The Power of a Newsletter

I have been told 1,000 times that a newsletter is one of the best strategies and/or tactics to engage with one’s audience and yet I have not always leveraged it to its utmost. In many ways I just thought that it was just another thing that I had to write for and since I do ample amount of writing every single day I wasn’t motivated to execute against it.

But recently I’ve found something very neat with the weekly newsletter (I use MailChimp) that I share on Tuesdays with my very small community surrounding my indie app, Desk. What I’ve discovered, most importantly, is that I do actually enjoy writing for it and my feelings for it have blossomed.

For starters I feel like my direct engagement with the reader is increased and enhanced. Whether or not this is actually true (i.e. the results of the “enhancement”) is left open to debate I suppose but I feel more attached to the words that I write in my newsletter.

It is, in the most simplest of terms, more personal. I think it has to do with the fact that these people have opted-in to hear something from me and that they have invited me into their sacred inbox.

But even more than that I feel like I have a controlled and somewhat curated and captive audience. These people really care about what I’m doing with my small app and so I feel like I have a limited and select audience. That’s nice and it’s a great change of pace from a blog (or Twitter) that’s completely open and free to the public – I mean, who’s to know who’s really reading and where they came from and why?

The kicker, though, is emails that I often get back from subscribers who are really impacted by my words. I’ll admit, that I’m often surprised how they glean some of what they get from the newsletter on Tuesday mornings but in the end I’m honored and humbled that they do.

For instance, take this email that I got yesterday:


Thanks for writing this. It confirms what I need to do today. I created a site for real-life antiheroes in NYC on the Newrainmaker platform, but the issue I came across is that they want to be anonymous while going through part of the recovery phase of their shame or haunted past…

Thank you for this update. Definitely a game-changing moment.

All the best on your new investment. I believe it will work out. It took Pressgram for Desk App to happen…
… and thanks for sharing your process. not many successful entrepreneurs publicly chart their course for more than the instantly-vomited ‘it takes hard work’ response.

you’ve been an inspiration for me since the tentblogger days. you were called to do what you do man. whether it’s code, text or an ikea crib (you seem like an ikea kinda guy), you’re a builder. you’re a harvester of ideas. you could be freaking farmer and you’d end up in outer-space saving the world (Interstellar, must see!)…

I gotta learn to keep these things short. and perhaps that ‘last line’ was all I should’ve written. but just know you’re changing lives man. changing my life.


You can check out Chris’ site here, btw:

Naturally I get the exact opposite as well from people who tell me (with just as much enthusiasm) to “go fuck yourself,” then unsubscribe and (if that wasn’t enough) they do me the kindness of labeling it as “inappropriate content” when they do:



I seriously cannot win them all! But for every one like this I get some great ones like I pasted above and it makes it all worth it. I can’t tell you though how disorienting it is to get some crazy positive feedback and then, literally seconds later, get one that is so filled with vitriolic fervor that I begin to question not only their sanity (why the hell did they sign up to begin with?!?) but mine as well. “Ricochet” is the right word for this.

All this to say, I’ve begun to rethink the usefulness of the newsletter and the power that it can bring. I’m quite happy about my cadence and rhythm so far (I deliver one a week on Tuesdays – sign up here!) and it’s a nice break from the ordinary.

And you know… it’s neat to see how impactful words can have on people when you share them liberally, with thought, and with great intent to serve and help others.

If your interested in what one is like, here’s a copy of what I shared yesterday (you can see the web view here):


Yes. But not because Desk is necessarily super-awesome-the-best-app-ever-created-by-a-mortal but because I decided to sponsor this week:


You can go read the entire thing here (give Gruber some click-love… although, he has a lot already…).

For starters, I’ll admit, it’s just neat to see something that I’ve done on Gruber’s blog. I’ve been reading his stuff for years and I thought it would be so neat for him to write something about something that I was doing.

But, I’ve never really had anything worth his attention (and perhaps Desk wouldn’t have been “worth” his attention either…). So, to check off this particular item on my “Bucket List,” sotospeak, I decided to sponsor this week.



You’re right. Sponsoring Daringfireball is not exactly the world’s cheapest marketing option and at roughly $9,000 it’s almost gag-worthy (some of you may have quite literally #facepalmed…).

It’s a gamble, for sure. Just like any marketing move or strategy or tactic there is nothing that is 100% guaranteed to work. I have no idea if this is going to get my money’s worth in sales and there’s a lot of doubt, anxiety, and fear associated with this decision.

But, I had to run the numbers and I believe that this type of sponsorship, although costly and risky, should be able to play out in the short and especially the long-run.

The way I see it is that Daringfireball’s online reach is huge and that the attention that his post will bring will give me access to sites, blogs, users, and ultimately customers that I would not have otherwise had the pleasure of encountering.

For instance, it’s already begun as many bloggers from around the world have pinged me asking for review opportunities:


Would I have had the pleasure of encountering Filippo and his Italian blog, There’s no way that I would have been able to do that on my own power and with my much-smaller network!

Thus, the direct sales play, if you will, from Gruber and Daringfireball alone is not really the only return I’m hoping for – I hope that this one large campaign will really start the engines running in a ton of different countries and that the “return on investment” will go way beyond the initial cost.

On the math side, though, I need to sell approximately 450 copies to break-even the cost of the sponsorship. Do I think that, over time, I can recoup the cost and find 450 new customers through DF’s reach? I think so, and that’s why I pulled the trigger.

(Also, when I asked my wife about dropping such a large amount of money on a single blog and website she just asked if I thought it was going to be “worth it” and I said “Yes”… and then she said “Sure, go for it.” So… there’s that too. My wife is amazing.)

Final Thoughts via T.S. Eliot

I had the pleasure of speaking at a conference a week or so ago and I shared this quote before I dropped a “bomb” on the audience:

Only those who will risk going too far can possibly find out how far one can go.

I have often-times done this for myself and for the projects and things that consume my time and attention. I want to see how far I can go, full-stop.

I don’t know what you’re facing nor do I know the risk that you’re undergoing (or thinking about encountering) but I hope you embrace it with all that you can muster.

Life is too short to not make it count, to not give it your all, to not leave it all on the table, sotospeak.

Sure, you might be thinking… “John, this is just a large marketing spend on a blog… big deal.” … but then you would have gotten it way wrong.


You see… this is my livelihood. This is how I make my meaningful living and how I pay the bills and support my wife and 2 daughters. ThisMUST work so that I can continue to improve the app and continue to grow sales.

This is so unbelievably personal to me.

So, spending ~$9k on a blog is a really big fucking deal. It’s not a hope-this-works-teehee type of thing… it’s kinda agonizingly-difficult to think through and pull the trigger.

Will my world collapse if it doesn’t work? No, and neither will yours when you make that attempt… or pursue that risk… but I really think it’s worth doing. I really think it matters that you try.

I don’t think you’ll regret it.


John Saddington
Developer, Blogger

Have a great one folks…! And, seriously, try doing a newsletter… you may really enjoy it!