It’s the holiday season again – my favorite time of the year! From Glühwein to Christmas lights and decorations, it’s the perfect time of year to tackle on many things that bring us cheer. When it comes to the people around us and in our lives, the holiday season is my favorite excuse to catch up with old friends and meet new folks.
‘Tis the Season to Reach Out
Outside the exciting, but tough world of venture capital and entrepreneurship, I enjoy spending time meeting brilliant individuals outside of the technology sphere. To the point, I made a New Year’s resolution half a decade ago that I’m going to meet one new person I’m crazy passionate about every single week. I’ve stuck with that resolution ever since. Obviously, it required me to find a way to get in contact with these amazing folks every week. From cold emails to calls to handwritten letters to knocking on their front door, whether it was going to be a success or not, each week provided me with a new challenge I get excited to embark. And I’ve found that I get the highest positive response rate out of my 52 weeks a year, the five to six weeks starting from Thanksgiving week until the first week of the new year – or in this coming year’s case, the new decade. Over the holidays, it’s true that people don’t check their inboxes as frequently, but it seems that most people who plan to reach out believe that too, and often stall until the new year, at least many of my friends and coworkers do – a sort of New Year’s resolution. Of course, I’m not saying there’s any guarantee in a positive response, but chances do seem higher.
I’d like to start off by saying that in the context of reaching out to individual people that I can imagine becoming friends with, I don’t have any holistic templates for cold emails, outside of a few sentences, which I’ll share in this post. To me, writing a cold email is a labor of love, and it really pays off when I make the content as relevant to the addressee as possible. On the flip side, if the purpose is to spray-and-pray or to gain leads in a funnel, this post may not be entirely pertinent, though there may be sprinkles of fortune scattered below in how I explore the mental maze in sending a cold email.
The Warm Up
Having spent almost a decade in competitive swimming, the first, and probably the most rewarding, yet most underappreciated, exercise I learned was visualization. Visualization comes in two parts: 1) Seeing myself win the race and get my desired time, and 2) Being prepared for any possible resistance or friction to winning. Don’t get me wrong; the race itself is important, but about a year into my swimming career, I started competing increasingly with athletes that were of a similar caliber as I was, where the margin between our best times existed in the milliseconds. And arguably, what makes or breaks the race is how mentally prepared you are before your race even begins – what all the 30-40 hour training weeks will amount to.
It’s the same when I send cold emails. I used to think I was special, having gotten into an amazing university, some of the most competitive and “elite” organizations on campus, and so on. Truth is it was all bullcrap! And sending those cold emails was one element that grounded me. A cold email is nothing but another tick in their inbox – nothing more, nothing less. I’m not allocated more real estate on the virtual battlefield. In fact, in some ways, you could even say I can’t even pay-to-win. If I’m punching above my weight class, then I was and am another competitor, competing for a limited, finite resource: attention.
Jeff Bezos once said:
“If everything you do needs to work on a three-year time horizon, then you’re competing against a lot of people. But if you’re willing to invest on a seven-year time horizon, you’re now competing against a fraction of those people, because very few companies are willing to do that.
“At Amazon we like things to work in five to seven years. We’re willing to plant seeds, let them grow and we’re very stubborn. We say we’re stubborn on vision and flexible on details.”
Although he said this in relation to building a company, it’s equally true in the competitive landscape of sending a cold email. You have to be willing to push your time horizon beyond any of your competitors. Or in other words, be prepared to go the distance – to play the long game.
What does that mean? Any permutation of creativity juices, like letters sent via messenger pigeon (or turtle doves for this time of year), and recurring emails works. The most important thing to keep in mind, when playing the long game, is cadence and commitment. My default is usually one email a week, usually Monday or Tuesday morning, up to three weeks, with each one showing the positive delta in knowledge acquisition compared to the past week, but still need help in their respective expertise on a particular topic.
Some of my friends and founders I met have tried more extreme versions of what I do. For example, one persistent founder I know once sent the same email every day at 9AM for three months to finally get a meeting with an executive at a major entertainment studio. Another sent the same pitch email to a well-renowned investor every week for a year, and now they’re best buds and play pick-up games every month. The disclaimer is that these may be edge cases, but do be cognizant to never overstay your welcome. If you’re asked to stop, stop.
When should I send a cold email?
On a macro scale, two overarching themes that run in my head are my personal resource availability and timing.
Personal Resource Availability
Outside of the obvious answer of trying to get in touch with someone outside of my immediate network, the question would be better phrased as: When can I not get a solid warm intro? I used to think all warm intros were the same, and that a warm intro is always better than a cold email. Truth is: it’s not always. There’s a huge spectrum to how great (or not) a warm intro can be.
Let’s think about it from the perspective of a Net Promoter Score (NPS). We may all be familiar with the question:
One a scale of 1-10, how likely are you to recommend this product to your friend?
We’ve most likely seen it when filling out a survey after you used or bought a product or service. It’s how businesses measure your satisfaction of their product or service. Although one might think that five is average, anything greater than five is above average, and anything less is below average, the truth is most people regress to filling out ‘7’. ‘7’ is a proxy for not offending anyone but at the same time, saying the the product or service was “okay.” Businesses usually measure 7’s and 8’s as okay, where the real breadwinners are the 9’s and 10’s. Similarly, when I seek or decide to give warm intros, it really comes down to: Can I get or give a 9 or 10-score warm intro? In my head, it subsequently creates a binary scale: a solid warm intro (score = 9 or 10) and a weak warm intro (score ≤ 8).
Subsequently, when should I send a cold email is answered by… whenever I can’t get a solid warm intro.
Solid Warm Intro > Cold Email > Weak Warm Intro
Now, it begs: what are the characteristics of a warm intro? This is decided in two parts: content and matchmaker.
I characterize content in three parts: the subject, the introduction, and the ask. The subject is meant to attract and describe the purpose of the email. The introduction is to explain who I am. The ask, and probably the most important bit, which has to be clear from the beginning, is what I want out of the introduction. With the first introduction, and also for the cold email, I keep it simple to one of two things, depending on the other person’s bandwidth:
- A 20-minute call or in-person chat (Note: If I go with this option, and the person accepts, I follow up with 2-3 questions I plan to ask during the chat)
- One burning question
To make it easier for the matchmaker, I often send them a short two to three sentences that summarizes the above, and can easily be forwarded along. My goal is to make it as easy and simple for both the matchmaker and the person I want to get in touch with.
The matchmaker, or the person referring me, is any one or a combination of the following:
- A subject-matter expert (SME) in my respective field, defined by having a track record for success and external validation by other thought leaders;
- Someone who knows me (and my work) well, capable of succinctly describing what I’m working on and me, and is excited for me;
- And/or, someone who knows the person I want to get in touch with well, where the matchmaker is either the first 100 names the person receiving the introduction thinks of, or the first five names in that given field.
Timing
Timing is crucial. And to measure it, I ask myself four questions:
- Where are they (in life)?
- Where am I (in life)?
- What is my purpose?
- How can they win?
Where are they (in life)? Is the person I want to get in touch with busy tackling a new project? Preparing for a new baby? Switching careers? On a holiday vacation? If the person has a large presence on social media, most of these can be found online. Take special notice of the inflection points and outliers in their life. Some are more obvious than others. Of course, they’ll be willing to talk about the moments in their life when their second derivative was positive, but I think there’s a bigger story behind the moments when second derivative was negative. Of course, it may be something I bring up later in the conversation depending on how openly vulnerable the person I’m reaching out to naturally is. If the person has a limited presence online, it’s best to ask the matchmaker or mutual friends and connections. Sometimes, I just can’t find evidence of his/her bandwidth anywhere, so I preface my cold email ask with:
I know you’re extremely busy as is. If this does surface in your inbox and you have the time to reply, I’m grateful if you could [insert ask]. Otherwise, I’ll reconnect in one month.
Leaving room for people to not feel bad to say no, and making sure to follow up have been the two hallmarks for me to potentially get a “yes” in the future. A “no” now isn’t a “no” forever.
Where am I (in life)? Have I done all the diligence I could possibly do before I reach out? Anything that is “Google-able” is not worth asking another individual, especially if I’m looking to punch above my weight class.
What is my purpose? Why am I reaching out? What makes this person special? Why might this person be the only one in the entire world who can answer my ask? If I’m reaching out in the networking sense, can I be this person’s friend for at least the next decade?
How can they win? Always give before taking. There’s plenty of literature online, explicitly and implicitly – on social media, in the news, in their public appearances – that would help arrive at what they might need. If I have to ask him/her how I can help him/her, then I’m already wasting that person’s time.
In closing
In a saturated market of information, product-market fit is defined by attention. So keep it personal. Keep it direct. And have some fun.
