How to cold email investors and leads

February 18, 2021
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Ever wonder why so many of your cold emails to investors and potential customers go unanswered? Would you like to change that? Today everyone’s inbox is overflowing and most people who get a cold email just ignore it.

So why is your email not breaking through? Because you don’t know how to get it opened, read, and acted upon. But there is a way to dramatically increase your response rates by becoming an “Email Ninja”.

To get responses to your emails, I’m going to break the process down into several core things you need to get right from making sure your social profile is strong to breaking the ice correctly, having a great subject line and making sure the email body is super compelling! So let’s dig in.

If cold emailing someone, the first thing I want you to do is “break the ice” before that email is sent. How? Use your social profiles and connect with them ahead of time.

My favorite approach is to start with LinkedIn. Before you send your LinkedIn request, make sure your profile is rich in substance,  up-to-date, and you have a photo. Once your LinkedIn profile is looking its best, send your LinkedIn connection request BEFORE your email goes out. HOWEVER, don’t just send a generic LinkedIn “Invitation to Connect.” Instead, make sure to add a short custom note to your LinkedIn request explaining why you are connecting and why the request is relevant. You can add a custom note on all versions of LinkedIn, including their mobile apps.

So LinkedIn is one way to “Break the Ice.” Another way -- start following the person on Twitter and other relevant social networks. That way, your target contact will get several notifications about you before they get your first email. So, technically, the “ice… it has been broken.”

About the subject line

Okay. Now let’s get into what your actual email should look like. To start with, you’ll need a KILLER email subject line! Don’t use things like Hello, Meeting Request, Intro, or never, ever leave the subject line blank. 

Instead create a short, really compelling subject line that has a “newsworthy hook,” giving the person a strong reason to open. Another great technique is to start the subject line with the recipient’s name like “Caya -- love to interview you for…”, and if someone referred you, make sure to include that in the subject line as this will dramatically increase your email open rate.

When writing subject lines, make sure to keep them as short as possible. There is a very good chance your email will be read on a smartphone where only the first 30 characters or so will be visible. So if you don’t have something compelling in the first 30 characters, there is a good chance you’ll be swiped off the screen and sent to email purgatory along with the 50,000 other unread messages in their inbox.

So let’s see where we are in the process of getting your emails answered. Social connections? Check! Killer subject line? Check! Now let’s put together an awesome email body. Something that’s personalized, compelling, clear, concise, and has a strong call to action.

The body of your email

Here are the key areas I want you to focus on when writing the body of your email:

First, you need to start with a VERY concise overview of what you are working on and what this email is about. Realize, the OPENING LINE of your email is critical! That’s the hook. With that first line they’ll either keep on reading, or boom, welcome to “Delete!”.

Your opening paragraph should be about 3-5 sentences, as concise as possible, have credibility, and try to BLUF. What’s BLUF? That mean’s “Bottom Line Up Front”. Don’t make the recipient read 4 paragraphs of text then at the end say “could I get 30 mins of your time for a demo?” Make sure to touch upon the ask in the opening paragraph.

Another critical piece to include in your opening paragraph: credibility. Were you referred by a warm intro? Make sure to point that out. If this is a totally cold email, do you have things you can mention to establish credibility? Perhaps venture or angel investors in your company they may know? Can you name customers already using your product? Maybe you went to the same university as the contact? Maybe you’re pre-product and have no angel investors but already talked to 3 interesting potential customers in the space. Mention the 3 customers you’ve talked to or are lining up to talk to in the coming weeks. Maybe there are milestones that you’ve hit: 3 interviews with Fortune 500 companies, 100 paying customers, 10,000 downloads, $50,000 in MRR, etc. Whatever it is, what can you add to that opening paragraph that shows credibility so you are taken more seriously?

What the mail is about

Next, I want you to think about how you can make the email “audience-centric.” What do I mean by that? Stand in your audience’s shoes and think about the WIFM statement -- “what’s in it for me.”

Usually when people send emails it’s all about them -- what THEY want. What they’ll get out of the meeting. Why they want to meet. But in a cold outreach email, you want to think about what’s in it for THEM?

So create a clear value proposition of what your recipient could get out of meeting with you. Further, if you want, you can try to add a bit of a FOMO. Could you say something like “I’ll be in Atlanta next month meeting with Coke and Delta Airlines with their heads of logistics and was hoping we could get together so I could share what we’ve learned from our discussions with leaders, get your input, and see what you think.”

Some other examples of a gentle “forcing function” to get things going? Maybe it’s a geographic forcing function like “I’ll be in LA next week meeting with 2 other investors”. Or maybe you could try to tie the forcing function in with some credibility with something like “Dell just bought 7 early prototypes of our product and we only have 3 left. Love to get 20 mins of your time to show you why they are so excited.”

What are you looking for?

Finally, the last part of your opening paragraph is a clear “ask.” What do you want? What are you looking for? Make sure to be very clear. Do you want a meeting? In person or online? How much time do you want?

By the way - a quick favor about your ask? Never, ever, put in that email an ask of - “I want to pick your brain.” That’s the most one sided ask you could ever make. You’re basically saying, “I want your time so I can get all of the benefits.” It just sounds so bad. Mention that you want to brainstorm, soundboard a concept, etc. But not “pick your brain.” Okay… end of rant.

Okay… let’s say your ask is for a meeting. Let me share some more “Email Ninja” best practices when asking for a meeting.

First, think about this: as your requested meeting length increases, your chances of a meeting decreases. Conversely as the requested time goes down, your probability of securing a meeting goes up! So ask for as little time as possible. My suggestion? For initial meetings, ask for just 20 mins and use your time wisely.

Finally, when emailing about meeting dates, assume you are communicating with an international audience. So  you should spell out dates such as “July 6th” instead of using just numbers. Because if you’re in the US, July 6 is 7/6. But if you are outside the US you would probably write it as 6/7. So be clear and just write out the date as month and day to reduce the chances of confusion.

How to close your email

As we get to the bottom of your email, I have one more suggestion for you. Put your email signature to work. So many times I get emails that lack the person’s full contact info. Their signature is simply...“Sent from my iPhone.” Ya know, that’s not helpful to you or me (but Apple thanks you for the free marketing!)  Have a rich signature with your name, title, email address, and mobile phone number.

As you are amping up your email skills -- just a few more quick points if you are working to line up a meeting. This is about calendar entries. Want to look like a total pro? Once you line up a time to meet or talk, send a great calendar invite.

So... my name is Steve. I’ve gotten invites from others and the calendar entry says “Meeting with Steve.” Okay - so like… that’s not helpful!

Be descriptive in your calendar invites. Who’s attending? What’s the meeting about so it makes sense on everyone’s calendar? In the calendar entry make sure to include the video conference link or phone number, or if a face-to-face meeting, put the exact meeting address.

Oh and if it’s a conference call and I need a code or password, for G-d’s sake include the meeting code / Password in the cal invite! And the last thing for calls -- make sure to specify who is calling who. Don’t put “Caya and Steve call”. Put “Steve calling Caya on … and the phone number”. Want bonus points? Copy and paste the email exchange in the calendar entry notes so it’s easy for everyone to get a quick refresh regarding what the call is all about.

Let's recap

I know that was a lot to cover, so let’s recap! Want to know why potential investors and customers are not getting responding to your emails? Here’s why and how to fix the issue:

1) Break the ice BEFORE you send a cold email and use some of your social capital. Have a rich social media profile and connect to people with meaningful, non-generic connection requests on LinkedIn. 

2) Your email subject line needs to be really compelling. Most are just not worthy of opening.

3) The body of your email needs to be concise, credible, compelling, have a clear ask, have a solid WIFM, and a reason for me to take action sooner rather than later.

4) You need to be super easy to schedule with. Ask for short meetings and send rich calendar invites.

And there you go. Follow the guidelines above and I can nearly guarantee you’ll be well on your email to becoming an Email Ninja and get a ton more responses. Your mileage may vary so let us know how this works for you by leaving your experience in the comments below.

I hope you’ve found this discussion on mastering cold emails helpful and if you did, please like and subscribe to the Slidebean and Dreamit Ventures YouTube channels. We both release great startup content weekly.

Steve Barsh
Managing Partner @ Dreamit Ventures
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