Cold Emailing Investors and Prospects - How to Become an Email Ninja

Ever wonder why so many of your cold emails to investors and potential customers go unanswered? It’s no surprise, everyone’s inbox is overflowing and most people who get a cold email just ignore it. In this Dose, Steve Barsh, Managing Partner at Dreamit Ventures, shares his pro tips on how to perfectly craft a cold email. To become an ‘Email Ninja,’ you'll need to master each of the following skills.

  • Break the Ice

  • Create a Killer Subject Line

  • Craft an Awesome Email Body

  • Be Easy to Schedule With 


Break the Ice

When cold emailing, the first thing you’ll want to do is “break the ice” before sending an email. You can do this by using social profiles and connecting with your target contact ahead of time. Steve’s favorite approach is to start with LinkedIn. You’ll want to make sure your profile is rich in substance, up-to-date, and you have a profile picture. Once everything is all set, send your LinkedIn connection before your email. Avoid generic invite requests. You’ll want to add a short custom note to your LinkedIn request explaining why you are connecting and why the request is relevant.

Another way to “break the ice” is to follow the person on other relevant social networks like Twitter. Doing so will give the target contact multiple notifications before they get your first email, so technically the “ice” has been broken. 


Killer Subject Line

Any good email starts with a great subject line. For starters, avoid using bland phrases like ‘Hello’, ‘Meeting Request’, or ‘Intro’. Never leave the subject line blank. 

Instead create a short, really compelling subject line that has a “newsworthy hook.” This will give the person a strong reason to open. Another technique is to start the subject line with the recipient’s name. If someone referred you, make sure to include that as well. Doing so will dramatically increase your email open rate. 

Keep subject lines as short as possible. There is a good chance your email will be read on a smartphone where only the first 30 characters or so are visible. If you don’t have something compelling in that short section, your email will likely be swiped off the screen and sent to email purgatory along with 50,000 other unread emails in their inbox.


Awesome Email Body

The body of your email needs to be personalized, compelling, clear, concise, and have a strong call to action. Here are key areas to focus on when writing the body of your email. Start with a very concise overview of what you’re working on and what the email is about. The opening line of your email is critical. It is the hook that the recipient will look at and decide to keep or delete the email. 

The opening paragraph should be about three to five sentences. Be concise, credible, and try to BLUF (“Bottom Line Up Front”). You don’t want your recipient reading multiple paragraphs of text just to ask for thirty minutes of their time at the end. Be sure to touch upon the ask in the opening paragraph. 

Another critical piece to include in the opening paragraph is your credibility. Include the shared connection if you were referred by a warm intro. If it’s a totally cold email, you can establish credibility by including venture or angel investors they may know, naming customers already using your product, a shared university, interesting potential customers you’ve talked with, or any major milestones you’ve hit. 

Next, think about making the email “audience-centric.” What Steve means is to stand in the audience’s shoes and think about the WIFM statement - “what’s in it for me?” Most people usually frame emails according to what’s in it for them and what they want, but in cold outreach emails do the opposite. Frame according to what’s in it for the recipient. If you want, add a bit of FOMO, and 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, get your input, and see what you think.”

Never use the email ask - “I want to pick your brain.” It’s the most one sided ask you could ever make. It is basically saying “I want your time so I can get all of the benefits.” Instead try mention brainstorming, soundboarding a concept, etc.

Finally, the last part of the opening paragraph is a clear “ask.” Make sure to be very clear in what you want, what you are looking for, if you want a meeting, and how much time you want.


Be Easy to Schedule With

As your requested meeting length increases, your chances of a meeting decreases and vice versa. So ask for as little time as possible. Steve suggests to ask for just 20 minutes for initial meetings and use your time wisely

Assume you are communicating with an international audience. Spell out dates, such as “July 6th” instead of just using numbers. The day and month are switched when writing numerically in the US versus OUS. So be clear and just write out the date as month and day to reduce confusion. 

As you get to the bottom of your email be sure to put your signature to work. Many times emails will be sent lacking the person’s full contact information, or the signature is just, “Sent from my iPhone.” Have a rich signature that includes your name, title, email address, and mobile phone number.

Another piece of advice is to send a great calendar invite once lining up a time to meet. Be descriptive in your calendar invites. For example, titling an invite, “Meeting with Steve,” is not helpful. Name who is attending and what the meeting is about so everyone is on the same page. Include the video conference link and the password if there is one. If it’s a phone call, include the names of who is calling who (e.g. “Steve calling Caya”). If it’s a face-to-face meeting, put the exact meeting address.


Founders need to be data-driven decision-makers. Cold emailing is no different. Apply these lessons and split test. Build, measure, learn, and repeat. Sharpen your blades Email Ninjas!


By Elliot Levy, Senior Associate, Healthtech at Dreamit Ventures

Learn more about Dreamit Healthtech, a venture fund and growth-focused program for digital health and medtech startups with revenue, pilots, or early product-market fit.

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