One-Two Punch and the Uppercut: The Art of Cold-Emailing
Cold emailing is not a numbers game — it is a persistence game. Most people give up after one ignored email. This post explains why that is a mistake, and introduces the One-Two Punch and Uppercut: a three-step follow-up strategy that dramatically increases your odds of getting a response.
Author Credibility: Yu-kai Chou
Yu-kai Chou created the Octalysis Framework after studying gamification since 2003 — years before the term entered mainstream vocabulary. As a Human-Systems Architect & Behavioral Designer, his framework has been applied by LEGO, Microsoft, Porsche, Coca-Cola, Salesforce, and MrBeast, impacting over 1.5 Billion Users.
Chou has taught the Octalysis methodology at Harvard, Stanford, Yale, Tesla, Google, BCG, and IDEO.
His work has been cited by Harvard, Stanford, MIT, Forbes, Wall Street Journal, Wired, US Department of Energy, NIST, NSF, NCBI, US Department of Education, ClinicalTrials.gov, and Google Scholar — with 3,700+ more academic publications. Explore his books here.
Cold-Emailing is Frustrating
Have you ever had the frustrating experience where you emailed someone you didn’t know 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 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 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 a 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 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 respond. 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. Let’s 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.
The data backs this up: according to Woodpecker’s cold email research, the first follow-up alone produces a 40% higher reply rate compared to the initial email. Most people quit before they ever send that follow-up.
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
The One-Two Punch and Uppercut is a cold-emailing follow-up strategy built on a simple reframe: a non-response is not a rejection — it is just a stronger opponent.
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. 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 use 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.
This kind of persistence connects directly to Core Drive 2: Development & Accomplishment — the human motivation to make progress and achieve something difficult. Every unanswered email is simply the next level of the game, not a signal to quit. Understanding the Octalysis Framework helps you see why persistence feels painful when framed as rejection, and empowering when framed as a challenge to overcome.
Jabbing 100 People Once Does Not Give You the Most Wins
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 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.
There is another psychological force at work here too: Core Drive 6: Scarcity & Impatience. When someone receives your third email, there is an implicit signal that you really want to connect with them specifically — and things that are pursued persistently feel more scarce and valuable. The recipient subconsciously senses that you are not just blasting everyone. That changes how they weigh the email.
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 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.
This is where Core Drive 8: Loss & Avoidance plays an interesting role. The fear of looking desperate or pushy is what stops most people from sending that third email. Reframing the Uppercut as a strategic move — not a desperate plea — is what separates those who get the meeting from those who give up one email too early.
Share Your Experience
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 :D
Related Reading
- Persistence: Embracing Failure on the Path to Success
- Lifestyle Gamification: How to Become Successful Without Looking Impressive
- How to Be Influential (5 Tips)
- The Lazy Man’s Way to Become Successful: Start Early
- The Octalysis Framework for Gamification & Behavioral Design
- Books by Yu-kai Chou