The Guy Behind Over 6 Billion Email Sends A YEAR (Episode 10 ft. Jay Schwedelson)

Welcome back to 21 Minutes With… (this time with emails, AI hacks, and a few typos that actually work).This week, Brittany and Christian sat down with Jay Schwedelson, founder of subjectline.com and host of the #1 Marketing Podcast in the US, Do This NOT That: Marketing Tips with Jay Schwedelson, whose strategies power over six billion email sends annually. From clever subject line experiments to the art of un-AI-ing your content, Jay shared lessons learned from scaling some of the most effective email campaigns and building a personal brand that breaks all the rules.We dug into why some “mistakes” become your best-performing campaigns, how to cut through inbox clutter in 2025, and why sometimes the most human, imperfect content gets the best results. Oh, and yes, we may have learned a few hacks you’ll want to test tomorrow (you’ll want to stay for these!).📧 Inside this episode:- Jay’s counterintuitive hack: why first-name personalization isn’t always the winner- How testing “broken” rules can outperform traditional best practices- The secret power of preheaders (and why emojis are your friend)- AI, typos, and un-AI-ing: why perfect content might be hurting your engagement- Personalization that mirrors your audience so they self-identifyThis episode is for marketers, content creators, and anyone who believes email isn’t just about clicks, it’s about connecting with real people in ways that surprise, delight, and perform. And trust us, you’ll never look at your inbox the same way again.