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Cover image for AMA with John Saddington
The Community Club

AMA with John Saddington

cole profile image Cole ・1 min read

Newsletters have proven to be a valuable touchpoint for community builders across the industry. They provide a space for curating quality content from/for your community, thought-provoking pieces, or announcing events, among other things. If you're thinking about starting a newsletter for your community, or maybe you already have one, John is here to answer your questions!

Join us at 4PM EST on November 13th for John's AMA on building out and maintaining newsletters. The AMA will happen in this post. John has been writing newsletters for 10+ years, recently starting a daily newsletter for community-minded professionals.

Discussion

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yenftw profile image
John @ YEN

yo. i'm fucking ready. let's do this.

a few high-level thoughts...

...newsletters are much more useful than just delivering content in one-direction; it can create a two-way communication channel between the writer and a (growing) audience of people who trust you to deliver insight that no one else can.

The real goal of a newsletter is to develop the currency of trust and once minted, you can barter, buy, and trade this for more insight for many more opportunities.

This isn’t strictly a “transaction” despite my use of the money analogy, it’s a real relationship and I have built many deep and abiding relationships via my newsletters over the 10+ years that I’ve been writing them.

Starting an email newsletter is functionally and technically very, very easy as I’ve laid out a step-by-step guide of how I recently built my most-recent one in just a weekend here.

Not quitting is the hard part.

So… ask me anything and I’ll tell you no lies — this shit is hard, but, it’s worth it if you know why you’re doing it.

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mac profile image
Mac

Always bringing the energy John!

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yenftw profile image
John @ YEN

appreciate you letting me share a few things!

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gabriel profile image
Gabriel Wilk

1st and foremost - We all wants to say how grateful we are for doing this - we all know that you grinding hard on that YEN.

So, thank you John. Thank you, thank you.

and let me kick off with the question to go all in with the stuff you do and build regardless if we taking of newsletter or dedicated community platform...

Would you recommend that to go all in?
For instance - leave everything behind, close one chapter and open a new one if you know what I mean, without security of having a job etc. and pursuit a dream of building "that thing" - I'm aware that it can be very personal but would appreciate your take on this.

Sorry for long format. 🙂

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yenftw profile image
John @ YEN

love the question. and of course, i'll answer it:

loom.com/share/622233304dd641f9b5e...

the short of it is that you should ALWAYS attempt a new project with OTHER people.

in other words, DON'T DO IT ALONE.

  1. you'll get faster and better feedback
  2. you'll get the encouragement and support you need (to not quit)
  3. you'll have more fun in the process

and... i think the outcomes speak for themselves.

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gabriel profile image
Gabriel Wilk

Thank you!

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rosiesherry profile image
Rosie Sherry

Is it bad luck to send an email on Friday the 13th?

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yenftw profile image
John @ YEN

i did it, so, i think my answer is pretty obvious! lol.

but.. i have more thoughts:

loom.com/share/281c1038ef754de193d...

in short, i think it's pretty cool to use moments like these as an opportunity to create new cultural rituals / workflows!

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brendanmcadams profile image
brendanmcadams

Hey John, this is great...and I'm looking forward to some schooling on this! Three questions:

1) There's Substack and Medium, and then are are a bunch of other newsletter tools out there. What criteria should one use to consider these, and is there an obvious choice? And does it differ at all if you're a coder vs a writer vs an artist, etc.? And do you even need a tool like that if you have MailChimp or ConvertKit, etc.?
2) What's the math behind deciding on a free vs paid newsletter? I'm all about free, but there is an argument for a paid subscription. What is that?
3) Are there any tricks to driving awareness and adoption? Like linking to other creators/twitter luminaries/etc.

Hope this made it in time!

Brendan

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yenftw profile image
John @ YEN

brendan!

thanks for the questions!

  1. BEST NEWSLETTER TOOL? wrong question. you don't need much at all. anything that gets in the way of your writing is a problem: loom.com/share/989ac2076fa445f2a0f...
  2. start with free. learn how to write. then, bifurcate. make sure you align with the WHY first... then the business, second: loom.com/share/666f0e384d4041048b1...
  3. yes, but, i focus on programming more: loom.com/share/3faaea15371b43f393c...
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user936 profile image
Mark K

Brendan, just to add to John's Q3 answer.

A lot of news sites and newsletters have started trending towards outrage headlines or just weird eye-catching titles. This is a “trick” I would avoid.

For regular media of course Mr T has become a great way to get clicks and add revenue. The issue with this is to keep people clicking you need to keep up a steady stream of these and this will, over time, create more outlandish headlines that less reflect the article underneath the title.

The world is stranger than fiction so their is really no need for this 🙃. More importantly (relating to newsletters) you have to look at a balance of

  • recruitment of readers
  • retention of readers

Retention is certainly more important medium to long-term; otherwise your recruitment is a wasted effort (don't fill your bucket if it has a hole in it)! These people do not need clickbait to read your work — they just need something that they can open because they perceive value in it.

Clearly titles are important to telegraph (no pun intended) your work, but the content is the Core and, as John said, Trust is the conveyor that gets people there.

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yenftw profile image
John @ YEN

love that mark. thank you for your response!

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user936 profile image
Mark K
  • what was the first newsletter you wrote and, looking back, just how bad was it?

  • what would you say is your favourite font and why?

  • how important is the integration of emoji's into our daily messaging clients 😀?

  • if you could give advice to someone growing coffee in Brazil, that would it be?

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yenftw profile image
John @ YEN
  1. here's a link to the first example: john.do/newsletter-peek/
  2. barlow black! and arial
  3. very much so!
  4. its really important to have buyers before you start.

in others, community before product!

loom.com/share/af564b59eb264927814...

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joshuadclark profile image
joshuaDclark

Hey John! Could you list out some instances where your newsletter has produced a profitable outcome or opportunity? If so what metrics are used to indicate the direction of a profitable outcome?

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gabriel profile image
Gabriel Wilk

Yo - hello brother - How is your newsletter going Joshua?

evshakeout.substack.com/

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joshuadclark profile image
joshuaDclark

Hey, it’s going great Gabriel - I continue to have a nice flow of signups and readers engaging with me on a personal level.

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gabriel profile image
Gabriel Wilk

that's great to hear brother - keep crushing it.

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joshuadclark profile image
joshuaDclark

Thanks for kind words

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yenftw profile image
John @ YEN

love that you two are connected. :) yenizens!

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yenftw profile image
John @ YEN

the power of a newsletter? yes: loom.com/share/7fae40ffbba5427095c...

i've written about it: john.do/power-newsletter/

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cole profile image
Cole Ask Me Anything

Thanks for doing this AMA with us John!

A couple questions for you:

  1. What secrets/tips have you discovered over the last 10 years of launching newsletters? Is there a certain pattern what works best for engagement?

  2. How much planning do you put into your newsletter issues? Do you have a list of topics written out ahead of time?

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yenftw profile image
John @ YEN

cole!

great:

  1. #1 tip: start, don't stop: loom.com/share/f2103eb85eee4748985...
  2. wow. fantastic. i go DEEP: loom.com/share/ceaaa24532bc4432b46...
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cole profile image
Cole Ask Me Anything

This was great!! LOVE the loom videos for answering questions.

I also appreciate the in-depth responses... lots to think about 😄

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yenftw profile image
John @ YEN

of course! love doing it.

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gabriel profile image
Gabriel Wilk
  • We often hear of the importance of experimenting - would you share some successful ideas and implications from your business?

  • What is the most important virtue of being a leader?

  • What's your biggest mistake and what have you learned
    from it?

  • What are some thoughts or quirks that you wish to know when you have started your Startup journey?

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yenftw profile image
John @ YEN

wow. some heavy questions, but, important.

i answer all of them: loom.com/share/14f80d7f53814889ba0...

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deepak910k profile image
Deepakkumar
  1. How often should I send the community newsletters? And how many?

  2. The role of automation. Wouldn't it be too boring to pick the trending topics every week and send just that as an email?

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yenftw profile image
John @ YEN

SUPER heavy topic: loom.com/share/9f57d88a50b24082948...

most-important, GOLDEN RULE of newsletter writing:

never ship a newsletter issue that you, yourself, wouldn't completely devour.

in other words, if you're not reading (and loving) your own stuff... you're doing it wrong:

loom.com/share/9f57d88a50b24082948...

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gabriel profile image
Gabriel Wilk

Hello Deepak - how are you doing?

How's your habitate.io/ going brotha?

Glad you are here.

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yenftw profile image
John @ YEN

i have to catch up with deepak too!

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yenftw profile image
John @ YEN

a tweetstorm for thought too:

twitter.com/yenFTW/status/13270295...

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mac profile image
Mac

When should you NOT start a newsletter? Sometimes it feels like the advice is always start a newsletter, start a podcast. When do you feel this advice doesn't apply?

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yenftw profile image
John @ YEN

wonderful question... and needs to be asked!

the answer: if you don't have the time.

the math is: for every issue that you create, multiply the amount of time you think it'll take you on average by 3.

so, if it takes you 1 hour per week per issue... set aside 3 hours to write, edit, and publish it.

loom.com/share/614e38298f384fc7954...

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gabriel profile image
Gabriel Wilk

What steps would you take having already a glimpse of "WHY?" and some direction but starting a brand new without having hundreds of followers on Twitter or IG and stuff?

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yenftw profile image
John @ YEN

here: loom.com/share/ec0142de4e8f4004b7c...

the answer: start with why... and start with one.

yenfm.substack.com/p/-dont-forget-...

most folks try to scale prematurely.. but, finding an authentic, true true believer is actually quite difficult.

The goal is not to surround yourself with everybody who needs what you have; the goal is to surround yourself with people who believe what you believe.

we have a lot of fans, but, very few TRUE followers. something to really marinate on.

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gabriel profile image
Gabriel Wilk

What's your take on paid advertising at the beginning of the project?

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yenftw profile image
John @ YEN

if it works, do it. but, it's unlikely to work until you have some sort of meaningful traction. but, the amount of traction required isn't as high as most folks think.

loom.com/share/221077a026854f5ba23...

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gabriel profile image
Gabriel Wilk

What are your views on borrowing money for business, financing projects?

In what stage of the project would you be looking for money? Any outsourcing methods, suggestions. VC, Tokenization?

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yenftw profile image
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gabriel profile image
Gabriel Wilk

How would you measure results and real growth apart of numbers (Signul-up's, visitors, conversion) on the very beginning?

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yenftw profile image
John @ YEN

you can't. if you're growing subscribers, that's one of the few repeatable metrics that you have.

what's most important is reviewing this over a long period of time... like 6 months. then, things will start to make sense.