Category: Email MarketingCategory: Email Marketing

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!

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.

From strategist and facilitator Caitlin Mayance,

Hey brands, why you still sending out storyless emails in 2026? You have direct access to a personal inbox – no algorithmic nonsense – and you’re leading with a promo or tiny lil ad?! Come on

When the bare minimum is copy and pasting your pre-existing marketing materials and hitting send to ALL is your strategy, expect bare minimum results.

Some of the most fascinating stories are being told on rented platforms, while email newsletters are filled with recycled social media images and [$NAME] placeholders.

I got a newsletter awhile back from a talented musician, and they casually mentioned they’ve got new music available, but if you want to hear it you need to reply to the email.

In one our Escape Pod Zoom calls someone mentioned how they leave “easter eggs” in their newsletters, usually a phrase that someone needs to include when they reply.

Parker Gates sent me this link (it’s an Instagram link, sorry!) about artist Jon Bellion and how he sent his fans to websites without linking to them (they had to type them into a browser from a screen shot), used message boards, and sent out music via WeTransfer.

Don’t just wonder who your biggest fans are – send them on adventures and see who makes it back alive.

Stuff we covered from a recent Office Hour Substack Live:

• The “boring stuff” that actually moves your career, like emailing people, following up, doing the unsexy work that compounds.

• Stop worshipping social platforms. Algorithmic reach is terrible, 90% of your audience doesn’t see your posts, email beats everything. RSS is even better.

• Audience-building for musicians. Embed your music, play live, collect emails in person, nurture your actual fans, don’t drive traffic to Spotify or YouTube.

• Let people pay you in multiple ways. Use Patreon, Ko-fi, PayPal, Stripe links; don’t make anyone jump through hoops to support you.

• Local, in-person proof builds trust — photos of real events, showing up in the world, and letting that strengthen the online side of your work.