Category: sethwCategory: sethw

Michael Gilbride of the MAD Records Collective and I sat down for an hour-long conversation about what actually matters when building a music career in 2026.

• Stop chasing vanity metrics. Having 50,000 Spotify listeners means nothing if you can’t reach those people when you have something to sell.
• We dove into lots of good stuff during this chat:
• Michael’s stark data point: 50,000 monthly listeners = one non-friend at his show
• Artists with small, engaged email lists are booking venues, selling out shows, making real Bandcamp revenue
• Sturgill Simpson released his latest album vinyl/CD/tape only—no streaming
• Creating friction isn’t a sacrifice, it’s smart business—increases fan commitment
• When fans go out of their way to support you, they convert from passive listeners to real fans
• Same principle for email: people who subscribe and open are demonstrating genuine interest
• Discussion covered economics of leaving streaming, potential comeback of physical mail, embracing business skills without sacrificing creativity

The core themes are this: stop building audiences you can’t reach (the Oatmeal is pushing his email list over socials), and don’t be afraid to focus on actually selling something!

From a recent Email Guidance client:

Decided to go through my “General” IG mailbox and send a version of this note: [REDACTED]

Picked up two new free sub’s in the first five mins.

This writer reached out to people already in his DMs with a note saying they could subscribe to his newsletter, and two people did that just that in the first five minutes.

I’m not saying automated systems cheapen the exchange, but honest communication certainly can’t hurt.

If you go by this post, “How Instagram creators are bringing their followers to Substack,” there are so many ways to get your Instagram followers to subscribe to your Substack newsletter! Video! Images! Text! Get creative!

In reality, however, your Instagram followers are likely very content to stay on Instagram.

Consider that best selling author Elizabeth Gilbert (Eat Pray Love) has 1.2M Instagram followers, but just 203,000 subscribers. Sure, 203,000 email subscribers is great, but it’s still less than 20% of her following on Instagram.

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On Monday’s Substack Live, I talked about lots of stuff, like putting the bulk of my work on my own site, and then when it comes time to send a newsletter, I never have a shortage of ideas to pull from. Something to consider with your own website, maybe?

On Wednesday, I had a conversation with label owner Michael Gilbride about the economics of leaving streaming platforms, why physical mail might be making a comeback, and how musicians need to think about learning business skills – woah boy!

On our Thursday call, we talked about Polymarket becoming a big thing on Substack, making promo stickers, the challenges of finding places to post our flyers, getting people from social media to subscribe to our newsletters, and lots more.

Then on this morning’s MINI ESCAPE POD Q&A we talked about the SEO game with Substack and our own websites. If people are searching for your specific project name (“Social Media Escape Club”), Google will usually surface it without big time optimization.

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From JA Westenberg’s “Communities are not fungible” piece,

“When a platform dies or degrades, its community does not simply migrate to the next platform, it fragments, and the ones who do arrive at the new place find that the social dynamics are different, the norms have shifted, and a substantial number of the people who made the old place feel like home are gone.”

This is what makes the “how do I move my social media followers to my newsletter?” a seemingly impossible task.

There are people that work at Meta who have multiple vacation homes because they are very good at their job, which is to keep users on their platform.

Make it addictive enough to keep people from leaving, and charge for things that used to be free, and you’ve got yourself a nice career.

Communities are not resources to be optimised and they’re not user bases to be migrated. They’re the accumulated residue of people choosing, over and over again, to remain in a relationship with each other under specific conditions that will never, ever recur in exactly the same way.

Some of your followers on Instagram are never going to subscribe to your newsletter.

Everyday, one of your followers logs into the platform for the last time.

Your followers are not yours, they are owned by the platforms who profit from your years of shouting “follow me on social media for updates!”