Cold emailing for startups: How to contact investors

By Denis Dovgopoliy

23 Apr, 2021

Photo by Stephen Phillips – Hostreviews.co.uk on Unsplash

Startups use plenty of communication methods to reach out to investors. Cold emailing contacts is not considered the most effective of them. Yet, Unicorn Nest is currently building a tool that could change cold emailing by helping startups quickly set up emails and manage all communications with funds (you can learn more and join the waitlist here). In this article, I show how our advanced cold emailing method can help you reach the right investors. 


A potential investor receives up to 600 emails any given day. A startup needs to break through this cascade of information and make sure the right person gets the right message. An entrepreneur also may need to write at least three to five emails to these select investors. This strategy can be called “the rule of five touches,” trying to make contact with a potential investor five times. Finally, startup entrepreneurs need to track their analytics, which will show how successful their email campaigns are.

The most essential metrics to track

The primary metric to track in the cold emailing strategy is the response rate. This rate can show how good your emails were or how good your startup’s products or services are.

Other metrics are related to the response rate: 

  • Delivery rate – % of delivered letters. It measures the quality of the email list.
  • Open rate – how many of the delivered emails were opened. This metric can be increased by conducting A/B testing of the subject line.
  • Multiple open – an important indicator that you have to take further action because email recipients opened the email multiple times without responding.

Working with a funnel 

As the conversion rate in cold emailing is usually low, your funnel should start with emailing at least 300 funds and 500 investors. It is also important to consider the geography of investors during the selection of potential recipients. For example, a startup’s headquarters could be located in “toxic” jurisdiction, like Eastern Europe, so this region has a limited number of investors. This problem can be solved by building a network of loyal contacts.


Unicorn Nest recommends using Reply or Revenue Grid for your cold emailing automation.


Before starting a cold emailing campaign, you have to do two things:

  • Check your sender score and email reputation that ensures high deliverability of emails (this will help you avoid having your emails end up in spam filters). Certain services like Sender Score help determine the sender reputation. You can delve into deeper detail here.
  • Warm up the emails from which the mailing will go in automatic mode (if you have a brand new domain without any emailing history). You can read more about warming up in the article by Reply.io.

Setting up a sequence of letters

To maximize outreach efficiency, a startup needs to use three mailboxes on its domain. The capacity of each mailbox is also important – for example, each should be able send 300 emails a day. 


It is better to have emails delivered to investors during the standard business day: within 7-9 hours of a working day with a 35-45-minute lunch break. A gap between emails can be random.


The optimal time to receive an email is Tuesday to Thursday from 11 to 13 local time of the recipient. On Monday, investors usually have partners meetings and this day has the lowest conversions during the whole week. Conversions are typically low on Fridays too.


It is better to send letters to your priority investors from 11 to 13, but for others, it could be any time during the working day. 


In case three working days a week is not enough to complete the outreach, letters can be sent after lunch on Monday and before lunch on Friday, but it is better to fit all emails in the Tuesday to Thursday period. 

Starting the waves 

We recommend startups to send three emails that will fall in the same thread in the recipient’s inbox. The second email serves as a reminder. The third one is a summary of key points from the first and second emails.


We recommend sending the second email out a week after the first and the third a week after the second. If the first email batch is being sent for more than a week, then the second wave will begin while the first emails are still sending out. Most likely, the first, second and third waves will cross.


Depending on the recipients’ location, email waves could be optimized in the starting time parameter. For example, for the United States, one wave can be sent according to the East Coast working hours and another according to the West Coast.


Important note: The optimal arrangement is when a fund receives one letter from a startup per day. This rule can help to cover most partners in two weeks. There might be some exceptions like Sequoia Capital that has dozens of partners. In this case, you cannot avoid sending more than one email per day. 

Switching communication to the CEO

When you receive a positive answer, you should transfer your communication to your main email address. You can use a couple of templates to do that. Here is an example: 

‘Good afternoon. Please accept my apologies, I’m currently ready to depart on a plane/train &, etc.’

or

“I’m in a meeting/at the bank, etc. I’ll contact you ASAP.”

Add your main address in a copy and your CEO will do the rest. This is an important step. Using mass emailing can cause a mess in an inbox, so it might be difficult to find the right message. 

Working with the answers 

Sometimes you will need to add the entire fund or a specific partner to a stoplist. Basic rules are the following:

  1. If the respondent asks to unsubscribe from the newsletter, it’s necessary to apologize and stop emailing the recipient.
  2. If the reasons for rejection are along the lines of “not interesting,” there is no need to exclude other fund’s partners from the mailing list. 
  3. If the reason for rejection is something like “We discussed the proposal and decided not to go further,” put the entire fund in the stoplist.
  4. If you received a positive answer, then add the whole fund to the stoplist.

Key points to remember

You can maximize the efficiency of your cold outreach by: 

  • Gathering an accurate database with emails of relevant funds and investors and checking the status of your domains
  • Warming up the email boxes that will be used for outreach (we recommend at least three boxes)
  • Create a schedule for 3-5 mailing waves, taking into account the working hours in specific time zones and ensuring that one letter goes to one fund per day
  • Segmenting the database so that high priority investors receive letters from 11 to 13 from Tuesday to Thursday
  • Setting up an automatic response, adding your main address to a copy, for an immediate response to answers

Luckily, we are now building a tool that will automate all these processes for you.

Join Unicorn Nest Connect waitlist to be the first one to try it out.

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About the Author

Denis Dovgopoliy

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