Substack’s Success in a World of Free Content
Substack has transformed how writers work, offering independence, community, and—most importantly—a paycheck, all outside the traditional media machine. But here’s the big question: could musicians have their own Substack moment?
I highly recommend this podcast if you haven't already. In it, Substack’s founder, Chris Best, recalls pitching his audacious idea to Jesse Brown, the host of Canadaland. Best’s pitch was simple: independent writers could thrive by building a small, paying audience.
Brown wasn’t sold. “If you wanna read blog posts on the internet, you’re drowning in free stuff,” he said. “Getting people to pay for it just sounded ridiculous to me.”
Ridiculous or not, Substack proved him wrong. Writers create steady income streams, bypass traditional gatekeepers, and deeply connect with their readers. Take Ted Gioia, for example: not only has he found financial stability, but also the freedom to speak directly to his audience without compromise.
Chris Best’s vision—and the skepticism he faced—feels all too familiar. I’ve had countless conversations about what we’re building at Sleeve, and the doubts often sound the same:
“Everyone wants artists to get paid, sure, but you can get all the music you want on streaming for cheap—or free with ads. So why would anyone pay for this?”
Fair question. But here’s the truth I keep coming back to:
When you make everything available for free, it’s not so strange if you don’t get paid for it.
For musicians, maybe it’s time to rethink what we give away and what we reserve for those who genuinely care.
Substack’s model proves this works. Subscribers aren’t paying for just another blog post but investing in a deeper connection. They want exclusive access, meaningful experiences, and the chance to be part of something special. As writer Jen Gerson puts it:
“We did the math on X, and the amount of time I was spending on there wasn’t providing ROI. (...) Our ability to grow on social media has officially collapsed.”
Gerson left behind the broken social media grind, and her supporters followed. Musicians can do the same—escape the streaming trap and build something sustainable by offering fans exclusive access to what makes their art theirs.
Imagine this: your raw demos, behind-the-scenes stories, or live moments are shared only with those who directly support you. That connection isn’t just a nice-to-have; it could be the foundation of a thriving career.
But here’s the rub: if you want to do this today, your options are platforms like Patreon, Substack, or OnlyFans. None of these are built for music, so you juggle a side gig to keep the system running.
If writers can find creative and financial freedom on platforms designed for them, why shouldn’t musicians have the same?
Stay tuned,
Anna
