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Email is a wonderful tool. It makes business more efficient and allows us to communicate with our friends and family faster. I often marvel that there was a time, not that long ago, that business functioned without the use of email. Once upon a time if a document needed to be executed, it had to be sent via overnight mail to the recipient, and then sent back for a total of two working days. And that was if the recipient actually got it and opened it the day it was received. Now, that entire operation takes all of five minutes. We also communicate via email to iron out business transactions instead of sitting on the phone for hours ironing out those very details. Often times email is simply used to follow up on what was previously discussed on a phone.

One pitfall of our reliance on email is the sheer number of emails contained in our mailbox. In just one of my email accounts, I have 26,946 emails and most of them are from within the last eight years. Keep in mind that I delete a lot of my emails and for a period of 11 months I was not able to send an email. To be sure, most of them can probably be deleted but our email accounts have become our de facto memory books. Doesn't everybody need to remember who they went to the movies with in 2012?

The other pitfall is that emails never disappear and can be taken out of context. When documents related to a business are subpoenaed by the government or even by a lawyer on the opposite side of a lawsuit, the courts have generally ruled that emails are not protected under the 5th amendment's right no not incriminate oneself. Just turn on the TV and we can see how many of the Trump campaign members are being forced to hand over emails to the special prosecutor. During the financial crisis, emails were used to indict and in some cases convict Wall Street bankers for financial fraud. Could this have even been an issue 30 years ago? Of course not. That's not to say any evidence of illegal activity is contained in these emails but the fact that they are being handed over to an adversarial party puts the author of the email at risk.

The real problem with anything written and in particularly as it relates to emails is the ability to take any email out of context. Imagine a phone call where a colleague agrees to advocate for you at a company meeting. Following the phone call you send him an email that says "love you man you are the best." Or imagine you take a client to dinner and the next day he sends you an email thats says "last night was fun, lets do it again!" Obviously to both the author and the recipient the email was in response to a phone call or a business dinner. Now imagine that the author of those emails is going through a nasty divorce. The attorney on the other side can easily take those emails and allege infidelity. True this may seem extreme but as someone who has had his emails dissected by prosecutors, opposing lawyers and even the press, I can tell you that this is precisely what takes place.

The sad truth is that any email can be taken out of context by an unscrupulous lawyer furthering an agenda as well as by a prosecutor trying to prove a crime. Obviously only a fool is going to document his crimes in an email (although I am amazed how many seemingly intelligent people seem to do so). However even the typical business owner or employee using email in the normal course of business has to be increasingly careful that anything he writes cannot be interpreted incorrectly out of context. This becomes increasingly difficult as even emails are increasingly informal and are written in a manner more akin to casual conversation.

I will give a personal example of an email that was taken out of context by multiple parties between the year on 2009 and 2015. As the perpetrator of the crime was hiding we in Miami were all panicking as we had investors to whom we were accountable. On Friday, October 30, 2009 was coming to a close,  I sent an email asking for some clarification immediately because "otherwise we are all done". Those five words were used over and over against me as "proof" that  knew I was involved in a major fraud and knew I would be going to prison. The problem was that everyone who read that email either decided to deliberately use it out of context for their own agenda or simply would not look at the 50 emails that led up to that email. Does ""done" mean prison or does "done" mean out of business. Well anyone who can read would have gone through my emails and concluded that this was an email sent in a state of sheer panic because I simply had no idea what was going on. And yet, over and over again it was used as "irrefutable proof" that a was a knowing and active participant in a fraud.

Here is another example. Scott Rothstein, narcissist that he was liked to be told that he was loved. He would insist that anyone that sent him an email closed with some variation of "love u!" Well, when all of my emails got into the hands of other lawyers, I was asked if Scott and I were in a sexual relationship. Now if someone is gay, that's their business, but personally, guys don't do it for me. The very notion that I would be involved in a homosexual affair was so ludicrous that I actually started laughing when I was asked. And yet, to the unknowing reader and taken way out of context, it was a plausible question. I can go on with so may examples where my emails were taken way out of context but the point has been made.

Being careful with what is put in an email is practical advice for everyone. Even if emails are not forced to be handed over in the legal context, there is the constant fear that email accounts can be hacked. Once an email has been sent, it can and will be used against you in a court of law or at the very least the court of public opinion.


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