How to Crush the Cold Email Game

This is likely not a secret anymore, as I haven’t been shy about sharing it, but I got my job here at Corigin Ventures through an original cold email to David Goldberg (email pasted below). In addition, I’ve used many cold emails to network with fellow VCs, and feel no shame or fear in doing so.

I have told many people before that I think there is real value in a cold email, so long as it’s done well. I’ve personally taken every meeting or call that’s come in through a cold email, so long as I think they’ve been thoughtful and put effort into it.

With that, I’ll lay out how I think a cold email can be written and executed upon well, and my major do’s and don’ts when it comes to sending them out.

I want to caveat this by saying that the cold emails I’m referring to pertain specifically to my field of work, which I define broadly as the tech/VC industry. I have no idea how it should be done in other industries, although I could probably guess. I would feel comfortable giving people this advice for reaching out for jobs (both startup and VC, like myself), for networking connections, and for startups looking for funding.

Strategy

I have two main points when it comes to the strategy around your cold email. If you don’t take anything away from this post, remember these two points.

1. The most important thing is to know who you’re sending it to. This may seem obvious, but it’s not executed very well in at least half of the instances that I’ve seen. An impersonal, vague, bland email won’t get you very far. Be as personal as can be. Look up the recipient on LinkedIn and refer to their past experience, or something they’ve blogged on. Look up their portfolio, and identify some companies that are particular relevant to what you’re doing. Look up their investment strategy and point out something you align with. Those are all examples, but are a bare minimum.

2. Don’t ask for something outright. Unless you have a specific ask that can be fulfilled with a quick note back, don’t just blatantly ask for something from the person you’re emailing. Chances are they’re smart and will be able to read between the lines and know what you’re getting at, but it’s much easier to start a relationship with someone if you’re not asking for something. In fact, to go one step further, try offering something.

I’ll use my job search as an example here, to explain those two points. I created a long list of VCs I wanted to get in touch with, and then tiered them. I reached out to each “bucket” separately, so I could be much more thoughtful on how I sent my emails. As a result, I made my emails personal and looked for something that could be unique for each investor. Then (and this goes more toward my recruiting technique), I didn’t ask for jobs, I offered up some work and deep dives I’d been doing in industries that were relevant, and asked if they’d be interested in getting on the phone to discuss, plus tell me about their experiences.

For founders looking for funding, I realize that you’ll need to tell the VC that you’re raising, and that sounds like asking for something. Mention your fundraise and what you’re up to, but then suggest a call to discuss the dynamics around the industry and the trends you’re seeing, plus the traction you’re getting, to explore whether further discussions for funding may make sense. In essence, you’re offering up your insider’s point-of-view, and a way to be helpful, while they also know that you’re seeking funding. It doesn’t come across as transactional. (more on this later)

It’s as many savvy investors suggest, “go asking for advice and you’ll get money, go asking for money and you’ll get advice.” I truly believe that if you’re humble, helpful and earnest, you can use a cold email to your advantage.

Structure

The best cold emails I’ve seen play a fine balance between giving enough context so the reader knows the gist of what you’re asking, while not boring with too many details or requests. In general, I like the following format, with about 1–2 sentences per section

1. Introduce yourself and lay out your intention

2. Loop back as to the relevancy of your cold email — i.e. how you found this person, what you find relevant, why they were the ones you decided to email, etc.

3. Explain your ‘ask’

4. Provide further context to why it may be worth their time to chat

5. Mention logistics — i.e. don’t leave the reader hanging. If you’re asking for a call, suggest times, but then mention that if those don’t work, you can be flexible around their schedule

6. Thank them for their attention and sign off politely

By far the worst cold emails are short, impersonal blurbs. They often follow this format: Hi Claire, my name is [x] and my background is [y]. I’m looking to get into Venture Capital and would like to talk to you about your experiences. Please let me know if there’s a time that works. Thanks a lot. Best, [x]

Do’s!

· Compliment the individual, without being too ass-kissy. Everyone is human and likes a little flattery, especially when it’s relevant to what you’re talking about

· Suggest ways to make their lives easier. This could be statements like “I’d be happy to come to your offices”, “I’m happy to send out an invitation to put it in your calendar” or “if there’s someone else I should schedule through, please let me know”

· Be personable, but also professional. A rigid email, especially in this industry, doesn’t always catch the attention of the recipient

Don’ts!

Again, these might seem obvious, but I can count many instances in which these are broken:

1. Please spell my name correctly. I often get “Clair” from “Corigan Ventures”. Sorry guys, but that’s getting a canned email back that I’m too busy or your request isn’t relevant to me. If you can’t spend the extra 30 seconds to look up the correct spelling of my fund, nor the extra one second to look at how my name is spelt, I can tell you have a low attention-to-detail and that you’re not that interested in me (you’re probably blasting out this email to many, many people).

2. Please spellcheck. When the recipient has all the leverage, you should always put your best foot forward. I’m not saying this is an absolute dealbreaker, because I’ve made mistakes too, but it doesn’t help. Why not spend the extra four minutes to proofread so that the recipient doesn’t have a small thing to doubt. Just take this right off the table.

3. This one is the absolute worst in my opinion: DO NOT HAVE DIFFERENT FONTS AND/OR SIZES. I can’t tell you how terrible that looks. It tells me that you’re copying and pasting a boiler-plate email out to 100 VCs. Be thoughtful. If you’re worried, physically type out each email. Then you won’t run into the issue above. And, I bet it’ll make you notice something in your text that may not apply to this particular recipient.

4. In this day-and-age, it’s not difficult to find out someone’s email address. Use Rapportive, that usually sorts it out. Don’t send an anonymous email to an anonymous inbox with the greeting of “To Whom It May Concern”. If you really can’t find someone’s email, send it to that inbox, but use the name of the recipient you’d like to speak with.

Samples

In the spirit of open-sourcing, I’ve pasted my original cold email below. Upon further review, I don’t think it’s very good. However, I think there are some good things in it. Therefore, I’ve highlighted the good and what I should have done better. I don’t give myself a very high grade for this one.

The good:

· I didn’t ask for a job. Especially in recruiting, it’s important not to outright ask for a job. I asked for a chat around industry notes (more in ‘the bad’ section).

· I gave some background into my focus and intentions, and I acknowledged that this was a cold email that I’d keep brief.

· I didn’t have any typos, mismatched fonts or incorrect facts!

The bad (unfortunately, there’s much more):

· I didn’t mention anything personal, or why I was interested in Corigin, or David’s background in particular. My email, sadly, reads as pretty formulaic.

· At this point in my recruiting cycle, I had put together a couple market theses. I didn’t mention those in this email (which I thought I had), but instead they were in further follow-ups, once I’d already chatted with David. I should have offered that relevant work upfront.

· I didn’t suggest any times, or help with logistics.

I have to give credit to Lou Stokum of EdFundr, for writing one of the best cold emails I’ve ever seen. While we didn’t invest at the time, we had some great chats and I think incredibly highly of the team there. With his permission (thank you, Lou), I’ve pasted his email below.

Lou has made this email incredibly personal, while giving a great overview of what they’re doing. You’ll notice that he didn’t ask for an investment, he asked for some time to chat, asking “I would love to schedule a call to tell you more about my company. We’re currently raising seed capital and I think we fit well with your portfolio, so any input you can provide on our strategy, growth plans, or pitch would be highly appreciated.”

Please send me any notes on what’s worked in the past, and what hasn’t, and if need be, I’ll post a follow-up. If you disagree with any of these points, feel free to let me know (in a constructive manner, please), and I’d love to get a discussion going. While there’ll always be some margin of error for personal preference, I believe these to be strong points to make in sending a cold email.

Thanks!