Disciplined Writing: Sending a really dumb email

From 35,000 feet

I promised myself I would write this entire piece while on the flight back to NY from SF, while also watching a movie on my right and staying up on work emails on my left. I was recounting a story to my friend about the dumbest email I ever sent during a hike this weekend and he strongly recommended I share it as lesson to others. The ultimate lesson from the story is to learn from your mistakes and I am not sure I have. To not repeat it over and over.

There are many old adages like “take a breath” or “sleep on it before you send” or even “look before you leap”, and many email programs and social media platforms have implemented delay or unsend features to reconsider what your sending. My most severe technique which I use is to create some fake email addresses like ray@dumbshit.com that I send a hostile and angry note, copying some others I want to see cringle or laugh, while the recipient does not really get it since they were at ray@gmail.com, but sending it was incredibly cathartic. All of these techniques help stop the impulsive reactions before they lead to misunderstandings, regrets and in the case of Ray, perhaps aggressive attacks or worse. The pauses promote mindfulness in communication, giving users a moment to think twice about their words or actions before they become permanent written stains on your relationships or business.

The one epic fuck-up I made which my friends wants me to retell is a little nuts. It was the Fall of 1999, before the dot.com bubble burst in March of 2000, and I was completing the construction of the Knitting Factory in Los Angeles. Our construction was overbudget and the contractor once again was trying to extort about $1.5m in additional costs in order to deliver our venue. I had no cash. With my good friend Andrew Rasiej, we had started a cool side hustle that was a great idea that leveraged what I was doing at the Knit, but at scale. It was called DCN, the Digital Club Network, essentially an internet channel to go club hoping watching streams of live music from venues all over the world. While my day gig was the Knitting Factory, I became the Chairman of DCN, Andrew the CEO and it was a hot new internet start-up. My ownership was in the name of the Knit and it was valued around $5m on paper.

Given the incredible pressure to come up with some cash for our physical business in LA to open, I convinced one of the early investors in DCN to buy us out for about $3m. In a perilous moment of needing to get permission from the Knitting Factory board, I sent an email that said basically (and I am embellishing a little here): “Dear Board, we need to move quickly and sell our ownership in DCN. This business is not worth anything, the internet is a fraud, and these guys are suckers for giving us any cash for the stock”. I really was trying to dramatically and quickly get the 7 people on the Knit board to agree, allow me to close, get the cash and pay the contractor.

Well, I hit the wrong group email I had recently created, and it went to “Board DCN” not “Board Knit”. Oops.

I immediately got a call from Andrew saying, what did you do”? What the hell were you thinking??!!”. I then followed it up with another email saying I was simply trying to convince my board at the Knit to sell, as they, like me, were actual real believers in the “dot-com”, that I was desperate, and was simply trying to convince them. I was graveling and shaking with nerves. Well, given the empathy of the group that was going to give me $3m, they gave $2m and wished me good luck. I had no choice but to take it as it was the only way to open the Knitting Factory LA. As it turned out, between the dot.com crash, record industry crash, and 9/11, the Los Angeles version of the Knit closed a few years after opening. And well, music on the internet has been doing ok since then…..:)

If only Gmail had the unsend or delay send features 25 years ago…..What I have learned from this--well not a lot. I probably take a little more time looking at what I send out then I did. But at the same time, like hitting “publish” with Substack, sometimes you just got to hit send and see what happens. You can’t control every reaction or protect every feeling. Kind Candor is good. So is perhaps, the unpolished email. Life is too short to re-read everything. I’ll certainly sign up for an AI software that creates some pop-ups while writing that says, “hey are you sure you want to say that” or “can’t you be a little nicer”, or “maybe all caps isn’t the best here”. But until someone writes that code, I will most likely be hitting send too soon on a few emails and posts. Sorry. That is the lesson. Learn to say I am sorry more. Publishing now. Back to work.