Kaizen 71: I convinced a popular YouTuber to "give" me $749

How to send a good cold email and thoughts on sharing on the internet and blogging

Hey friend 👋,

Welcome to the 71st edition of the Kaizen Newsletter ⛩, a weekly newsletter where I share my thoughts, new ideas I learn and make weird connections between self-improvement, productivity, product, tech, sports, anime.

As you may have noticed, I’ve been experimenting a bit with my email titles. I realized how important they were and wanted to see how short I can cut it until people stop recognizing it’s the Kaizen Newsletter! This week, I have a really cool issue. I decided to give out this YouTube thing a try and enrolled in Ali Abdaal’s online course. This story is how I convinced him to “give” me $749 by sending him a cold email. Hope you enjoy!

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Two weeks ago, I made a $749 mistake.

Instead of browsing Twitter, I decided to work on my weekly newsletter and missed Ali Abdaal(a popular productivity YouTuber)'s announcement that the prices for his course would double.

By the time I saw it, it was already too late.

Instead, I reluctantly purchased the essential membership at the same price – $749$ – I would have paid for the premium membership (now at $1498), had I seen the announcement a few hours earlier. (In case it isn’t obvious, the premium membership is a step up from the essential membership!)

I took a chance by tweeting at him but didn't get any response, apart from a few likes from supportive tweeter friends (thanks!!!)

I was pretty bummed out when I realized I’d missed the deal – and even got mad for a bit.

"I thought Ali would be a cool guy and just respond to my tweet to bump up my membership. It wouldn't even take him any time!"

How egotistical is it to think that Ali Abdaal, a productivity YouTuber, doesn't have anything better to do than respond to future students crying about how they didn't register for the course earlier.

There are probably a thousand others sending him questions and different requests.

And that's when it hit me. I can put my copywriting learnings into practice and craft one hell of an email to grab his attention and make him bump me to the premium membership!

There were four core components that I knew were important when writing the email:

  1. The email title

  2. The lead

  3. The value

  4. The ask

The email title

This is when you realize how important email titles are. Regardless of how good the rest of the email was and how much value was given through the document, if Ali doesn't bother to open the email, it was game over.

Here are the titles that I wrote down and eventually settled on the bolded one above (thanks Stew for the help).

The headline represented exactly the purpose of the email. I (a future student) wanted to get the premium membership, so there was a very high chance that he would at the very least open it up.

The other titles were either underwhelming, confusing or just way too salesy/cocky (looking at you "Future Student looking to make $749”).

The lead

When you send a lengthy email, you want to make sure to grab the reader's attention right away, so they're intrigued and will read through your email to discover what happened.

I decided to start the email with "Last Tuesday, I made a $749 mistake" (seems familiar??)

Using a big enough dollar amount combined with the word "mistake" invokes curiosity in the reader.

Someone who opens the email and sees this right away will be like "Oh, how did he lose $749?" and will want to continue reading.

As proof, if you’ve read up until now, then it means my lead worked!

The value

This is obviously important because if you can't provide enough value, then forget about your ask.

This is the moment where you want to convince the person that this email was worth his or her time.

In this case, I knew (from this tweet) that Ali valued feedback for his course and because I took a lot of other online courses, such as Write of Passage, Building a Second Brain (BASB) and I’m currently taking the writing fellowship at On Deck, I figured that I could offer some good ideas on how he could improve his course.

I also knew that he was a mentor for BASB, so I wanted to make sure to offer ideas that weren't from the courses that he was already aware of.

Thus, The bulk of my ideas came from my writing fellowship at On Deck and from my writing group, Compound Writing.

Here's what it looked like:

The ask

Technically, this is the easiest one.

If Ali opened the email, read through the email and received lots of value from the document, then as long as the value provided was way more than the ask, then it should be an easy yes.

In this case, it was a relatively small ask, because he wasn’t actually giving me $749 (sorry for the clickbait). But he would be offering the equivalent of $749 by bumping my membership to the next category.

This is how I phrased it:

"My only ask is if you believe that this document provided you with good enough value, that I can be bumped up to the premium membership."

Finally, after everything was compiled together, was the stressful part: Sending it to Ali Abdaal.

So after sending it to myself twice to make sure I didn't make any stupid mistakes, I pressed "send".

Deep breath

Then, I waited…

And after refreshing my inbox at least 100 times, I see this pop-up in my inbox.

I couldn't believe it. I did it??!!

I honestly thought I would be a lot more ecstatic than I was when I would get it, but I also have to say that I was pretty confident that this would happen.

It might be cocky, but the moment I knew this email was good was when I asked my girlfriend to let me know her thoughts.

And this is what she responded: "I would never have the balls to send this!"

I grinned because that's when I knew I had a high chance of getting what I wanted.

What sending this cold email taught me was the following:

If you want to stand out, you can't do what everyone else does. You have to take risks.


🤔 Thoughts

🌐 Thoughts on Sharing on the Internet

Reason #124545983459 why you should start sharing what you do on the internet.

Patricia was an ex-PM at Stich Fix and Door Dash who really had a passion for mindfulness, philosophy and building products.

So she worked on projects that would fulfill her passions:

  • She started a bi-weekly newsletter called Wellness Wisdom where she shares resources and thoughts on start-ups, personal development and philosophy.

  • She started building Mind Streaks, the Strava for meditation (which by the way I've been using every day for the past couple of weeks).

And because she was continuously building in public, she eventually got a position at Calm as a Senior Product Manager.

Which to me is crazy because it blends her passion for mindfulness and building products together.

How can you not be inspired after seeing that?

👨‍💻 Thoughts on Blogging

Enjoyed reading Andrew Chen's post about what he's learned from his 10 years of blogging.

His most powerful idea is the following:

Thinking of yourself as a journalist that’s covering interesting ideas, trends, products, and everything that’s happening around you leads to much better/stronger content.

As creators, we often struggle because we want to write about something that is "new". But using the lens of we're only a journalist that's covering interesting ideas, a lot of the pressure is taken off thanks to that way of thinking.

🐦 Tweets

The only Ls I take are lessons.

Not true for everyone, but I'm definitely of this mindset.

Cuteness overload.

🙏 Shoutout

Shoutout to Mark, Pranav, Rishi and James for the good convos this past week!

Also thanks to Parthi Loganathan, Elisa Doucette, Alexandra McQueen and James McGirk for providing feedback and edits to this newsletter.


👋 End Note

If you want to know what I'm up to now, you can check it on my website here.

If you enjoyed the Kaizen Newsletter, then it'd be cool if you can share it with your friends.

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See ya next Tuesday,

Alexander ✌️