Retaining vs Deleting Emails

Conventional wisdom is that deleting old emails regularly is the best way to avoid issues down the road.

My experience has been different.

I’ve been involved in a few legal matters over the years where email discovery has been done.

Going back and re-reading emails you sent years ago is a pretty enlightening experience.

What I have found is if you have the right intentions and act reasonably and responsibly, old emails often show that to everyone and can be valuable.

Being able to go back over old emails is also a great way to jog a foggy memory.

So while I understand the challenges with having a lot of written and discoverable emails “on file”, I would argue they they often can be quite valuable.

#life lessons

Comments (Archived):

  1. Michael Weiksner

    It’s also really hard to truly delete emails. Think about the Patreaus scandal. He and his mistress shared a gmail account, and sent messages in draft emails that they then deleted. They were still caught:…By deleting the drafts, he did not prevent the prosecutors from gaining access. But he did rob himself the chance to refresh his memory beforehand about what might be discovered.Sadly, you basically have to assume that you are living your digital life completely naked.

    1. jason wright

      i’ve often wondered if web email services are capable of retaining typed text not saved or sent, as a real time capture. i wonder if agencies of government have that technical capability?

      1. Michael Weiksner

        I think that the government needed Google’s cooperation. However, they *might* be able to do it if he was using a government computer with key logging enabled.

      2. Lawrence Brass

        In that line of thought I’ve wondered if an unsent email that is auto-saved as a draft has any legal value or meaning.

    2. LE

      Think about the Patreaus scandal.The vast majority of crimes (or civil actions for sure) in everyday life do not rise to the level of ‘search for OJ’s murder weapon in the garbage dump’. As such what happens in a major case with a large amount of scrutiny would typically bare no resemblance to what is done in a civil case or even a lesser known criminal case. As a broad generalization.Noting this in the Petraus case in particular:According to the Wall Street Journal, the original red flag that caught the FBI’s ear was a series of anonymous, threatening emails sent to Jill Kelley, a Florida woman who organized military social events. The FBI then traced those threatening emails to their origin—probably with an IP address given up by Google—to Paula Broadwell. The FBI then got a warrant to monitor those email addresses, and eventually stumbled upon another email account where Petraeus and Broadwell left drafts of messages for each other

      1. Michael Weiksner

        Perhaps. But the trend is for this kind of forensic analysis to get radically cheaper over time. This exceptional case today can easily become the normal one in 5-10 years.

        1. LE

          This is correct however there are and will be protections in place which should prevent that type of forensic analysis being used unless there access is granted by court order.For example cars have for years had devices that log your speed and actions (g forces) as well as where you are driving which is logged by other devices which you have. But it is not available to authorities who are merely on a fishing expedition. So the cost (or technology) is not the factor at all. It is cheap and it is easily available but it is not accessible. Or take Ezpass. It definitely knows when you are speeding and can easily compute that by the time it takes you to pass between two toll readers. But nobody has ever been issued a ticket for speeding that way. Tech is not the reason it’s not done. God knows they could enforce traffic laws by using that, right?In the case of Petreaus (at least by the story I have highlighted) someone sent a series of anonymous threatening emails. So the bigger point is that you don’t have control over what anyone else does that may come back to haunt you in some way by simply being associated with them. That is really the danger (as opposed to forensics).

  2. LIAD

    “It’s better to have a gun and not need it than to need a gun and not have it” – Clarence Worley, True Romance.Find_All: Gun. Replace_With: Email

  3. Richard Reisman

    I agree completely. I was involved in three major patent litigations (as inventor), and having that record served me well (even if it added to the discovery work). It is a great aid to memory, and excellent proof of integrity.

  4. Petri Aukia

    On a related thought, I’ve come to find that sending a quick email to document verbal agreements has saved my bacon on multiple occasions. It has also made it very clear that some people I’ve worked with have preferred the fuzziness of verbal agreements and the leeway that gives the party more willing to haggle.Always email confirm your important verbal agreements.

    1. PhilipSugar

      No, always write them down and sign them.

      1. Petri Aukia

        That would depend on your jurisdiction. In many jurisdictions unsigned emails are just as valid as statements of intent as printed, paper based documents are. Obviously, if you are living in an area, where emails are insufficient. you need to print more stuff.

        1. Vasudev Ram

          >That would depend on your jurisdiction. In many jurisdictions unsigned emails are just as valid as statements of intent as printed, paper based documents are.Interesting. I had read something along these lines a while ago, that emails are considered legal evidence.

        2. PhilipSugar

          I can assure you I can make another email to your response. Not a good idea.

          1. Petri Aukia

            You are right, no question about it: signed pieces of paper are good if you deal with potential criminals.Email is good, if you deal with people, who do not commit fraud intentionally, but have a tendency of remembering only the details that suit them, either intentionally or unintentionally.I’ve never had to deal with contract fraud in my ≈30 years in business and forcing everyone sign all change orders would have been an expensive endeavor.

          2. PhilipSugar

            My point is this. If you deal with a potential criminal it doesn’t matter if you have an agreement signed and notarized with the best attorneys. They don’t care.How much extra time does it take to say sign this or I suppose even respond: “I agree and understand this is the final agreement”, then store it in a file system. And the first one is an acknowledgement that email is not a commitment system, here is how we make commitments.I will guarantee you this: infinitely less than for all of those combined than one, well: I know you sent that email I sent this one and going back and forth through a giant search. Lawyers love doing that at $600/hr.And BTW: Lawyers are like nuclear weapons, I have mine you have yours, if either of us uses them we are both screwed.It is so easy. If it is small and you don’t care? Well you don’t care. But we are talking going to the mattresses here.

  5. William Mougayar

    Indeed. Searching old and recent emails is very rewarding.I wished I could go back to ones dating from 1995 to 2000.

  6. Josh Goldberg

    Great note. As a former lawyer now entrepreneur, it’s also a good reminder to folks to make sure that when sending emails, we all think about how we would feel if that email came up in discovery or showed up in the Washington Post. Emails are easy to send, but often live forever.

    1. creative group

      Josh Goldberg:It appears that there are applications that allow a person to set a time to delete emails sent. Wonder if those emails can ever be retrieved.Captain Obvious!#UNEQUIVOCALLYUNAPOLOGETICALLYINDEPENDENT

    2. jason wright

      i’d be delighted. you just can’t buy that volume of publicity.

    3. LE

      we all think about how we would feel if that email came up in discovery or showed up in the Washington PostWashington Post? Understand how you are using an outlier to make a point but that is a bit extreme The extra overhead required to make an email conform to possible disclosure in a public newspaper could be enough to remove the benefit of sending emails. After all why not just not send emails at all?Sure you should be careful what you write. But if you want to remove all risk in life you should also not fly in airplanes or drive cars or for that matter exceed the speed limit and so on.For that matter Fred has a risk by writing a blog everyday which is public and in theory could be used against him at a later date.On the other hand maybe I am underestimating the lack of common sense in the people who would need to be reminded to simply be careful about what they write.Separately what holds up in a court of law (in an email) and what shows well in a NY Post story are two entirely different things.

    4. awaldstein

      Good rule.The most careful of us, the most seemingly benign email taking out of context is damning.Context is everything

    5. Vasudev Ram

      > if that email came up in discoverySince discovery (a legal term) [1] was mentioned, thought I’d just say that xtopdf [2], my Python toollkit for PDF generation from other formats, was (maybe still is) used for e-discovery by the Software Freedom Law Center, USA. I got an email from a lawyer/programmer who worked there, saying so, some time ago.[1]…[2]… – xtopdf overview… – xtopdf project

  7. Guy Lepage

    I have a similar experience as well Fred. I feel those with something to hide lean toward the deletion path. Those who do their best to be as transparent and ethical as possible should have very little to hide.

  8. creative group

    CONTRIBUTORS:A thought on retaining and deleting. The platform we use is very important and value based depending on our usage.This brings us to the trust we provide to the platform we use. Evernote was a incredible tool that we used. We migrated everything to Google Keep. That appears to have been a great decision. Most of Evernote executives have left and it appears to be a matter of time before those doors close.Captain Obvious!#UNEQUIVOCALLYUNAPOLOGETICALLYINDEPENDENT

  9. Jeremy Shatan

    In my business (nonprofit fundraising), each year often follows a similar cycle. For that reason, I save (almost) EVERY email so when that thing we did last year that we’re going to do again this year (only if it was successful, of course!) comes around, I can simply search for those emails and set the whole thing in motion again. It’s also easier in my work flow to simply file the email away than to take time to consider whether I’ll need it in the future. I can’t tell you how many times this practice has saved me time and effort – and made me look like a hero to those colleagues of mine who delete too many of their emails!

  10. Ravi Kurumety

    There are multiple facets to this. I agree with what’s been said about the benefits of keeping the emails especially for those that live life with right intentions. The biggest concern I see though is in regards to security. My emails tend to have sensitive information that has been communicated with accountants, business partners, legal advisors, etc. This accumulates over time. All of this is exposed if someone breaches the email security and gains access to my emails.

  11. Pointsandfigures

    had a ceo that told me they never delete an email. his company won a treble damages case recently. wonder if this came into play.

  12. jason wright

    it’s about having a ‘nose’ for which emails are going to be worth keeping, which is mostly about the economic value of the subject matter.i recall having a legal dispute over a domain name. i made a Freedom of Information (FOI) request for copies of emails sent by the other party to a public agency. the copies included sections of text redacted using a black ink marker pen. these were the critical sections of text. using a technique i will not bore you with i was able to ‘penetrate’ the blackness and read the text. i won.emails can be very important. cultivate that nose.

  13. LE

    Personally though I have won many battles by having the most complete set of information and documentation vs. an opponent (company or individual) who is in no way as well prepared to dispute my claims. I have always found that having more information gives you more power and leads to getting what you want. But I also don’t think this applies to everyone as not everyone is as skilled in the practice of retention of documents (whether email or printed).

  14. LE

    Conventional wisdom is that deleting old emails regularly is the best way to avoid issues down the road.However the question is what is the best policy for a company where others may not be as skillful in writing the emails that are to be discovered or may be used? That is why it’s ‘conventional’ wisdom. It’s ‘wisdom’ that is meant to apply broadly to a wide range of people that have different skills and competence. What I am wondering is what should be done with other employees at USV or companies that you invest in. [1] <— Read this first.Separately and to other’s points in comments yes there is another side to an email that could be discovered but that is an entirely different process and may not always happen w/o the original email (or what it contains).[1] Not that I think it’s a good idea to disclose that publicly.

  15. JLM

    .Emails are business correspondence which is considered a “record” for such matters as taxes or litigation. As a general proposition, a business should have a records retention and safeguarding policy. This is true even if you are a 2-man plumbing shop.This doesn’t mean just keeping them on an individual’s hard drive somewhere. It requires a business to segregate them and to safeguard them. This was one of the HRC problems related to the records retention policy of the Dept of State and the Federal gov’t – neither of which she came close to complying with.As a general proposition, business records should be retained for at least:1. Seven years for tax purposes2. Beyond the statute of limitations for the longest limitation for the most serious crime the business or a principal might be accused of which is ten years except for murder which is not germane hopefully, and3. Longer than one might be engaged in any civil controversy.For tax purposes, the IRS would generally say seven years though the statute of limitations on failing to file a return is six years.For criminal statutes of limitations, the Feds would typically say five years, but since VC involves the funds of public institutions the statute of limitations would be ten years for a slew of things (fraudulent inducement of a financial institution, as an example).For business interests, the time period would be some time period after there is life left in the investment (same time period after dead investments, seven years for “worthless securities”).A public company has to have a written records retention policy and a disaster recovery plan which mandates a duplicate for all records.A public company is supposed to have a custodian of records and its auditors may review the policy and its compliance with the policy.A disaster recovery plan mandates an off site duplication of the computing capabilities of the company and its records. This is a huge pain in the ass and, again, an auditor may want to take a look at this.After 9-11, American Express was back in business within less than a week after losing some substantial amount of their computer system because they had a good disaster recovery plan.The status of records and disaster recovery should be footnoted on an US SEC Form 10K Annual Report though I have read a lot of big company 10Ks which are silent on the subject.With the state of digital record keeping, there is no real reason why a business would not retain its records forever.Records are never important until they are important.JLMwww.themusingsofthebigredca…

    1. Pete Griffiths

      Well said

    2. Vasudev Ram

      Wow, Jeff, do you have a supercomputer to help you look up all these facts for writing in comments? Or are you the supercomputer yourself? :)(This is like @PhilipSugar commenting on @GirishMehta’s ability to bring up relevant quotes, a while back.)And it’s not just isolated facts, otherwise some handy reference books or Google might do. One has to collate them, know what to look for, know how to organize them, how and in what context to present them, have the deep background knowledge about the subjects involved, and more. I guess all your years as CEO and investor, etc., have a lot to do with it. Cool.

  16. rfreeborn

    I agree 100% – and having that complete retention thought process in the back of my mind forces 2 actions: 1) Don’t put anything in writing you wouldn’t want “the wrong person” to read i.e. don’t make crass jokes or comments at someone elses expense…2) Keep personal and work email 100% separate. I have *no* personal email coming to the work account and vice/versa. Heck, I only do personal browsing in Chrome and work in IE/Edge. Separation of church and state keeps things clean.

  17. Richard

    It’s also a great way to celebrate an anniversary and remind yourself how amazing life can be.

  18. Donna Brewington White

    How does this square with your email bankruptcy policy?

    1. fredwilson

      Email bankruptcy is about archiving them out of the inbox

  19. BillMcNeely

    Having been in government and government contracting saving emails, warts and all have been way more beneficial than not. See Agility Logistics.…. When this story first came out it was Page 1 of the Wall Street Journal sometime in 2007/08.On the other hand, the most shady business,in violation of the Federal Acquisition Regulations, I worked at, produced over 1,000 emails in the short 1 week I worked there. So that was not going to end well for them.

  20. Chris Phenner

    Fred’s post that shares his email exchange with Paul Graham (debating Airbnb as an investment opportunity) is one of my favorite AVC Posts of all time. I wish he created a separate tag (at minimum) or Weekly Ritual (like Feature Fridays).So much of AVC is about thinking through whether you might be right. Where things are headed, whether to buy/sell/hold and what contributes to great firms’ growth.Sharing ex post facto decisioning (via old emails) is so great,

    1. BillMcNeely

      I still look back on occasion on my email exchange with Ryan Graves back in September of 2011 when I was interviewing to be the Operations and Logistics Manager in Boston and what that could’ve meant for me, career wise. #justabitoutside

      1. JamesHRH


  21. jason wright

    duplicate comment. see above. disqus!

  22. jason wright

    when i’m engaged in an email exchange on a subject i will sometimes send an additional email to myself where i’m ordering my thoughts on the issue at hand, my view of the other party’s position, and how i’m going to move forward. potentially useful, but just don’t send it to the other party in error. that doesn’t work.i sense that there’s still opportunity to innovate in the email space, that there’s a third and a fourth dimension of possibilities not being seen, and that we’re missing something here that is potentially BIG. that’s my view of the present state of the emailing experience.

  23. PhilipSugar

    I am going to disagree. If you have a commitment (legal, or otherwise) then that should not be in email.And yes. Email or for that matter commenting here is forever.But every legal document I have signed says something like “all past correspondence is null and this is the agreement” Now I believe as the great Myles Bass would say just write down the intentions because that is what every lawyer wants in litigation and put those in the agreement.Here is why I refuse the “email or text commitment” What was said afterwords?Sure you have an text saying I would do something: Fix your truck let’s take an example. Text: Hey can you fix the starter. But then you called and said hey Phil, I know you said the starter on that 200k mile truck broke and I pulled it from Tractor Supply on a Holiday weekend, but you really should get a new air conditioner idler pulley, ok with a new belt for that too?Cool. Thanks for the help. Don’t come back to me and say well I only said the starter.