The Art of the Cold Email

Part 1 – How to find almost anyone’s email in less than 1 minute:

Step 1 – Once you know who you want to email, find the website of the person’s employer.

Step 2 – Go to (sign up for a free account), enter the website from Step 1, and skim the first few results to determine the most common email syntax.

Note – using the name John Smith as an example, I find that about 90% of the time it is either john.smith@, johnsmith@, or john@. Most of the rest of the time it is either johns@, smithj@, somehow involves a middle initial, or is generally unguessable or not worth the time to figure out unless the results make clear the harder to guess syntax.

Step 3 – For better than 90% of people, you should now have a best guess email address that will work better than 75% of the time.

Note – if your first guess does not work, go back to and see if there were any other common syntaxes, or else make educated guesses based on my note above. can be used to test email addresses rather than sending and getting them bounced, however, it is only sometimes useful (all green means confirmed, any red means failed, and often it is green & yellow which doesn’t tell you one way or the other).

Part 2 – Considerations for the cold email:

Anyone who has recruited for an internship or job in investment banking or another networking necessary industry likely is already familiar with some version of the process above. It is not at all difficult or complex. What is difficult is getting people to respond, so what is complex is trying to figure out how best to do so. After sending hundreds of cold emails, being fortunate enough to get a job in banking, and then receiving hundreds more, I have come across one important realization and a few things I believe one can do to improve the rate of response on cold emails.

My important realization was that regardless of what you say in the subject or body of your electronic mail, the outcome of whether the person responds or not is entirely up to and dependent on that person, not you. You can write the perfect email, whatever that looks like, but if the person to whom you are sending it is home sick vomiting with a fever while simultaneously running behind on a project that is totally consuming their week, you simply are not going to get a response. This is important to remember so as not to waste too much time striving for perfection. I hear a lot of successful people saying done is better than perfect. That certainly applies here.

That said, the few things that I do believe you can do to give yourself the best rate of response in aggregate are as follows:

1. Keep it brief. This person does not care about you, not even enough to care to read about why you are telling them they should care about you. They get these emails all the time and they all look mostly the same. It is bold to be brief. No one ever lost interest and stopped reading halfway through a tweet. Use that length as a parameter.

2. Attach your resume. Since you are keeping the email brief, you will not have room to tell them much if anything about yourself. Attach your resume in case you are lucky enough to get their attention and interest in who you are. They might care enough to open it but not enough to ask for it, and they might respond if they like it but they won’t like it if they never see it. To avoid wasting a sentence telling the person my resume is attached, I often either put “(resume attached)” after my name at the end or don’t mention it all. They can see the attachment.

3. Check the time. Jeffery Fox in his book How to Become a Rainmaker says the best time to sell is on Friday afternoon. This has stuck with me for years and in many regards I buy it. People are happy on Friday afternoons and they tend to be open and careless and kind. At the same time, some people also will stop checking their email for the weekend and may not want to give you the time of day on a precious Friday so I like to send emails Thursday afternoons as well. I stay away from most mornings when people generally like to get cracking on their to-do lists and are less tolerant of distractions. I especially stay away from Monday mornings, the most generally hated time of the week. Don’t worry too much about it because you never know. Just take a moment to put yourself in the person’s shoes and think about timing for a second.

4. Be persistent. You will not annoy anyone by following up on your first email even if the person does not respond. No one cares. Emails from anyone can be annoying for everyone. The person is not going to hold a personal vendetta against you. You have nothing to lose and it is unlikely they will even remember your name. If you were emailing me, however, I have found that a second email from the same person makes me more inclined to respond. I respect persistence in almost any case and this has worked on my behalf as well. Ask for what you want, and then ask again.

In closing, these are the things that I think about when I send cold emails, and my cold emails tend to work well, better than most I can confidently say. I have made connections with billionaires, bankers, venture capitalists, CEOs, authors, and others through cold emails. Don’t be afraid to reach out to anyone. Email the CEO instead of an associate. When it comes to the cold email, as with so many other things, it pays to have guts. Good luck.