On Newsletters

Wed, Nov 10, 2021 10-minute read

What and Why?

Personally, newsletters are the new blogs. While I don’t write or curate my own, I read a lot. And I am over-subscribed too. I subscribe to about 15 different newsletters but manage to read 1 or 2 in a week. That isn’t good. Luckily, I don’t yet pay to subscribe for any of them – and precisely for this reason.

The only newsletter that I pay and subscribe to is the Blackbook newsletter by Vijay Anand. When I wondered how I would organise and streamline my newsletter subscriptions, there was a post on the Blackbook discussing the very problem in good detail. Perhaps, I was mulling over a problem that hadn’t been solved very well for the first time. Of course, even as I write this, I am sure dozens of startups are solving this and probably very elegantly too.

Anyway, I continue to wonder how I want this solved. I’ve approached this problem in multiple directions. I’ve considered all the ideas listed in the post as well. But there is something that continues to bother me. So I’ve not made any appreciable progress on this. Until today, that is.

Over the last couple of days, I’ve had a few thought blurbs. They are disconnected, and they don’t solve anything. One thing I learned during my stint at IIT is to chase down each of the rabbit holes to see which one leads to a solution. And of course, none of them may lead to the “promised land”. And that is completely fine. For a long time, I have been holding this idea very close to my heart. In my mind, this would be my ticket to entrepreneurship. But something clicked in my head today. So I am setting it free. This might not be it, but I’ll collect the thoughts in public, and hopefully, someone will pick it up and solve it better than I imagined.

How (all)?

The basic premise of all the ideas below is this: Newsletters (however old they are), as a concept, is like the phoenix risen again. It probably rose from the ashes of RSS/Atom Feeds. I love the feeds stuff – but just stating this reveals how old I am. I haven’t come to terms with the fact that the resumes I get for hiring and internships are kids born in the 2000s! These kids probably don’t know feeds at all. So pushing that medium is plain silly. I still love my feeds, though.

And most kids today have terrible email habits. Again, email is a medium built for a different era. And newsletters have heartily embraced that medium. I don’t like to check my email. I use “hey” and have turned off all notifications. So email arrives when I care to see. Kids are living in the era of disappearing messages. They don’t care to hold gossip sacred. Newsletters over email seem doomed to start. Some old-schoolers like myself might keep this alive for some more time. But to survive, the medium might need to change. Right? Maybe, maybe not.

The first thought blurb: IM

What if newsletters are delivered over instant messengers – WhatsApp, telegram, signal or Facebook messenger. There is nothing holy about this list, though. There are others like WeChat or Line that probably are just as interesting. The point is, the next-gen of readership is perhaps not over email or feeds. I consume more content over WhatsApp than over email. I cringe at the content, but that’s a different problem.

And maybe they should be disappearing too. Not to create urgency but to maintain relevance. There are very few things that need to be timeless. The vast majority of stuff we hoard won’t stand the test of time. Newsletters may not be very different.

But then it is not that simple either. We don’t want to scroll six pages on a WhatsApp message. Today’s newsletters are well crafted long-form mediums. Consuming long-form content on a short-form platform is a challenge. I am building something (using Twilio) to dump the newsletters I receive to my WhatsApp. But I don’t expect the experience to be that good. It will be interesting to see if I read more, though. I’ll share the details if I get to it.

This report gives you a better idea of what I tried to say here.

The other problem is, how many non-tech oriented Indians consume newsletters? A vast majority of them don’t even read emails. Besides, the tech community in India is a minority. India has a very young population which means much of the target markets for newsletters could be from India. And yet, there isn’t much done to reach out to them.

In this sense, perhaps reaching out over a messaging platform like WhatsApp will increase adoption in countries like India. I frankly don’t know what African countries are like, but I won’t be surprised if they have the same composition as India.

The second thought blurb: Audio

I consume way more audio content than any other form. I read a lot over the internet, but I listen more than that. I have a dozen podcast subscriptions for just Tech. And I have all the same problems with podcasts that I have with newsletters. And recently, a fellow Twitter citizen raised the same concern too!

For me, background audio is an effective mechanism to retain focus on my work. Many times, I’d be listening in on Netflix shows while I work. I rarely watch them intensely. So much so that I know a lot of Korean words that I learnt when I rewatch the shows later in the night or at weekends :-). Not proud, but that’s just how I work. I have to plough through stuff, and there is very little thinking involved.

I often listen to podcasts when I work. Podcasts are very efficient because I learn quite a bit in a very passive manner. And podcasts are better because there isn’t visual content that you need to focus on. At least, I consume only audio podcasts.

A week’s worth of newsletters may work out to be a single podcast episode – about 45 mins long, say. That’s a very, very efficient way to consume this content. Again, maybe – maybe not.

A couple of years back, I hacked up a simple script to fetch a bunch of feeds and use the OSX say command to record it as an audio file, transfer it to my iTunes and listen with my phone when I walked to work! Like most hacky stuff, it worked with a lot of rough edges. Then I had to move, my mode of transportation changed, and basically, the script stopped being feasible. I should have it in my drive somewhere. Maybe I’ll publish it to my GitHub one of these days.

It should be possible to do this even now. But the actual problem is somewhat different. I picked some ideal blogs that shared full text over RSS (like Seth Godin) when I first did this. These blogs don’t have ads in their feed text. Newsletters, on the other hand, are positioned as a viable source of income to the creators. We either pay the creators or allow them to monetise over ads. In fact, in many of the newsletters I get, there will be an ad or two. I respect that and don’t try to block it. I am not sure if it will be good to have a command read out a banner ad for us! Some creators, though, write their own copy for the ad. This stuff is ok – like the Twit podcast; I enjoy the ads there and won’t mind at all. Reading those out can’t hurt much.

There is a second problem, though. Because it was a hack, I didn’t mind how the readout content sounded. There were misspelt words, mispronounced names, terrible intonation, incorrect pitch and more. I am not even an expert, and I felt these. But thanks to the IKEA effect, I didn’t mind it at all. But if it were to be for a larger audience, we need a way to make it sound acceptable. Tools like Amazon Poly make this somewhat feasible, but automating it takes more effort. Again, it’s on my list, and someday I might get to it.

Third thought blurb: Kindle

This is the biggest blurb I’ve had so far. I had it in my shower today. If I go by the statistic, shower thoughts are generally more profound than the others. Maybe this one is a winner in that sense.

Like you might guess, why not collect all the newsletters for a week and build it as a simple Kindle book (or epub/imobi/whatever else) and sync to the reading device? Most of us consume books over Kindle. Having a new book every week (or having the same book replaced every week) seems like something I’d do. This should put us in the reading mode – or why else are we in that app or device – and we get distraction-free consumption time for all our newsletters.

So why Kindle over email? Because email feels like work. Kindle feels like leisure. Secondly, email is cluttered. Unless you are paying $$ for superhuman (which I don’t know as better), I don’t think email is a suitable medium. It gets the job done, but it should be limited to just that – getting a job done. And eBook readers come with tonnes of goodies. They are easier on our eyes, have page tracking and bookmarking enabled – making it simple to resume over multiple breaks.

I spent a couple of months working on the epub format in a previous job. It has all the elements I hate – XMLs interspersed with hairy HTML and pulled together as a zip file with a META file that identifies itself as a book. But that said, it is a very well-published format, and there are libraries to help us handle the details. This is the latest idea on my list, and I might do this one first – my favourite consumption for written content is still ebooks because it puts me in that reading mode. It is better to get my content as a kindle book.

But I won’t be the first to think of this. There was a pretty popular app that brought feeds like a mag: Flipboard. I used it for a bit, but it didn’t stick. I have about 200 feed sources making my Flipboard look never-ending. Just add TechCrunch and Mashable to the board, and you’ll see what I mean. Just the sheer volume of content put me off. In the case I am presenting, though, it will be a limited set of articles. I have 15 newsletters, so maybe 15 chapters in a book. Most newsletters are a 10 min read per article – that’s just 2 hours of content – with bookmarking too 🙂


I have poured out everything I’ve been thinking about in the last couple of months on this topic. This post is incoherent and is all over the place. Bear with me; that’s how I think. I didn’t want to spend the time to streamline or polish it up. It’s a mind-dump if you will.

There is an interesting pattern I am just noticing, though. I am averse to adding more apps to my device. But that’s the millennial in me, perhaps. Maybe, kids these days do love their apps. I always want to piggyback on whatever is already available and working. In my opinion, it makes for a more straightforward adoption. Of course, there is an exclusive branding opportunity lost when you don’t have your app. But so long as someone pays for the service, the branding can happen elsewhere. Or maybe there can be an app too.

There might be a startup hidden somewhere there. Or maybe none of this is good. I am going to stop judging and leave it here.

Happy newslettering!