I work on an email marketing product as my full-time job, but I must confess, in my day-to-day life I’m the kind of person who uses adblock and opts out of marketing messages whenever possible.

However, since starting my job at Mailchimp and diving into the world of digital marketing, I’ve been paying much closer attention to the ads that I used to glaze over. In fact, I now voluntarily sign up to be on email lists (using a burner email, of course).

I’ve learned that studying marketing is a lot more interesting than being marketed to—as marketing marries my interest in human psychology with my interest in making money 😉

Since Black Friday is probably the biggest sales event of the year, I decided to pick out 3 emails that jumped out to me in my inbox this season and do a mini-analysis of each one.

1. Skillshare – “The ONLY TIME to get 50% off is right now”

Skillshare’s 50% off email

Subject line: The ONLY TIME to get 50% off is right now
Preview text: Cheers to a year of learning (& saving money!) Get 50% off a year of unlimited learning.
Lead type: “Offer” lead
Why it stood out: Skillshare actually sent me 3 different emails within a 2-day span, with the following subject lines:
- Your Black Friday Savings: 50% OFF
- The ONLY TIME to get 50% off is right now
- Get our BIGGEST DISCOUNT For a limited time
The reason why this one stood out (and was the one I actually clicked) was because it had the strongest claim while specifying the offer details. Claiming that this is the “ONLY TIME” to get this deal added a much stronger sense of scarcity/urgency compared to the other two subject lines. Using a number “50% off” made the subject line easier to digest and more actionable than the subject line that only mentioned this was the “BIGGEST DISCOUNT” (leaving me to wonder how this discount would be structured—too much thinking required!)
The offer: Following up on the promise in the subject line, Skillshare provided a discount code for 50% off, expiring Dec. 3, 2024 (Cyber Monday).

Skillshare Membership Benefits
Why it works: Emails that start with offer leads are generally targeted to people who are already well aware of the product that’s being sold. Most people already know that Skillshare is an online learning platform, especially if they signed up to receive emails. So instead of trying to slowly ramp you up into why you should start learning new skills this year, this email focuses on delivering a clear, direct offer and doubles down on scarcity messaging all throughout the email to get you to buy now.
Actionable takeaways: Use the following subject line template when running the biggest discount of the year: “The ONLY TIME to get [XX]% off is right now”

2. Patagonia – “A deal that lasts”

Patagonia’s “A deal that lasts” email

Subject line: A deal that lasts
Preview text: Our Black Friday spiel.
Lead type: “Proclamation” lead
Why it stood out: Amongst the 100s of “50% OFF BLACK FRIDAY SALE – LIMITED TIME ONLY” emails that arrived in my inbox this Black Friday, Patagonia’s claim that they have “a deal that lasts” stood out in its lack of urgency and scarcity messaging.
The offer: After a brief recognition that this email was sent during Black Friday season, Patagonia reveals their “deal”: instead of a steep price discount, their offer is their continued commitment to supporting environmental causes, as outlined in the following graphic.

Patagonia’s “offer”
Why it works: Timing. Patagonia strategically sent this email during Black Friday season, knowing that it would stand out amongst the 100s of other emails going on around this time. But instead of going with the grain and offering their own sale, they chose to double down on their brand messaging, building customer loyalty and no doubt getting a couple of people who decided to click in and buy some new Patagonia gear. This isn’t the first time Patagonia has leaned into this kind of messaging: on Black Friday in 2011, Patagonia famously placed its “Don’t buy this jacket” campaign in the New York Times.
Actionable takeaways: Be mindful of the brand’s values when crafting email campaigns for Black Friday. Brands that focus on sustainability may not be a good fit for typical discount offer emails, which give off a consumerist image. Use counter-intuitive messaging to stand out and amplify the brand message around sustainability instead during the Black Friday season.

3. Deya – “how to slay 2025”

Deya’s “how to slay 2025” email

Subject line: how to slay 2025
Preview text: Plot twist: The people who are going to slay 2025 aren’t waiting for January 1st to roll around.
Lead type: “Promise” lead
Why it stood out: All lowercase letters and the usage of “slay”.
The offer: After building up some suspense in the lead – Deya reveals that her offer is a free gift that comes with a purchase of her Digital Business Management Bootcamp.

Digital Business Management Bootcamp free gift
Why it works: Deya has created a personal brand built on her digital business management freelancing experience, and as a Gen Z herself, her brand is marketed towards a Gen Z audience that’s comfortable with (and even drawn to) less formality online. Using slang like “slay” immediately catches the attention of this audience, who might otherwise glaze over the message.
Actionable takeaways: By using a brand voice and tone that’s uniquely tailored to your personal brand and uses the language of the target audience, you can stand out amongst a crowded pile of emails.

Closing thoughts

I’m still learning and not an email marketing expert (yet 🤞) by any means, so take my analyses with a pinch of salt. However, if you’re like me and you’d like to start a business in the future, I hope you enjoyed this exercise!

At the very least, you might find advertising to be a lot more interesting than in the past, especially when you look at it from the perspective of the business instead of the consumer 🙂

That’s all for now, see you next week!
Tim

P.S. I’ll be writing this newsletter from Europe starting next week, so expect to see some more travel-related posts!

♥️ My favorite things this week

🦃 Thanksgiving meals: I met up with friends and family throughout the Thanksgiving holiday, and it was nice to be able to take time to intentionally connect and spend time in a group setting. For my family’s Thanksgiving meal, we met up with some family friends for lunch. I remember when I was younger I wasn’t a huge fan of these gatherings, since I was “one of the kids” and didn’t have many people I could connect with. This year, I had some pretty interesting conversations! One high schooler I talked to was passionate about public transportation and urban planning 🤩 I hope they run for office one day.
🚗 Road trip(s): In a spontaneous turn of events, I joined some friends (hi! 👋) on a couple day trips over the weekend to Carmel-by-the-sea and Mt. Tam with essentially 1 day of planning. We had some great conversations along the way and bonded over shared experiences. I also realized I should probably brush up on my Chinese a lot more lol. I’d love to have more spontaneous activities like this in the future, which means I need to either move to a city or get a car 😂 Stay tuned on which one I go for!
📕 Great Leads: The Six Easiest Ways to Start Any Sales Message: Part of what inspired me to write this post was reading through this book. The core idea is that the hook aka the “lead” is the most important aspect of any marketing campaign, and it categorizes leads into six different types that range from most direct to most indirect. It provides helpful examples and principles that explains how to use each lead effectively in different situations. If you want to nerd out about marketing, I recommend checking this out!