The Skeleton Key for Cold Outreach

Jason Yeh
January 23, 2024

I hate cold outreach, but given the right language and circumstances, it can work. 

There's no magic formula that turns a random email into a qualified fundraising lead. HOWEVER, I've recently discovered the closest thing to it. I'm calling it the 'cold outreach skeleton key' 💀.

Fundraising and Certainty

Fundraising is all about a founder's ability to provide some semblance of certainty to investing in an early-stage startup, which itself is a very uncertain action.

At any stage of investing, from a friends and family round idea on a napkin all the way to IPO, an investor is betting on some version of the future that no one can definitively guarantee. At the pre-stage, it's "Hey, I have this idea. I can build it into a billion-dollar business." At the pre-IPO stage, it's "I have this company that's running and is huge, but I can at least double it in size in the next two years."

Both situations carry a ton of uncertainty. However, when a founder is great at fundraising, they can sprinkle signals into the situation that make the investor feel like the chances of that future happening are greater than not happening.

First Impressions and Warm Introductions

The first impression an investor has of you is crucial. Because of that, I often promote warm introductions being the key to a smooth and successful fundraise.

If you're able to reach an investor via a warm intro, you have the opportunity to capitalize on the credibility of the person introducing you. Or at the very least, you demonstrate to the investor your ability to reach them through a method that offers comfort and requires more effort than a copy-paste email. 

The Cold Challenge

When your initial connection comes from a cold email, all you have is the text within your email or possibly a WhatsApp message to generate some interest from the investor about your opportunity.

You're already behind the eight ball in this endeavor because investors receiving a cold email will inevitably ask themselves, "Why couldn't they reach me via warm introduction? Is it because they/their opportunity isn’t good enough?"

Balancing Warm and Cold Outreach

While I encourage people to focus on warm introductions, I realize that even for founders with extremely strong networks, there will always come a point where the effort to arrange a warm introduction exceeds the downside of resorting to cold outreach.

Usually, this happens when the time needed to set up a warm connection is longer than what you have before you need to launch your fundraise.

In these situations, crafting the best cold outreach you can becomes essential even though there are no guarantees.

The 'Skeleton Key' to Cold Outreach

This skeleton key, in other words something that will unlock any email door, is relatively simple. 

Mutual affiliation 💀🔑

By mutual affiliation, I mean something that you and the investor have in common. Including some form of mutual affiliation in your email has a mind altering effect on minds.

This connection enables the investor to think, "They're just like me. And if they're just like me, they might be worth talking to, investing in, good enough to win."

Some of the stronger mutual connections range from having worked at the same company, worked for the same person, or growing up in the same small town. The investor might think a little more highly of you if you went to the same university, making them more receptive to hearing from you.

But you might be surprised to hear that even affiliations that seem superficial could potentially unlock a conversation with an investor. 

For example, living in the same city or having a shared hobby, such as golfing or surfing.

There are countless scenarios along these lines, but I recommend trying to integrate some aspect of mutual affiliation into your cold outreach. I guarantee it will, at the very least, boost your response rates in your cold outreach. Try this and let me know how it goes.


  1. Cold outreach can be effective if done thoughtfully.
  2. Prioritize warm introductions when possible for smoother investor interactions.
  3. If cold outreach becomes necessary, enhance its effectiveness with the "Skeleton Key" approach—include shared affiliations with the potential investor. This addition can unlock deeper engagements and yield better responses.
  4. Implicitly refer to this "Skeleton Key" in the opening line of your email to grab the reader’s attention.

Be chased,

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