Milestone roundup: Writers reflect on their years on Substack
Takeaways from another year of publishing on Substack, and more
Writers from, , , , , , , , , and share insights that every Substacker could benefit from, from sustaining her income and family life, to generating enough paid subscriber growth to cover his child’s day care, to turning Platformer into a full-blown media business.
For more one-year reflections, check out our previous summer ’22, spring ’22, and winter ’21 roundups from the past year.
Did we miss a good milestone reflection post? Share the link in the comments.’s goals are focused on finding out what’s really going on in the venture capital industry, in service to his readers. He celebrates two years of his newsletter, , including a breakdown of his business, hiring his first staff, surveying his readers (and sharing that survey in this post), and thoughts on going independent and what the next year holds. He also offers a discounted subscription as part of the party.
Key takeaway: Eric says the greatest driver of growth for his 2,200 paying subscribers is simply great stories. This includes cross-posting with another Substack writer, Gergely Orosz.
For all my coverage of cash-burning, venture-backed startups, I’m enjoying building my business on the back of real cash flow. It means that I’m making sustainable moves, hiring when it makes sense, and not just throwing money at my problems. I’m sure I could have grown faster if I were blowing money on Newcomer Twitter ads or buying email distribution lists. But given customer growth has been hard-fought, I can say with confidence that this is a business with real customer demand.
Read more: 🎉 Two Years of Newcomer! 🎉of looks back on why starting his Substack was easy from the get-go. Two years in, he reflects on why newsletters, and niche media, are “having a moment,” and how the secret sauce of product, audience, monetization, and expansion has led to “the most rewarding work [he’s] done.” Congrats, Brian!
Key takeaway: Take your time and don’t focus on distribution hacks or Twitter threads. Brian didn’t experience any rocket-ship launch, but averaged 8% month-over-month growth and consistent 50% open rates.
Back in October 2020, I was leaving my job of a decade and figuring out what I wanted to do next. I knew I wanted to take an independent path and start a new publication focused on building sustainable media businesses, using my experience both covering the industry for many years and as president of Digiday Media. I found it a good match for my experience and also something that’s societally important. What I wanted to find out was:
Could I make a product I found rewarding and needed?
Would the people operating media businesses find it useful?
Is there a business model in doing this?
Two years in, I’m confident the answer is yes on all three. Here’s the progress report.
Read more: Two years inof is more surprised than anyone to find her Substack is now her third-longest relationship ever. She takes a moment to look at favorite posts, thank readers for their support, and marvel at the fact that her writing can support her family while helping her “connect with people at a time when I feel like we’re all more disconnected than ever.”
Key takeaway: Ijeoma didn’t think she’d have time for a newsletter while writing, editing, and promoting her new book. But soon her Substack became a life raft during a time of turbulence—and could become a more sustainable income than other ventures.
I started this newsletter because I wanted a way to write and connect regularly with readers, without having to go through the fancy rigamarole of … you know … editing or spell check.
Seriously, though. Many of you know that I’ve been working on my next book for FIVE BILLION MONTHS, and when I’m working on a book I don’t usually have the bandwidth to add formal freelance writing—especially since I also pay the bills with regular speaking work. I missed y’all. And I missed being able to go off at length on things that are on my mind. So I looked for a platform that was more writer-focused and landed on this one, and I haven’t looked back.
Read more: We’re A Year Old Now!
Two years ago,quit his full-time job at The Verge to start . As he heads into year three, he’s happy to report the business is more sustainable than ever. His detailed post on the past year (also one of his biggest reader hits) covers balancing investigative journalism with posting cadence, launching a podcast, and knowing how to uniquely serve his readers. If you’re keen to know how to turn your Substack into a full-blown media business, this post is a must-read.
Key takeaway: For Casey, the big hits are still growth drivers: breaking news and big analysis pieces that resonated with readers increased free and paid subscriptions more than anything. But that doesn’t mean those hits shouldn’t be as complex as they need to be, allowing for nuance and uncertainty in an age that emphasizes fear and outrage.
I think all this speaks to the need for independent, reader-supported journalism about some of the biggest questions of our age: about the relationship between social networks and the world around them; about how technology ought to be built and governed; and about some of the seismic changes that result from innovation.
I also think it underscores the appeal of this newsletter’s design: one big idea a day, delivered straight to your inbox at a reliable time, without any ads, affiliate links, pop-ups, SEO bait, or any of the other now-familiar features of our digital landscape. Platformer shows up, tells you a few things, and ends. I think the value of this is still somewhat underrated.
Read more: How Platformer is changing in year three
After a year of publishing on Substack,of has generated enough paid subscriber growth to cover his 2-year-old’s day care, and feels he knows the four key ingredients to making a newsletter successful: post consistently, be on Twitter, have a clear value proposition, and “write about stuff you’re obsessed with and make your readers not wish they were dead.” Max believes he only does one of these things really well. He understands that readers want value and joy—to be made to laugh as much as to learn and think.
As for next year, Max says he should probably announce a podcast or hire an intern. But what he can promise is only more “weird mysteries, vague discomfort, internet sociology, ill-advised diagrams, action-movie recommendations, and some very strongly held pointless opinions.”
Key takeaway: If you write obsessively and passionately about what you love, your readers will feel it and come back for more.
When I sent out my first post, it remained an open question to me whether or not it would be possible to build a sustainable newsletter operation with no Twitter presence at all. The flip side of this conundrum, of course, was whether I’d want to do a newsletter at all if it meant being on Twitter, shoving my Substack down everyone’s throat and mixing it up with various guys named Glen/Glenn. As subscribers know, I’m not above regularly embarrassing myself in front of medium-size audiences, but there are only two possible outcomes once you become A Social Media Personality: emigration to a country without extradition or a series of Apology Videos. Could I launch a successful newsletter without being on Twitter? Could I attain the elusive dream of “financially independent content creator with normal brain”?
After a year, the resounding answer is: Probably!
Read more: A year of Read Max
A year ago,of decided to turn a long-held idea of a blog into a Substack. She remembers being broke and manically depressed. Now with 40,000 subscribers (five of whom are famous famous) and more than 1 million reads, Rayne celebrates her first year on the platform by looking back at how it started and sharing some behind-the-scenes facts. Plus, a flash sale for new sign-ups.
Key takeaway: Some of your best posts can start as a notes app file on your phone while you are crying in your family basement bedroom over the holidays. Some of your best ideas take flight during the most difficult times in your life.
i have a note on my phone from pre-launch where i wrote that my goal was to get 1500 subscribers in six months. isn’t that crazy!! i feel so lucky every day.
the first nice thing i purchased with my new substack money was Replica’s Under the Lemon Trees, which devoted readers will identify as my current favourite / signature scent. it’s very sentimental to me for exactly that reason. it feels silly to say this about something you buy at Sephora, but as i picked it out and realized i could actually afford it, i remember feeling certain for the first time in a while that my life was actually starting to turn around. and i was right!
Read more: thank you + celebration sale <3
Unlike the volatile stocks he reports on,of confirms that in its first year, his publication has grown steadily and exceeded expectations. Since its launch, TKer has sent out 157 newsletters, with an open rate of between 50% and 70%, and has more than 10,000 subscribers.
Key takeaway: TKer relies on word of mouth as well as the Substack network for its growth.
Free and paid subscriptions have increased every month, and growth shows no sign of plateauing.
I’ve had the good fortune of interacting with some subscribers, which include financial services industry professionals, entrepreneurs, journalists, students, and many other folks with financial exposure to the stock market.
Many subscribers already follow market prices very closely but read TKer to keep current on macroeconomic matters. Other subscribers follow the economy pretty closely but read TKer to get a better understanding of why markets move the way they do.
Read more: Telling the story of how the stock market usually goes up, year 1 📈🎂
Mountain runner, coach, and authorstarted her Substack as a place to share her upcoming races of 2022, which were giving her a sense of purpose and motivation in midlife. One year on, she says, now her newsletter also nourishes that sense of purpose.
Key takeaway: Starting a newsletter can do so much more than provide space to cover a topic or niche. It might just lead to a feeling of life purpose.
The conversation and online discovery of Substack newsletters that ensued sparked an internal drive similar to what I felt the first week of journalism grad school in my twenties—that feeling of, I have so much to read, write, and do! The inspiration to mothball my old blog and start fresh on a new platform, with a new mission and a commitment to publish at least weekly, filled me with ideas and purpose. The community aspect of Substack—a network of writers and readers supporting each other, who practice and celebrate longer-form writing in this age when Instagram captions pass for essays—appealed to me as well.
One year ago, I launched this newsletter with a title more practical than clever, “Colorado Mountain Running & Living,” and the tagline “personal essays with practical advice about trail running, mountain living, and midlife grit.” Since that day, I have published 71 posts and grown a subscriber base nearing 1,000. Thank you for being a part of that.
Read more: One Year in the Substackverse
Despite missing his deadline of hitting 1,000 subscribers by 10 months,of says this actually helped him focus on a more significant aspect of growth: progress. Michael advocates not fixating on numbers but understanding that steady is better, community is important, and social media is overrated. Plus, celebrating incremental wins as an independent writer is a good idea.
Key takeaway: “Perfection is the enemy of a good newsletter.” And his newsletter is best when it takes chances.
The bribes didn’t work, but Situation Normal continued to grow because every week a handful of readers would share my story with their friends. That’s when I realized that growth comes in two flavors: Get Rich Quick and Compound Interest.
The growth I saw from Morning Brew fell into the Get Rich Quick category. Like winning the lottery, a subscriber windfall is great, but you can’t bank on it because you can’t control when, or if, one of your posts will go viral.
On the other hand, Compound Interest growth is something you can control by putting out consistent work and asking readers to share stuff they enjoy.
Read more: I hit 1,000 subscribers. Here’s what I learned
On reaching the milestone of 100 subscribers, writerof recalls an important lesson from his training as a horseman. His post covers art, criticism, taking advice and feedback, and plowing on, and it is well worth the read.
Key takeaway: Be careful about taking in feedback and advice from your critics, even when they appear to be successful experts or it comes from those you admire. Learn to trust your hard work and experience and assess what you hear to make your own choices.
I knew what the coach had demanded of me would harm my horse and the humane training I had so carefully cultivated. It would betray the kind of horseman I wanted to be. If others were comfortable accomplishing their goals through fear and abuse, that was on them. I would do it differently or fail trying. I’ve had similar experiences with my novel when agents and others tried to convince me to cut a third of it for the arbitrary reason of “genre standards”; alter facts and terms consistent with the historical period to conform with political ideologies I don’t share; submit to the whims of sensitivity readers, etc. These would have been betrayals of the kind of writer I want to be. If other writers are ok with having their creative efforts manipulated in this way, that’s up to them. I will do it my way or fail trying.
Read more: On meeting the 100 subscriber milestone
Congratulations, too, to the following writers and publications celebrating milestones this season:celebrates one year of , a newsletter and podcast. marks the milestone of 20,000 total subscribers to by updating its About page . . .
. . . as inspired bydoing the same for Newsletter. and the team at are celebrating their 10th anniversary.
For more writers’ milestone reflections, see our summer, spring, and winter roundups.
Are you writing about a milestone in the life of your Substack publication? Send us a note about it at email@example.com, and we’ll consider it for a future milestone post roundup (just make sure your post is available to free subscribers). It doesn’t have to be at the one-year mark, but we’re most interested in writing that shares thoughts about what you’ve learned along the way.
Milestone roundup: Writers reflect on their years on Substack