The Upside of Struggling to Break Through

For today’s episode, we revisited a timely topic—breaking through the noise. 2024 was a big year for newer artists in music who gained attention, but there’s still a gap between them and the biggest artists in the world.

You can listen to my conversation with Tati Cirisano here, or read below for why despite the trends in music (and other forms of media), I’m optimistic for all the people who put out excellent work. Let’s dive in.

I’ve been writing this newsletter for a while. It’s been seven years, as of last week! I’ve met plenty of people who have started and stopped their own newsletters in all sorts of industries. I know all the trends on what works and doesn’t work. I could write a whole book on it.

This year though, I’ve heard more from people who feel like the “best days” are behind us. The email marketing platforms have made it easier than ever to spin up a newsletter and get started. Having a newsletter is now table stakes. The inbox is more crowded than ever. Social media algorithms no longer promote threads, which can lead to thousands of new subscribers. Plus, video captures more attention from audiences than ever before.

But the newsletters that last have actually built a company around their work. There’s a brand that resonates with its target audience. The company is focused on a market that’s willing to pay for what they offer. And operators need to have the endurance to continue. Believe me, I’ve made my fair share of pivots, and have experienced some of the same evolutions.

The encouraging part is that most people don’t have the endurance. Like Jay Z says about his career, “The most genius thing is that we didn’t give up.”

These conversations about newsletters sound like the discussions in music for the past few years. By 2021, TikTok began to saturate, record labels realized that many of the acts they signed from viral TikTok clips wouldn’t pay off, and the algorithms became stronger.

It became harder for new acts to break through. The newer artists who do break through, like Sabrina Carpenter, Chappel Roan, and Shaboozey, aren’t really “new.” It took them years to get where they are. The biggest stars from the late 2000s and early 2010s rose up because of their talent. But the reason that many of them are still the biggest stars today has more to do with their timing than their talent.

This is why I revisited our episode, Can New Superstars Ever Surpass Old Superstars? A few things have changed since our December 2023 recording, but the sentiment still holds.

Despite these trends, I believe that now is still the best time to be an artist. I feel similarly about most forms of media, even newsletters.

The truth that few want to admit is that these long-lost “glory days” had elevated a lot of mediocrity. There was plenty of mediocre writing, newsletters, podcasts, and video series that gained traction because they were new, or because of the well-known name attached to them. That doesn’t mean they were good! It’s not just the biggest artists in the world who thrived off of monetizable mid.

It’s harder for mediocrity to break through, but excellent work that’s uniquely positioned can still find its audience. It may take more effort and resources and is still subject to market timing, but it’s possible. That’s what pushes successful independent artists to still pursue greatness. That’s what pushes me to still make the best podcast possible week after week. And I hope that’s what pushes you with your work in your respective fields.

For more on this topic, you should follow artists managers, and indie label owners like Barry Johnson, Kei Henderson, and Zeke Nicholson. They’ve managed some of the most successful artists and are transparent about the realities. Like most things in music, the topics they discuss today will likely be similar in other industries.

Listen here:​​Spotify​ | ​Apple Podcasts​ | ​Overcast

Chartmetric Stat of the Week

Following her Super Bowl halftime performance and the release of the deluxe version of SOS, SZA's Spotify monthly listeners have surged to 97 million as of March 11, 2025. No wonder the concert tickets for SZA's tour with Kendrick Lamar, who has 111 million listeners.