Nobody teaches you the rules of email, and people are usually too polite to tell you when you violate them. But understanding and following them are crucial to ensuring you get investor meetings (or, indeed, meetings with anyone).

Below, I give you four of these essential rules.

1. Move to Bcc

When you have been introduced to an investor via email, make sure you move the introducing party to bcc. Here’s a sample email to demonstrate this principle:

Subject: Matt<>John

Matt – meet John. John is a 25 year veteran of the venture capital industry and exclusively focuses on Saas companies. I told him about Software Co. and he loved the idea. So I thought you two should meet.

John – meet Matt. Matt is a serial entrepreneur with a decade of experience in building Saas companies. His last business, Geekware, is now listed (NASDAQ: GEK). As I explained yesterday, he is currently building out Software Co.

I’ll leave the rest to you!

Eric

Let’s say John responds first. His response will likely be: 

Subject: Re: Matt<>John

Thank you for the intro Eric (to bcc)

Great to meet you Matt! Blah blah blah

Notice that John has now moved Eric to bcc. This means that Eric will now be excluded from the subsequent email chain, which will likely include an exchange in which John and Matt attempt to find a mutually convenient time to meet in person or talk on the phone. Eric has no interest in being part of the logistics conversation, hence being moved to bcc is a welcome courtesy.

2. Always Get a ‘Double Opt-In’ Introduction*

*Credit to Fred Wilson for this nomenclature.

Let’s continue with the same example. Before Eric introduces Matt and John, it is crucial that he asks each of them whether they are interested in the introduction. Once he has buy-in from both sides, he can go ahead and connect them.

The situation you must avoid is introducing two people without prior context or approval. Without buy-in, one or both parties are less likely to want to invest in the interaction. Especially if the goal of the introduction is for one person to help the other out, the person expected to do the helping is far less likely to do so if he has not first bought in, and is simply copied on an email with a person he has never previously met.

Below is an example. Assume that the sender (Johnny) has asked neither party whether they are interested in the introduction):

Subject: Tom<>Marc

Hey Tom –meet Marc. Just like you, Marc’s an entrepereneur. Marc’s looking to raise some money so I thought you could be really helpful in making introductions to investors.

And I know you guys will really like each other.

I’ll let you two take it from here!

-Johnny

Absolute train wreck. Tom has no idea who Marc is. And yet he is expected to give him some of his precious time. When put in Tom’s position, many are annoyed because they have been obliged to do something they did not agree to do. And it is difficult to decline without being rude.

There are a few typical conclusions that result from this kind of introduction. The first is that Tom begrudgingly takes a meeting, and the relationship is poorly colored by these shaky beginnings. The second is that Tom finds a way to defer the meeting, and then doesn’t ever take it at all. The third is that Tom never replies at all.

The double opt-in will avoid all of these suboptimal scenarios.

3. Optimize Your Send Time

The time you send an email to an investor has a significant impact on the likelihood of reply. So you must send your email at the correct time.

Here are some bad times to send email to an investor:

• Anytime on Monday. Monday is the day that investors have ‘partner meetings’. They are busy all day, and hence accumulate a lot of emails.
• After midday on Friday. If the investor doesn’t get to it before the weekend it may be lost forever.

Emails sent on Tuesday, Wednesday and Thursday are likely to garner higher response rates. Sunday evening can also be a great time, because many folks try to clear out their inbox before the week starts again on Monday.

4. Use Eye-Catching and Memorable Subject Lines

Remember that an investor’s inbox is always overflowing, and there is no way he can open, much less read, every message.  As a result, your subject line is extremely important: it ensures your email will stand out in a busy inbox and enables investors to find the email again if he reads it and needs to return to it later.

How do you create a great subject line? Be very specific and use memorable language. Quote your name, company name, or include eye-catching verbiage to ensure your email is not lost. Examples of terrible subject lines include “Startup,” “investment” or “Introduction.” Avoid generic wording at all costs.

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