Hello there! This is the latest edition of my Q&A series where readers ask me questions and I do my best to answer them.

But there’s a catch: while the answers are free to read, only the paying subscribers get to ask the questions. If you’re a paying subscriber who wants to ask a question for the next edition, you can leave it in this thread over here.

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Ok, let’s jump into it…

Assessing the success of my newsletter

The first questions comes from Sarah Bean

How has the journey of building your newsletter been vs what you expected? Where have you experienced the best community, feedback, growth channels?

I would divide the history of my newsletter into two distinct eras. The first era stretches from roughly 2014 to February 2020. That’s when I used the newsletter mainly as a distribution channel to drive people to content elsewhere. I sent it out sporadically, usually only when I had a new longform essay or article that I wanted to point people to. As a result, growth was slow. By February 2020, it had about 1,200 subscribers. I wouldn’t say that I had any coherent strategy or expectations during that era.

In February 2020, I launched the paid version of the newsletter, and that’s when I more or less started trying to turn my newsletter and podcast into a full-time gig. Between then and now, I grew the newsletter to 4,597 (free) subscribers. The podcast averages around 1,000 downloads per episode.

So let’s get to the first part of your question: “How has the journey of building your newsletter been vs what you expected?”

Let’s say I traveled back in time and told 2020 Simon where his newsletter would stand in May 2022. Would he be disappointed or encouraged?

If I’m being honest with myself, I’d say he’d be pretty disappointed. I always assumed that there’d be some sort of tipping point that led to accelerated growth. Instead of only expanding my list by a few dozen a week, I would suddenly start growing the list by the thousands. I would then convert a sizable chunk of those incoming readers into paying subscribers, and then before you knew it I’d have my 1,000 true fans.

But while I certainly did have good weeks when I saw spikes in new signups, those spikes always leveled back toward the norm. I never managed to hit that hockey stick growth trajectory that you often read about in Creator Economy profiles  —- the ones where a creator suddenly goes from thousands of views to millions over a period of just a few months. Every time I felt like I was building momentum, I’d suddenly hit a slow growth period where I was once again wading through molasses.

I’m probably sounding pretty down right now about the business, but the truth is that I’ve been incredibly optimistic these last few months. In the beginning of 2022, I finally admitted to myself that I wasn’t going to build a sustainable income through paid subscriptions alone, and in March I announced both sponsorships and an $800 online course. We now have 20 enrollees in the course and my sponsorships are sold out until August. For the first time since February 2020, I’m making something close to a living wage from my content.

I’m also starting to achieve some of that elusive momentum that I’d hoped for. Between March 1 and today, my newsletter grew by 544 signups. Over the same time period prior to that date, it had only grown by 245 signups. That’s a 120% increase in the growth rate. I’m finally beginning to see the benefits that come from having a very large archive of high-quality content.

Ok, now on to the second part of your question: “Where have you experienced the best community feedback, growth channels?”

Some people are going to consider my answer super lame, but some of my best engagement has come from my Facebook group. I’ve been extremely disciplined about only promoting it at the very bottom of my newsletter. I also implemented an automated question that forces people to tell me where they found the group. I reject anyone who doesn’t list my newsletter as the source.

As a result, the signal-to-noise ratio is pretty good. Nearly every person in the group works in media and is a fan of my work, and they’ve been generally excited to chat with me about industry news. It also helps that Facebook prioritizes group posts within the Newsfeed. I don’t have any hard data to back this up, but I’d be willing to bet that members of the group are more likely to open my newsletter, convert into paying subscribers, and recommend it to others.

Now, every now and then someone scolds me and says I shouldn’t be building an audience on Facebook’s land. They tell me that I should instead migrate the group over to a more decentralized platform like Slack or Discord.

I just don’t buy this argument. First, I don’t put more into Facebook than I get out of it. I spend no more than an hour or two responding to the comments each week, and if it disappeared tomorrow my business would be largely unaffected.

Also, for better or worse, Facebook is the most-used app on the planet and is already built into people’s daily habits. Every time I get added to someone’s Slack group, I’m all gung ho about posting there for a few days before it quickly falls out of my website rotation. I’m not going to launch a community on a platform I don’t regularly use myself.

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Is Substack still my go-to choice?

The next question comes from Mignon Fogarty

If you were starting a newsletter today, would you still use Substack, or do you think there are better options now? A comparison of the options would be helpful too!

So I actually wrote a piece back in April titled “Substack's biggest competitor isn't who you think it is.” You should definitely check it out to get my full thoughts of where Substack fits within the competitive landscape.

But to answer your question directly: Yes, if I were starting a newsletter today, I’d still use Substack.

Before I talk about why, I should start by acknowledging that there are two types of newsletter creators:

1. Those who want as much customization and control as humanly possible. These are the people who host the content on their own domains and use multiple best-in-class tools. A typical creator in this cohort might host their content on Wordpress, distribute the newsletter via Mailchimp, monetize with Stripe, and grow their list with Sparkloop.

2. Those who want to spend as little time as humanly possible on tech/design and focus most of their attention on creating content.

If you fit into the first group, then you definitely don’t want to use Substack. But if you, like me, fit into the second group, then Substack is the best option. And I’m willing to bet that the vast majority of creators fit into that second group.

So now that we have that out of the way, let’s talk about why Substack beats out its competitors:

It’s free

I think this is one of the most underrated features of Substack, and it’s something its biggest critics fail to acknowledge. I can sign up for an account and send my newsletter to an unlimited list, and the platform won’t charge me a dime, at least until I start monetizing it through paid subscriptions. Most other email tools start charging you right away, with the price going up as your list grows.

There are only three tools that I know of that are completely free from the get-go: Tinyletter, Revue, and Substack. And I wouldn’t really consider Tinyletter an option, considering that it doesn’t allow for paid subscriptions and it’s basically been dying on the vine for years. I’m honestly surprised it still exists.

It looks good on the web

Substack is often referred to as a “newsletter” platform, but it honestly looks really good on the web — as good as Medium, Wordpress, Blogspot, or any other CMS. There might not be a ton of design customization available, but you can rest assured that any reader who lands on one of your articles will find it easy-to-read and aesthetically inoffensive.

Honestly, I think Revue lags in this area. To get a feel for what I mean, compare this Substack article to this Revue post. The latter just doesn’t look very good, and the auto-loaded thumbnail looks bad when you try to share it on social media. I would give Revue’s article web presentation a C-.

It has the most robust set of features

This is where Substack really breaks away from the pack. It just has so many more features than your average free publishing platform, and it’s shipping new ones every week.

For instance, in addition to distributing newsletters, Substack will also allow you to host and distribute podcasts, both free and paid. It revamped its analytics dashboard so you can segment lists. It launched a “recommendations” feature that makes it easier for newsletters to cross-promote each other. It operates a mobile app. And it also has a pretty decent customer service team who will answer your subscribers’ technical questions.

The icing on top of the cake

Lastly, I think it’s important to point out that I’m never truly wedded to Substack. At any point, I can export both my free and paid subscribers, so if I ever find a truly better platform, I can just leave. That’s really why there’s no downside to starting an account on Substack and utilizing its free email features; if you’re ever dissatisfied, you can pick up and go. That feature alone is why I value Substack more than every single other social media platform combined.

How to get yourself listed in PR databases

From Tim Benjamin

As a newbie publisher, I’m keen to better understand how media release services (e.g. Business Wire) work. There’s a TON of articles about how to write and distribute media releases — but little on how small publishers can use these services to (quickly) find useful content. A related topic is how small publishers can get PR teams to include them on media release distribution lists.

The PR distribution platforms are the bane of my existence and you should thank god that you’re not on their radar. I would seriously pay someone $100 to remove me from all these platforms permanently, and I spend a significant portion of my week wading through badly targeted press releases sent by people who have no idea who I am.

These platforms do nothing but promote laziness within the PR industry, because instead of doing actual research, flaks will just filter through broad categories and then blast an email out to hundreds of unsuspecting victims. The PR firms who use these databases charge huge monthly retainers to their clients, and for the most part that’s money that would be better spent on content marketing.

Sorry, I know I didn’t actually answer your question, but I’m doing you a favor, really.

Quick hits

Most crypto startups are glorified pyramid schemes, but there’s something particularly dystopian about “play to earn” games. [Vox] From the article: “You don’t literally own an item. You own a pointer to an image on a game company’s servers. They can alter it or delete it. If they go out of business, it’s gone. It’s purely a marketing term”

Instagram shares revenue with video creators but not still photographers. Why? Is there something inherent in still photography that makes it non-valuable? [Insider] (this is a rhetorical question. I believe Instagram should share revenue with all its creators).

Amazon became an advertising behemoth in just a few years. Now Microsoft is poised to do the same. [Digiday]

VCs are investing in media again, only now they're making lots of small bets through holding companies rather than dumping hundreds of millions of dollars onto a single outlet. [WSJ]

"Theatrical movies … tend to perform better on HBO Max than movies made exclusively for the service." [WSJ]

Man, Hank Green did an excellent job of calling bullshit on Instagram's claims that it wants to "figure out a way" to help creators making a living. [Hank Green]

An interesting look at the Facebook strategies for local TV news stations, which tend to have way more reach than their newspaper counterparts. [Nieman Lab]

ICYMI: Why a Hell’s Kitchen print magazine pivoted to newsletters

Phil O’Brien realized that distributing a print magazine during the Covid shutdown would be impossible.

Let’s spend more time together

This newsletter only goes out once a week, but I’m dipping into my Facebook group several times a day to chat with readers. I only promote the group at the bottom of this newsletter, which means that it only has members who are as obsessed with the media industry as you are. You can join here: [Facebook]