When a Millionaire Dares You to Cold Email Them

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Hey folks, Kabir here, bringing you another round of "Kabir Cold Emails Millionaires" - the series where I share my attempts to reach out to some of the coolest and most successful folks in the biz via cold email.

In today's episode, we're looking at an email I sent to Nick - a challenge he threw my way after a cheeky YouTube comment I made. Now, this email is a bit of a departure from my standard fare and boy, did it get a reaction!

So buckle up, grab your popcorn, and let's dive into this madcap adventure of cold emailing.

So, here’s the scoop. I was tuned into the My First Million podcast - a pretty regular occurrence in my life - and up pops Nick.

Now, this guy was something else. He had this infectious energy, a brand of humor that could make a monk crack a smile, and an overall demeanor that was as impressive as a peacock in full strut.

Then came the real zinger. Shaan attempted to blow up the concept of AI-driven web pages for local businesses like it was a piñata at a kid's party.

But Nick, cool as a cucumber, skillfully steered the conversation back on track, championing a more measured, tortoise-beats-the-hare kind of approach. I was nodding along like one of those bobblehead dolls on a dashboard.

Inspired, I hopped onto YouTube and left a comment. Something along the lines of “Such positive vibes, Nick. I’m going to cold email you.” 

And wouldn't you know it? Nick shot back with “Do itttt” which I took as more than a challenge - it was an open invitation to a digital duel at dawn!

So there I was, in the wee hours of the morning in drizzly Delhi, crafting this email like it was the next great American novel. Well, here goes nothing...

The subject line: “Friends Newsletter”

I ventured into a fresh strategy on this occasion, which differed from my usual approach in three significant ways.

Firstly, I had already informed the individual that they should expect an email from me. It was a challenge thrown at me, and I accepted it.

The second unconventional tactic was that this was in reply to a newsletter. It wasn't one of those standard cold emails I was accustomed to sending. Instead, it was a new approach where I was actually responding to his newsletter.

Lastly, the third unique aspect was the length of the email. This wasn't your typical short and crisp cold email. This was a more extended version, more detailed and comprehensive.

All of this led me to write that subject line.

Now, the opening line: "Nick, you dared me to cold email you (on a YouTube comment), it’s 1:30 AM on a rainy day here in Delhi, and I’m doing exactly that."

This line is personal, relevant, and has a dash of humor. It ties directly to our YouTube rendezvous. A continuation of a conversation - more like a late-night chat show episode.

Next: "Just finished tuning into your episode on the My First Million podcast. Totally dug the whole chat, especially that bit when you wrangled back the conversation after Shaan tried to obliterate the concept of making web pages for local businesses with AI. Classic Shaan!"

This line shows that I paid attention to the podcast, and I’m not just throwing out generic compliments. I’m referring to a specific moment in the episode that connected with me and explaining why it stood out.

Then comes the whimsical part: I dished out some juicy personal nuggets about myself - like the fact that I'm "5 foot and something," and the reality that my wife and I have been buddies since we were in 3 years old.

Oh, and I threw in a fact about my buddies getting lost in the labyrinth of dating apps, despite the buffet of 1.4 billion potential love interests on the planet! Of course, this was all by design. Why? Because it's relatable, it's funny, and it takes the "corporate" out of the corporate email.

In the next chapter of this wild email ride, I shifted gears to talk shop. I wrote, "Aside from my romantic adventures, I helm a personal branding venture for founders, and have been moonlighting on a spanking new AI writing software that morphs founders into contortionists, letting them create content in any voice—be it Shaan, Greg Eisenberg, or even Neville Medhora!" 

Now, I knew Nick is friends with these folks, so dropping their names was not just a random name-dropping exercise. It was a strategic move to create a warm fuzzy feeling, to show I've done my homework, and to add a hearty dash of credibility to my pitch.

Then, I turned the conversation towards my newsletter: "Caught the cold email fever recently and launched a newsletter dissecting emails I’ve dispatched to mega-rich individuals I look up to or wish to learn from. Not exactly the epitome of scalability, but I’ve heard many intelligent people say ‘do things that don’t scale.’" 

This was my way of not just introducing my work, but also aligning it with something Nick likely resonates with—doing things that don’t scale.

Next came the proposition: "Would really appreciate the chance to be an observer of your journey and get to know you better. If there’s an avenue where I can lend a hand in your endeavors or showcase my worth, I’d grab it with both hands." 

Here, I wasn't just asking for a favor—I was extending an offer to assist in any way that made sense, while emphasizing my eagerness to earn my place in his network by demonstrating my value.

As the curtains fall on this email, I wrote: "Wishing you the best and looking forward to staying connected. Kabir Krishn." 

Beneath this, in an unassuming, smaller text, I slipped in a little sneak peek: "Next week’s newsletter – How I signed Sam Parr’s fitness coach as a client for my agency." 

This showcased a recent triumph, looped back to Sam Parr, so as to pique Nick's interest in my newsletter, offering him another incentive to delve deeper into what I'm all about.

So, there you have it. A detailed look at my email to Nick. This was an unusual approach for me as I responded to his newsletter, included a personal touch, and went longer than my typical cold emails.

And what do you know? Nick responded in just two minutes!

Although he hasn't gotten back to me yet, I'm pleased with the connection and I'm planning on following up with something valuable to continue the conversation.

Thanks for reading, and may your cold emails be ever successful! Stay sharp, my friends!

Message From Kabir…

Hey reader.

I'm Kabir Krishn, the founder of upTalkk. I believe that Cold email provides the most asymmetric edge one can have.

Every week, I pen countless cold emails, each a stepping stone towards connection, growth and success.

• Are you doubting your cold email game? This newsletter is tailored to help you level up and command the inbox like a pro. Drop a comment and I’ll respond.

• If you're hunting for that personalized touch, I offer 1-1 coaching. Just drop me a line at [email protected] and together we can refine your approach.

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