Happy EntStrategyGuy Sixth Anniversary! With 17 Tips on Writing a Newsletter

Share on facebook
Share on twitter
Share on linkedin
Share on whatsapp
Share on email
(Welcome to the Entertainment Strategy Guy, a newsletter on the entertainment industry and business strategy. I write a weekly Streaming Ratings Report and a bi-weekly strategy column, along with occasional deep dives into other topics, like today’s article. Please subscribe.)

Last week marked the sixth anniversary of the Entertainment Strategy Guy website, which later became this newsletter. To celebrate, I’m doing the slightly-cliched thing: offering advice to my fellow Substackers. Frankly, I love reading articles like that, and I have advice to give, two years after I put up my paywall and six years of writing total. 

In classic EntStrategyGuy fashion, I’m also going to twist things around. I’m not just providing advice for writers today: I’m also going to offer advice to Substack itself. It’s a great platform, but I think it could add a few features to make my life (and other writer’s lives) even easier.

But first, a thank you and news about EntStrategyGuy’s future, including a price increase for new subscribers…

A Sincere Thank You to the Subscribers 

Years before EntStrategyGuy, I wrote online for a long time, and I was fairly successful, finding a fun little niche and getting published in multiple, high profile places. (I’m being vague on purpose.) Unfortunately, I made almost no money, aside from a handful of lame Google Adsense ads that didn’t even cover my hosting fees.

If Substack had launched in the early 2010s, honestly, I might never have started this website because I probably could have become a successful writer in my previous niche, without the stopover in streaming land. Honestly, I don’t know what would have happened, but the ability to earn a living from writing as an independent journalist/analyst is only possible because of Substack. It truly is a sea change in how creators can make money these days. And it’s not just me earning a middle class income, but my full-time researcher/editor as well. 

Of course, while Substack made it possible, paid subscribers make it a reality. And that’s why I can’t thank all my paid subscribers enough. Even anyone who signed up and cancelled, thank you for giving me a shot. The trust, faith, belief and support of this audience is incredible.

Thank you.

The Year Ahead

The plan for the rest of 2024 and beyond is to keep publishing the best, most informative deep dives and analysis you won’t find anywhere else.

Still, some changes are in the works.

First, in June, the monthly Entertainment Strategy Guy newsletter price will be going up to $15 (or $150 a year. That’s up from $14/$140 per year). If you’re already a subscriber, your price will not go up. Once you’ve started paying, you’re locked into that price going forward.

So if you want to lock in the lower price, upgrade to paid now. (Reminder: paid subscribers will keep their lower prices.) 

Second, I plan to add advertising to the newsletter in the next year, fingers crossed. But it won’t be ridiculous. I probably won’t ever include more than two ads per article, at most, if that. Frankly, many other Substackers have advertising and adding it to my revenue will help me increase the quality of my content in the future. Of course, it goes without saying that advertising will not impact my honest take on streaming ratings. (If and when I start advertising, I’ll have more to say on this.)

If you would like to advertise on this newsletter, send me a note on info [@] entertainmentstrategyguy dot com. That’s the best way to stay in touch. If you work in “For Your Consideration” advertising and have advice, please reach out as well.

Third, I’ve debated cracking down on folks who share the newsletter widely. Not a handful of shares, but with dozens or hundreds of others (especially on internal distro lists). Right now, I’d just repeat that if you share the newsletter that widely, please don’t. If you’re interested in a group subscription, please reach out. I’m working on that upgrade as we speak. I’d also love to offer discounts to certain groups, like union members of IATSE or SAG-AFTRA, as just two examples. So again if you manage subscriptions for a large corporation or organization, reach out to see if we can work together.

So You Want to Substack/Write/Podcast/Newsletter?

I love advice articles, especially if they offer advice that’s specific and actionable. Everyone should focus on regular, sustained self-improvement. You can always get better. Heck, even for myself, writing out this advice gave me some great ideas for areas I need to focus on.

Of course, it does beg the question, “What gives you the right to give advice?” I’m a bit hesitant to share actual numbers, but as I wrote above, this newsletter provides enough for two people—me and my editor/researcher—to make a middle class living.

And I think a lot of other people could and want to do the same. That’s what I have to offer. 

But let’s start by discouraging new writers…

Only Do This If You Have the Passion

Like a lot of people in Hollywood, I’ve observed the aspiring artist scene in Los Angeles. Every year, a ton of people come to Hollywood dreaming of becoming an actor, musician, writer, comedian, director, or what have you, and 90% of them fail. Maybe 99%. And when it comes to doing things online, the same fail rate applies. Stephen Follows has a graph showing that the vast majority of people on Patreon have less than five patrons. Now, this was from 2017, but the point stands:

A lot of people don’t make it.  

Don’t start a newsletter if you don’t have a passion for writing (or podcasting or making video) and a passion for the subject matter that you’re covering. If you’re just trying to do it to make money (or more oddly, become famous/influential) then you shouldn’t bother. (Especially for the reason I lay out next.)

If you can’t imagine not writing or making videos (or acting, making music, etc) then go for it. (But be honest with yourself.)

That said, I do believe that passion can be developed. If you asked me ten years ago, I don’t know that I would have told you that writing a weekly report on streaming viewership would have got my creative juices flowing. Now my editor/researcher and I spend way too much time talking about TV show ratings and the streamers and strategy and so on. We love it. And we have a passion to share the actual data in this little media niche.

Take the things you like and develop an even greater passion for them. 

Now, even if you love writing and you love your subject matter, there’s more bad news.


  • To make it, you have to have the passion for that niche.
  • Find the area you have the passion to create.

If You Post Regularly/Consistently For a Long Time, You’ll Gain an Audience…But Be Prepared to Work For Free For a Long Time)

Here’s some bad news:

It’s going to take a while to quit your day job. 

I spent four years writing as the Entertainment Strategy Guy before I ever made a dime. Could I have put up a paywall earlier? Maybe, but then growth would be that much harder.

But there’s good news! I’m firmly convinced that if you post regularly/consistently for a long time, you will at some point build up an audience, either through links from other people or Google search traffic or social media shares. And the higher quality the content that you produce, the quicker you’ll build that audience.

To repeat:

Post regularly, and you’ll build an audience. 

It’s literally the best and only advice you need. What does “regularly” mean? It depends on you. For some people, it’s daily posting. For others, it’s twice a week. Maybe it’s less, maybe it’s more. But just be consistent. 

The even better news? You can monetize your audience now through Substack. I’ve gotten to this point twice in my career, except as I wrote above, ten years ago, I couldn’t monetize that audience.


  • Write and post regularly. 
  • Prepare articles/posts/newsletters ahead of time in case you get sick or need to take a vacation.
  • If you’re young, start writing in college or right afterward. Start building your profile as soon as you can.
  • To be clear: posting on social media, where you don’t control your relationship with the audience, is not what I’m talking about. (And it’s a crowded field.)

You Need To Be A Writer (But You Might Be Able to Become One)

Okay, here’s more discouragement:

You need writing talent.

Years ago, on the Scriptnotes podcast, John and Craig made the point (in an episode I won’t even try to find) that almost every professional screenwriter they knew had a background in writing, like writing for their college paper or getting great grades in English. The same thing definitely applies to writing newsletters. As someone who scored a “5” on my AP Lang and literature tests, I have that ability. 

Is that you? 

Be honest. Because if it’s not, good luck trying to make it as a writer. 

I’m a bit conflicted about writing this. On the one hand, yes, I’d like to think that almost everyone could become a “good enough” writer with enough dedicated practice. My editor/researcher just spent nine months working with a client to write a non-fiction book and in that time, the aspiring writer went from unable to write at a professional level to writing at a near-professional level. (He was already a voracious reader.) On the other hand, I think for some people, that’s just not true. My editor/researcher also spent years of intensive, daily practice with another man who wanted to be a writer, but due to various issues, didn’t like reading. But the client liked the idea of selling a screenplay because he loved watching TV shows. He did not become a good writer, let alone a passable one. 

I could want to be a male model all I want, and work out and get six pack abs, but it’s not going to change the fact that I will never be a male model. 

Here’s a rule of thumb: if you don’t like reading—be honest—you’re probably not going to like writing. (Especially since most writing is rewriting.) 

If you have the natural aptitude, that’s not enough. You also need to hone your craft. (I know I needed to.) You need/should read books on writing. You need to read, read, read. But mainly: 

If you want to be a good writer, you need to rewrite your work a lot. 

When I first started writing, I was pretty bad. Unimaginative prose, boring sentence and paragraph structure, and more. I spent years on that other writing project, literally writing and rewriting over a million words. And I mean rewriting. I read, rewrote, and edited every post at least four times, sometimes over a dozen times. Within a couple of years, my writing had improved exponentially. And it improved because of that rewriting.

If you want to be a professional writer, that’s what you need to do as well. Maybe not that exact path (perhaps your writing skill is starting at a higher level) but you need to start writing and focus on improving that writing. 


  • Honestly assess if you have a natural aptitude to be a writer. If you don’t, I’d consider doing something else. 
  • Read all the books on writing you can. (You can also listen to podcasts and read stuff online, but I’d stick to the physical page as much as possible.)
  • Read as much as you can. Preferably offline.
  • Rewrite as much as you can.
  • Rewrite at least two articles a week for five years. By the end, you’ll be a good writer.

Find Your Lane/Pick a Niche

A lot of people have opinions on popular topics (like, say, movies or politics) then try to start a newsletter to discuss those things, often just sharing their personal opinion and that’s it. Best of luck, because other people do that sort of thing better.

You need to pick/find a lane. A unique lane. 

We live in an incredibly complex, complicated world. There’s tons of niches out there for you. And a bunch of them could be quite profitable. Or interesting. And depending on what you charge, you really only need a thousand people to be willing to pay for it. So find a niche that could have at least 1,000 to 2,000 people who are willing to pay to read about your niche.

How do you, the reader, do this? I know that my approach was—twice—born out of frustration at bad media coverage about a particular subject I knew quite well. If you become an expert in a subject that you’re passionate about, I’m sure you’ll find an area or perspective that the rest of the media isn’t covering very well. 

I would also argue that you need to have a unique perspective. A distinct point of view. Frankly, if you’re just going to say what 90% of other people have to say, I guarantee that there’s a super star reporter/pundit/columnist who’s already saying that thing more eloquently than you are with a bigger platform. 

Now, I’m not arguing that you should have crazy opinions just to be different. Find out what other writers/reporters get wrong. (It’s not out of malice. More, I think accurate reporting is just really hard. And it always has been.) You’ll discover this as you gain expertise in a subject. Plus a lot of people tend to herd around the same opinions, which especially happens on social media today, but has always happened in the mainstream press. Breaking from the herd is lucrative.

Be different, especially if the data supports that. 


  • Don’t be a generalist; pick a specific niche that you can be an expert in. 
  • Pick a subject matter that the media doesn’t cover well.

Be An Expert (Or Become One)

Unlike my concerns about writing, it’s easier to become an expert these days. To quote Jason Crawford, if you read three books on a subject, you’re practically an expert, especially compared to 99.9% of the country. 

So start reading!!! 

In all seriousness, just become an expert in something. Now, that can mean reading, or it can mean conducting deep dive research into some niche topic. The internet is literally a repository for an almost endless amount of information and data…use it!

To relate it back to me and my personal experience, I have an MBA in business. I worked in the entertainment industry, so I have real life experience. And my readers want and need that experience. When I started writing, I combined deep MBA-style strategic analysis with the news stories of the day.

But the real unlock, for me, was shifting focus to streaming ratings/viewership a few years into this newsletters existence. Not only was this a completely uncovered lane, but I built up a dataset and expertise with content that few other entertainment strategists have.

A lot of people hate on higher education (and its exorbitant costs, which, like, fair enough), but I also think if you pick the right field, with the right instructors, it could be be quite valuable. Of course, you don’t have to go to grad school, as long as you work as hard as if you were going to grad school, which means reading and researching voraciously. 


  • Read as much as you can. 
  • Read one book on a subject each week.
  • Go to graduate school. (And actually study.)
  • Find bespoke research that you can do.

Be a Broadcaster on Social Media, Not a Consumer

I don’t really like social media, for a lot of reasons. It can become a giant time suck that prevents truly deep work, a distraction from the hard work that will make you better than your competitor like researching something in depth or rewriting your own work. Instead, you should read newsletters, books or listen to podcasts.

Even worse, I think social media, with its reinforcements loops, encourages a lot of herd mentality and groupthink and what did I say above? Be your own person with your own voice.

Should you use social media to advertise your stuff? Yes. But be a broadcaster.


  • Don’t waste time on social media.
  • Don’t let other people’s opinions influence yours. 

My Seven Improvements for Substack

I have advice for Substack, not because I dislike Substack, but because I love it. (This is something many people don’t seem to get these days; you criticize the things and people you like more, not less…And obviously I depend on Substack.)

And anyway, these aren’t huge changes, just some (hopefully) quick fixes that will make the platform better.

1. Indentation

Seriously, I just want to be able to indent a line without making a bulleted list or using that weird blue line. Perhaps there’s a technical explanation for why this isn’t possible, but please, just make this change. I would have used it throughout this article. 

2. Create Customized Paywalls

When I have the time, I write a customized paywall for my readers, telling the free subscribers what’s in the rest of the paywalled article. To do this, I have to upload, re-format and post the same article twice, but send it out to two different groups of people. Which takes a bunch of extra time.

In the same way that you can have customized buttons, I’d love to have a customized paywall so readers know what they’re missing out on in the rest of the article. I guarantee it would help convert people into paid readers.

3. Allow For Internal Links Before Publishing

I write long articles and I’d just love it if I could add in internal links (to headers and subheaders within the article) before I publish, especially so I could make a table of contents at the beginning of some articles. Again, technically this may not work for emails, but it would be great if it did.

4. Allow for Multiple Images in Notes

On Twitter, you can do threads and include multiple images. As someone who uses lots of images in my articles, I’d love to be able to use three to five or so images in a note, to really convey a point that I’m trying to make.

5. Make the Free Option First (On the Left) When Subscribing

This design choice by Substack really bothers me. Look at my sign-up page:

I’ve had several people sign up for a paid account without intending to after they accidentally clicked on the paid link, and then they want a refund. This is bad customer service. I want to give people what they want. In Western culture, since we read “left to right”, we naturally expect prices to go up from left to right as well. This order of options has no coherent internal logic, and that’s why it sometimes tricks customers into signing up, and immediately unsubscribing.

6. Let Writers Sell E-Books

If I were Substack, instead of focusing on engagement or recommending more Substacks, I would focus on monetization. For example, you know what a lot of writers want to do?

Sell books. 

You know what I can’t do on Substack right now?

Sell books. 

So you know what Substack should do? Sell books. 

Physical books? I don’t know, that sounds pricey. But e-books? Sounds like a no brainer to me. If Substack weren’t just the home to my newsletter (and, someday soon, my podcast) but also my e-book market place, I’d make more money. Right now, I have two or three different series I’ve written—my Future of Film series, my annual content recaps—that I could turn into short e-books that I could sell on the same platform. So let me do just that! (This would be especially good for aspiring novelists.)

(And if Substack has a world class e-book store that rival newsletters services don’t, it makes it that much harder to leave Substack.)

7. Sell Merchandise

Does EntStrategyGuy sell merch right now? No, because it’d be way too big of a hassle. I’d have to find someone to sell it, make a design, possibly order merchandise ahead of time…ugh, it sounds horrible. Sure, there’s other services you can use, but it’s not integrated with Substack.

But imagine, as a content creator in the 2020s, if there were a one-stop shop where you could post newsletter, host podcasts, and now create videos, and also sell t-shirts, hats, mugs, whatever? What if it was as easy as uploading a design and then I had my own merch store?

Guess what? I’d sell merch. Tomorrow. 

(And if Substack has a world class merch store that rival newsletters services don’t, it makes it that much harder to leave Substack.)

The Entertainment Strategy Guy

The Entertainment Strategy Guy

Former strategy and business development guy at a major streaming company. But I like writing more than sending email, so I launched this website to share what I know.


Join the Entertainment Strategy Guy Substack

Weekly insights into the world of streaming entertainment.

Join Substack List
%d bloggers like this: