The Toxic Nature of Email

Posted on May 11, 2010 | 248 comments


I haven’t written a blog post in a week.  I travelled for a couple of days for work and decided to get some sleep on those days rather than staying up into the wee hours as I often do when I travel.  I closed one deal (I’ll talk about that soon) and issued one term sheet (I hope to talk about that soon, we’ll see!).  It has also coincided with the kickoff of our Launchpad LA educational series which has taken some of my time.

But what has really killed me is email.  I live in email hell.  And for the last few evenings I decided to get through email rather than blog.  I’m always so completely behind on email.  I have a love / hate relationship with email.  Actually, mostly hate.  Email is a chore.  I’d much rather spend time conversing with people in a lighter weight venue.  I’ve always been a big fan of IM (instant messaging) which is why Twitter has been so appealing to me.  I love the restriction in terms of message size.  And I find that platforms like Twitter, IM and even Facebook carry much less “obligation” to them.  People expect too much when they email you. Your email is your recipients social obligation.

I email people – don’t get me wrong.  It’s just that the whole email system seems to be out of balance.  I’ve written about the topic before when I wrote the post “I emailed a VC but never heard back.”  As in, what do you do now that you’ve written them.  Should you bug them?  Is it normal to not hear back?  Are all VC’s just a-hole’s?  If you’re interested in that topic have a read of my previous post.

It was interesting for me to read Fred Wilson’s email bankruptcy blog post this morning.  I think I’m permanently bankrupt on email with no solution.  I don’t think any GTD method will work.  My volume is simply too big to handle.  It’s like spaghetti – the more I process the more it seems there is.  I’ve talked with a lot of VCs about this and all said the same thing, “we simply don’t get through it all.  There’s no way to.”  Actually, there is a way.  If I never spent time with my wife & kids, which I’m not willing to do.

When I read Fred’s post it resonated for two reasons: 1. He ends up spending personal time trying to get through email.  This is my life, too.  And probably yours.  We all want to be responsive  people.  2. He makes in clear in his responses in the comments section that he wants to review the email directly himself where many people recommended an assistant read through it.  I think we both feel we want to be accessible to people.  Not all VC’s feel this way in my experience.  Some love the filter.  In my mind that’s OK for some people.  It preserves more of their scarce time to deal with the people and companies with whom they want to interact.  I’m on the side of wanting to be more accessible.  It’s who I am.

But here’s the problem:

1. Anyone and everyone can email you.  When email nomenclatures are obvious you’d be surprised how many people feel entitled to just email you.  It’s not just the spammers or marketers trying to sell you products or services.  I understand that.  But it’s the person at undergrad who has a project in entrepreneurship and just wants your quick comments on their project.  Really.  I get those more often than you think.  And when I have time I try to write back.  Often I just can’t.  It’s the alum from University of Chicago who realizes I got my MBA there and feels a sense of kinship.  It’s the entrepreneur who’s buddy is a lawyer who wants an intro to you and who doesn’t think about whether it makes sense to ask you whether you want an intro before sending it.  It’s all of these things accumulated that adds up to such a huge mass.  And that’s in addition to portfolio companies, colleagues at work and legitimate deals you’re working on.  It’s just too much cumulatively.

2. The sheer volume / math doesn’t work. If you think of it this way.  Let’s assume I get 200 emails today.  Let’s say I can delete 100 as unsolicited with just 5 seconds work / email.  Then 30 are ones I can read quickly and delete or store (I only use one folder – “storage”) with no actions.  Each of these takes 1 minute.  Let’s say 30 are these sort of “unsolicited” emails that have some expected action associated with them.  Let’s call these “optional” and if I get time they take 2 minutes each to read and respond.  And then there are 30 “real” emails for which I really should read, process and come up with a sensible response.  Let’s call these 3 minute emails.  And the last 10 are the “big effort” emails.  They’re from lawyers or CEO’s requiring analysis before a response.  Let’s call these 10 minutes on average.

So that’s:

Marketing / conference invitations – 100 x 5 seconds = That’s still > 8 minutes.  Let’s say I read the text on 2 of them so round up to 10 minutes for “marketing junk” email

30 x 1 minute = 30 minutes for “read and store” email

30 x 3 minutes = 1 hour, 30 minutes of “real” email

10 x 10 minutes = 1 hour, 40 minutes of “big effort” email

30 x 2 minutes = 1 hour of “optional” email

==> 3 hours, 40 minutes of email / day plus 1 hour of “optional” email.  Let’s call it 4 hours.  Who has 4 hours / day to process email?  Let’s assume that I’m super efficient and can process these in 2 hours?  Many days I have a breakfast meeting, back-to-back meetings all day and then an evening event.  Or I’m at BOD meetings or conferences.  I can normally “just about” manage my emails until I pile up 2 days traveling and then I have a crazy email traffic jam.  If it’s more than 3 weeks old it’s unlikely that I’ll ever see it unless I search on it later (which is why I’ve started using X1 a lot more).

3. People who email you expect a response. Let’s face it.  In the old days if you wrote people a physical letter, first it was a big effort to actually write and send the letter.  So many things were filtered out.  But second I think there wasn’t an expectation that people would write you back.  Now everybody expects a response.  Based on the email math problem this just isn’t realistic for many people.

4. I WANT to be responsive and open. I really do want to get back to everybody who writes to me.  Sometimes I find myself trying to help the college student with a quick response.  Sometimes I do offer that University of Chicago person some quick advice.  So it really pains me that some people write me and I don’t write back.  I don’t want to be “that guy” who doesn’t respond to emails so people think that I think I’m above it all.  I’m not.  I sometimes dread going to conferences where I know people will walk up to me and say, “I send you an email a few weeks ago” and I’m struggling to remember it.  I have at least read or skimmed most of them.  But not always.

5. Social networks exacerbate the problem. People now write me on Facebook, Twitter and LinkedIn.  Luckily I haven’t signed up to Formspring and don’t spend time on Quora.  I actually tell some people to write me on Twitter.  Given that it’s constrained to 140 characters it’s easier to process.  But there isn’t a permanent record or any way to “mark something as read” so some stuff falls through the cracks.

6. Blog comments. Why don’t you just blog less or not respond to everyone’s comments? I do get that sometimes from people.  If I did that then I’d be letting email make me hostage to other people’s agendas.  I enjoy the creative outlet of blogging and being able to build relationships with people in a lightweight way that often lead to in person meetings or phone calls down the line where appropriate.

Anyway, so for now I have to live with occasionally not living up to other people’s expectations.  And to telling people to bug me multiple times if I haven’t responded to an email that they deemed as important.  If that’s you – I apologize now, in advance.  I’m willing to accept that I’ll never be a black belt in email.

  • http://bothsidesofthetable.com msuster

    Yes, the problem goes well beyond VCs. It's pervasive. I wonder if the cultural norms need to change more than the technology.

  • http://bothsidesofthetable.com msuster

    Yes, the problem goes well beyond VCs. It's pervasive. I wonder if the cultural norms need to change more than the technology.

  • http://bothsidesofthetable.com msuster

    Ha! That's because you probably get 50 alone from me / day!

  • http://bothsidesofthetable.com msuster

    Ha! That's because you probably get 50 alone from me / day!

  • http://bothsidesofthetable.com msuster

    Outlook for work and gmail for personal / semi-work.

  • http://bothsidesofthetable.com msuster

    Outlook for work and gmail for personal / semi-work.

  • http://bothsidesofthetable.com msuster

    Wouldn't that be nice! ;-)

  • http://bothsidesofthetable.com msuster

    Wouldn't that be nice! ;-)

  • http://bothsidesofthetable.com msuster

    I enjoy my life perfectly as it is and have hobbies. That's the point. If I answered every email I wouldn't!

  • http://bothsidesofthetable.com msuster

    I enjoy my life perfectly as it is and have hobbies. That's the point. If I answered every email I wouldn't!

  • http://bothsidesofthetable.com msuster

    When I first started the blog I said exactly that. I felt I was having one-on-one advice sessions all the time and thought if I published them I could have one-to-many conversations.

    Also, a reader pointed me to this article from Jeremiah Owyang that says it well. “Pay yourself first” http://www.web-strategist.com/blog/2007/07/06/p

  • http://bothsidesofthetable.com msuster

    When I first started the blog I said exactly that. I felt I was having one-on-one advice sessions all the time and thought if I published them I could have one-to-many conversations.

    Also, a reader pointed me to this article from Jeremiah Owyang that says it well. “Pay yourself first” http://www.web-strategist.com/blog/2007/07/06/p

  • http://www.echosign.com Jason M. Lemkin

    Just do what other Important People do – hire 1-3 people to read your email for you, respond to most, then print out the key ones in a nice, tidy stack for you to read.

  • http://www.echosign.com Jason M. Lemkin

    Just do what other Important People do – hire 1-3 people to read your email for you, respond to most, then print out the key ones in a nice, tidy stack for you to read.

  • http://bothsidesofthetable.com msuster

    LOL. I'm sure some senior execs in “industry” still work this way.

  • http://bothsidesofthetable.com msuster

    LOL. I'm sure some senior execs in “industry” still work this way.

  • http://www.venturevoice.com gregory

    Why not go full Gmail for your domain? I spent two days switching from Outlook to Gmail last summer for my work email and it's been great. Taking back the two second delay Outlook has in filing messages, not to mention the time of searching for emails, makes a big difference. You might still be bankrupt, but perhaps not so deeply in debt.

  • http://www.venturevoice.com gregory

    Why not go full Gmail for your domain? I spent two days switching from Outlook to Gmail last summer for my work email and it's been great. Taking back the two second delay Outlook has in filing messages, not to mention the time of searching for emails, makes a big difference. You might still be bankrupt, but perhaps not so deeply in debt.

  • http://sisyph.us/ ErikSchwartz

    It's really a no win situation for you guys.

    Even if you do something sensible like filter via closeness (using twitter or linkedin or disqus) there's still going to be someone out there who never hears back from you and publicly complains.

  • http://sisyph.us/ ErikSchwartz

    It's really a no win situation for you guys.

    Even if you do something sensible like filter via closeness (using twitter or linkedin or disqus) there's still going to be someone out there who never hears back from you and publicly complains.

  • http://shanacarp.com/essays ShanaC

    I’m under 30, I still use email. I’m tempted to junk it except for real people that i want to talk to, because I find it harder to use it for that very purpose every day….

    I find the best medium, and the one I grew up with-
    Chat
    and now
    Video Chat.

    Amen.

  • Philippe Cases

    Makes perfect sense. We are still a one trick poney in the sense that we are spending most of our time texting and emailing. We should learn other approaches: comments on blogs,….. that are more one to many, updates and put less pressure on the reader.

  • Philippe Cases

    Makes perfect sense. We are still a one trick poney in the sense that we are spending most of our time texting and emailing. We should learn other approaches: comments on blogs,….. that are more one to many, updates and put less pressure on the reader.

  • Philippe Cases

    I agree. We are still one trick poney in the sense we are using emails. With text and Twitter, we are learning to be more succinct and send updates, hopefully, this will help.

  • Philippe Cases

    I agree. We are still one trick poney in the sense we are using emails. With text and Twitter, we are learning to be more succinct and send updates, hopefully, this will help.

  • http://jpm.cc/ Jose Paul Martin

    Dylan, this is infact something I was toying around with… read the post: http://jpm.cc/kill-spam-junk-email-and-informat

  • http://jpm.cc/ Jose Paul Martin

    Dylan, this is infact something I was toying around with… read the post: http://jpm.cc/kill-spam-junk-email-and-informat

  • http://jpm.cc/ Jose Paul Martin

    Imagine the amount of money that could be made! (especially for those handling 800 to 1000 emails a day!!! Time is certainly money. Let's respect that fact.

  • http://jpm.cc/ Jose Paul Martin

    Imagine the amount of money that could be made! (especially for those handling 800 to 1000 emails a day!!! Time is certainly money. Let's respect that fact.

  • http://jpm.cc/ Jose Paul Martin

    or checking both… defeats the purpose.

  • http://jpm.cc/ Jose Paul Martin

    or checking both… defeats the purpose.

  • http://twitter.com/nemra nemra

    Sorry for commenting 3 days later. Had lot's of meetings and then spent all the time on cleaning up my email inbox :) It is really toxic…

    Small solution to the problem, which can be added to any email, IM, social chat: a piece of software, that will group / order emails by priority / answer expectations / trust. Consider usage scenario:

    1. Anybody who send's email, might specify when he/she expects an answer (options: ASAP, in few hours, in a day, in a week, etc…). This requires additional field to the email/message, filled with default value.
    2. Inbox automatically groups emails by expected answer time so you can view IN A WEEK folder later. Each day emails can move between folders, thus indicating that it is time to answer.
    3. Since some people could consider always putting ASAP in any email they send, receiver could manually change expectation time. The system will automatically collect all that “changes” info and next time ignore ASAP message from those people or mark them for later answer. Simple “learning” system, based on the receivers input. The opposite also works, important people's emails will be in ASAP folder, once I made system to learn that.
    4. Messages inside groups can be grouped by preferences, for instance short emails first. Other options might also apply, like extracting some “tags” and auto-grouping by topics.

    Bottom line its time for some kind of smart assistant, but in can be really a small addition to current systems with minimal effort. I will implement it in our chat/messages later, will see how useful it might be :)

  • http://twitter.com/nemra nemra

    Sorry for commenting 3 days later. Had lot's of meetings and then spent all the time on cleaning up my email inbox :) It is really toxic…

    Small solution to the problem, which can be added to any email, IM, social chat: a piece of software, that will group / order emails by priority / answer expectations / trust. Consider usage scenario:

    1. Anybody who send's email, might specify when he/she expects an answer (options: ASAP, in few hours, in a day, in a week, etc…). This requires additional field to the email/message, filled with default value.
    2. Inbox automatically groups emails by expected answer time so you can view IN A WEEK folder later. Each day emails can move between folders, thus indicating that it is time to answer.
    3. Since some people could consider always putting ASAP in any email they send, receiver could manually change expectation time. The system will automatically collect all that “changes” info and next time ignore ASAP message from those people or mark them for later answer. Simple “learning” system, based on the receivers input. The opposite also works, important people's emails will be in ASAP folder, once I made system to learn that.
    4. Messages inside groups can be grouped by preferences, for instance short emails first. Other options might also apply, like extracting some “tags” and auto-grouping by topics.

    Bottom line its time for some kind of smart assistant, but in can be really a small addition to current systems with minimal effort. I will implement it in our chat/messages later, will see how useful it might be :)

  • http://twitter.com/vrevzin Vadim Revzin

    Hi Mark,

    Huge fan of your blog. Also recently saw you in TWiVC and just love how much helpful/valuable content you're able to pump out.

    In response to this post: In your previous entry on the topic you mentioned that you try to convert “incoming emails to “to do’s” rather than leaving them the in-box.” I agree that this is a super effective way to clean up your email and am actually doing some work for a startup that tackles that problem specifically. Right now the tool (Boomerang) works in Outlook but work is underway for a gmail firefox plugin as well. You can check it out at http://www.baydin.com/boomerang

    I'm confident that email will become much more manageable as technology gets smarter but for a lot of folks a simple tool that helps you stay organized can go a long way.

  • http://twitter.com/vrevzin Vadim Revzin

    Hi Mark,

    Huge fan of your blog. Also recently saw you in TWiVC and just love how much helpful/valuable content you're able to pump out.

    In response to this post: In your previous entry on the topic you mentioned that you try to convert “incoming emails to “to do’s” rather than leaving them the in-box.” I agree that this is a super effective way to clean up your email and am actually doing some work for a startup that tackles that problem specifically. Right now the tool (Boomerang) works in Outlook but work is underway for a gmail firefox plugin as well. You can check it out at http://www.baydin.com/boomerang

    I'm confident that email will become much more manageable as technology gets smarter but for a lot of folks a simple tool that helps you stay organized can go a long way.

  • http://blog.dylansalisbury.com/ Dylan Salisbury

    Cool! I think it would have to be implemented with an entrepreneurial opt-in solution instead of forcing a carrier charge. People could 'federate' and let anyone they want onto their free list. For example:

    So an average person sets her inbox price to $0.25, lets her 50 most frequent contacts and some mailing lists in for free. The economics of spam are totally gone, and if somebody else wants to reach her, it only costs a quarter. And if you're a friend she'll probably add you to her 'free' list after that.

    A tech celebrity or a well-known VC sets his price at $5 and donates everything to charity. It gets a lot of buzz and his contacts are quoted saying they have no problem getting in touch with her and she seems to be more focused recently.

  • http://blog.dylansalisbury.com/ Dylan Salisbury

    Cool! I think it would have to be implemented with an entrepreneurial opt-in solution instead of forcing a carrier charge. People could 'federate' and let anyone they want onto their free list. For example:

    So an average person sets her inbox price to $0.25, lets her 50 most frequent contacts and some mailing lists in for free. The economics of spam are totally gone, and if somebody else wants to reach her, it only costs a quarter. And if you're a friend she'll probably add you to her 'free' list after that.

    A tech celebrity or a well-known VC sets his price at $5 and donates everything to charity. It gets a lot of buzz and his contacts are quoted saying they have no problem getting in touch with her and she seems to be more focused recently.

  • http://jpm.cc/ Jose Paul Martin

    Bingo! I can already hear the tills ringing!

  • http://jpm.cc/ Jose Paul Martin

    Bingo! I can already hear the tills ringing!

  • http://facebook.com/lane.rapp lanerapp

    I feel better about staying in and reading my screen. thanks.

  • http://facebook.com/lane.rapp lanerapp

    I feel better about staying in and reading my screen. thanks.

  • http://www.blitzlocal.com dennisyu

    I LOVE email– it creates a paper trail and forces you to think in an action-oriented “what's next” sort of way, if done properly. For me, email is like writing code– it requires precision, as opposed to meetings that can go on forever with no action resulting.

  • http://www.blitzlocal.com dennisyu

    I LOVE email– it creates a paper trail and forces you to think in an action-oriented “what's next” sort of way, if done properly. For me, email is like writing code– it requires precision, as opposed to meetings that can go on forever with no action resulting.

  • http://sharelomer.blogspot.com SharelOmer

    Dear Mark,

    I can relate to your pain, and to the pain Fred is raising, and it hurts me to read it…

    We have a social relationship, and from time to time you respond to some “Seek advice” mails i send, and i want to encourage you, and tell you that it does make a difference, and a big one!

    Your blog and mail inspired me to do great things, learn grow and seek my vision. since i live in Israel i am not connected to the changes in the state of mind of the industry, but i have a vision i have an ability to execute, and with your posts, accumulated wisdom and helping tips we are getting close to making a dream a reality.

    I want to encourage you to keep on writing, and answering mails when you can, since it really make a difference in people life, state of mind and approach, for example your post of JFDI or Entrepreneur DNA or “most-common-early-start-up-mistakes” are post which are writeen with blood, i knwo that i personally avoided many mistakes thanks to it, and adopted the approch of JFDI as a way of doing things.

    I see you as a person who is really passionate about helping and mentoring others, and I want to encouraging you to keep on writing, keep on replying to emails and inspire others to make a difference in the world, i know it can be a pain, but i hope that seeing the fruit of your labor can encourage you :)

    Thank you for all,
    Sharel

  • http://sharelomer.blogspot.com SharelOmer

    like it, i also use mail as my own to do list… :)

  • http://sharelomer.blogspot.com SharelOmer

    Dear Mark,

    I can relate to your pain, and to the pain Fred is raising, and it hurts me to read it…

    We have a social relationship, and from time to time you respond to some “Seek advice” mails i send, and i want to encourage you, and tell you that it does make a difference, and a big one!

    Your blog and mail inspired me to do great things, learn grow and seek my vision. since i live in Israel i am not connected to the changes in the state of mind of the industry, but i have a vision i have an ability to execute, and with your posts, accumulated wisdom and helping tips we are getting close to making a dream a reality.

    I want to encourage you to keep on writing, and answering mails when you can, since it really make a difference in people life, state of mind and approach, for example your post of JFDI or Entrepreneur DNA or “most-common-early-start-up-mistakes” are post which are writeen with blood, i knwo that i personally avoided many mistakes thanks to it, and adopted the approch of JFDI as a way of doing things.

    I see you as a person who is really passionate about helping and mentoring others, and I want to encouraging you to keep on writing, keep on replying to emails and inspire others to make a difference in the world, i know it can be a pain, but i hope that seeing the fruit of your labor can encourage you :)

    Thank you for all,
    Sharel

  • http://sharelomer.blogspot.com SharelOmer

    Dear Mark,

    I can relate to your pain, and to the pain Fred is raising, and it hurts me to read it…

    We have a social relationship, and from time to time you respond to some “Seek advice” mails i send, and i want to encourage you, and tell you that it does make a difference, and a big one!

    Your blog and mail inspired me to do great things, learn grow and seek my vision. since i live in Israel i am not connected to the changes in the state of mind of the industry, but i have a vision i have an ability to execute, and with your posts, accumulated wisdom and helping tips we are getting close to making a dream a reality.

    I want to encourage you to keep on writing, and answering mails when you can, since it really make a difference in people life, state of mind and approach, for example your post of JFDI or Entrepreneur DNA or “most-common-early-start-up-mistakes” are post which are writeen with blood, i knwo that i personally avoided many mistakes thanks to it, and adopted the approch of JFDI as a way of doing things.

    I see you as a person who is really passionate about helping and mentoring others, and I want to encouraging you to keep on writing, keep on replying to emails and inspire others to make a difference in the world, i know it can be a pain, but i hope that seeing the fruit of your labor can encourage you :)

    Thank you for all,
    Sharel

  • Mazmazi911

    hey,do you also invest in Europe?(germany)