The Double Opt-In Email

A hotly debated topic in Venture Capital is the “Double Opt-In” email. This has been well illustrated with these tweets between Jeremy Liew from LightSpeed and Jason Calacanis.

An example of a double opt-in email would be when a founder asks me for an introduction to an investor, the investor would like me to ask them if it’s a fit before sending the introduction email. This requires two emails on my part, rather than just the simple one that says “You two should talk, and here’s why.”

I’m glad that it’s being talked about, because I’m in the camp of “Just send the intro”. Over the last few years there have been numerous Venture Capitalists who lash back ‘suggesting’ that I get them to opt-in before sending the email, and this required me to move toward Double Opt-In being my personal standard. So basically I acclimated to what I believe the standard to be, rather than pushing what I believe to be the most efficient way, or best way. I would much rather have people just introduce me to people, and then I select whether it’s a fit or not.

It’s funny this is a conversation around digital etiquette, which is a ridiculous concept to discuss in the digital era of rebellion. It’s the same concept of my Mom telling me to keep my elbows off the table during dinner, or not to chew with my mouth open. (Sorry Mom) Double Opt-in emails are a conversation around “Digital Rudeness.” Rudeness generally assumes that people are interrupting a societal norm. Seeing as the idea of a “societal norm” on the internet is hilarious because they change so often, I think that progress and flow of information should be paramount and ideas move faster if all inboxes are open.

One of the difficulties I have had with going with the societal norm is that every investor has a different preference, in the same way some people care about elbows on the table and some people do not. Some are ok with the open door policy, some are not, which leads you to check with everyone, because no one remembers who is ok vs. not ok. This is why societal control becomes a thing, you default towards not being “rude”, when all you wanted to do was facilitate an interaction. This friction stalls introductions from being written at all in my experience.

I understand the investors who believe this is an attack on their time, making it a rude gesture. How else are people supposed to get to you though? Without some friction or rudeness you may just be speaking with the same people all the time. The open communication network of TCP/IP wasn’t designed to disallow certain people from connection, the etiquette of Double Opt-In kind of fights the whole reason that the system was built. It’s the world wide web, not the “Selected introduction web.”

I’m going to stop doing double opt-ins. I don’t think it fits with the way I hope the world works.

You can respond or not. You can push back or not. But meeting random people through random channels is a part of the job, and if you feel that some societal norm has truly made you more successful, great, because building relationships through cold opt-ins has made me more successful.

What I do promise is that I will think before sending the email about whether it is a good connection. My intention is to drive valuable interactions, not to just off load some introductions. I apologize for my digital rudeness, but I believe direct messages is the best way to facilitate conversations.

There is another conversation around trust and building credentials of trust in networks which I think is really the core problem in this whole debate, that maybe I think about writing about in the future.