          2. bsoist

            I had an old friend complain about Outlook on Facebook and I left the comment “people still use Outlook?” I’m not sure I should have said anything because I ended up spending quite a bit of time helping her sort out her email issues.and I’m pretty sure I’ve seen you leave this same comment before πŸ™‚

          3. JimHirshfield

            I tend to repeat myself…I tend to repeat myself…

        2. William Mougayar

          Can you search by fields: To, From, Subject, etc… I can’t see that on my Android. The iPhone version used to have that, but they took it out, to my bewilderment.

          1. JimHirshfield

            Yes, just like on desktop:From:william…works.But usually, all I have to do is search without the to:/from: parameter and it works.

          2. William Mougayar

            Looks like an IPhone thing or older Androids which I’m on.

      2. pointsnfigures

        There was a company in Chicago TechStars that made an app called FindIt. It helped with searching Google Gmail. But, when I searched for it on the internet of course I couldn’t find it. Maybe they are OOB.

    3. fredwilson

      really? i find it to be as good as web email search.

      1. William Mougayar

        Maybe it’s an iPhone thing. Gmail search took a step back recently with iOS 7.

  11. Donna Brewington White

    I guess I’m old enough to remember what life was like before email and for that reason I love it.What I hate about it is that it doesn’t provide enough opportunity for instant signals and ways to communicate beyond what sometimes feels like the laborious act of composing and sending.I want to be able to press a button to acknowledge receipt, or to nod agreement or send a reminder to read the email. I have to sometimes send a text as well as an email to make sure I get the desired attention or response. Maybe what I want is a hybrid version of email/sms/IM, etc.

    1. Andrew Kennedy

      totally agree. a hybrid version would be great. it seems the world is shifting that way. email is void on any social gestures and text messaging although efficient is totally inappropriate in many situations. Texting to me requires a very strong relationship that is current and even then it still lacks a sense of professionalism in my book.

      1. Donna Brewington White

        Yes! Everything you said! These were all the thoughts in my mind as I was typing that comment. We need something along the lines of Disqus for communicating beyond blog comments — something conversational, flexible, that allows for the various social and business relationships.

        1. Andrew Kennedy

          I am not a shill, but that is exactly what I am working on. Arnold has been a great advisor and outed me today; would love for you to take the early product for a spin if you are interested as it would be great to get your thoughts on the app. Anyone else that reads this is welcome to participate as well.Link to AVC Test Group is here:…If you have ios app, saying yes to push notifications is quite important and we need to highlight that better.@wmoug:disqus @awaldstein:disqus @donnawhite:disqus @JimHirshfield:disqus

          1. awaldstein

            You’ve worked hard and smart, built something that is part of all of our futures so hell yes, let people know about it.

          2. Donna Brewington White

            Works with Android?

          3. Andrew Kennedy

            yup, I like the android app better than the ios app.

          4. Donna Brewington White

            I am soooo going to check this out. And then getting @awaldstein:disqus ‘s endorsement. Doesn’t get much better.

    2. William Mougayar

      Good ones. Have you tried the Signal plugin for Chrome/Gmail by HubSpot? It tells you when the recipient opens your email, and you can tell if they forward it if you get multiple notifications. Kind of creepy sometimes.

      1. Donna Brewington White

        Will check it out!

        1. Abdallah Al-Hakim

          There is also Yesware which does similar things to Signal plugin and is free for limited use

          1. Informerly

            Yesware / Signals / ToutApp are one of the best kept secrets in email. It’s kind of scary to watch someone open an email you’ve sent 3-4 times as you can almost watch them “thinking” about how to respond. Especially for anyone in BD, they’ve completely changed the efficacy of email.

          2. JLM

            .Well, you can take some comfort the NSA is reading it, no?When I recently lost a hard drive, the NSA was so kind to give me a backup they had.JLM.

          3. Donna Brewington White

            I am actually responding to your other comment that I don’t want to scroll down on my phone to find. Where you said “rich man problems” or something like that. Almost every day I think of how you often say “Isn’t this a wonderful time to be alive” Yesss.One of the reasons I enjoy discussing this problem is that I know with certainty that someone will fix it. And perhaps someone we brush shoulders with here at AVC. Knowing this excites me. Not so much about fixing email but just all the possibilities in general. We ARE rich!

          4. JLM

            .Also the world has gotten so small we are everywhere in our pajamas.I cannot believe how small the world has gotten.JLM.

          5. Peter Beddows

            Totally agree.

          6. Peter Beddows

            @JLM:disqus Are you serious? You got a backup by asking the NSA to provide it for you? If that does not sound like Big Brother is in fact even more pervasive than any of us previously believed, this surely proves that it is. Whoa nelly – to use an old British ‘polite’ expression of concern!

          7. ShanaC

            i’m now seeing crms with this capability too

          8. Donna Brewington White

            And you are experiencing exactly what I mean… saw your email. .. thought “yay!” but was in the middle of a long string of calls and tasks. And then 50+ others came through and yours is buried in my Outlook that I can’t access from my phone when I might actually be able to respond. So now I’m using Disqus to tell you this! Some of it is a need for better organization on my part and reconfiguring my email accounts. But this won’t fully fix the problem.

          9. Abdallah Al-Hakim

            This wasn’t the intention of my comment! But it is a great example :). I will wait for your response and will bug you again if I don’t hear anything.

          10. Peter Beddows

            BTW: Dare I mention that “is buried in my Outlook” is exactly why we love and use BlackBerry – It integrates perfectly with our Outlook so we can respond from desktop or BlackBerry with equal ease and functionality.And, btw, since we are ‘hating on email’, may I also add that I do not like iPhone or anything much about Apple products including not liking iPad. We can do more, and do it more easily, with our BlackBerry Playbook. OK: So I guess we are out of the closet and admitted freaks with this admission but whatever floats your boat; these tools work great for us!!! πŸ™‚

      2. PhilipSugar

        Is there a way as you the recipient can see if somebody is using (Signal says no). That actually is really creepy.

        1. LE

          Only way for that to work is by embedded images unless it’s something that is tied into some specific system that has that featured programmed in.In other words if you are running your own email system (which I do) and I read your email using imap unless there is some image in the file which I loads (small 1×1 pixel etc.) no way you will know if I read your email. And if I don’t load images you won’t know I opened your email.There is a way to see if an email was delivered to the inbound SMTP of the recipient by monitoring your outbound logs if you run your own mail servers. I do this sometimes for troubleshooting. But getting accepted and put in someone’s email box is not the same as them opening the email which of course is separate from them reading it.Separately nothing on the signal plugin website indicates how this works other than making a broad statement that is works.Oh, ok I was right, here it is, found it:Signals uses the same pixel-based tracking technology that marketers have been using for years, and makes it available to sales and services teams for smaller scale, one-to-one and one-to-few conversations.So they imbed an image and then track that image. I did this as far back in the 90’s with my own email when I wanted to know the ip address of the person who I was communicating with so I could figure out who they really were.

          1. PhilipSugar

            Yes, I know the 1×1 pixel. Not reliable as in preview mode, but I would think there is a good opportunity to test for it.

          2. Vasudev Ram

            They are called web beacons or web bugs.Googling for the term shows many results explaining what they are.

          3. ShanaC

            the problem is the beacon makes it less likely to go directly into inboxes, at least with google.

        2. William Mougayar

          I don’t think you can tell.

      3. jason wright

        like readnotify?

        1. William Mougayar

          perhaps. i’m not familiar with readnotify. it’s a bit like yesware, but more lightweight

      4. Donna Brewington White

        Ha! Edited my previous response when I asked if this was for Android. Blame it on jet lag.

    3. Troy Jenkins

      The thing I dislike about email is the yahoo email system. Unfortunately I am locked to it so hating the way the emails are organized has become a daily ritual. And now this post makes me believe I am not the only hater out there πŸ™‚

      1. Donna Brewington White

        I am such a sickeningly positive person that getting to be a hater even for a moment is truly a Fun Friday. And Fred picked a good one to draw out the hater in most of us.I have a yahoo account that I never use…came with my internet. Oh I hate it. But maybe it’s improved since MM took the helm.

        1. Troy Jenkins

          Oh I thought it got messed up post-MM. MM made it hard for me to even log out of yahoo πŸ™‚

        2. Peter Beddows

          We also have a Yahoo account that came automatically with using AT&T to provide web access services but NEVER use Yahoo or its email ‘cos do not like either.

      2. Marissa_NYx

        Hey Troy, I had an old yahoo account which was hardly used but I went to the trouble of cancelling it about a year ago (finding the instructions as to how to do this was a challenge) when yahoo had a massive spam & hacking problem. Someone was hacking my account and sending badly worded fake emails under my name to people in my contact list, it was very embarrassing and a huge violation of trust. It took Yahoo what seems to be a very long time to get it under control. Shows how vulnerable we all are!

    4. fredwilson

      ooh. i like that idea donna. i use the favorite button on twitter to let people know i saw and liked their tweet. i would love to do that with emails as well. replying to email means i might get another reply back. which is the last thing i want.

      1. Donna Brewington White


        1. Aviah Laor

          just reply with πŸ™‚

        2. Robert Holtz

          Neat idea.

      2. Joshua Baer has a “Like” button for email that serves exactly that purpose. It’s pretty great!

    5. Sriram Yadavalli

      Associating actions with emails is something that is being built as a part of standard. Some sites have already implemented the needed JS snippet for this functionality.

      1. Joshua Baer

        I love the stuff Gmail is doing with!

    6. Ryan

      Thats a great idea Donna.Is there any work being done on email as a protocol? It seems like it hasn’t changed since the early days of the internet. My startup RadiumCRM built heavily on the Gmail API and even that was lacking compared to Google’s other APIs. It just seems like one of those things that people are always complaining about but little is being done to fix it.

      1. Donna Brewington White

        I’m not the best person to ask — but some people in this thread have mentioned things they have built/are building. I’m wanting something that is not gmail or iOS dependent.

      2. kidmercury

        the great innovations that customers actually want are difficult at the protocol level. that is why all the messaging innovations are occurring at the platform level where all message participants are on the same network using the same app.

        1. Ryan

          I agree, the innovation is going to come at the platform level. It’s just sad that there doesn’t seem to have ever been any work done at the protocol level, at least anything notable.Here’s a great snippet from a Paul Graham talk that’s very relevant. Great speech in general btw …

          1. sigmaalgebra

            Nice talk.Moore’s law themeThree approaches:(1) There long has been ‘very long instruction word’ (VLIW) architectures where basically one instruction could be, say, 320 bits long, that is, 10 instructions each 32 bits long with corresponding 10-way hardware, i.e., 10 register sets. This is supposed to be ‘finely grained parallelism’.Last I heard, could take traditional ‘serial’, single-threaded code, wash it through a special VLIW compiler, run the result on a 24-way VLIW computer, and get about 9:1 speedup.There has been at least some DARPA funding.From time to time there have been commercial versions. Now that clock speeds are not increasing very rapidly, maybe interest in VLIW will return.(2) Graham did mention ‘lego block parallelism. Good: Maybe there should be more attention there.E.g., so, maybe have some semi-specialized parallel hardware for some parts of database. There have been some efforts with, say, a central clock (often important for database) and broadcast of cache invalidates.Of course, for a database that needs high performance, there are some approaches available now. In part can have a ‘front-end’ that is read-only and a back end that accepts writes. Last time I looked at this was a while back, but just with SQL Server can do a lot there.(3) One of the problems with parallelizing current software is the ‘paradigm’ of nearly all commercially important programming languages designed without parallelism in mind. So, design a new language that is not much more difficult for a programmer but much easier for a paralyzing compiler, i.e., the ‘grand’ compiler Graham mentioned.CollegesPerhaps the college accreditation groups would permit a college to modify their requirements for a Bachelor’s away from the traditional in classroom courses, credits, and grades to just testing for a grade in the course. Or an independent organization could do much the same, e.g., as for the subject matter tests of the CEEB and GRE. This approach has been available for decades but has not caught on as a replacement for attending class in a university. Yes maybe the AP courses and corresponding CEEB tests are catching on and, thus, letting students start college at least with ‘advanced placement’ if not college credit for the AP work in high school.’Advanced placement’ has been easy for a long time. E.g., as it turned out, I taught myself freshman calculus, never took it, never got credit for it, and started with sophomore calculus. Worked fine. All I needed was just permission to enroll in the sophomore calculus class — no biggie.Of course, getting college credit for a course would be more difficult but, also, more progress.Then, how many students would really just teach themselves, say, at home, save the costs of attending college, and then just take tests for, say, their credits for their first three years and maybe attend for just their last year? My guess, few.Really, as far as I can tell, what Graham and others would like to see is colleges doing more in, say, vocational training. Colleges will resist that and say that we have community colleges for such material.UniversitiesIt’s not commonly made clear, but in a major sense the real challenge, ‘bottleneck’, in running a famous university is the research record of the graduate school faculty. Getting ‘world beating’ research done is not so easy; there are many thousands of researchers eager to make a big splash, and competition for big results and grants is high. Each instance of research is mostly done by one person sitting alone in a quiet room, and revolutionizing this process needs more than the Internet.For what Graham said about e-mail, I still mostly don’t ‘get it’: As I posted in…in this thread, a lot could be done on most of the issues mentioned just by sending/receiving e-mail via POP3 as now but writing some software to handle the results as stored on the user’s computer (server, whatever).E.g., Graham regards a current e-mail in-box as a ‘to do’ list and wants to block just anyone from putting an item on his ‘to do’ list. But as far as I can see, for this he doesn’t need to change the e-mail ‘protocol’. Instead, just go ahead and receive the e-mail, spam, etc. and have software in effect ‘block’ that stuff after it has been received. Some progress on that is old and is in the old 2003 copy of Microsoft’s Outlook I am still running.If I were to do build a better e-mail system, with most of the features mentioned in this thread and by Graham, for myself, then I’d keep each e-mail sent/received in its own directory, index the contents with, say, several B-trees using, likely some old B-tree software, have some relatively simple, individual programs for the operations, and for the user interface use just a good text editor with some macros. Not a biggie.But likely Google+ or whatever Google called their e-mail efforts worked hard, and it appears that still people are not satisfied. I can’t guess why Google could have a big project just for e-mail and fail to meet common needs.It appears that somehow we are not being very clear, in this thread and/or in Graham’s talk, on just what we want that would be better; i.e., else Google would have done that, already, right?

      3. Joshua Baer

        If you’re passionate about email as a protocol, come to the next Inbox Love conference in October.

    7. Brandon G. Donnelly

      I use Mailbox simply for the ability to “snooze” emails. It’s a killer feature for me because I found I was checking emails after hours and then losing track of them if I didn’t respond immediately (which I don’t want to do after hours).

      1. Donna Brewington White

        I don’t read your blog as much as I’d like to or as much as it deserves. I am never disappointed when I do. However, I do remember the love email post and how much I resonated with it. And obviously with the second one as well.

        1. Peter Beddows

          Agree with both of you @donnawhite:disqus @aaronklein:disqus

      2. Joshua Baer has a Like button for email today πŸ™‚

      3. Jeff Steinke

        And I love the asynchronous nature of email – interruptions (e.g. Phone calls, stopping by my desk, IMs, etc) while I’m deep into a project kill my workflow.…Totally agree on an email Like/Favorite button.

    8. Peter Beddows

      Totally support this notion @donnawhite:disqus. Well expressed; reflects my view exactly – and I’m obviously much older than you; I even still remember tube fired computers, telex and ammonia based copiers!!!.

  12. pointsnfigures

    Yes to all you mention. I also have to bear in mind that no one can mind read or see emotion in anything that I write-nor do I see emotion in what they write (unless I know them extremely well). My biggest beef is spam email and lists I didn’t sign up for or “I am a marketing agent, will you post this on your blog”

    1. Andrew Kennedy

      oh yeah. all painful.

    2. LE

      Disagree that you can’t see emotion in what someone writes. I interpret emotion frequently in email. I can tell by the words that someone writes many time where their head is at with a deal or a price.Here is one that came yesterday it’s pretty obviously there is money on the table here, right?:I appreciate the reply. Is it simply just not for sale at this time? Our buyer may be able to come up on the offer. Let me know if you have an asking price or perhaps a range we would need to get to in order for you to be interested. Feel free to call me if you’d like to touch base. [1]Likewise, I communicate emotion in emails all the time. If I know that someone is offering a number that I will accept (and I don’t want to go bust and lose the deal) I will say something that indicates I want something more, but in a way that doesn’t scare off the person so they go elsewhere or get to frustrated.What I like about email for this is that I can exactly precisely convey what I want which is really hard to do verbally.As far as verbally I have many cases where I won’t pick up the phone and will allow someone to leave a voicemail so I can hear the tone in their voice to see where their head is at. (And I have been known to tape record conversations in order to play them back and analyze further).[1] They could have just as easily said “I don’t think my client will go higher” (or nothing) and then waited a week and got back in touch before saying “may be able to come up on the offer”

      1. pointsnfigures

        Prof Nick Epley of UChicago did a lot of research and I am sure would dispute your opinion. You need to know the person really well to “mindread” emotion.

        1. LE

          Telling me that an academic has done research which proves me wrong is like me telling you that some academic has said that people can’t sense the mood on the old trading floors by the noise level or verbal and non verbal cues. Not my venue but yours. I’ve heard that and perhaps you could confirm. [1]But with my point I’m not talking about something that I’ve read or I have been told.I’m telling you about something that I’ve actually done, multiple times, for many years, and (if I needed to) I could show you the exact play by play in emails that led to a particular outcome based on wording used and what I sense as a result of that wording and my decision process.I also (to go further into this) take into account other factors. Such as how quickly someone replies, when they reply (time of day/weekend), and to what extent the reply is out of character with previous replies (delta in reply time) when I make a decision.Are you talking about this book:…A quick read doesn’t show the tie in to the subject of email.[1] If I’m wrong about that of course that’s fine. I’ve never been on a trading floor but have heard that a few times (or perhaps read it) so I will use it as an example.

        2. ShanaC

          to some degree. You definitely can get the basic gist of emotional stuff from an email.

          1. pointsnfigures

            actually, it goes back to confirmation bias. a lot of times you read what you want to be there, not what the true intent is.

          2. Andrew Kennedy


  13. Cam MacRae

    I hate the way people use email. I want you to tell me who you are (if I don’t know) and what action you want me to take. That’s it.Instead we get bacn waffle. (Actually that does sound kinda good).I miss the days of plain text email.

    1. Donna Brewington White

      You had me until plain text.Although, what’s bacn waffle?

        1. Donna Brewington White

          You’re funny. You are also quite educational. Thanks to you I now realize that I have an inbox embarrassingly full of bacn. As my Gran would have said, my eyes are bigger than my stomach.

    2. fredwilson


  14. Andrew Kennedy

    Email groups really bug me. Trying to communicate with groups of people via email? It’s such a sterile experience yet it dominates still. What amazes me is how listserv is still the default for group communication. Would be nice to have a “mute” and “unmute” button (following posts not people) to avoid a string of responses to an email that I don’t want clogging up my inbox and to have them segmented in pre-sorted “folders” labeled by topic. Lists and folders are a pain to manage.

    1. pointsnfigures

      Yes, or if someone sends a group email and someone responds “Yes” with a Reply all. Then my email box fills up with scads of email, one word answers….

      1. bsoist


      2. JimHirshfield


  15. Jack Barcroft

    Two things 1) If you turn off conversation viewin Gmail & organize your inbound with rules, one can get really lost quickif 20 people respond to an e-mail chain: 2) Lost in translation – Writing aquip or sentiment into an e-mail doesn’t always work. Not everyone readsyour e-mail the way it sounded in your head when you wrote it.

  16. bsoist

    I hate the laziness of it all and the expectation of immediate response.I remember my dad teaching me a couple of things about the telephone. In the days before voicemail, he found it the epitome of arrogance to call someone, wait 18-20 seconds for them to answer and then HANG UP! ?He also taught me at an ealy age – if you ignore the ringing, it will stop. :)Email reminds me of that. On the one hand, I LOVE that it’s asynchronous. Theoretically, I can get to it when I get to it, but not everyone plays the same game. I get a lot of these – “Hey Bill, I know we’ve never met, and you probably have no idea who I am but I sent you an email yesterday. Did you get it?” Sometimes I actually reply to those with something like “yes, I distinctly remember deleting that email”And the recruiters looking for Java programmers or Windoze systems admins. The only way you could convince me to do either of those is to pay me enough to hire someone else to do it. :)I know we’ve talked about this before in the comments, but we sometimes make the situation worse with our own behavior. The first time I emailed Fred Wilson, he responded in a matter of hours. Now, I have to be careful not to expect that every time. πŸ™‚

    1. fredwilson

      replying to email is an invitation to get another email. which i really dislike. i want to be responsive but i often delete instead of replying because i just can’t take the idea of starting yet another conversation

      1. bsoist

        Well, I don’t want to make your email situation worse πŸ™‚ but you are more responsive than most, in my experience. and I just checked emails between you and I – avg # messages/thread = 4, you get the last word almost 50% of the time when you do reply. Works for me.

        1. fredwilson

          getting the last word works for me πŸ™‚

    2. kassner

      That’s exactly why I love the e-mail. Asynchronism. People want to reach you immediately, but they forget that you are doing something else, maybe focused at work, maybe playing football with you son, maybe just resting. And I’m supposed to not enjoy my life because someone couldn’t wait 5 minutes or 2 hours to receive a very superficial information.

    3. PhilipSugar

      Its also asymmetrical and this is a big problem. It means that there are some people that almost get none and others that are flooded. It means you can compose one email in 30 seconds and send it to 100 people, and if it takes each just 10 seconds to look your 30 second investment just burned 1,000 seconds of time.Like many I would sit there and listen to people complain about how many emails they received and think it was humblebragging.But I now understand it. I belong to a charity where the average age is much older than me and the average profession is blue collar (i.e. no email at work). I had to setup a separate box because as much as I love these guys when they all found email a meaningless reply all was greeted with more reply-alls because getting an email was fun.

      1. LE

        where the average age is much older than me and the average profession is blue collarOlder people are more likely to feel that if you write to someone you deserve a reply. Period. No such thing as ignoring contact. Doesn’t happen and really has little to do with a flood of email but with the way you were raised.I was raised in a way that said it was rude to not reply to someone. Was never told this it just was the way it was. You know “call your aunt and thank her for the birthday gift”. When birthday gifts were shirts that you didn’t even care about.I’ve noticed though that many others were not raised this way and don’t operate like that.Yesterday I came home and asked my 11 year old stepson a question while he was at the kitchen table on a computer doing school work. He totally ignored me. Doesn’t hardly ever happen but it did this time. I asked again and he ignored me again. So I shut the computer and said “when I talk to you, or any adult does, you need to reply. Quickly. It’s not optional. And your friends as well but particularly an adult. And if you don’t, forget watching the game on TV”. And the punishment does happen I won’t take any shit from him. (Lest the problem gets worse). Same with my step daughter. Same with my kids (who are older and in college.)

        1. PhilipSugar

          No they are cool. The only problem was this has led a bit of figuring out what I do. I am happy just being the guy that serves the food and washes the dishes.

        2. sigmaalgebra

          For couples, E. Fromm (‘The Art of Loving’) has four, knowledge, caring, respect, and responsiveness.By ‘knowledge’ he means “give knowledge of yourself” to the other, i.e., what you are thinking, feeling, wanting, hoping, fearing, worried about, afraid, frustrated about, etc. Call it ‘intimacy’ between the ears.For caring, care about the other person. This is intuitive, natural, and not nearly new: E.g., last night watched a DVD of the original ‘King Kong’ and noticed how right at the beginning of the love affair of the first mate and the girl, he cared about her, e.g., wanted her safe from the natives on the island.For respect, you gave several examples.For responsiveness, you were teaching that.These four are good ‘criteria’: If know a couple and get to observe them and watch for these four, then might learn something surprising and important.Maybe the woman has a motto, “Don’t tell them ANYTHING” where “they” includes much of the public, say, at her church, and also her husband. So, she is denying him important intimacy. Not good. Strike one.If she doesn’t care about him, e.g., doesn’t try to help him on his diet, another strike. Maybe he will die of a heart attack, but in the meanwhile she gets to appear in front of the neighborhood as a wife who feeds he husband plenty of food — cares more about that part of her image in front of the neighbors than her husband’s health. Strike two.In addition, if she doesn’t respect him, e.g., makes fun of him because, like 25% of men, he is partially red-green color blind, then strike three and likely out.And if he tries to talk to her and she just doesn’t respond in any meaningful way, then another strike.You observed that some of these four also apply to children within a family. Good. You were correct to insist on respect and responsiveness.Application: Consider a young man dating a girl. She looks terrific and invites him to her house for a few days. He goes and the family looks terrific. But looking a little more carefully, just watching, maybe not saying much, he notices that the girl’s father and mother are bad on this list of four items from Fromm. Not good. How can the family still look “terrific”? Because there can be a LOT of really good acting, maybe as in E. Goffman, ‘The Presentation of Self in Everyday Life’. So, with the acting, they are making their ‘presentation’. Do people commonly do such things? Hmm!The girl, likely she will do well on all Fromm’s four as long as she still ‘has stars in her eyes’. I.e., Fromm’s four are quite natural. But, after about three years, then what? I mean, if the boy marries the girl, then he signs up with a very serious “’till death do we part” legal and financial obligation, and maybe already after three years she starts following her mother’s example and doing poorly on Fromm’s four.Or, ‘talk is cheap’: Maybe she has big smiles when he does something nice for her on their wedding anniversary. Since that is easily just put on or a short term thing, he has a less intrusive means of evaluation — Fromm’s four.Fromm’s four are good criteria, within a family, especially for a couple, maybe sometimes elsewhere, and stand to be good to teach children.

      2. bsoist

        getting email was fun, like …an international network of hugsbut then …it became less like careful letters and became more like an avalanche falling on your head every morning(both quotes – Merlin Mann, Inbox Zero talk at Google )

      3. James Ferguson @kWIQly

        I may be weird, but I have never sent an email copy more than say 15 people.To do so is to broadcast. I accept that in the consumer world broadcast has a certain lowest common denominator effectiveness.In my world an email takes a while to craft, and is sent to those that need it (or may appreciate it).I do wish the rest of the world thought like me on this, meanwhile I don’t mind making my own futile gestures in clinging on to what I value – my word !

    4. LE

      “Hey Bill, I know we’ve never met, and you probably have no idea who I am but I sent you an email yesterday. Did you get it?”We have customers who send us an email and then 2 minutes later they call about the same issue. Or send a fax and say “did you get the fax”. Doesn’t relate to importance of the issue either many times.And the recruiters looking for Java programmers or Windoze systems admins. The only way you could convince me to do either of those is to pay me enough to hire someone else to do it. :)I look at anyone who is non spammy as opportunity. I’ve had people try to sell me something and then I sell them something. Actually, now that I’m thinking about it, one case was someone spamming me to buy some domains from them and I ended up selling domains to them. Was a lot of money. As the saying goes easiest person to sell is a salesman (and a dreamer).The first time I emailed Fred Wilson, he responded in a matter of hours. Now, I have to be careful not to expect that every time. :)I find that it’s important to manage expectations in the sense that if someone writes you have to be careful not to respond to quickly so that they think that is the norm. And in some cases if I do write back quickly, or there is a particularly long interchange, I will even say “I am leaving and won’t be able to reply back for some time” or something like that.

      1. bsoist

        Exactly. We set the wrong expectations sometimes.RE: opportunity Agreed. The reason the spammers bother me so much is because I DO take emails seriously ( until I’ve learned my lesson ). The same recruiter asking me about the same position over and over again gets old. πŸ™‚

    5. Donna Brewington White

      Laziness or restlessness? Or maybe both.

      1. bsoist

        restlessness may lead to the need for immediate replies, but I think laziness definitely drives a lot of first emails

        1. Donna Brewington White

          I was thinking restlessness as in knowing or having a hunch that there must be a better way.

    6. Donna Brewington White

      And about those Java programmers…

  17. bsoist

    I have to believe there is an Android equivalent ( hope so, planning to switch ), but I use iOS and I deal with my Cal invites in the calendar app. I have the emails filtered out of my way, but I get the appts in the calendar and I can accept or deny there.Maybe that’s worse for someone who gets many more than I?

  18. Martin tipplr

    I’m glad I’m not the only one who doesn’t like email as it is now. My particular frustration is sending and getting cold emails. I rarely get the answer. So I put together something that could help: It’s a Chrome add-on for Gmail. Let me know what you think.

  19. Rick_Robinson

    back in AOL land users could “unsend” mail as long as it was not yet read by the other AOL recipients. awesome.

  20. Pablo Cerrilla

    Couldn’t agree with you more, Fred. Email as the main form of communication altogether. Can’t wait for the day when A.I. can just manage these inefficiencies in communication for us, and just have us review and approve on order of importance.For me, in particular, is the lack of consistent email etiquette, makes it hard to understand tone and original intent in communication. I think, personal voice should be kept to in person interactions, email (written) communication is complicated enough already, as displayed by this post.

    1. bsoist

      I’ve found that I have to explain to people I’ve just started working with how I do email so there are no misunderstandings later.

  21. thebigmix

    I hate that email on my PC is not the same as it is on my phone….if someone could invent some sort of mechanism to make sure I see the same account, no matter which device I use, that would be awesome…..I’m thinking along the lines of “in sync” or “synching” the phone…..oh wait…..In all seriousness – I hate how email has become a proxy for work/creativity. You did not spend all day working, you spent it responding to emails. 2 very different things, ideally.

  22. Dave Pinsen

    Not an issue for me, but for someone like Fred, what about an email system where emails only appear in your primary inbox if the sender has reached a certain level of connection with you via other social media? E.g., say you get 1 point for a response from the person to one of your Disqus comments, 1 point if they favorite one of your tweets, etc., and when you have x points, your email appears in their primary inbox.

    1. fredwilson

      i want to be open to someone i have never met and who has no connections to me. that is a huge part of my inbox problem. i understand that. but that’s how i want to live my life

      1. LE

        You are actually quite the hustler and would have done very well if you had started a business yourself as you see everything as a potential opportunity and don’t just concentrate on the usual suspects.That said it’s tremendously difficult as you get older to be able to keep track of all the people that you meet and the connections and so on. And to be able to pull that info up when you need it to your advantage.I’m working on that issue right now trying to build a way to be able to keep all the contacts and/or people that I’ve met.When you are younger this is really easy it’s all in your head. When you are older it becomes quite a problem.

  23. Daniel E. Espinal

    Trying to figure out the chain of events on a chain of emails where I receive the most recent one last. It’s a pain.

    1. Andrew Kennedy

      Big pain point. Hey Dan.

      1. Daniel E. Espinal

        Andy! I wasn’t sure if this was you, nice to see you reading the finest quality literature! I recommend this blog to everyone who cares about startups, entrepreneurship and Venture Capital

        1. Andrew Kennedy

          Nice to see you in the comments!

        2. Donna Brewington White


    2. JimHirshfield

      Oh, yeah. Don’t you just love scrolling down forever until you’re into the abyss of email signature after email signature zone?

      1. Daniel E. Espinal

        It’s the worst..

      2. fredwilson

        yesss. adding this to my “things i hate” list

        1. Donna Brewington White

          That list seems to be growing during the course of this thread.

      3. Drew Meyers

        def a big annoyance to me. gmail seems to be particularly bad at this…

        1. JimHirshfield

          It’s universal. Every email app slaps the signature on the end of the thread. But gmail actually has a feature that inserts the signature after your individual email. So that solves the signature graveyard problem.

      4. LE

        Surely you remember those tag lines or quotes that everyone put after their sig in the 90’s. Then one day a memo was passed out and everyone stopped doing that.

        1. JimHirshfield

          Most have not gotten that memo.

  24. Pat Clark

    Hate how I can’t unilaterally select to opt out of a group email (and instead, you need to rely on a sender to un-loop you). Just because someone cc’d me on a thread doesn’t mean I should have to be in the next 42 replies. I have the same gripe with group text messages using native iMessage.

    1. Andrew Kennedy

      Pat, I feel your pain on this. I hate this also. I am building a product that solves this problem; a multi-threaded group messenger that allows for responses to be muted. Would love you to test it out if you are up for it.

  25. markslater

    i wake up to this every morning. I’ve lon ago given up on trying to put the order in to the chaos – now i simply get here earlier and wade through stuff from top to bottom….its hell

  26. Tom Labus

    If you’re not inundated, mail is great. Very pro

  27. markslater

    i just used – it was awesome. go give it a try – its free and takes 10 minutes.

    1. ShanaC

      i still get way too many emails

  28. Abdallah Al-Hakim

    Email is terrible for managing group projects. That’s one of the selling features that apps like Asana keep on emphasizing. Still, the problem remains in that different people use emails for different reasons and I find that I need to identify who responds better to email versus other outlets such as social media, sms, etc…

  29. Daniel E. Espinal

    I also hate, well that’s a strong word, I “dislike” being expected to respond to emails in real time (especially when I’m creating content or in deep on something else). Also dislike being on the “CC” chain.. particularly when someone wants to demonstrate all the fine work they’ve done.. In the army it’s called “a spotlight ranger”!

    1. Susan Rubinsky

      I use CC on large projects when an underling isn’t responding/following through. I’ll CC that person’s boss. It’s sort of a little fire under the ass. I had one case where a guy’s boss asked me to do it every day because the guy was not following through and they needed a record for HR to prove the guy wasn’t following through.

      1. PhilipSugar

        That is the exact behavior I don’t allow. We setup a plan and commitments, This is not done in email. Trying to manage through email is wrong. You say this is what we commit to get done and get it done. No congrats, no trying to light a fire under somebody. Get your work done. If you don’t email for hours at a time I understand you are working.

        1. Donna Brewington White

          I love your no BS, grownup approach Phil.”Trying to manage through email is wrong.”Word.

          1. PhilipSugar

            I’m telling you I watch this all of the time. I stomp it out. No different than talking bad behind somebody’s back, using leading questions (don’t you think Phil is ……)If you need a record for HR, then you are letting HR manage your business not the other way around.My five rules never change.1. Hire and retain the best people (you need to do that yourself)2. Don’t let one department drown out others (you need to orchestrate, I always say you can never write a check you can’t cash)3. Have a commitment system and have people do the tough stuff (using email???? Wow that is bush league)4. Serve the customer (that means you go visit the customer, pre-sales, implementation, post sales)5. Set the strategy. What you do and don’t do.Not tough. not hard. just do it.Gossip, Politic you are fired.Meetings?? The only meetings we have that are not with a customer are to set commitments. Should be once a month to once a quarter, no more, no Monday morning 6ams, no “scrums. Just get your work done. Friday at 3:30, we blow off steam. You saw my biggest disagreement with Mark Suster was when he would say you come to a decision before the meeting…..bullshit, then don’t have the meeting. Also when you say people have said Phil is……whatever, no bullshit.

  30. CJ

    Email should be smarter. When someone sends me an email with a phone number and I actually use that phone link to call them my email client (gmail) should automatically create a contact for that person with an email address and phone number linked. I waste so much time searching gmail for phone numbers that are embedded in the body of an email over a huge amount of correspondence.It should be simple, I click the number, make the call, when it hangs up I get a prompt, would you like to create a contact for this person: email address and phone number already populated, name too if it comes along with the email address.

  31. leigh

    i’ve gone to zero with mailbox, i use sanebox — it helps a bit — but it always ends up with my gmail being 80% filled and a 1000 emails in my inbox. I like the thought about calendar invites staying in my calendar vs. coming in as notifications in my inbox. that might save 30% of all of my email traffic.

  32. Henry Glover

    How many emails do you get per day?

    1. fredwilson

      well i filter out most of them via google’s “important and unread” feature. anything that doesn’t get into the “important” section of my inbox goes unread. the only way i’d ever see it is via searching for if i only count what gets into “important” that is about one a minute during prime work hours. i probably get around 500 emails during prime work hours. but since i do a lot of work in europe and the west coast, i get a fair bit of email from 3am to 9am from europe and a fair bit of email from the west coast from 6pm to midnight.all in all, i figure its about 700 to 900 emails into the “important” section every day

      1. Andrew Kennedy

        800 a day by 365 = 292k. a lot of email.

        1. fredwilson

          Less on the weekends

          1. Andrew Kennedy

            Disqus notifications count as part of email or separate? You must get +/- 100 a day via avc/Disqus.

      2. Henry Glover

        wow that is a lot of email – I would hate it too. I am not dealing with as much volume as you. I do have two rules for email.1) Limit Notifications: filter all emails addressed to me into one label marked “To Me” – that way it bypasses my inbox and notification and I control when I can check email (3 or 4 times a day or when I have some downtime – standing in line etc). Any sender I want to make it to my real inbox (with notifications), I can set a rule for that.2) Take Action: When I do check my inbox… archive things I might like to keep, delete things I don’t care about, mark spam or unsubscribe. Anything that has a 3 min or less response I handle right then. Everything else I send to Asana with a due date and if applicable let the sender know.This way I am not a slave to my inbox but instead work off my Asana task list based on due dates and importance. It also allows me to set follow up dates for things that need a response.

      3. sigmaalgebra

        Good grief! I don’t yet have an e-mail problem, have some ideas, outlined elsewhere on this thread, for some of what to do If I get an e-mail problem, have some ideas for still more, but for 700 to 900 messages a day, I wouldn’t know what the heck to do. Maybe some simple ideas could get the list down to 200 – 300 but at some real risk of your missing something you would have liked to have seen.Since I have a project, I’m not interested in another one, certainly not e-mail, e.g., in competition with GMAIL, but there are, what,100 or so major VCs who may have about the same e-mail problem you do? Hmm — charge what P. Graham mentioned in his video in this thread, $1000 a month per person. So, say, five persons at each of 100 VC firms, get half the market, and get revenue of5 * 100 * 1000 * 12 / 2 = 3,000,000dollars a year. Hmm …. Not too exciting. Maybe add on an average of five persons at each of the Fortune 1000 and get half of that and add on another factor of 10, that is,$30 million a year. Still not too exciting. And, without some more thought, there’d be no barrier to entry and Microsoft, Apple, Google, Facebook, etc. could look at the resulting product and clone it in a hurry.Hmm …. Instead, maybe sell some software components and APIs so that, say, you could hire someone for a month to apply these components to your e-mail. Then if you need a new feature, call the person back and give them a week. Not a lot of revenue, but selling just tools, and the end user gets terrific customization.Maybe someone will pick up this ball and run with it, but not me. But for 700 – 900 for all the best known VCs along with others in with a similar problem, something should be doable and done.

  33. Dale Allyn

    Like @donnawhite:disqus , I like email and rely on it heavily. I’m not a target like you are, Fred, so the experience is different. I don’t use calendar invites though (hate ’em too).One of the biggest problems with email is finding a good email client to address some of the points you raise. I’m an Mac OS guy, so use Apple Mail as my primary client, but I will tell you that recent iterations of the app suck in comparison to older versions. Still, smart folders and search are very effective for me. Having OS level search and application level search is incredibly important to me. These provide very important and accessible archiving for my needs.I maintain several email accounts (15 at current count, although 5 which are important daily) and find the process very effective… well except for Apples total f*^k up of the app recently.

  34. Susan Rubinsky

    I love email. But, hell yeah, would love to see some improvements. I use Google Apps and it syncs nicely across all devices. Google needs some richer feature sets: better search/sort; auto-add contact that intuitively knows that a contact already exists but append new info to it. I could go on…I wish I could create my own filters in Google. I subscribe to a lot of email lists but I don’t want to look at those emails until I have time, or when I’m sitting on a train or I have a client that needs something.But on top of all this I still want my Scopeware (old software startup that died in web 1.0) which gave me the full stream off all disparate things related to me in a timeline with little clickable icons and boolean search to change what was in the stream. You also could set up your own custom streams and save them.

  35. cmackge

    Mail on multiple devices — which is a requirement in modern times, is a path to chaos and lunacy. Lost emails in inboxes, lost sent mails, etc., etc. Calendar invites across platforms (and acreoss calendar servers – iCloud, Google, Outlook, I call you out). It is a cascade of chaos. Life was better when I was in an Outlook only corporate job, but as a freelancer, things come in from all sorts of paths, and there’s no way to organize it anymore. I went to the effort and expense years ago to set my email up on iMAP, but different mail clients interract with IMAP in “Unique” ways. Its a PITA>

  36. Adam Steiner

    Fred — The closest thing I’ve found for the lost reply problem is Boomerang (http://www.boomeranggmail.c…. When I send an email I just tag it to come back to my inbox in a day or two with a filter to highlight/label it (I use a @Boomerang label so its near the label list) as an extra reminder. Downside? You’re not tracking the email per se…so you can’t get a list of all emails you’re waiting on, you just know that it’ll pop up again at a set time.Other things I hate — a good and quick way to unsubscribe from mailing lists or services I signed up for. Every now and then I spend a half hour unsubscribing but usually just delete messages. Would be nice to start with a clean slate…

  37. Jon Michael Miles

    If I were to say one thing about email, it would be that it’s like search results for me. If it’s not ‘above the fold” on or the first page, it’s gone forever. A tabbed solution has always worked best for me, but this goes out the door on mobile.

    1. Andrew Kennedy


  38. msuster

    RelateIQ solves point 1 beautifully. What It also helps me with reminders of important emails I received but never responded to – which sadly is higher than it should be.And … Sadly I’m not an investor in RelateIQ.

    1. fredwilson

      but that means i need to use a separate app to manage my work. i would prefer not to do that.

      1. LE

        I know you would never do this but I will throw out the old school approach to solve some of your problems.Back in the day when a company needed software for a specific purpose and the purpose was important they wrote their own software to handle the problem.My guess is that today people are so wrapped up in the fact that things have to be free they don’t always even consider that possibility..For the amount of email that you have, and the importance, it wouldn’t be off the table for you to spend some money to write exactly a piece of software that solved your problems and provided you a benefit. [1] And if that software was good for others then you could get someone else to commercialize it. If you wanted but that isn’t the goal here. The goal is to solve a problem that you have. Re-read that.I had a need to be able to send emails from the command line (from both Linux, Solaris and Mac OSX) for a particular purpose.So I wrote something to do that. And I’ve been using it for a long long time and it solves a particular problem that I have. And it works really well for me and saves me time.While I did write it myself, I would definitely have paid someone else to do it for me if I had to. The benefit of writing it myself is that I can tweak and modify it without having to explain what I want to a third party. And it’s fun to do.In the 80’s I did the same thing by writing a quick and dirty estimating and job management system. It wasn’t something I would ever commercialize but it solved a problem that we had at the time and was “good enough” for us to use internally. And the people who bought the business laughed at it but continued to use it for 5 or 6 years past purchase after they realized the benefits and the cost to replace it with commercial software. It solved a problem and worked. Which is different from having a fancy interface.[1] The current thing I am doing is writing my own dropbox so I can access certain files that I need without having to rely on dropbox, google or anyone else. So I control everything and tweak it so it’s exactly what I need. Lots of fun to do this. And it already has helped me save time and provided benefit and it’s nowhere near complete.

      2. markbarrington

        That’s one of the frustrating things about email and workflow management. My email is locked up in either a Microsoft or Google dungeon. Seems like the choices are either to be restricted to their ideas about task management, to do lists, document management and workflow or alternatively to use other applications that lose the link and context with the original email.

  39. Mario Cantin

    My pet peeves are your items number one and three. Hopefully someone at Google is listening this morning…

  40. Raffaele Colella

    At Cannonball ( we’re working on email UX and we started from scratch as (like somebody here said), email was not invented to handle all this. We redesigned it so that people can easily answer a friend, find a travel plan, browse their last 10 newsletters and easily delete them with one swipe. All in the homepage, no hidden folders.We try to be the most non-invasive interior designer for your inbox, facilitating the flows to set you free but always leaving you in control. We combine visual gestures, default rules, custom interfaces based on the context of the message and algorithms so that with quick gestures like swipes or tapping you can’t get as much as possible done without typing.We completed the design of our iPad app around our users in the last 6 months we were live in the Apple store… If you feel trying it we will love to hear your feedback too.And we just started with our iPhone beta and feel very excited for bringing the app in the hands of people 24/7….the app has been thoroughly redesigned to provide you the same experience the larger screen ;)Happy Friday to all of you,Raffaele

  41. daryn

    I’m glad it has become irrelevant enough that you no longer call out Spam Arrest as a thing you hate πŸ™‚

  42. LE

    So those are some, but not all, of my pet peeves about email. What are yours?My biggest has to be people who either can’t type, or reply to emails by mobile and don’t provide sufficient information for me to understand exactly what they need or what the problems that they have are that need to be solved.This results in creating extra work for me in order to cover multiple ambiguous possibilities in my reply.Such as “if you mean this, then here is my answer if not, then this is my answer”. Problem is there are so many forks you can take if you don’t know exactly what the specific question or concern is.People who know about a particular subject think of all the nuance in the subject and need details in order to help a decision maker. The person who needs help doesn’t know what they need, but even if they do, what I find is that they are simply to lazy to put the effort into composing an email.Imagine if I wrote to Arnold and said “Can you recommend a good wine?” Or JLM and said “can you give me the name of a good restaurant in Austin?”.I’m sure Arnold would think “what do you want to spend, what is the occasion, what wines do you typically like, is this a gift, is this for a dinner, where are you” and so on.

  43. kirklove

    Gonna have to add @hater redirect as well now it seems

    1. fredwilson

      you knew that long before this post

  44. TedHoward

    I would never receive a calendar invite if it wasn’t an email or a TXT. There is no other system I interact with where the main user task is just to look at it and see what’s there. Similar to calendar-related notification via email, folders are essential for auto-sorting bug and source control emails.No multitasking? That’s a pretty awful email client you’re using. Try … any email client. The web browser is not an email client. I hate Gmail because their paradigms (such as anti-folder) break email clients, forcing me to use their web page. And their web page has issues such as no offline support and no multitasking and every problem that every web page has always had.

  45. Twain Twain

    If email let us swipe which also re-orders for priority:* up = must reply* down = bin* right = read later* left = archiveI’d be happier and more email effective.The whole “scroll the list”, sub-categorize into folders, metatag with labels annoys me for its inefficiency.Also, I’d like email to be a lot more visually appealing.

  46. Dave Hendricks

    I wish email programs would pull in the contact info from the sender more efficiently and add it to my address book. I have tried Brewster, Plaxo, etc. I think that if someone could crack the contacts thing in a simple way they would rule the world.Fred your #1 complaint: Know what I’ve sent and reminding me to/prioritizing followup (or answer) mail to/from important contacts is another thing that could be a life improving innovation.

  47. JTDALY4

    Mr. Wilson what jumps out at me from this post is the fact that you use gmail. Why?This entire dialogue is about something that is free. Has anyone ever heard the expression you get what you pay for?Email is very much like tap water. Tap water is free but annual bottled water sales are 11.8 billion in the US and globally its 60 billion.To rephrase my question. Why does a best of breed VC drink tap water? Is there a highbrow “FIJI” email system that you know about or use to communicate with a certain set of contacts?If I may suggest a future blog post maybe it could be the following. Instead of asking what sucks about free water.Maybe the question should be what would everyone be willing to pay for a QUALITY email service that was AD free. Maybe we could rank our dream features from 1 to 5. After each feature each person could state what they would be willing to pay for each feature.e.g.1. an automatic RTS(return to sender) feature. The feature would work like this. After 24 hours it automatically sends a reply to emails you haven’t opened and says “Mail not read.” it takes it out of your inbox and puts the ball back in the senders court . where it belongs.. thats worth $10.00 a month

    1. fredwilson

      Because it is the best thing out there. And I have tried everything. And we pay for Google apps at USV

      1. JTDALY4

        We have been in stealth mode for two years developing a solution to the multiple protocol communication problem. If you are interested in our work, I would be happy to share it with you. Please email me at [email protected] I would email you but your inbox is clearly full!!!

  48. matthughes

    All legitimate gripes.I’m still a believer in email.My email newsletter is growing much quicker than a blog might.Simply put, it’s a daily push notification in a reader’s inbox.I agree email has many problems but think it’s undervalued.

  49. sigmaalgebra

    I don’t have any problems handling e-mail, but then I don’t send/receive all that much e-mail. And the anti-spam laws cut way down on the junk.E-mail 101 by Example.When e-mail started to get popular, I had for e-mail one of the dumbest programs ever written, fully in line with a graphical user interface (GUI) with the ‘paradigm’ of ‘direct manipulation’ on the screen of data ‘objects’ so that each e-mail message was an ‘icon’ (can’t spell it, can’t look it up in a dictionary, can’t pronounce it, don’t really have a meaning for it, can’t usefully send it to others — semi-, pseudo-, quasi great idea, and that’s being generous). Great for someone who sends/receives at most a dozen e-mail messages in several years and has nothing much else to do with a computer!We can have a competition: We put down our bets; you name the worst program you ever saw; and I will name a worse one and win the bet!So I got out the Internet engineering task force (IETF) requests for comments (RFCs) on e-mail, took out an afternoon, and wrote my own post office protocol 3 (POP3) e-mail software to send/receive e-mail. Used the software for years, and it worked great.Lesson: Sending/receiving POP3 email is dirt simple, about the simplest little TCP/IP socket program could ever hope to write. Did I mention, dirt simple?Okay, now you can send/receive e-mail but want some additional features. Fine.Here’s how to proceed: Put each e-mail message in its own file system directory (the overhead for a directory is small, and disk space is cheap) and there also convert the attachments from base 64 encoding (the way they are transmitted, that is according to multi-media Internet mail extensions (MIME)) to the file types indicated in each attachment’s ‘header’ line (permits using file search tools, say, Grep on Unix or Findstr on Windows, that will not do the base 64 conversion itself).Now you have your e-mail data in good shape for more in programming desired features.Then, think of all the features you want and program away. Maybe search, organize, connect via(A) e-mail time/date stamp, e.g.,Date: Wed, 30 Apr 2014 13:47:44 -0600(B) e-mail address,(C) person’s name,(D) text in the e-mail subject line,(E) etc.So, for an idea, each search returns a ‘list’, and then can search again just on that list. So, could search on person’s name, get a list, and then search the list for keywords in the subject line, get another list, and then search by a range of dates in the time/date stamp. That much ‘drill down’ should be enough new functionality for finding stuff for a while.Should be able to do more making use of the e-mail header lines.If e-mail gets to be a big problem for me, then I’ll write software for a solution.

  50. CaliforniaMomVC

    If you hate calendar invites – check out The company presented yesterday that the Alchemy Accelerator demo day at Citrix in Santa Clara. Founders are out of Berkeley. All calendar activity happens on the back end – doesn’t require a user to download and save.

  51. Rob Underwood

    i hate long emails

    1. fredwilson

      me too

      1. John Revay

        There should be an app that limits the number of characters in a given transmission…..For some reason 140 sounds like a nice round # πŸ™‚

    2. ShanaC

      me top, but my dad loves them. drives me bonkers

  52. Jeremy Toeman

    Self-serving (yet totally relevant) indulgence here: about half the complaints you and others have can be fixed with one of my previous endeavors (still alive) called NudgeMail – Works a lot like Mailbox, but no download/client/app required, just use email. For example:Fred: “- There is no easy way for me to keep track of the emails I’ve sent where I really care about the response.” – just BCC “[email protected]” on these, and in two days you’ll get a reminder to follow up.Others who complain about Snoozing emails: just forward them to when you want to receive them, such as “[email protected]” or “[email protected]” or “[email protected]” and they’ll return to you then. AND with a snoozebar.

  53. Stephen Beck

    No easy way to quickly confirm that you’ve read and/or agree with an email you’ve received other than sending a reply. A simple ‘acknowledged / yes / no’ set of buttons would save so much time and cut down on useless follow up responses.

  54. Retellity

    It would it make life much easier if we were able to input certain words and key phrases that would automatically presort any email coming in, just like in regular mail if we see standard postage we know it’s junk.

  55. jason wright

    “These important responses get caught up in all of the other email and I often miss them.”then there needs to be an inbox fork and marker options before sending.

  56. Oz Nathan

    I get spammed by every single service I sign up to by default.

    1. ShanaC

      it is an effective marketing channel

  57. Glungie


  58. Matt McCormick

    Keeping track of emails I sent where I cared about a response or a result used to be a big problem for me.About a year ago I found out about So now if I send someone an email and want to follow up in a week with them, I BCC [email protected] and archive the message.A week later followupthen send the email back to me. Perfect solution to the problem.And it’s free.I’d say this is the single greatest email support tool I’ve ever come across.

  59. Niv Dror

    I usually spend about 2 hours a day connecting with people and making intros – all via email. This is a very high leverage use of my time that I enjoy doing.The other side of email is calendar invites, more scheduling, company email lists that are 1% relevant, and unsubscribing from marketing spam.I feel so strongly against the latter that I recently left a dream job a couple of weeks in because of it, and in favor of spending more of my time doing the former.To summarize: for direct communication/reaching out to people email is great. For everything else… use Asana or more of Slack.

    1. ShanaC

      how are you using asana for emails? I’ve been hearing about people doing this, and I want to know how they are doing this.

      1. Niv Dror

        Not sure, I actually haven’t used Asana. Was trying to make a point that companies need to move as much non 1-1 conversation as possible off of email, to things like Asana, or other software solutions that facilitate the sharing of company wide and group conversations.

  60. LaMarEstaba

    I’m one of those dreadfully annoying people who have achieved inbox zero. I do not get 700-900 important emails a day, like Fred does. I have used Gmail for years for personal use, and I have a lot of filters.I had to adjust to Outlook at work. Once I got a rule paradigm set up (if sent to me specifically, TO ME, else FOLDER OF SENT TO (X, Y, Z LIST)), my life was great. It’s interesting that a lot of the features that people are asking for in the comments are things that I de facto have in Outlook (follow up later, read receipts for mostly tacit acknowledgement, send later). I also use FYI+Low Importance for “Thanks” emails or purely informational, no response required emails. I know that some people preface such emails with NRR, and I would love to do that if it became part of my company’s culture.I am honestly not a Microsoft fan (I’m typing this on a Mac), but I’m happier with Outlook than a lot of people here are with their email client.

  61. ShanaC

    I think we need personal crms – its a way better way to organize email stuff (and this is from someone who remembers when gmail threading was considered a huge step forward in email organizing

  62. davidu

    Try SquareOne

  63. Matt Zagaja

    That people do not read it. It is amazing how many times I can send an important piece of information via e-mail and when failing to read it results in a negative consequence for someone they do not believe it is their fault. In law school they drilled into us that managing our inbox was an ethical and legal obligation because if we miss something clients can lose lots of money or go to prison.I use Google Apps for My Domain with Mailbox app and it is a great combination. I hit inbox zero in both my work and personal inboxes almost daily. Many messages do go unread but that’s fine, much of it isn’t important, unfortunately.Edited to clarify that it isn’t just work, and that it results in a negative consequence because re-reading it made it seem not clear at all.

  64. lunarmobiscuit

    Full agreement Fred. But for email follow-ups, I finally found a solution. Have you seen SaneBox? You just bcc 1week@ or 2days@, etc. and if you get no response, the system tells you (by email of course).Plus I t’s key feature solves yet-another problem you missed, sorting the important email for the less important. Gmail is good enough for that, but only on the web interface. On my phone and tablet, the email was unsorted. Now only the important email are seen on those devices, the others labeled “later”.I can’t recall where I first found this service, but it’s one of the few impressive enough to be worth paying for. I’ve no investment or interest in the company short of enjoying its benefits.

  65. Aaron Troublefield…Success Is Waiting For You -You Can Genuinely Receive $100β€²s To$1000β€²s Each DAY Follow Our Simple,Proven System To Your Success.100% FREEE

  66. Adi Dagan

    One thing i do love about emails – Boomerang for Gmail. A life-changer

  67. Robert Holtz

    Fred, I hate all the exact same things you do EXCEPT for Labels. Labels have saved my life. Firstly, I have a label called “- PRIORITY -” that puts that label with white text on a red background on emails that I actually care about. The great thing about that label is it persists with the whole thread so when someone responds to something you’ve marked with that label, you KNOW it matters because the prioritization is not automated in any way. I manually mark it that way as a conversation becomes important and it stays connected to the thread. As the conversation becomes less important, I can shut it off at will by simply unchecking the priority label on it. Even if you don’t use labels generally, try that one on as for this one function if nothing else at all, you will find it revolutionizes the way you look at your inbox. Right away, when I open, I know what needs my prompt attention versus what can wait its turn. I have a love/hate relationship with email. It has MANY shortcomings but it is still better than any other tool I’ve tried and you know that there has been countless attempts at dethroning email and while IM and text now co-exist, email is still the backbone.

  68. Matt Zagaja

    Another e-mail pet peeve: banks and other organizations that feel the need to communicate only via what they deem a “secure inbox” located on their website. So then you get an alert to go to the website to check your messages. I don’t want people hiding the ball, put the thing in the actual e-mail. Among all tech companies in the world I have a hard time imagining many can surpass the level of security that Google is providing me in my e-mail inbox.

  69. Marissa_NYx

    What I love about Line, the Japanese messaging app is that they sell emoticons and cute badges & icons which you can share with those you message. It makes communicating fun. It may be just a Japanese thing but I for one love animation and color. Brightening up the drab grey gmail which I have open all the time, is the thing I’d like to change. Maybe someone will take what Line has done so well and hugely successful with and apply it work on email ?

  70. Kirsten Lambertsen

    Like @donnawhite:disqus , I like email. It is indeed my to-do list and also my filing system. I have emails going back years, and I like being able to keep the timeline of events at my fingertips. (I don’t use GMail.)I can imagine what it’s like to be someone in your position, though. Email must feel like a relentless task master.Seems like you could use something that would almost be like ZenDesk. Something that would give you a customized dashboard view of what’s happening in your email, with only conversations in process showing up in your actual inbox feed.You could sit down for a 1/2 hour and say, “now I’m going to go through email from new people that’s over 5 days old,” or “now I’m going to review new email from people I regularly email with,” etc.

  71. Roland Pokornyik

    I wonder that nobody mentioned Rapportive – which is a superb Add-on for Gmail. Thanks to that, you can instantly see each and every social profile of the sender of the current email you are reading.(if he uses the given email for other online profiles as well) It works great for me, I would strongly advise it for anyone.There’s one more interesting tool out there (also for Gmail), called Boomerang. With this you can “Boomerang” emails back to yourself, in a given time frame (4 days), add conditions (Boomerang if “no reply”), can track opens (if the person opened your email or not), and may schedule messages.These two tools together increase my efficiency in sending and dealing with emails at least by 30% I think!

  72. Joshua Baer

    First there were viruses in email. Then spam. Then graymail. I’ve filtered it all away. What I have left is email from real people – and that’s the hardest to deal with. I need ways to automatically respond to some types of messages and make it faster to choose how to reply to others.Fred, to your first point, check out They do a good job pulling out the important emails you need to reply to or that you’re waiting on a reply for.

  73. #vjgrover

    After reading your post, I cleaned my mailbox by first removing all the filters and allowing Gmail to arrange in the five groups. It does a pretty good job. And then I can keep moving messages to folders, this way atleast I have a chance to read all messages and no message goes unnoticed.

  74. anand

    What I’d really like to see is email better integrated into an Evernote/Onenote type of app – really would be useful.

    1. Rishit Jhunjhunwala

      try, integrates with both Evernote and OneNote (disclosure – see bio)

  75. Sahil Parikh

    Hate delegating tasks and sharing files via email with my team. So inefficient

  76. Linda Chung

    Have you tried the Mailbox app for mobile? It’s easier to boomerang emails that you want a reminder to follow up, or to remind you to read later and you can boomerang sent emails. The Email Game is similar for desktop and it’s more like a fun game with timer to make email more efficient.

  77. James Alexander

    Non-mobile optimized email is a frustratingly poor customer experience. >51% of email is now opened on mobile devices (26% on iPhones) yet every day I get email that requires pinch and zoom to read. It makes the senders and their vendors look bad and no doubt impacts engagement rates. A visually rich, HTML email is arguably the de facto homepage of your site for that email recipient at that moment in time. Marketers can be doing more to test their email campaigns for responsiveness. And companies like Constant Contact should be leading on this but they’ve been slow to respond. For anyone interested, I just posted about it with some stats and sources at

  78. Gregory Magarshak

    I think email should be replaced more with subscriptions to streams published by various people, kind of like forum threads. Google Wave was a nice idea, but something with a much simpler mental model should be there. Also, there is no reason why this “inbox” couldn’t be used for more than just email messages, but notifications of all kinds.In my opinion, the main problem with email is that it’s still about the same things it was about in the 90s. Text messages that arrive. What you really want is notifications which pull you back into some collaborative “stream”. Then email would be an endpoint whose main job it would be to manage your notifications, curate content, organize your contacts, and make sure you’re responding to everyone. It would also solve the major problem of spam. Something like this:

  79. Sean Saulsbury

    Flagging for follow up is a big one for me. Too often I send out an email and it disappears into the ether. I’d like a reminder to pop up X days later if there is no response. Why doesn’t Outlook or Gmail do this?

  80. LE

    I put all email that are important (as well as a ton of other things I figure out) in a wiki that I keep on a colocated server so I can access it from anywhere.The only thing I have been meaning to do is write something so I can forward the email to an address and have it automatically added to the wiki so I save several clicks.The other thing I was working on was a way to “one click” an email, have it saved as a pdf, and then have that pdf synced with my cloud colocated server for access anywhere or easy searching.Once again I want something that works for exactly precisely the situation that I need it for without feature bloat and relying on someone else to tweak and change.

  81. Andrew Kennedy

    Good point

  82. Aviah Laor