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.





