A Look At My Email Inbox
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As communication technologies go, email is a first-ballot hall-of-famer. I love my personal inbox. I love that it’s highly customizable in terms of what I receive and gives me the ability to control if / when / how I interact with messages (a key feature that I think Slack and Facebook Newsfeed lacks today). With some purposeful curation and a bias to use the “unsubscribe” button, I try to make my personal email a feed of content I legitimately look forward to receiving.
About every 6 months or so, I let my personal inbox fill up to take stock of what I’m receiving and any changes I want to make. This post is an analysis of my latest look as of May 2020. My goal is to share my approach and hopefully inspire you to check out some of these newsletters (or find some of your own that you enjoy). Think of it like a personal email State of the Union — a full list of the email content I subscribe to, the framework I use to think about the content I’m receiving, and some closing thoughts on what I find exciting about the future of email.
First, I try to have my inbox reflect my own interests. It’s ultimately a place where I receive written content that I want to continuously learn more about, from people I think are smart and / or great writers. My interests break down into these categories:
- Business analysis, with a particularly focus on tech
- DTC brands / e-commerce / hardware
- VC / company building
- Investing / markets
- Author grab-bag (people whose writing I simply like reading)
- Life interests / hobbies (music, watches, food / drink)
- Politics / staying informed
Here’s a list of all the newsletters I subscribe to. I read 28 publications, of which 5 are paid and 23 are free. This amounts to about 5–6 emails a day, with a larger bulk received on Friday for weekend reading. The paid newsletters total $664 per year ($55.33 per month). That’s a decent chunk of change, but I’m fortunate to have an employer that helps subsidize it through our learning & development grants. It’s also less than the average cost of cable TV per month (I do not have cable TV) and I personally get much more utility out of the newsletters.
To better understand how I think about the content I’m receiving, send frequency is a helpful variable for me to organize and understand common characteristics.
Daily:
If an email is going to fall in this frequency bucket, I think two criteria apply. One, you should truly look forward to reading it every day. And two, it should provide a clear reason for being sent daily which usually is that it’s topical / tied to current events.
I subscribe to 4 daily emails. For me, this bucket is predominantly about staying informed. The content of the newsletters I receive daily tend to be quick hit summaries. They’re tied to topical current events (like this John Hopkins COVID-19 daily newsletter) and very skimmable. They also give me the information I want without linking out to another article. This is a huge reason why I prefer the New Paper over other daily email newsletters — I believe in their mission to “overcome sensationalism in media by making straightforward, factual news easy to consume” and I trust them on the 5 things I need to know every day without baiting me with links.
This bucket also highlights Stratechery by Ben Thompson, my favorite newsletter and the only long form content I subscribe to that is sent on a daily frequency. Most long form content is published at a frequency that allows quality to stay high. For many people that means “when available”, though some who are more dedicated can do it a few times a month or weekly at most.
Ben’s Stratechery is published daily and is consistently some of the best technology analysis available. His publishing frequency and consistently high quality is a testament to his ability both as an analyst and as a writer. It also allows him to adapt to current events and provide “breaking” long form analysis, which is incredibly hard for other writers to imitate.
Weekly / few times a week:
15 of the 28 newsletters I subscribe to fall in this frequency bucket. It’s dominated by content aggregators — emails that consolidate a collection of links to related stories. A weekly / a few times a week cadence feels acceptable for a newsletter to ask for attention and provide quality content to read without being overbearing.
The frequency is also where the lines start to blur between content aggregators and original writing into “hybrid” newsletters. It’s easier to aggregate articles on a weekly basis than it is to write quality content every week (much less daily). But if you can create great original content every week, your subscribers are typically more loyal (and more willing to pay).
Some newsletters like Divinations achieve original writing quality and a weekly(-ish) frequency by having more than one author (Nathan Baschez and Adam Keesling frequently share the publication load). Other newsletters like The New Consumer achieve original writing quality and a weekly frequency through years as a professional writer — author Dam Frommer was a tech and business journalist at publications like Recode before striking out on his own.
Not everyone can be Ben Thompson, but the idea of being a good writer and having something valuable to say that other people want to read is appealing. This pushes some publishers in the process of becoming more prolific writers to do both — maintain newsletter frequency through link aggregation, but sprinkle in original writing when it’s ready. This is where newsletters like 2PM and Drinking from the Firehose tend to play.
Few times a month / when available (alerts):
I subscribe to 5 emails newsletters in this frequency bucket. It’s dominated by long form content from people who are great writers and experts in things I’m personally interested in. “Personally interested in” is the optimal phrase and makes this category different for everyone. Since the content will only be published when it’s ready, I’ve found that it tends to be lengthy. Due to the level of engagement it requires per piece, it better be aligned to your individual tastes or written by someone who you’ll read almost anything by in order make the engagement effort worth it.
If you clicked on the email newsletter links that I subscribe to, you’ll notice that quite a few of them are hosted on a website called Substack. With some closing thoughts, Substack is a major reason why I’m excited that email newsletters might continue to play a larger role in how we consume media.
At it’s core, Substack is an email newsletter publication platform with a business model that incentivises high quality content. Writers can build their audience of paying subscribers through great writing. Substack makes money by taking a percentage of subscription payments for providing the publishing and distribution platform. Substack doesn’t play a critical role in building audiences.
This model is set-up to foster great writing compared to a publishing platform like Medium. Medium is a publishing platform that centralizes traffic / eyeballs to their website and drives that traffic to its hosted content via tools like their homepage, search, etc. Writers are incentivized to write content that appeals to as many eyeballs as possible, which in the world of Facebook feeds and Buzzfeed, leads to a lot of clickbait headlines and writing about personal development. Medium makes money by putting posts behind a metered paywall and asking readers to buy a content subscription after reading a certain amount of articles each month. Medium does play a critical role in building audiences.
As a consumer, I much prefer Substack’s model due to the quality incentive in their business model. The flip side to their business model is the challenge of discovery. How do users find highly quality newsletters that align to their interests and are worth subscribing to?
First, Substack just creating a place that encourages great writers to write and own their subscriber base, and prove out their platform is capable of sustaining great paid publications. They’re doing this through adding great texting editing functionality, publication landing pages, and easy email sign-up / payment functionality. They also promise that should a writer decide to leave the Substack, the writer can take their subscriber email list with them. This reduces the fear of not “owning your audience” and makes the platform more attractive to new writers.
Second, once Substack has a healthy base of high quality content, two potential paths to increase discovery excite me. Bundling is one. Publications with similar audience interests could be bundled to increase total subscribers. Divinations recently did this with the publication Superorganizers, and published a great analysis on the theory behind bundle economics. Substack could focus on deeply knowing their subscriber base, providing robust reader analytics to publications to identify shared audiences and high bundle success pairings.
The path I find more exciting though is focusing deeply on knowing their publication base and promoting more Ben Thompsons. There is obvious scarcity given the constraints outlined above — it requires subject matter expertise, a deep analytical skill set, and being a fantastic writer.
But imagine if Substack could quickly identify and promote the Ben Thompson equivalent for COVID-19? Or the Ben Thompson of the Impeachment hearings? That’s a highly compelling media platform business — finding and promoting incredible “breaking” long form analysis at the right time, where quality is incentivized through the subscription model, and individual authors aren’t as easily influenced by the slant / business of the publication they work. In a world where media polarization is a huge problem, creating trust at the “by-line” layer, promoting great individual writers, and building large audiences at relevant coverage points feels like the holy grail goal of email newsletter business. Hopefully, Substack can pull it off.
I’m bullish on email newsletters (clearly), and am excited that there’s still room for great content. I haven’t found a sports publication that balances the quality + frequency correctly yet. The Athletic is close, but I still find their email frequency too high for content that reaches to be interesting. I also think there’s white space for top Wall Street style company analysis, effective recipe / cooking newsletters, and newsletters that lean more into pictures or visuals more than words (shoutout to 2PM for developing their own visual / graphics identify and Hodinkee for the best product photography I’ve ever seen). If anyone has recommendations in those areas, please feel free to send them my way :)
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