Jesse Anderson went from zero writing ambitions to 70,000 newsletter subscribers and a social media following of hundreds of thousands, all while working full-time in tech and raising three kids. The kicker? He did it completely by accident.
I wrote a deep dive on Jesse’s story mid-2023, but there’s a huge change that recently happened which is going to change everything for him. We’ll get into that later, but first we wanted to hear more about what’s happened since 2023 and where he sees the business going.
We recently sat down and chatted about finding your niche, some challenges around staying authentic as you scale, and building a business around helping others navigate challenges you’ve personally faced.
We recorded the full interview and put it on YouTube if you’re interested in listening as well.
The Accidental Start
He joined Ship 30 for 30 in March 2021, he had zero ambitions to become a content creator. No dreams of writing a book, no plans to build an audience, and definitely no intention of turning ADHD education into a thriving newsletter business.
“I had no ambitions to be a writer or a creator,” he told us. “I saw Ship 30 for 30 and thought, that sounds like a fun thing. I think I’ll do that.”
His plan was to write about design and tech (and his role at his day job). But he decided to include a few essays about ADHD since he’d been diagnosed a few years earlier.
Those ADHD posts changed everything.
“I did one or two ADHD essays, and immediately it was like, oh, this is what people don’t know about. That’s the content people are connecting with and replying to.”
The timing was perfect. Ship 30 attracts entrepreneur types, and studies show entrepreneurs have significantly higher rates of ADHD. Jesse accidentally found his ideal audience.
Building the Newsletter
Following advice from his Ship 30 cohort, Jesse started a newsletter on Substack. His strategy was refreshingly straightforward:
Take the ADHD atomic essays he was writing and send them out each week.
“I’d do a weekly newsletter that was like, ‘Here are the four things I wrote about ADHD this week,'” he explained.
What made Jesse’s content special wasn’t just the ADHD information – it was his authenticity. He wasn’t positioning himself as an expert. He was sharing his own journey of trying to understand his brain.
“People felt really seen because they felt like I got them. I understand what it’s like living with ADHD, especially undiagnosed. I wasn’t diagnosed until my mid-thirties.”
The “Seen and Attacked” Content Formula
Jesse has this ability to connect ADHD experiences to universal moments that hit deep. His followers constantly comment things like “I feel both seen and attacked.”
I’ve definitely left that exact comment on his posts.
“I seem to be good at connecting the ADHD experience to everyday situations,” Jesse said. “I get a lot of replies from people saying exactly that – they feel seen and attacked at the same time.”
He’s found a sweet spot. Content that makes people feel understood and called out simultaneously.
This content has a natural leg up when it comes to being share-worthy.
Because not only are those people feeling that, but they can share it with friends who might also be going through the same thing, or their partner, to help them better understand why they do certain things.
Multi-Platform Growth Without Burnout
While building his newsletter, Jesse was also growing across social media. His approach was surprisingly sustainable:
Jesse created short, tweet-like content which ended up working across platforms. He shares the same posts on Twitter, Instagram, Blue Sky, Threads, Mastodon – all automated through Buffer.
Most professional creators will tell you not to do that, but it’s working for Jesse, and it’s much more sustainable than trying to recreate the wheel for every platform.
Instagram Success with Text-Only Posts
Here’s what’s wild in my view: Jesse built a massive Instagram following by screenshotting his tweets and posting them as static images.
“I’m the weirdo where most people who follow me on Instagram don’t even know what I look like because I’m just not posting that sort of content there.”
While everyone else creates reels and stories constantly, Jesse posts text images and crushes it, to the tune of 129k followers.
I love his style because it’s just so approachable. Will it work for everyone? No. But he gave it a shot and it worked for him, so he just kept going with it.
Data-Driven Repurposing
For a long time, Jesse would not repurpose past content because he felt weird doing it.
“I was really precious about not wanting to repurpose content, and now I’m fully in on it. Every time I post something, I still get comments from people clearly seeing it for the first time.”
Jesse’s smartened about repurposing now, though.
He exported all his Twitter data and built a
Makes sense, right? You have all of this content, it’s about time you started reposting some of it and stopped trying to recreate the wheel.
And then best part? He said he hasn’t been called out once for resharing stuff – in fact, some of those older posts do better the second time around.
The Support System
Jesse built this while working full-time and raising three kids (ages 8, 12, and 14). His secret? Being honest about who makes it possible.
Most “solopreneur” success stories have someone working behind the scenes. Jesse’s just honest about it.
“My wife is amazing and does a lot for our family. That’s something I think a lot of people forget to mention, especially white males talking about grinding to get stuff done. For me, it’s my wife working behind the scenes.”
Having ADHD made family scheduling even more challenging, making his wife’s support crucial. And he doesn’t hide that at all.
The Course Launch Strategy
Jesse just launched his first major course using a “founding cohort” model. He sold the course before creating it, then recorded modules weekly based on student feedback.
This approach let him:
- Price it lower to attract more students and testimonials
- Adapt content based on real student needs
- Create a recorded asset for future launches
- Build community among students
That community aspect is crucial for his ADHD audience. “When you have somebody you can talk to that gets it, you can talk about things that are embarrassing to tell someone neurotypical and get understanding instead of blame.”
What’s Next for Jesse
Since 2021, his growth has been substantial:
- 70,000 newsletter subscribers
- 400-500K followers across all platforms
- 85,000 YouTube subscribers
- 400 paid Substack subscribers at $8/month
But here’s the plot twist: Jesse recently got laid off from his tech job.
Instead of immediately job hunting, he decided the universe might be telling him it’s time to give this full-time creator thing a shot.
“I was like, if I jump into another job right now, then I’m never gonna do this. It’s just never gonna happen.”
So, he’s giving it a go, and trying to make a full-time living from his newsletter business.
5 Lessons from Jesse’s Journey
While we were chatting with Jesse, I pulled out a number of interesting ideas and lessons from his journey over the last 4 or so years.
1. Start with authenticity over expertise
Jesse’s early success came from sharing his personal journey, not positioning himself as the ultimate ADHD expert. He documented his own learning process rather than trying to be the world’s leading authority.
This is huge because he admits he fell into the “expertise trap” as he scaled.
“When that number gets high enough, you start to overthink – should I be more streamlined? Should every newsletter be exactly a strategy with three takeaways? But now AI can spit that out like that. That’s not the value I’m going to be adding.”
When you position yourself as the “learner” not the expert, it takes a load off of your shoulders from trying to be something you’re not quite yet.
It also helps people resonate more with your content because you’re showing the process of learning that thing.
2. Repurpose strategically
One piece of content can work across multiple platforms if you understand each platform’s preferences. Jesse proved this by taking tweet-style content and successfully posting it everywhere with minimal adaptation.
He was initially “really precious” about not wanting to repurpose content, worried people would call him out for posting the same thing twice. That never happened.
In fact, he discovered something counterintuitive: “Every time I post something, I still get comments from people clearly seeing it for the first time.”
The reality is your audience isn’t following you on every platform, and even if they are, they’re not seeing every post. And even if they are, they are going to forget the post existed before.
Jesse now has a massive
3. Community beats courses
People want connection with others facing similar challenges, not just information downloads. Jesse discovered this when course participants consistently asked to continue the community aspects after the educational content ended.
“Every time, they’re like, oh, I wish we could keep doing this. And they’re like, I’m the idiot that, like, no. We can’t. Bye.” Jesse was literally walking away from people begging to pay him for community access, which is he rethinking now that he has a bit more time on his hands.
This is especially true for topics like ADHD where there’s often shame involved. “There’s so many things with ADHD where it’s so easy to feel immense shame because you have these intentions, and your actions so often don’t meet what your intention is.” Having a community of people who “get it” is incredibly valuable.
4. Don’t overthink the format
Jesse worried about changing his newsletter structure, but readers care more about value than consistency in format. He spent mental energy perfecting formulas when his audience just wanted authentic, helpful content.
“I feel like it’s so easy to get in your head and think everything is permanent. Like, I have to have the perfect format where I’ve got this here and then this thing, and then I do that there. And then if I change it next week, everyone will be upset for some reason, and no one cares about that stuff.”
The overthinking actually made writing harder for him. For months, he dreaded writing his newsletter because he was trying to force everything into a perfect formula. When you dread writing something, your readers can feel that energy. Better to write something you’re excited about than something that fits a template.
5. Build relationships, not just audience
The most engaged followers become customers when they feel genuinely connected to your story and mission. Jesse’s success came from people feeling “seen and understood” rather than simply educated.
Jesse’s content works because it creates this specific emotional response: “I feel both seen and attacked.” That’s not just educational content – that’s relationship building. His readers don’t just know facts about ADHD, they feel like Jesse understands their daily struggles.
When you focus on building relationships rather than just growing follower counts, you end up with people who are genuinely invested in your success. They’re not just passive consumers – they become advocates, customers, and community members who stick around for years.
Bringing Back the Real-Ness
Jesse is focused on recapturing the authentic voice that built his early success while creating sustainable revenue. His plans include:
- Launching a community that emerges from his course
- Creating an evergreen version of his course
- Simplifying his tech stack
- Getting back to personal storytelling
“I really need to recapture what I was doing in my second year when the newsletter really started to grow. Getting back to what I loved about writing – talking about things I’m learning and excited about rather than following an exact formula every week.”
For creators building around personal challenges or niche communities, Jesse’s story shows the power of leading with vulnerability and shared experience rather than expertise.
The best creators aren’t the ones who have everything figured out – they’re figuring it out alongside their audience.
