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💡Learnings from 140+ newsletter editions

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If a friend forwarded you this email, sign up for a Free subscription. Inbox Hacking is packed with marketing insights, tools, & tactics (& 2.4 laughs on average). 

A slow Humpday might have you crying “uncle!” Luckily, a good cry helps. 

We’ll carry on with today’s Feature, which lays out 35 of the biggest things I’ve learned through writing over 140+ editions of Inbox Hacking. That will set the table for…

  • The Knowledge Base 
  • Self Help 
  • Facts & Stats 
  • Get Hacking 

Alright, let’s get to those 35 learnings from over two years of writing this marketing newsletter.

Insights from Two+ Years & 140+ Editions of Inbox Hacking

I thought I knew a lot when I started writing Inbox Hacking. And I did😁. But little did I know all the extra info and intel I’d pick up from researching and writing a marketing newsletter.  

The Work Involved in a Newsletter 

#1 There’s a mountain of work setting up the technical aspects of an email newsletter – better have a pro to turn to for that.

#2 Building an email list takes patience (and meditation) (and beer).

#3 Email software can be glitchy. Worse? An ESP can act erratic at the worst moments!

#4 Freedom given by the bosses to write a newsletter how you see fit is a blessing.

#5 Grammarly is an awesome helper tool but isn’t perfect and isn’t human, so it shouldn’t be agreed with on all its suggestions.

#6 Printing out a newsletter checklist is the best way (not fool-proof) to prevent looking like an idiot to readers.

#7 You know I don’t think much of ChatGPT, but even if you do and believe you can add human stylings to AI writing – I believe that would take as long as writing a newsletter yourself.

Email Marketing Learnings

#8 Sadly, most email marketing articles rehash the same concepts over and over (segment your list, clean your list, A/B test, yada yada yada). 

#9 The best uncommon advice I’ve seen on email marketing is from Inbox Mailers’ John Gardner (engagement segmentation).

#10 Automations are a handful, so it pays to have an expert handling automated workflows.

#11 There are endless email acronyms to be aware of, and new ones popping up on the regular.

#12 Litmus, Really Good Emails, and Validity are great additional sources of info for email marketing.

#13 “Keeping subscribers happy” sounds vague, but should be the #1 goal of an email newsletter.

#14 Email metrics can give you a headache (depending on the ESP you use).

#15 Brilliant subject lines don’t always prove to get the highest open rates (perhaps they weren’t so brilliant🙂)

#16 Don’t rely only on your own email marketing checklists (Oracle has you covered)

Thunderous Headlines Have Never Been More Critical

#17 Marketers in the 1950s knew how critical headlines were, and that was before readers had 100x the distractions we have today.

#18 Old-school tactics in headlines still work on modern people (3 of them below👇 )

#19 See, it worked☺ – use numbers in headlines, stick emojis in subject lines, & become more curious to maximize your ability to make people reading your headlines curious.

#20 Read and note epic headlines for swiping (not stealing).

#21 Never use “demystified” in a headline – ChatGPT ruined that word forever, as I’ve ranted about before (tell your bot of choice to avoid words real people don’t use when talking to other real people!).

How to Make Your Content Unique 

#22 “Be yourself” sounds – what’s the word? Stupid. But I stand behind it. 

#23 Sounding unique often only takes changing a single word at the end of a sentence.

#24 Mix in stories only you have. The key is to weave them into a world-class story structure with the help of experts like Donald Miller or Matthew Dicks.

Newsletter Productivity 

#25 Get up at 4:50 AM – the best productivity hack for newsletter writing or any task requiring quiet time.

#26 The only way you can repurpose content efficiently is if you organize your content so it’s easy to find what you wanna repurpose.

#27 Writing comes easy. The research and keeping up with the latest news is what chips away at your time.

#28 Inserting your newsletter (or marketing/sales emails) into your email service provider and website can bog you down too (formatting issues, double-checking links, etc.). 

#29 Get ahead so you have a couple of emergency editions of your newsletter in the can.

#30 Getting ahead also improves your email newsletter because you have more space between writing it and editing it.

#31 Have a consistent file naming system for your newsletters and accompanying sales emails. Again, being organized is a huge help.

Email Deliverability

I’ll wrap up the Feature with critical notes on getting your email newsletter to the inbox. First, remember to make at least a piece of your newsletter fun. 1440 is a serious newsletter, real buttoned-up, but still sprinkles in fun or unique links at the end of most editions.

#32 Check email blocklists (nearly 1 in 4 emailers didn’t know if they had been blocklisted).

#33 Invest in good list hygiene tools (over half of emailers are not using any such tools as of September 2023 – yikes).

#34 Hire a deliverability expert if you aren’t confident in your deliverability knowledge (2 in 10 email marketers are not confident in this arena).

#35 An easy ROI win can come via small improvements in your email deliverability.

Onward to our Knowledge Base after we stop some sales slippage…


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The Knowledge Base

We leaned into videos and podcasts this week – enjoy:

Your customers’ brains on “story”

Don’t bother with social media unless you do this

A lesson in loyalty programs done right (Dominos Pizza)

Empathy + authority = customer trust

What SEO experts need to get good at in an AI world

In the trenches to get in shoppers’ minds

Are websites becoming obsolete?

Keywords don’t matter, says former Googster 

The history of advertising in 60 seconds


Self Help

I aim to turn 50 in a few days. 

Wish I had some epic life advice for ya. I can’t do much better than the title of this section, though.

The following ain’t bad advice either… Ask about and care about other people’s experiences. That’s not mine, it’s from my Pop. He never went to high school but was plenty wise.


Facts and Stats

  • 58% of people’s 1st stop on the web each morning? The email inbox. *2nd most→ search, 20% of people (Snov)
  • Cross-sells make up 7% of e-commerce store visitors & account for over 26% of their revenue (Investpo)
  • 32% of companies report they are taking no climate-related actions (CMOsurvey.org)

Bonus: What makes a memorable ad’s product ironically forgettable to consumers? Answer – Not linking the ad’s concept to the product/service.


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Get Hacking

Today’s Hack is timely. If your email open rates are dropping, test a time change. Instead of sending at the top of the hour or on the 30s (ex. 9:30), schedule your emails a few minutes earlier (or later). Example: send at 8:41 AM instead of 9 AM sharp.

And please save yourself the trouble of reading all the reports on the best time to send marketing emails. Spoiler alert – at the end of all those articles is a disclaimer: “Timing depends on your specific audience, so please A/B test to find the best time to send.” 

Aaaand – your ESP could be hindering your email campaigns. See link below for more details on how some ESPs are better than others for deliverability and inboxing. 


Thanks for making time for us. If you know another brilliant marketer, please share Inbox Hacking with them.

5 of the Best Editions of Inbox Hacking:

How your ESP affects deliverability

Why subject lines with sizzle often fizzle

12 days of email deliverability (what Spamhaus says) 

Are you building loyalty programs into emails?

Don’t lose your subscribers’ attention (14 tips)

Preceding message contains sponsored offers we think you can benefit from. Thank you for supporting our sponsors.

Shane McLendon, Copy Kingpin – Inbox Hacking