The Email Whisperer Speaks: Jay Schwedelson on Subject Lines, Event Emails & Marketing Myths You Need to Skip

In this episode of Event About It, host Megan Martin sits down with email marketing legend Jay Schwedelson, founder of SubjectLine.com and Guru Media Hub, to talk all things clicks, subject lines, and the art of making your event emails impossible to ignore. They cover everything from Jay’s obsession with Celsius to his greatest email pet peeves (looking at you, “register now” button).

It’s a wildly insightful, and wildly hilarious, conversation for marketers tired of the same old strategies. Jay dishes on what works now (hint: emojis and weird send times), what’s outdated (first-name personalization), and why your post-event email might be the most important one you send.

💡 Themes and Takeaways for Event Marketers and Email Strategists

1. Stop Saying “Register Now.” Try “Save My Spot” Instead

Jay’s #1 vent? The overuse of “Register” in call-to-action buttons. It’s sender-focused, not audience-driven. He recommends CTAs like “Yes, I want in” or “Save my spot” for a 20%+ lift in click-throughs.

🔑 Takeaway: Flip your CTA to be participant-centric—what’s in it for them?

2. Email Is Not Dead—It’s Just Underutilized

Jay argues email is the only marketing channel that lets you communicate with your full audience instantly. But most marketers underperform because they’re stuck in outdated rules.

🔑 Takeaway: Your email database is your most valuable marketing asset. Treat it like one.

3. Send Times Should Be Weird (And So Should You)

Sending emails at the top of the hour? Skip it. Most marketers do this, and it buries your message in the inbox. Try sending at 8:04 or 11:12 instead.

🔑 Takeaway: Non-standard send times boost open rates by 15%. Don’t be basic.

4. Subject Lines: Personalization ≠ First Name

Personalizing with job function, industry, or interest gets significantly higher engagement than using someone’s first name.

🔑 Takeaway: Try subject lines like “Just for Event Marketers” or “CXOs Only” instead of “Hey Megan…”

5. Weekend and Off-Hour Sends Work—Especially for Decision-Makers

High-level executives spend more time on emails on Sundays than any other day. Long-form content and invites? That’s your golden window.

🔑 Takeaway: Rethink “off-limits” send days. Weekend emails may outperform weekday noise.

6. Post-Event Emails Are Your Best Opportunity—Don’t Blow It

According to Jay, most event marketers go dark after the event. Big mistake. You have 48 hours of peak emotional engagement to nurture, convert, and keep the energy alive.

🔑 Takeaway: Plan a 3-touch follow-up series:

  • Within 3 hours: emotional thank you or highlights
  • 24 hours: early access or VIP invite for next year
  • 48 hours: community pop-up, content bundle, or exclusive recap

7. On-Demand is Killing Your Urgency—Use “Earned Access” Instead

Rather than promoting on-demand access before the event (which gives attendees an excuse to skip), require a minimum attendance to unlock content.

🔑 Takeaway: Turn on-demand into a reward, not a marketing feature.

8. Don’t Check the Box—Check the Relevance

Great marketers never just “get the email out.” They ask: Is this actually useful? Is this awesome? Or is this just average?

🔑 Takeaway: Every email you send builds—or erodes—brand sentiment. Don’t waste inbox space.

9. Get Funny, Get Real, Get Clicks

Jay’s blunt advice: humor > corporate stiffness. In the era of AI-written monotony, emails with personality (and memes) win.

🔑 Takeaway: Even in B2B, you’re marketing to humans. Be worth reading.

10. Bonus: Don’t Ever Start Your Subject Line With These Words

Words that tank open rates:

  • “Register”
  • “Reminder”
  • “Discover”
  • “Learn”
  • “Webinar”

✅ Instead, use: “Invitation:”, “Just for [job title]”, “Only 97 spots left…”

🎤 Final Thought

Whether you’re running a 10-person webinar or a 10,000-person trade show, the email rules still apply: be relevant, be interesting, and don’t let your CTA be “register.”

For marketers ready to level up their event campaigns, Jay’s mantra is simple: stop being boring, test everything, and write like a human.

🎧 Catch the full episode of Event About It with Jay Schwedelson at EventAboutItPodcast.com
🎟️ Learn more about Eventastic
📩 Visit SubjectLine.com to test your next email

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