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

**Dave Gerhardt** (0:00)
Hey, it's me, Dave. Today's episode is brought to you by Webflow. Webflow is a website platform for the Agendic Web, built for modern marketing teams to build fully custom sites that perform an AI search, no developer needed. Your website isn't just your home page anymore, it's actually the first thing an AI agent is going to read about your company, and from there, decide whether or not to recommend you to a potential customer, before a demo, before a sales call, before anyone on your team even knows that buyer exists. Which means if your site isn't structured to show up in AI search, you're not in the buying conversation, it's as simple as that. Webflow is the platform marketing teams use to fix that. You can build a fully custom site without a developer, optimize it for AI search, govern your content and actually see how agents are reading and interpreting it all in one place. Make your website your biggest growth engine right now with Webflow. Check them out at webflow.com/four/exitfive.
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Hey, it's Dave. We've been having a lot of fun recently with our live session strategy lately at Exit Five. Don't you dare call them webinars. And this conversation I had with Jay Schwedelson a few months ago is a big reason why. Jay is the founder of subjectline.com and Guru Media, and he's one of the sharpest tactical minds on email, webinars, live content. And we get into the word, we get into why the word webinar kills registrations. I thought this was really interesting before you even started what to do. Instead, tactics for improving the webinar experience overall, including how to dramatically increase show rates and a bunch of email plays that you can try that are easy to test. We even talk about our mutual love of Bravo, Summerhouse, big, big stuff going on there, and the many great marketing lessons from Bravo and Andy Cohen and the gang. And this is a good one for anyone running live content or email programs who want to squeeze more out of what they're already doing. Enjoy my conversation with Jay Schwedelson. All right, excited to do this episode, Jay Schwedelson. We got connected through email content over the years. Love your energy, expert in all things email, events and virtual events. We were just talking backstage, but let's kick off this. You actually, you created this virtual events business. We're just talking about how to explain to your lawyer friend, like what a virtual event is, right? Can you kind of like recap the events of maybe the last 30 days? And that's a good way to introduce you and tell the story about your business.

**Jay Schwedelson** (3:46)
Yeah, for sure. So I have a media business called Guru Media Hub. And some of the things that we do is we put on a really large scale, completely bonkers, very different virtual events, ones that you actually might want to go to. We do them at scale. So we have one that's about events called Eventastic. That's about 15,000 people. But our biggest one is called Guru Conference. It's about 30,000 people. It's all about email marketing. It's a virtual event. We just had it. We had Nicole Kidman there, whatever.
So about whatever. Yeah, right. That's my flex. You like that?