Learnings from publishing 100 Substack articles in 100 Weeks
Looking Back 2 years of Serviceable Insights
I used to struggle consistently putting out content. I would publish an article after hours of painstaking effort, then before I could put out a second one, I’d get busy and years would go by.
This pattern persisted until I came across a few insights:
90% of podcasts don’t make it past 3 episodes. Releasing 21 episodes means you will put out more content than 99% of other podcasters
Mr. Beast, Alex Hormozi and countless creators put content out daily or weekly for years before cracking 1,000 subscribers/followers
Most content is bad. Even before LLMs, the internet was drowning in slop. There are so many unremarkable books, movies and shows that generate plenty of views
With that Serviceable Insights launched March 15 2024 with one goal:
Publish 100 articles in 100 weeks, offering readers at least one useful thing each post.
As of March 2026, SI has ~1,200 subscribers, and generates100,000 views per year.
I don’t know what these numbers will look like two years from now, but Serviceable Insights is just getting started and remains a Day 0 newsletter.
Whether you are a long time reader or discovering me for the first time, my objective remains the same. Inform and entertain. This will not change. Why? Because that’s what I would want to read, and if I don’t want to read this, why should you?
This week’s article will share some of the lessons I’ve learnt along the journey to 100 articles with the hope of inspiring current and aspiring content creators alike.
Keep reading to find out!
If this week’s article does not interest you, please check out some other recent ones:
Pre-Launch
Lesson# 1 —“Victory is secured by choosing battles on your own terms, exploiting terrain, and forcing the enemy to fight where you have the advantage.” Sun Tzu
Lesson # 2 — “Be So Good They Can’t Ignore you.” Calvin Newport via Steve Martin
It takes anywhere from weeks to months to establish a habit. If you stick with something long enough, it becomes second nature, like brushing your teeth or engaging in petty thefts.
Don’t write to maximize Subscriber, Likes or Comments. Write great articles on topics you enjoy. If you are going to commit to producing content on a regular basis, you are signing up for a marathon. Even successful creators regularly burn out.
I knew I couldn’t write 100 articles on one topic, which is why I decided to run a generalist account. This goes against conventional advice. Most people will tell you to specialize in one niche, where you get known as the best writer for that vertical. Subscribers know what to expect each week and you are more likely to get discovered by people looking for that that topic.
Despite knowing this, I decided my interests are too varied. I came up with the title Serviceable Insights because it was sufficiently broad enough that as long as readers learnt something, I would have achieved my mandate.
In terms of cadence, I went with weekly to get into a consistent groove. It also works out nicely to ~50 articles per year. More than that is excessive for an employed person earning zero income from this.
To make it as easy as possible to turn this into a habit, I wrote 6 articles before I released my first post. Four of those articles were a series related to startup equity, one an article explaining Mimetic Theory, and another a look back at of Peter Thiel’s book Zero to One. Sufficiently varied but with some consistent themes.
I schedule sent them and Serviceable Insights began.
Early Days
My early articles sucked.
There were some interesting premises but the writings were too long and not optimized for an email inbox. I was writing novels without having built nearly enough credibility with my audience to expect that much patience.
There was good information in there but it was overwhelming. Even if people opened the article few would read to the end. It took me a while to appreciate this.
In the first two months I only gained about 50 Subscribers and none of my articles made it to 200 views. I was only being read by people who knew me. Friends, family members, work colleagues, Linkedin connections, stalkers etc.
I started getting regular comments and interactions from fellow Substackers, who were nice enough to occasionally promote their work as would I with theirs.
I started to see a steady climb by month three. After a 5,000 word article on Henry Kissinger surprisingly bombed, I knew I needed a different approach. I worked on that article for 3 weeks and nobody cared. Seeing this, my next few articles were shorter, and on more universal topics. Business and life lessons from Game of Thrones, Succession, a summary of The Richest Man in Babylon. These articles only took a few hours to write and resonated much better with my audience.
I followed this up with my first relative big success at the time with an article explaining how to sell. This was my first article to reach 1,000 views within the same week and it generated me almost as many subscribers as all my previous articles combined. This was a more dense article compared to the last few weeks. This told me, I could write longer articles, if the writing was good enough.
Considering I wrote this from a generalist blog, expert sales people coming across the article were willing to afford me more tolerance compared to if it came from a sales blog. People who normally wouldn’t be interested in sales, were willing to give it a chance and then were happily realized this knowledge could help them.
My Subscriber count was trending towards 200, and 50% were opening my newsletter each week. I was starting to assemble a loyal following. My next few articles didn’t do as well but they were still getting more views than the prior month. In late July, I got hit with inspiration, cranked out an article in 3 hours. I didn’t think much of it at the time, but what came next was unexpected.
Going Viral
Lesson # 3 — “What is an expert anyway? Just some guy from out of town?” Mark Twain
Lesson # 4 — ‘The greatest victory is that which requires no battle.” Sun Tzu
The best creations flow easily. Mark Twain, Cormac McCarthey and Rick Rubin all expressed this. It’s difficult to predict what will resonate with an audience but pain on your part does not guarantee enjoyment on theirs.
When Mark Twain wrote The Celebrated Jumping Frog of Calaveras County, he didn’t think much about it. He was shocked to see how much readers across the country resonated with his story.
I don’t deserve to be mentioned in the same breath as Mark Twain, but I had a similar experience with Sorry Jocko, Discipline Is Overrated. In response to an unintentionally funny Youtube video from 5+ years prior, I wrote down some quick thoughts outlining my perspective on discipline versus building systems to achieve goals. I didn't say anything new but for whatever reason, the article was a hit.
Sorry Jocko, Discipline is Overrated
Many internet thought leaders have built their livelihoods diagnosing why many people feel disillusioned, fat, poor or less successful than they would like to be.
The day it came out it, it generated 400 views. This was slightly better than my previous best but nothing shocking. To that point, my articles would usually generate most of its views within the first 24 hours, then gradually taper off by the end of the week. Instead of view counts dropping off, they started accelerating. By the fifth day, I had already gotten more views and likes than my previous 4 articles combined. People were sharing, re-stacking and commenting. I was even getting hate messages. Within a month, it had amassed 6,000 views and generated 100 subscriptions.
This doesn't sound like a lot but keep in mind, I only had 200 Subscribers at this point and most articles were getting around 200 views. The article also directed traffic to other articles, generating me additional subs and engagement.
Every few months, some decent size Substack account would share it, and I would get another engagement boost. This is still paying dividends nearly two years later. As of this writing, it’s been viewed 12,500 times, has 200+ likes, 45 comments and 30 re-stacks. That’s rare for an account with 1,000 subscribers, let alone 200.
This came after only 4 months and 20 articles. To this day, I still don’t think it’s one of my best but it doesn’t matter. Enough people on the internet thought there were enough useful learnings and it was worth the time to read, comment and share.
When you have a strike of inspiration, jump on it. Ride the wave and see where it takes you. Not every article needs to be perfect. There is so much bad content out there on the internet, you would be surprised what rises to the level of good or useful. Content you consider mediocre might be a revelation to others.
The Slog
Lesson# 5 — “Stay in the game long enough to get lucky.” Naval Ravikant
A lot of success in life comes from sticking with things long enough to bear the fruits of your persistence. This is true in finance, business, politics and content creation. Giving up guarantees your failure. The ability to keep going even when the evidence of success isn’t there, is what separates eventual winners from current losers.
After the viral article, I didn’t have another article crack 1,000 views for 6 months.
Subscriber counts continued to grow but article views were flat. Some of my best work, such as Robbing Banks is a Rich Man’s Sport came out during this stretch, but the data was uninspiring.
Robbing Banks is a Rich Man's Sport
Heists and major robberies, once dominated by the poor and working class, have become nothing but an expensive hobby for rich men unwilling to go to therapy.
It’s frustrating to feel like you are putting out better content without anything to show for it.
Nonetheless, I kept at it. I knew it was going to be a grind before I started, here it was. It had only been a few months; the Discipline article gave me a false sense of the work that was required to break through on the internet. So I kept at.
Putting something out each week can feel daunting. You get busy with other things, you get tired but you still need to find a way to get 1,000-2,000 words out. Instead of approaching it as 2,000 words each week, break the work into manageable chunks. If the intro and each section is ~150-300 words, look at it as writing 300 words, 4-6 times. Anyone can write that much and you can squeeze those out in 30 min blocks.
If you are stuck, start writing ideas down. They don’t need to be connected or even coherent. By putting them on a page, your brain will try to make sense of it. It can’t help it. If the words aren’t flowing, just keep throwing down more ideas until the floodgates open. Before you know it, you’ll have too many words and you might need to divide them into several sections or even multiple articles.
Start earlier in the week so you don’t find yourself the night before your weekly release cadence with nothing written. 2,000 words in one evening can be difficult, especially when you don’t have the spark of inspiration. I do my best thinking in the sauna. I can normally connect all the ideas and the articles before I sit down to write. If not, sometimes writing one section or the introduction is enough for me to fill in the blanks throughout the rest of the week.
The Hot Streak
Lesson # 6 — “Luck is what happens when preparation meets opportunity.”
As I continued putting out articles, I would pick up things and incorporate it into my writing. 2024 might have finished with a whimper but 2025 started with a bang.
My cold streak of articles without 1,000 views ended with Should I go into Debt for a Rolex? It didn’t reach the heights of Sorry Jocko, but it performed really well on Substack, reaching 3,000 within the first week. Huge accounts were commenting and re-stacking it, eventually getting it to 5,000 views.
Why did it do so well? I hit the trifecta.
Great title: It needs to make people want to click on it. Whether their goal is to tell me how stupid I am or if it’s something they are actively contemplating, it did a good job of peaking people’s curiosity. If the title was less provocative like “Luxury watches are expensive”, it wouldn’t have performed as well.
Thumbnail: Visuals catch the eye more than a title will. By having Zuck sporting his oversized gold chain and expensive watch, it stood out compared to other articles on Substack. There’s a reason you see a lot of thirst traps on social and print media, it catches the eye. Anytime I’ve posted Margo Robbie, Sydney Sweeney, a cute girl or dog in the thumbnail, the article has reached at least 1,000 views. Photos of Rick Rubin or overly niche memes haven’t done as well.
Strong Introduction: If you’ve managed to get somebody to open the article, you only have a few seconds to capture their attention before they click off. Long time readers might afford you more leeway, but you have no goodwill with readers discovering you for the first time. If you can’t hook them in the first few lines, you’ll lose them. This extends to the entire article, but the deeper somebody gets into it, the more willing they will be to finish it. You need to get them far enough long they will want to read to the end. To do this, eliminate fluff.
Beyond this, the Rolex article did well because I didn’t hedge. I took a position and I stuck with it. If you want somebody to read your writing, you need to be credible. Don’t kill your own credibility with words like perhaps, sometimes, potentially etc. Get the facts and information then make your claims.
You aren’t writing a Phd thesis defence, you can make some bold statements that aren’t immutable laws of physics. The benefit of writing is you can follow your line of thinking. If you have good sources and your arguments are logical, it doesn’t really matter if you are wrong. Plenty of great writers, authors, academics and investors have made many wrong calls without losing face or respect.
If your goal is build an audience you need to take positions. Readers will respect this more than offering no opinion. Just don’t take dumb takes with the goal to get dunked on. You’ll get views, without respect. Just look at Taylor Lorenz. My articles started popping off because I took strong positions and backed them up.
Should I go into Debt for a Rolex?, Is Skiing a dying sport?, American Tourism is Getting Wrecked, and Is Pretty (Male) Privilege a Thing? are some of my best performing articles to date and they are all examples of that. They all came out within the first half of 2025 about a year after I started.
Since then, most of my articles reach 1,000 views. Not always within the first week or even from Substack. Now I get up to >1,000 monthly views from Google and other search engines, some on articles written two years ago. Between Substack, my subscribers and reader sharing, I get anywhere from 5,000-20,000 views per month.
The Future
It’s already been 2 years and 100 articles, but I feel like I haven’t even started yet. Looking back at old articles, I’m shocked anybody was willing to tolerate such awful writing. If you don’t look back at work you did 6 months ago and think it sucks, you aren’t improving quickly enough.
Nonetheless, I love my articles. All of them. Even the bad ones. They aren’t all gems and that’s fine. 100 articles in 100 weeks will do that. I learnt something writing each one and as a result, I’ve improved immeasurably in the past two years. I’ve only distilled a tiny portion of those lessons in this article with the hope this will help current or aspiring readers.
I want to thank my 1,210 subscribers, everyone from those that have been with me from the beginning and those who subscribed recently. This includes friends, family members, professional acquaintance and complete strangers on the internet. A special shout out to Giacomo Falcone Paul Drake Inverteum Capital Asmy J.K. Lundblad Les Barclays and many other Substackers regularly engaging and sharing my work as well as publishing great content themselves.
Here’s looking forward to another 100 articles, that will only get better. In the meantime heed these lessons
Lesson # 1 —“Victory is secured by choosing battles on your own terms, exploiting terrain, and forcing the enemy to fight where you have the advantage.” Sun Tzu
Lesson # 2 — “Be So Good They Can’t Ignore you.” Calvin Newport via Steve Martin
Lesson # 3 — “What is an expert anyway? Just some guy from out of town?” Mark Twain
Lesson # 4 — ‘The greatest victory is that which requires no battle.” Sun Tzu
Lesson # 5 — “Stay in the game long enough to get lucky.” Naval Ravikant
Lesson # 6 — “Luck is what happens when preparation meets opportunity.”
Thank you for reading. If you liked this article please Subscribe below. I publish articles on a wide range of topics from business, books, current events or anything on my mind.
Good tips and thank you for sharing!
Congrats Ben!! I love reading your articles ever week and I can’t wait for the future ones you’ll write!