How to Upgrade Your Webinar and Email Strategy for 2026 with Jay Schwedelson (Founder, SubjectLine.com)

#329 | Dave is joined by Jay Schwedelson, Founder of SubjectLine.com and GURU Media Hub, to break down why most webinars and email programs underperform and what to do instead. They talk about how packaging drives performance, why the word “webinar” kills registrations, and how small tweaks like renaming your session, shortening it to 22 minutes, or adding an “attend to receive” hook can dramatically increase show rates. Jay also shares tactical email plays, from using white space and tighter subject lines to increasing reply rates and improving inbox placement.

Timestamps

• (00:00) - Why packaging matters more than the content
• (01:43) - Jay’s virtual event business and the GURU acquisition
• (04:29) - Why you should stop calling it a “webinar”
• (06:24) - The “attend to receive” tactic to boost show rates
• (08:58) - Why on-demand is hurting your engagement
• (13:07) - Why Fridays and Sundays outperform for B2B email + webinars
• (16:40) - How to choose webinar topics based on your goal
• (17:07) - Why 22-minute webinars and shorter podcasts win
• (26:16) - The white space + no preview text email hack
• (34:28) - The “reply with GUIDE” tactic to boost engagement
• (36:14) - Final takeaways and wrap-up

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