Email Fail

I've been struggling with email for years but lately it's gotten way worse. I am now routinely not replying to many emails and most weeks I get days behind and then spend a good part of my weekend catching up.

I know that there are techniques that I should be using, including outsourcing some of the email to my colleagues and administrative team. I am not enthusiastic about any of this.

I've been searching for a better email client. I was on entourage (which is unstable for large mailboxes like mine), recently went back to outlook on paralells (but crashed my virtual machine somehow), and have been on gmail all week.

Gmail has promise for me. At least I'm not likely to crash it. But I cannot get used to the collapsing of conversations in email and I've tried at least a dozen times now.

This morning I downloaded thunderbird and connected it to gmail. That didn't work either because I have years of email in gmail and Thunderbird is trying to download them in buckets of 250 messages.

The whole experience is a complete and total failure. I've been down the email bankruptcy road a few times but that's getting old too.

I really think it's time for me to walk away completely.


Comments (Archived):

  1. Keenan

    Walk away, Fred walk away. We all should, and then maybe someone will come up with something good to lure us all back. I’m to the point were hundreds of emails just go unanswered. It used to be more than that.One thing I’ve done to help is I have multiple accounts. Personal, business, blog, etc. I can then prioritize them accordingly. It’s helped.If you come up with a new approach, love to hear it.

    1. fredwilson

      i may need to set up a new account. i really hate to do that used to be the one thing that i would make sure to complete in its entirety.once i stopped feeling that about it, it’s become a very slippery slope.

      1. Mike

        OtherInBox might be a good solution for you. One feature that I really like is that you can set it up so it lists a daily summary for you at the end of the day of unread mail, which then allows you to skim through and decide what needs a response now or later.

        1. kenberger

          OtherInbox did sound like a very compelling solution when I saw it launch… and since then I’ve been too busy using old email to ever get around to trying it !I’d love to hear folks’ reviews of it.

  2. stone

    I hate to throw water on the idea of using gmail but it is Google least reliable product imho. We use it for personal and business and routinely run into glitches. Very un-Googly but true.

  3. Bryan

    Note that Gmail allows you to append your username with “+something” to help with filtering. In other words, “[email protected]” will still land in your inbox, and you can create a filter that automatically labels messages with that “to” address. Then all you have to do is read, then click “Archive.”I recently weaned myself off Thunderbird because it’s much much easier to click “Archive” than it is to drag something into a folder. And, with the better gmail extension, Firefox is actually a pretty good client.The goal is to decrease the sorting-to-writing ratio. But I don’t know of any technology that lessens the time spent actually writing email …

    1. MarinaMartin

      You’re clicking “Archive”?? Hit ‘y’ on your keyboard (when the message is open) or ‘xy’ (to select the message in a list, then archive).

  4. Roger

    I have thought about this too as many others have to use some sort of machine learning technique to priortize emails so the most important or relevant ones can bubble to the top. Let me know if something like this interesting to anyone, perhaps I could start this as a project.

  5. vruz

    did you try Thunderbird + Gmail IMAP ? (instead of POP)

    1. fredwilson

      No, but I willThat’s what the consensus reaction on twitter wasI’ll do that this weekend

  6. Brad Birnbaum

    There is always I made the switch from Entourage recently and haven’t looked back.

    1. kenberger

      I’m pretty sure that Fred, like many of us, still relies on MS Exchange integration. would have to resort to IMAP polling (like some of the other solutions mentioned here).

  7. robjohnson

    if you stay in gmail for any period of time i highly encourage learning the keyboard shortcuts. they are from unix-based text editors and they really make the whole gmail experience faster, smoother, & better.

  8. BmoreWire

    I’ve actually gotten used to gmail but i recently tried their offline option. That sucks. It’s super slow and times out all of the time and gets confused as to what I deleted online or offline. They really need to tighten that up.

  9. Max Kennerly

    I will leave the client issues to the techies, and the DMZ/bankruptcy to the GTD gurus, but I will recommend dictating e-mails and/or using Dragon NaturallySpeaking, which is finally useful.I never realized how much pain and fatigue in my hands and forearms kept me from responding to e-mail. Given the handful of corrections you have to make, voice recognition is not necessarily faster, particularly not for e-mails shorter than a paragraph, but it is not nearly as draining as typing everything out, even for fast and efficient typers like me (and I assume everyone else here).

    1. nickdavis

      But don’t underestimate the fatigue that dictation can cause on your voice, which is generally not used to speaking for long periods of the day…..

  10. markslater

    This is how i have tackled it as i use two different machines (PC desktop and mac laptop)My company mail is hosted on a remote exchange server – this allows for smooth reconciliation across outlook and entourage (in fact really good – read mail replication, the lot) – obviously also has web access. – i have Xobni on my outlook profile which does tremendous stuff for the conversations.I then have my investment banking email come through POP to gmail along with my personal mail and the start up mail.I have canceled all mobile email. (pop and BB) – i have concluded that there s absolutely nothing that comes via email that is so time sensitive that i need to be stumbling down the street like a moron stopping traffic buried in my minute form factor – i also hate the things in meetings and on the golf course. I am rarely away from a screen for more than an hour a day, so can check regularly – and if there is an emergency (wife pregnant etc) – i get………called.!you can bang on about productivity and blah blah – i have been a BB users longer than most (most bankers have been) and i love the technology – but i have come to appreciate partitioning my time properly, and switching off when i want to – i have a better quality of work life balance, i have lost absolutely nothing in terms of productivity.i usually spend 2 hours in the morning emailing – an hour or so reading and responding to blogs like this, the majority of the day meeting and conversing, and repeating this at the end.All my personal stuff is now pretty much in facebook – i will move that to our new start up as soon as we are ready, because frankly i don’t have 170 friends and no desire to stand i a high school hallway and scribble on the wall. The 10-20 i spend most of my time with will be through a new service where we can geolocate, and do stuff that real friends do.So no personal email anymore, business email in the cloud and cross platform.walking down the street or driving a car is,……just that. Meeting face to face. i take devices very seriously when they are brought in to a room.

  11. awatterson

    What’s causing the lack of enthusiasm about outsourcing? Isn’t that how people in the past dealt with large physical / voice mail inflows?You could even set up an auto-filter / forward to a dummy account for all the people who it’s critical you get their mail, that way you could just manage that personally and have your team deal with the rest of the stuff.It’d be a real shame I would think to get off email. I’m sure it’s a challenge for visible/influential people, but Obama felt it was important enough to make a big to-do about it, and I think that says something about email (and Obama)

    1. fredwilson

      I don’t want someone managing my inbox. I would love someone to write a set of rules and algorithms so that I could auto forward the mail that I don’t need to be managing. But when somebody writes me, I feel that they should hear back from me.

      1. awatterson

        Sorry, I guess when I thought manage, I was thinking about mostly filtering and prioritization , de-spaming. I can understand the desire/need to “own” the actual communication.As far as rules and algorithms, doesn’t there come a point in human-human communication where they find their limits?

      2. caveman1

        Fred – it seems like your issue is really dealing with mail from people you don’t know, which I assume is ample. You don’t want to just let it go, and you don’t want to leave it to an admin. That’s admirable – I think most people who get become “known” for whatever reason just give up on living up to that.Perhaps you could give a word to all of the people you know that they could include in a subject line to you – something like PERSONAL or UNION or MUSIC. The idea is that senders provide the context for your relationship in the note. Then Google sorts those for you, so you look at those first. Then, when time permits, you shuffle through everything else.At least then you’ve solved 90% of the signal to noise problem. I don’t have a solution for the other 10% beyond slogging through it.Good luck!

        1. bernardlunn

          Yes, that is what I do. As “press” (ReadWriteWeb) I get tons of mail. Anybody who is not in my contact base gets into a different category. I can still look at them, but choose when and how to do that. And that may prompt me to put that person in my contact base. It is sort of like “following” somebody now that I come to think of it.

      3. Satish Mummareddy

        You can make the rules/software smarter or you can request your public email to add tags so that you can deal with them better. You have a safe list of people from whom you will receive all email. Make a list of reasons why people contact you and create a tag for each of those reasons – NewPitch, Meet4Coffee, TryMySoftware etc. If other people want to contact you, they need to use one of the several tags you ask them to use on your contact page. Based on the tags people use in their email they could be forwarded to different email addresses for your use at a later time. When someone from that communication becomes important and a frequent person you communicate with you can add them to your safe list.

        1. fredwilson

          I am not anywhere nearly organized enough to make this workI need AI

          1. TweetProbe

            Today’s AI will just melt it up more 🙂 If you have a simple desktop client allowing you to organically build your filters over the years, then you would not be in bk again. If twitter will add a new status object pointing to a payload, this as u darn well know, forces the sender to focus their intent in to 140 chars. Wanna bet this will change the World?

        2. Andy Ranley

          my experience with filtering rules has been so-so when trying to utilize one all-in email address…sometimes important email can be inadvertently put in the wrong place. i have found tremendous success and ease-of-use by offering my inner-circle (family, close friends, long-standing professional folks) one address and using another for all my more public/outward interactions. It’s rare that someone really makes a transition from one group to the other other. on top of creating that initial filter using two different email addresses, using filter-rules within each account can be invaluable within each category. convo threads in gmail also took a little getting used to, but they are last suggestion Fred is that you just stop being so smart, sought after, and in demand :-)a

          1. fredwilson


  12. stuart

    I’ve heard a lot of buzz about Postbox – but I haven’t used it personally yet. I’m highly committed to Eudora. I’ve tried many times to ween myself off, but nothing ever compares. It has very a very powerful rules engine that automates many tasks for me. Unfortunately, the interface may be a bit clunky for somebody expecting a modern GUI experience

  13. John Thomas

    I use my own Cyrus mail server (, but you could use fastmail if you want someone else to handle the brain damage) and its sieve mail filtering language (programed via a webgui in Horde) to automatically sort email into folders. I use thunderbird for general purposes and Horde for web reading (fastmail has its own webgui). The system is amazingly fast and efficient. Your email to me would have to meet very specific criteria to make it into my inbox. The filtering will take some work to set up, but after you set it up, you are golden.Thunderbird on Gmail was terrible, when I tried it. GMail, it seems to me, has tried to layer IMAP on top of their server and it did not work very well for me. Using a true and fast IMAP server with IMAP specific clients will be different.

    1. fredwilson

      I need to hire someone like you to hack up a custom email solution for me!

      1. daryn

        I guess the real question is: Do you have any thoughts on what would work for you / what is missing from the current solutions in your opinion?I hear three main points:1. You can’t keep up with the current mess 2. You want to read and respond personally 3. You don’t want to spend even more time and effort on email by trying to manage rules,etc.From a process perspective, I think you could probably benefit from having an assistant screen and collate your incoming firehose. Rules could do it, but I think a human would be most effective, and seems reasonable in your situation. The assistant doesn’t need to reply to anyone, and I wouldn’t overly complicate it to start, just filter things into a handful of buckets (pitches, intros, replies, etc.).Have fred@usv go to the assistant. Have another address/mailbox that the mail gets filtered into, and that you can hand out selectively to friends, colleagues, and anyone who gets to “jump the line”. This is the folder you should be looking at on your BB.Technologically, I think the key to efficiency isn’t lots of segmentation on the server/filtering end, but rather a few folders, and a better perspective with which to view each pile. You’re probably not going to get this perfect on your mobile, but if we can come up with a view (keyword heatmaps, sender “rank”, replies etc..) that you quickly navigate at a glance on your desktop, I bet it would go a long way.Be careful if you go with a homegrown mail or webmail solution. You’ll miss your favorite features, and anyone who says it’s an easy problem didn’t spend 4.5 years building and running one 🙂 If you can get used to thunderbird though, you can definitely take it to the next level with a plugin or two.

        1. andrewparker

          This is a good outline for a human-capital based solution (which I agree is ideal) and reminds me of how I heard Bill Gates manages his email. Well worth considering, if I can work for a former Fortune 500 CEO.

    2. kenberger

      @John- I think you’re on the right track of a compelling solution. To make it even better, the system could incorporate an agent that continually gets trained and after a while becomes very good at knowing what goes where. Some might call this AI (artificial intell), and Gmail has this to some extent for spam management.I use spamassassin heavily with excellent results. Its Bayes filters that you train to help it recognize spam are even more useful than its copious heuristics tests. I think a system could be devised to similarly learn to organize things the way you want, based on content. You’d have to work it daily, which could be partially automated, but it would be well worth the small effort.

  14. Dan Lewis

    I’m going to echo what I’ve seen others say: It’s not the email that’s the problem, but the blackberry.Here are my rules for mobile email:* Never start a conversation unless absolutely necessary. I actually use the notepad on my ipod to jot down cribbed notes about emails I want to send later. Most often, I don’t send them at all. I rarely, if ever, initiate email conversations on the blackberry.* Try to limit the amount of instances in which you reply to things on the ‘berry. If it can wait, let it wait. Again. most of the time you’ll end up not replying at all. (You’ll feel guilty about it the first few days you do this.) You’re *not* going to end up neglecting the emailer — just not replying to that specific email. Trust me, at some point you’ll end up thinking, “I haven’t replied to this person in a while” and reply, even though you would have archived otherwise. That’s exactly what should happen, and exactly what you should do.* As you get used to the above, Archive Often.What you’ll end up doing is managing *relationships*, not *email.* And that’s really what communication is about. Very few relationships are so important that the other person should be an immediate priority. I don’t see why technology should change that axiom.

    1. markslater

      exactly – you put it much better than me

    2. bernardlunn

      Absolutely, Blackberry is both the biggest time-saver and the problem. I am actually testing something new this weekend that may solve the problem (sorry, I am in embargo land on that one). I try to do what you do, only use BB for mails that don’t need to be properly tracked. The answer is Either: push email from webmail vendors that replace BB push or b) some great CRM-lite tools that buil using a native BB interface. Methinks a) is more likely ie open standards always win in the end.

    3. awaldstein

      “mapping relationships not email” is what I do without the articulate title. I keep conversations within my networks–FB, Twitter, work email and don’t push anything to my personal email unless its justified. Technology is not going to solve this. Me understanding my networks is. Good point Dan.

  15. Roel

    Gmail is something you either love or hate. The collapsing of conversations is one of those things. I used to have a folder ‘To do items’ in my pre-Gmail mailbox, and an Inbox overflowing with e-mails. Gmail worked well for me once I understood the Gmail Inbox was the exact opposite of my previous Inbox: – the Gmail category All mail = my previous Inbox – the Inbox = my previous folder of To do itemsJust review the e-mails in the Gmail Inbox, and either just archive or reply and archive (there is an option in Gmail Labs to have a Send & Archive button). Everything I cannot immediately reply to I leave in the Inbox. Use Canned responses for standard replies (these can also be found in Gmail Labs) to save time. And rely on the filters: those are really good.The keyboard shortcuts are also a lifesaver, and you can customize those through another Gmail Labs option to suit your preferences.(And if you’re going to use Gmail and Thunderbird, definitely use IMAP instead of POP3. It will make your life so much easier. Especially if you decide to switch to another e-mail solution later on. )

  16. e.p.c.

    I maintain two email addresses, one which I use publicly (ie, what Disqus would show if it displayed email addresses) and one which is “private”. I use the “private” one solely for inbound mail from vaguely security sensitive things like financial institutions, insurance, personal information. A few select people have the private address as well. Everything else gets dumped into the public address (which is what I send from as well). I then use filters to segregate mail from people I “know” (for now anyone in my address book) from people I don’t know. It’s not perfect, the segregation can break down if the “select” people forward a mail on somewhere or one of the institutions stupidly resells my address. The key thing is segregating mail from people you know away from the deluge of mail the general public.It worked well for me up to about 500 emails per day, at which point I had to allow other people I worked with to browse & handle the “public” email, if only because most of the time (in the role I was in at the time) the mail from the public at large was either spam or was something I’d just forward onto my team anyway.These days as a non-public person my inbound mail volume doesn’t really call for the split mailbox approach but I keep to it since it’s what I’ve grown accustomed to. I use this method across Gmail, and Outlook on Windows depending on my mood of the day.If you use GMail just make sure that you’ve got a stream of mail going to some backup mailbox, at least for the private/personal mail if not for the “public” mail.

  17. ceonyc

    I think it’s a process problem.A few suggestions:Do the Thunderbird thing and setup a new personal account… [email protected] or whatever. Don’t even give it out… Have 25-50 people get forwarded to that account. When you reply, using Thunderbird, just remember to reply to [email protected] way, Joanne can get responses from you quickly.Setup an autoreply that asks people to redirect the message. Tell new pitches to send to Andrew or Eric, b/c that’s the best way to get them looked at. Figure out what other kinds of redirects…Take all notifications out, like comments, and put them into a daily digest of some kind… or again, fwd them to a separate account.

    1. fredwilson

      Those are all great suggestionsBut if I am reading the email from the new account in the same inbox, how does that help me?

      1. ceonyc

        You don’t check em at the same time.I have a seperate account that nextNY e-mails get fwd’d to, but I only check it once a day…

        1. fredwilson

          I can’t have two inboxesI can’t manage what I’ve got now

  18. Carl Rahn Griffith

    I have some 5 years of emails available via entourage, with dozens of sub folders, etc; i was perpetually frustrated with outlook/windows – frequent crashes, slow, fraught database rebuilds/poor search ability/etc – but i must say one of the better experiences i have had since migrating to mac a year or so ago has been regarding entourage. very pleasantly surprised. at any time i typically have a couple of IMAP accounts active and several POP3 accounts.famous last words maybe, (i hope not), but, it’s always been quick and reliable, for me and offline functionality is absolutely imperative.

    1. fredwilson

      I was on entourage for the past few years and I just couldn’t take the weekly crashes and rebuilds that took 12-18 hoursToo much downtime for me

      1. Carl Rahn Griffith

        wow – that is like what i frequently experienced on outlook/windows. can understand the frustration; even though my rebuilds were never quite that protracted.just checked and my database is currently ‘only’ some 4GB so i imagine is still within the logic constraints of entourage – your DB is somewhat bigger i’d imagine, fred!

        1. fredwilson


          1. Carl Rahn Griffith


  19. Jay Cuthrell

    Fred,Nothing is a magic bullet but…Pay the $50 for a Google Apps account.My personal anecdote is that I use it with IMAP clients on a variety of platforms, mobile, and web… and have moved +12 years of email there.You can search more effectively there than with any desktop app I’ve found. The filters vs. folders world shift for me unlocked things I had forgotten about — and I understand the threading concerns but would submit you can try it and see what you think. Getting back is as simple as having someone change the MX record in DNS for the domain of your choosing. The export and import of filters gives me the power I shared with others when I was deep in Outlook/Exchange as well. It’s good stuff.BTW, my Core Conversation at SxSW was “Too Much Text: When I was your age we sent email” so this is an area where I am quite passionate.

    1. fredwilson

      Thanks JayI’ll consider your approach

  20. mattmaroon

    Have you tried Clear Context? A few of my friends who have a lot higher email volume than me swear by it. I’m still at the level where Outlook + Exchange + good filtering gets me by.

    1. fredwilson

      I think I tried it once

      1. Jeremy Kloubec

        I would give it another try. Their new Pro product has evolved quite nicely and is something I cannot live without. I was not as impressed with some of their previous versions.

      2. mattmaroon

        You might want to give it a shot. I liked it, and there are definitely a few features of it I miss, such as the ability to easily grab contacts from an email or create a calendar entry from one, but I just felt like it was overkill for my volume and in the end not worth it. I imagine you’re an order of magnitude above me though, so you might find it helpful.

  21. iderdik

    Fred, You can probably get Outlook to work for you via Parallels. Try moving older archived mail to its own .pst file within Outlook so that Outlook doesn’t feel the need to chug through it in you main inbox. It’ll see be there and searchable, but your main inbox will run much better.

    1. fredwilson

      It was working but then it crashed hard and I’ve got someone working on bringing it back

  22. C

    Agreed. That companies like Xobni and boxbe are attempting to address some of these issues in 2009 speaks to a broken model and an antiquated metaphor. It will be interesting to see how networks like Facebook, LinkedIn and Twitter ultimately play into the messaging mix. There is clearly a product opportunity here. I’m reminded of a quote from back in the day: “Just because all the water comes into your house in the same pipe doesn’t mean you want to drink from the toilet.”

  23. kenberger

    I’m assuming you’re using Exchange on the back end? IMAP can ape a lot of the functionality compared to using an Exchange client (like Outlook, Entourage or iPhone), but not nearly as robust or smooth in most cases, and won’t sync things other than mail (contacts, calendar, etc). Sorry to say that proprietary trumps open source here.Also VMWare Fusion is the way to go, not Parallels– you put it in “Unity mode” and you’d swear Outlook was an actual Mac app. I have an extra copy I could give you. Caveat: on a MacBook, best to have 4GB RAM and consistent hi-speed connections.Agreed on Gmail. Although Firefox crashes plenty, taking Gmail with it.

  24. bernardlunn

    Fred, I saw your earlier Tweet about Entourage/Outlook and was going to reply there but it actually takes more than 140 characters. I switched from Outlook to Gmail about 9 months ago. I wrote about it on RWW (just Google “breaking free of outlook” to avoid me posting links). I cannot imagine going back to a Outlook/Entourage. But then, less than 6 months into using Gmail (which is great) I realized that what I really needed was a CRM system (just think Contact Relationship Management, even if you don’t have Customers, it is just about keeping all your contact threads organized. I looked at Salesforce, Zoho and others. All too heavyweight. Then Dmitry at Relenta found me. At first when he said “you gotta switch from Gmail” I was “no way Jose”) but Dmitry persisted and I did switch. I wrote about that experience also on RWW (Google “switching from gmail to relenta”). I only use Gmail as back-up now.The really interesting bit comes when we integrate email with social media. That is the thread I started to explore with my “this messaging fragmentation is crazy” post.Sorry for a long post. But I sense that I have been down a path faced with similar issues to the ones you are facing. Hope it helps.

    1. fredwilson

      So relenta is the product you use?

      1. bernardlunn

        Yes, Relenta.comTell me if you want to get a demo from Dmitry, he would be thrilled. I can show you how I use it, but the I would have to figure out how to use DimDim or some other screen sharing utility (which I have been meaning to do)

        1. Dmitri Eroshenko @Relenta

          Thanks Bernard. Fred, I will be thrilled indeed, except now I am afraid to email you 🙂

  25. musigny

    agree completely and i’m in the same state. for the life of me i can’t understand why gmail doesn’t just add an option to turn off the conversation mode. at this point, i’ve basically resigned myself to putting follow up tags on emails that i know i MUST get back to and then work from there.

  26. GB

    Eudora has served me well through the years, so I would strongly suggest giving it a try.

  27. Seth Lieberman

    This is not a technical problem. This is a time problem. No tech solution, no matter how good will fundamentally alter your desire to do such a diverse set of thing that all require time and focus. The natural, and *only* result is a sure but steady increase in constraints on your time. Better management of communications surely helps, but I think your email headaches are a symptom not the problem. I wish it wasn’t so, but I fear it is.

    1. fredwilson

      That’s sort of my final point

  28. Giovanni De Stefano

    Fred, have you tried Just to use Gmail’s IMAP on a IMAP capable email client?

  29. Paul Edmondson

    Gmail + Plus mastering the keyboard commands + Filtering has been the best for me. Second, is to change your email habits. Mark stuff you have to get done that you can’t do right now. Do what you can do right now. Only reply if it requires a reply – each reply generates more mail. Put time on your calendar to do mail.Mail has been a pain point for me for some time. Years ago, I’d get so much that each ding of Outlook made me cringe. When I left my big co job, my email went down to a handful a day.So, if you really want to really see your email become manageable, start a company – you’ll at least get a few month slow down:)

  30. TedHoward

    Try Outlook 2007 with SP2. The press release, so ‘grain of salt’ there, reports a 35% increase for ‘large’ mailboxes and 26% faster for ‘common’ tasks. It’s worth a try at least.You sent in the crash report for your Parallels crash, right? 😉

    1. Druce Vertes

      SP2 for Outlook 2007 just came out this week, so I would maybe give it a little time to season… but I’ve heard good things. Outlook 2007 is the one Office application that actually works better than 2003, especially when used with Exchange 2007.Email is a train wreck and needs to be rethought from the ground up….trust model to prevent spam…semantic model to allow automated handling of meeting requests, contacts, other workflows… better database models to eliminate duplication and corruption…modular client that could incorporate features and different messaging protocols like SMS, twitter, etc…secure transmission.

  31. Kostis

    I’d suggest to keep using Gmail. The concept of the collapsed conversation was also very bizarre to me at first, but after a couple of weeks or a month you’ll get used to it. And after that, I have to say that it’s the best thing Gmail ever did for email.

  32. needcaffeine

    I’ve been using Gmail for serveral years now, and am now running into the issues of too much email as well…I’ve started to use labels & colors more(through labs) and am learning the boolean search terms. Recently I did “is:unreadh in:inbox from:twitter subject:following”, this helped a lot as before I’d just search for twitter & get deleted or archived emails.I’d look through the “labs” there are a lot of useful tools in there

  33. ade

    Is this about trying not to use Outlook on a PC? I use Thunderbird and its a dog compared to Outlook, i really should just pay for it.

  34. MarinaMartin

    Hi Fred,I’m an efficiency consultant and have been helping people solve similar email problems for years. There is a better way, but it’s not Gmail (filters are seriously lacking in complexity, for one) or autoresponders or declaring bankruptcy. If you’d like some help this weekend, please let me know. (I was going to email you this offer but figured this comment had a better chance of being seen!) We could make some serious headway in 30-60 minutes. Good luck!

    1. fredwilson

      Not going to work on this over the weekendBut I am all ears

  35. Dmitri Eroshenko @Relenta

    Amen! Email failure is probably problem #1 for many businesses today, but most people don’t know they have it or just wouldn’t admit. The Radicati Group estimates that 41% of knowledge worker’s time in 2009 will be spent on managing email. The cost of email mismanagement? Try Basex’s information overload calculator:

  36. Mike Elliott

    I feel your pain. I’ve been through entourage (used it for a week), thunderbird (a year), and numerous other web based email services. At the beginning of this year it all came back to Gmail, customized with some lab addons and greasemonkey scripts – it’s now the only thing i use or ever plan to use again. I finally gained control of email management when I implemented the GTD (“Get Things Done” – Dave Allen) system for my labels. This combined with multiple inboxes is a powerful combo. There’s a firefox addon that actually sets all the labels up for you automatically.

  37. banane

    I imap a few accounts into Gmail, and roughly have 2 active inboxes I check (I know you don’t want to do that) one is professional, and for services (banking, etc.) the other is purely personal/fun, and most of my social networks key into that one.I can’t believe you’re using client-based email. Seriously, the spam filters are AMAZING on web-based emails, and that may be one of your problems.Also, if you remember, adding yourname + [storename/service] – sub-addresses, helps with organization.I check mail on my iPhone but I rarely reply. Just a “FYI” kind of thing. I also take driving and walking seriously, or perhaps I’m not gifted in that area, ha.I also unsubscribe to things periodically to clean out my inbox. Good luck.

  38. alexismichelle

    One of the biggest challenges with email is expectations management. People expect a response, and expect one quickly!While I haven’t had a chance to implement the system yet myself, I’ve heard *wonderful* things about AwayFind (, which is a tool and system that deals with email overload, and is particularly effective in managing the expectations of others.

    1. fredwilson

      that’s a great suggestionthanks

  39. pfreet

    I have been using Thunderbird with GMail for two years with no difficulty. Yes, took a bit of time to download all the headers form Gmail into Thunderbird, but was worth it.Think about having different email addresses for different contexts/identities. Takes a little time to get used to, but lets you choose how to prioritize your workflow. I have 12 myself.

  40. jose

    Try AOL… it is imap, web based, unlimited, and no colapsing of conversations. Works with iphone and blackberry and probably everything else.

  41. OurielOhayon

    i manage a nearly zero inbox with hundreds of email received per day. it took me some time to set but used rules in Gmail, one at a time. I also use text expander for repeat answers which saves so much time.Gmail should add a killer feature: prioritize emails according to your tracking history. if the email comes from someone you talk a lot with then it should be highlighted and prioritized automaticallyTry mailplane for a desktop gmail client

  42. Robert

    My issue is that all my news ways to connect and interact come with an inbox – Facebook, LinkedIn, Twitter, etc. It gets cool when I can put all this stuff in one place instead of being informed in my inbox that I have a message in another inbox. Why is it that every application eventually has to have an email capability? Stop the madness!

  43. coldspring

    Fred – sent you some thoughts in an email 🙂 I’m here all week…Seriously though, I do IMAP through Outlook / Blackberry and let gmail hit Spam and then check it every now and then. I miss a few emails but they are rarely critical ones. With IMAP, if I hit it on Blackberry then it shows up in my Outlook client.

  44. obscurelyfamous

    I’ve been using Apple with Google Apps mail IMAP for 1.5 years or so now. There are quirks, yes, and many things I don’t like, but overall effective.One of the biggest factors in this was my heavy email use on the iPhone Mail client. I like the Gmail client OK because of the conversations, but it’s not really suited for large volume of mail.

  45. rfreeborn

    First thought – 15GB in outlook is the prime reason for dog-a$$ performance. No matter what MS says, my experience has shown you need to keep all .pst files under 2GB.Fred, you MUST invest at least a little bit of time in your email filters – at least comments from Disqus, etc.As far as email clients – I’m a nerd and willing to try just about anything once. Postbox….not ready for prime time. Thunderbird….ehhh. Outlook….no matter what, there is NO other way to unify your life the way Outlook does – that’s if you are a schedule nerd (both personal and biz are managed through Outlook calendar) and have BB access…..sorry, nothing else is as seamless as Exchange/BES….at least not yet.Yahoo! Zimbra Desktop – testing this out for my offline Gmail account access… far, so good.Lastly, you’ve had a number of “operational” notes here so I figure that I’ll toss in my own. Read this .pdf…I’m guessing the book he wrote is simply an extension of the same ideas, but I haven’t read it yet…In closing – Some bonus for Gmail online – you slowly “unlearn” the concept of filing and start to rely much more on efficient search to get through the day. I’ve been doing it for ~ a year now and only play with desktop clients for my personal mail because I like to….not because I need to.r.

    1. josh

      You could install RT. It is traditionally an “issue tracking” system, but it has a variety of features that you may like, including customization and the ability to collaborate with others, and of course as much automation as Perl hacking allows. You may even find someone willing to host a server for you and do the programming for cheap. You would need to combine RT with spamassassin, etc, of course.

    2. fredwilson

      oyi am a packrat, totally disorganized, and run my life to maximize the amount of serendipity and chaosthat’s how i try to find things that others don’tmy concern is all these approaches, like bit literacy which i’ve read, don’t work for someone like me

  46. Seenator

    Dont worry Fred. Help is on the way.There is a guy called Ev Williams who “been pondering a way to revolutionize email.”…You may want to get in touch with him 🙂

  47. kevinmurphy

    its nice to hear that I am not the only one who uses my email as a sort of filing cabinet (years of emails)- which by the way I am constantly told is the “wrong way” to use email- it works for me, but like you Fred I am vulnerable.I find one lingering question however- How can we walk away when registering on most sites requires an email address?

    1. fredwilson

      i can’t walk awaybut i can let everyone know that email is not the best way to communicate with mei did that with the phone a few years back and now i do very few phone calls where some other form of communication would be preferable

  48. RacerRick

    If you ditch email, you should setup a regular time, via IM or chat or ustream etc, that you can still interact with the people that you don’t know personally.

  49. Aruni S. Gunasegaram

    I know what you mean. I have 3 email accounts and have people send me links to their ‘we will solve all your email problems’ businesses. But all seem too time consuming and even less intuitive than what I do now – Outlook and iPhone. It’s probably because I haven’t really had time to evaluate them. And for some strange reason although I use imap on my phone, the emails don’t delete when I delete them on my phone and then they re-download. I haven’t had time to figure that one out yet.I guess someone needs to invent another form of communication…it’s sometimes just as hard to return voicemails. Texting and twitter are good but not really for the email issue.

  50. bsaitz

    took me a while, but once you get hang of gmail, the keyboard shortcuts and blackberry or iphone client, you won’t look back.

  51. Josh Power

    I use gmail as my effective”” exchange server” — for all Mail. Have pulled all legacy accounts into gmail via smpt and pop. Its searchable and stable for my 100K messages/year for 5 years. I pull down all business and tier-1 personal mail to my mac mail client (super stable for 25K volume/year) and can go back to gmail to search for anything as its a comprehensive archive. perfect. no issues. bit literacy helped in terms of maintainence opex.

  52. Deepak Das

    Well its a bit far fetched, but in the near future, I predict that “email” as we know it will be road-kill. Not that people will stop using it, but a different method of effective inter-personal communication will have to replace the overload associated with existing emails clients and their methods. I see so many people online and even on twitter commenting on email fatigue. Something has to give.Some stats that I have collected from here and there.# 35 Billions emails are sent worldwide everyday. # More than 94% of all emails are spam. (recent NYT article)# On average only 8% of emails in inbox is relevant to your work at hand **# Over 60% of your inbox is either spam or not relevant to the work at hand **** Quoted by Padmashree Warrior (CTO of CSCO) speaking at Voicecon-09 in Orlando recently** She added – Dont set your priorities by your inbox# A recent sudy by Lexis-Nexus showed that over 43% of respondents actually said that email/IM creates information overloadAs much as we found email helpful and productive in its early years, I think it is time for change. People are not leveraging the address book interface for communications effectively. Especially in enterprise where any time wasted sorting through dreaded email gridlock is a drain on productivity. Micro-expression for collaboration lacks certain key features in enhancing productivity. It requires a key facet of goal/task oriented exchange to establish context and relevance. Internal wikis such as those established by some organizations tend to accumulate unnecessary information if not moderated.For a non enterprise user facing the same overload situation, essential communication that is relevant is the exchange between the close inner circle (those in your address book). Using email and other methods to filter out some of the noise manually. For ex; Currently I use hotmail (personal), yahoo (tech related) and gmail (SN related) to keep a handle on the situation and have filters to keep out spam. I know its not the most effective way, but its one way I am managing now. In your case, you already communicate via email and to some extent effectively via your blog & twitter.Note: We never got to finish our conversation that we started about effective communication and the importance of leveraging the address book back in Feb. 🙂

  53. David Cottingham

    Hi Fred,Microsoft Research have two plugins for Outlook:- E-mail prioritizer:… (automatically gives a certain number of stars to each message, adapts if you decide that e-mail from certain people should be more/fewer stars.)- Social Network And Relationship Finder (SNARF):… (again, automatically adapts, separates out list and personal mail, allows more efficient triage.)Of course, neither of these helps with Blackberry use, but I’d go with previous people’s suggestions of using some type of filtering (e.g. GMail labels) to put certain messages into an IMAP folder. Then you tell your BB to look in that folder, rather than synchronising with your entire Inbox. E-mails with a particular GMail label all appear to an IMAP client as being in one folder, hence it should be fairly simple to set up (and the beauty is that everything is in reality still in your central inbox). That’s a halfway house between one inbox for everything, and two separate inboxes (personal and business).Good luck!

  54. Jon Michael Miles

    For me, Email is a failed technology. And thus, an opportunity.As we have no real AI (yet), might I suggest two bio-tech solutions:1. A human — Delegation is important. There are plenty humans out there, and they’re pretty cheap nowadays.2. A prescription for

  55. Prokofy

    I think the key is to have several accounts, a mixture of Yahoo or gmail, Microsoft Outlook, etc. I cease using Outlook because I’m tired of how hard it is to back up the files and then later find them, tired of how easy it is to overwrite your entire email (even computer gurus do this by mistake), tired of everything about it. Yahoo Mail is at least always there and easy.However, I want to redesign email completely, to “email without walls”. Take off all its frames, boxes, folders, etc. And make it into a stream that you then push around on a cloud on your desktop:http://secondthoughts.typep

  56. Greg Solovyev

    The best search capabilities ever in Zimbra Desktop. So far my favorite features of Zimbra Desktop are searching, filtering and calendar… mm… and the fact that I do not have to use Outlook, which I hated for slowness with large mailbox. With Outlook, whenever I had to find an email that is a couple of years old, I felt like turning off my computer and going to do something else. With ZD – it’s a breeze. Really. One drawback – initial sync (or import) and initial indexing of all messages may take some time, but then it becomes pretty robust.

  57. Mukul

    outlook 2007 works like charm on my mailbox of over a GB

  58. Daniel Odio

    Fred, I also manage copious amounts of email. Mac Mail via hosted IMAP w/ Google Apps was growing unstable at my level of usage – about 50 gigs for the email package alone.My solution, which has worked very well, was to put all email older than 18 months in a specific folder and instruct Google to not synchronize that folder with my mail client (this “non synching” is possible via a new Google Labs feature).When I have to find an email that’s older than 18 months, I’m able to log in to my branded gmail interface to find it, but it’s very much worth the trade-off of a smoothly functioning Mac Mail interface.On a somewhat related note, I’ve hooked Google Voice into my iPhone voicemail. Here’s a video on how I did that:,DROdio

  59. Stephen Bates

    Fred, I haven’t read all the comments here, but the bottom line is Gmail is the way to go.The way to power through Gmail is to master the keyboard shortcuts, label things, and archive them. Use filters to auto-archive less than time sensitive emails, when you can go through them at your leisure.Unsubscribe from any informative newsletters, etc..and use Google Reader and RSS (again, keyboard shortcuts)Install Google Gears for off-line access.

  60. Jim

    Fred — I have read “Take Back Your LIfe” which is book/toolset with techniques to get through email easier. It’s not a total solution, but if you can scan the book, you might find 5-10 things that you can adopt. I took the class and read the book and adopted about 1/3 of it in processing email.Good luck — lots of great ideas from your readers in this forum!

  61. tamccann

    I used to work on the Exchange team at MSFT and have been a long-time user of Outlook. I have tons of shortcuts, rules and strategies on dealing with email inside Outlook. When we started Gist, we started using Gmail as our mail system, so I have been using the Gmail interface more recently and liking it, especially all the keyboard shortcuts which make it incredibly fast to “process” mail. Yes, conversations take a bit of getting used to, but that it the way Exchange and Outlook are going as well with the new versions… (my brother designed most of it for Exchange), as it is more efficient ultimately to keep the key stuff in view.We are Gist ( are also trying to tackle some of these issues with federating messages from multiple places (email and twitter) as well as providing some smarts on “priority”. While we have not set out to build a new email client just yet, we are working on the problem space on helping you control to flow of information and making it more actionable.

    1. fredwilson

      I sure hope gist can help me. I’ve got the invite. Thanks!

  62. Michael Grant

    Fred,Another idea. Here’s what worked for me (also on a Mac):- Use Apple linked to your gmail IMAP account. I find it works flawlessly.- Once every 3 months I archive all my mail for that Qtr using Mail Steward. MS is a fantastic email archiving program on the mac built on a embedded SQL database. Whenever I need to search past email, I just launch MS and search away! Also handles indexing attachments etc.- For dealing with current email, I simply set up a master ‘Mail Archive’ folder that sits within my gmail account. Once I read an email, I either 1) immediately archive it to the Mail Archive folder using drag and drop, or 2) I tag it using Mailtags (a plug-in for Mailtags really couldn’t be easier to use and if you keep your tagging VERY SIMPLE, you don’t get hung up by the process.- Running Outlook in a VM and having your mail locked in a .PST file seems crazy to me.Check out: Mail Steward & Mailtags. They are your friend. ;-)-m

    1. fredwilson

      This is where I’m headed. Outlook in a vm failed me

      1. Michael Grant

        I should have added that I use’s smart folders to group mailtags tagged messages instead of creating some byzantine organizing folder structure that requires a lot of discipline to keep up with. I have created a VERY simple tagging system that actually works for me. Having tried more involved systems, I often found the process getting in the way. My tags involve projects I’m working on (could be deals or portfolio companies for you) and then simple priority tags such as ‘Action’, ‘Waiting On’, ‘Delegated’. The nice thing about Mailtags is that it is VERY fast and doesn’t get in the way. It also maintains tags across machines if you need to check your IMAP mail from another Mac. Finally, Mail Steward supports indexing Mailtags so that you can search your archived mail by tag as well as other criteria.I’ve tried a lot of systems and I know that some people swear by just using the gmail web app since it supports many tagging type things as well. But I find to be the right combination of simplicity, features, and OS integration. Mail Steward saved me as I was doing my archiving by exporting to .mbox – a standard mail interchange archiving format – but unable to adequately search my archives.Not sure if you are aware of it but Merlin Mann has a nice ‘Inbox Zero’ article over at That might help as well.-m

        1. fredwilson

          I’m headed to gmail/imap and so this is a good tipthanks

          1. Michael Grant

            Sorry Fred, one more thing, and it was a BIG one for me. I don’t particularly like’s window layout for reading mail with the mail message below the message list. I MUCH prefer the Outlook style of the message list parallel to the actual message text. With a landscape monitor, this gives you the ability to use more screen real estate effectively and to see more of the message. Also critical for composing long messages in my opinion. How do you get this in Meet your other new friend:…Hope this completes your initial training young grasshopper. Feel free to email me directly if you need any advise or help with your setup.-m

          2. fredwilson


          3. NICCAI

            You might be interested in this article then:Achieving Email Bliss with IMAP, Gmail, and Apple Mail

          4. fredwilson

            I’ve moved to gmail’s web app and after a couple weeks and learning the shortcuts I’m starting to like it

          5. fredwilson

            I’ve moved to gmail’s web app and after a couple weeks and learning the shortcuts I’m starting to like it

          6. fredwilson

            I’ve moved to gmail’s web app and after a couple weeks and learning the shortcuts I’m starting to like it

    2. Mark Essel

      Thanks Michael, I’m guessing the future…The iPhone 4G will run full mac software and this type of setup will be standard (and brilliant). Found this comment from following Fred’s friendfeed btw, good stuff (I missed the original post/comments)

      1. Michael Grant

        Mark,Let’s hope for some improvements to the iPhone’s mail app. I find it to be frustrating with no search capabilities. Given the richness of the underlying platform OS, I suspect Apple has a real opportunity to take on the Blackberry for the mantle of ‘best mobile email’, but they have yet to get there in my opinion. The coming 3.0 landscape keyboard will be very welcome. And while they are at it, Apple needs to improve the calendar services on the iPhone. Not being able to deal with meeting invites is a big problem. Again, I think 3.0 addresses this along with a bunch of other things that have been missing.I’ll be surprised in the 4G phone will run mac software however. I think Apple is keeping the brands separate.-m

        1. Mark Essel

          I’m retraining myself to believe in a future full of the marvels of technology, driven by competition to provide incredible consumer satisfaction, contrary to what my pessimism predicts. I’m convinced this is one of the secrets to success: continual positive thinking in the face of current limitations 😉

  63. Adrian Palacios

    Just for the benefit of anyone who stumbles into this comments section after the fact: Gmail announced a rollout of a tool that makes it easier to import contacts/emails from other accounts http://gmailblog.blogspot.c