yukai chou gamification

One-Two Punch and the Uppercut: The Art of Cold-Emailing


Cold-Emailing is frustrating

Have you ever had the frustrating experience where you emailed someone you didn’t know very well, and never got a response? Feels pretty bad right? No one really likes cold-emailing, but in order to strive for more opportunities that wouldn’t regularly show up at your door (customers, mentors, advisors, investors, etc etc), you are often required to contact people you’re not already buddies with.

But what if they don’t respond? Should you email them again? But haven’t they already implicitly rejected you by not responding? Aren’t you annoying them? The entire experience can be very demoralizing.

A story of Yu-kai Chou RECEIVING cold-emails

However, before you give up hope, I want to share a couple quick stories. In 2007, I went to an entrepreneurship event hosted at the UCLA Anderson School called StartupLA. I signed up for the spontaneous 1 minute pitch at the event. After the event, I was catching up with a lot of work so I only made sure I followed up with a handful of key people that I had to meet.

However, I got an email from a struggling entrepreneur that the judges didn’t really like during that time. He said it was great meeting me and wanted to catch food/coffee sometime together. Being in my stressful catchup mode, I felt warm about the email but ultimately ignored it (I didn’t want to appear like an asshole and reject such a polite and sincere offer).

A couple weeks later, I received another email from him, saying that he knows I am busy, but it would be great if we could catch coffee sometime. I actually did kinda mean to respond to that, but it sat in my inbox for almost a week, and it felt a bit awkward responding with “Sorry I didn’t get back to you earlier…” so I also kinda let it go…

LUCKILY, this guy had the persistence of the Uppercut (will talk about soon!) and emailed me again! By this time, there was no excuse for me and I was compelled to respond to him IMMEDIATELY. We then scheduled to get some dim sum together.

I’m so glad he sent me the third email, and that I responded to it. We became great friends afterwards and helped each other out in everything we could. Possibly due to his persistent personality, his company took off. Today his startup is extremely successful and making some good, scalable money for him.

As you can see here, if he got discouraged and upset from the first or second email “rejection” and gave up our friendship would have never happened.

A shorter story of Jun Loayza receiving cold-emails

Jun Loayza is long time friend of mine and CMO of VoiceBunny, and he regularly gets a lot of service providers that want to sell them stuff. Needless to say, most of them are ignored or rejected.

However, there is this one firm that continuously contacted them. At the beginning, Jun was complaining how they were very spammy and annoying. But as time goes by and as they continue to politely request a phone conversation, Jun finally got hit by their persistence and decided to schedule a meeting with them. He was kinda annoyed by how they wouldn’t retire, but also respected how they stayed on target for as long as they did.

Now since that’s Jun’s business, I’m not sure how the talk went (and hence a shorter story). But hey, they managed to turn Jun from being annoyed to having a phone conversation, and that’s pretty impressive. Except, what they did involved no real “skill”, no real learning-curve, and every one of you can do it if you have the willpower and discipline.

The Secret of Cold-Emailing

Since me and many of the people I know have a lot of similar experiences like these from the receiving-end of cold emails, I slowly derived a conclusion that could be semi-insightful for highly motivated individuals.

Now a lot of people say that cold-emailing is a numbers game. You email 100 people, and X% of them would response. Once you tried that 100, you move on to another 100. Sure, there are concepts of doing a lot of research and changing the cold-email to a warm-email(which I definitely support if you have the time), but unless they already know you, it’s going to be lukewarm at best. Lets still include that as cold-emailing for now.

So the potential insight I had about cold-emailing is: the odds of your cold-email getting a response from someone you already cold-emailed before is often higher than the odds of cold-emailing someone new.

This idea is similar but in reverse to the fundraising concept of how people who have donated before have a much higher chance of donating again. This says that the people who have IGNORED you in the past have a higher chance of responding to you this time.

Now obviously this assumes everyone you targeted at the beginning is relevant to you. If they ignored you because you were trying to sell pads to old men, then you are ridiculous and my blog does not apply to you. Yes, even if you were trying to sell it to young men. And yes, even if you planned to sell pads in gift-wrapped form so men could give to women as gifts.

The One-Two Punch and Uppercut

So I call this cold-emailng “technique” the One-Two Punch and Uppercut. If you know a little bit about boxing, basically it means that the first email you send out is the weak jab. The second email you send out is the stronger right cross punch. And finally, that third email you send out is the Uppercut that can defeat most opponents.

Again, there is nothing special or skillful about this technique. The key difference is a change in mentality. Normally when you send out cold-emails, you take the first nonresponse as a failure. While you are a little depressed, you might muster up the courage to send a second email. Once that one is ignored, you are done and a failure in life. You are too insignificant in life and no one wants to talk to you, even after your carefully crafted email straight from the heart. And then suddenly some autumn leaf blows over your head as the sky becomes quiet and gloomy, I might add. Very depressing.

Well, in the One-Two Punch and Uppercut mentality, you want to defeat as many opponents as possible. Some opponents are weak-sauce and once you hit them with a jab, they lose and respond to your email (metaphorically! I fully encourage you to be these cool people who respond to people the first-time through). Some opponents are stronger, and you need to do a jab AND a forward punch before they are defeated and send you an email.

And finally, if your opponent sustained through the first two punches, then you must seal it with the uppercut, which is often strong enough to knockout most opponents. Come to think about it, I don’t think I have ever ignored ANYONE who tried to contact me three times. I guess I have never survived through an uppercut 🙂

When you utilize this mentality, you no longer see being ignored as a rejection. You just identify the person as a stronger opponent that requires the full-combo. In that way you maximize your chances of getting a response from them.

Jabbing 100 people once does not give you the most wins in cold-emailing

With this concept, you can easily see why cold-emailing a lot of people once and moving on to more is not ideal. If you found 100 opponents and jabbed each of them once very fast, I doubt you will have too many victories. Only a few noobs would fall and you will begin to think you kinda suck and get depressed. If you instead found 30 opponents to do the complete One-Two Punch and the Uppercut, you would probably defeat a lot more opponents and feel better about yourself.

What if the Uppercut fails?

If you have finished your combo but have yet to get a response, it’s completely up to you if you want to continue fighting or just give up for now. I would say that in most cases the odds of the fourth email getting a response is actually lower. If your opponent took your 3-hit combo and still stands firm, they just might be too high level for you. Like your 3-hit combo technique would definitely not work on President Obama as his level is too high. You can’t really damage him no matter how many emails you send.

In that case you’ll just have to first level up before you try again. If you become Bill Gates, Oprah, or Arnold Schwarzenegger, then you actually might have a good chance succeeding with the One-Two Punch and Uppercut on Obama.

And just remember, there is really no harm in trying. The worst that can happen is that you never talk to this person, which is by default the result if you never tried at all. Actually, the worst that can happen is that you make an asshole feel very good about himself, maybe brag about it to his friends, and ignore you like an asshole. It’s okay if you make someone’s day today. Keep leveling up, and one day you’ll knock him out.

Time for you to share

What about you? Have you ever had someone contact you three times and you still ignored them? What was the reason you didn’t give them a chance? Also, have you had any experience on being successful on the third attempt? Please share with me and fellow readers 😀

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19 thoughts on “One-Two Punch and the Uppercut: The Art of Cold-Emailing”

  1. It seems like you’ve had a recent experience where you found yourself on the receiving end of an uppercut during a confrontation. Your resilience and ability to respond constructively are commendable. If you’re open to sharing more details or seeking advice on how to handle such situations, feel free to provide more context, and I’ll do my best to assist you.

  2. I used to really like reading what you had to say, but your recent writings have been quite dull… Your brilliant articles are much
    coreball missed. These last few postings are completely off topic! I mean, really!

  3. Came to read the post based on a tweet today about it. It may be an oldie, but it is good advice as I was already planning on using a list and cold emailing to a few hundred at a time and then moving on. Now I will plan a 3 part attack. I did wonder what you meant by “pads.” Something you would give to women but not sell to men. Assuming maybe something was lost in translation 😉 but curious as to what you meant, because I have no guesses.

    1. Pads is the feminine care product that women need to purchase regularly. I was saying that if you are emailing a man multiple times trying to sell them this product, it would not work no matter what 🙂

  4. This is a comment from Allison Carpio. It was in my wordpress but not sure why it didn’t go on LiveFyre.

    “Very interesting. I used to think following up  with the cross punch was the last step–never thought of an uppercut.I came across this article () about how to get the attention of a busy person. It states offering something in return–nothing monetary, but offering to teach something or share an experience they would find valuable. 
    Smart people always want to learn something new, so your chances of getting a response from a busy VIP is higher if you could add value to them somehow.”

  5. Very interesting. I used to think following up  with the cross punch was the last step–never thought of an uppercut.
    I came across this article (http://www.fastcompany.com/3015627/leadership-now/the-key-to-getting-meetings-with-insanely-busy-people?partner=newsletter) about how to get the attention of a busy person. It states offering something in return–nothing monetary, but offering to teach something or share an experience they would find valuable. 
    Smart people always want to learn something new, so your chances of getting a response from a busy VIP is higher if you could add value to them somehow.

  6. I Liked the player power analogy, life is like that, sometimes you need to level up a bit before taking on the ultimate boss.

    Thanks for the article, I enjoy reading your stuff.

  7. Hey Lashonda.

    Thanks for the great feedback! I’ve been off my game in terms of blogging for sure. Can you let me know what are the old posts that you thought were great, and what are things I can improve with newer posts? Thanks!

  8. Great post Yu-kai!

    I’m new to the Bay, and thus have been reaching out to a lot of unknowns over — and I’ve noticed something interesting: The ‘level’ of the person I email is in NO way related to their propensity to respond (or predictive of how many swings they will require).

    Often times, the person who I’d think least likely to reply can be the easiest to start a dialog with. I’ve found the most important factors to be my sincerity and quality level of the dialog which I’m trying to start.

    Keep it up, best of luck with the angel fundraising.

  9. Thanks a lot for the comment and the consistent support. Even though we’ve never really met, you are considered a really good friend of mine. The powers of social media 🙂

  10. Thats my favorite picture of Muhammad Ali. “First round, first minute” Solid advice Yu-ki. Thanks for providing. I like the direction Viralogy is going.

  11. Sounds advice here. Makes sense when you break it down like that.

    Your advice also matches up with what many sales experts will tell you except that they talk about cold calling where you’ll need more like 5 to 7 jabs (points of contact) before you land the uppercut.

    1. Thanks Xurxo for the comment!

      Yea, you can only do the uppercut to people who are ignoring you, so it’s not realistic to jab too many people and suddenly land an uppercut 🙂

  12. I thought I was the only person who hits the mat after the upper cut. Great post and very timely as I just responded to a guy after he laid me out with an uppercut!

    1. Hahaha, very timely indeed! It’s always nice to see how systematically people can actually be defeated by the uppercut. But hey, someone worked this hard just to talk to you. Why not just talk to him right? 🙂

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