Podcast Summary: The Dave Gerhardt Show (Exit Five)

Episode: How to Upgrade Your Webinar and Email Strategy for 2026 with Jay Schwedelson

Date: February 13, 2026
Host: Dave Gerhardt
Guest: Jay Schwedelson (Founder, SubjectLine.com, Guru Media Hub, Host, Do This, Not That Podcast)

Overview

In this highly tactical episode, Dave Gerhardt chats with email and virtual event expert Jay Schwedelson about real-world strategies to upgrade webinars and email marketing in 2026 and beyond. Jay shares why most webinars fail due to dull packaging, how live energy beats on-demand every time, fresh hacks for subject lines and newsletter anatomy, and how B2B marketers can revive stale channels with smart experimentation, genuine engagement, and better human connection.

Key Discussion Points & Insights

1. Reinventing Virtual Events: From Boring to Bonkers

• Jay describes his media business Guru Media Hub:
  • Organizes large-scale, unique virtual events like Eventastic (~15,000 attendees) and Guru Conference (~30,000 attendees), recently featuring Nicole Kidman (03:05).
  • Virtual events attract high-caliber celebrity guests more affordably than live events.
  • Acquisition by Constant Contact: Validates the power of virtual events (04:44).
  • Notable Quote:

    "You want to show up and see what she has to say. I think that's part of why people get virtual events wrong. They think you have to follow this boring ass playbook that nobody cares about." — Jay (03:55)

2. Webinars Aren’t Dead—The Word “Webinar” Is

• Packaging Matters:
  • Stop calling them "webinars" (“the worst word in the human language”) (05:47).
  • AB test titles: “Live panel” or “Live insider session” outperform the word “webinar” by ~35% in registration.
  • Quote:

    "The biggest mistake in marketing: you have a webinar...you send out an email. The first word you put in your subject line: 'webinar:'. Boring, boring, boring. Nobody cares." — Jay (06:20)

3. The “Attend-to-Receive” Method for Higher Show Rates

• Key Play:
  • Offer exclusive resources or rewards only to live attendees ("attend live, get X").
  • Works only if it's a lead message, not buried in copy (09:17).
  • Staying for at least 50% of the time triggers the reward; increases show up rates by 30%+ (09:04).
  • Jay’s Stance on On-Demand:
    • “We’ve turned marketing into Netflix. It’s there whenever you want...that’s how you wind up scrolling and never watching anything.” (10:00)
    • Jay’s events require attending live to unlock on-demand content.
    • Allow FOMO: It’s better to have fewer, more engaged live attendees than inflate numbers with passive viewers (11:46).

4. Emphasizing Human Energy in a Remote, AI-Driven World

• Live and In-Person Events Matter:
  • Human connection is harder to achieve online, and B2B companies must prioritize in-person or live experiences (13:49).
  • “If you don’t have an in-person motion for your business...I think you’re going to be left behind.” — Jay (13:49)

5. Tactical Webinar and Email Marketing Plays

a) Rethink Timing:

• Fridays and Sundays are prime real estate:
  • Registration and attendance rates on Fridays have soared post-pandemic.
  • Long-form emails perform better on Sundays around 11:00 am.
  • Quote:

    “Sundays is the only time I can really look at my email...click through rates for business to business emails on Sundays is up like 60% year over year.” — Jay (14:23)

b) Content & Format Choices:

• Purpose-Driven Webinars:
  • Be specific about the funnel stage:
    • Top-of-funnel = generic, broad appeal topics.
    • Mid-funnel = product/problem-focused, specific, fewer but higher intent leads (17:04).
• Optimal Length:
  • 22-minute webinars get higher attendance; 22 (not a round number) feels real/manageable (20:08).
  • “If you’re doing a 60 minute webinar...you are out of touch. Nobody wants to put that on their schedule.” — Jay (20:08)
• Podcast Lessons:
  • Shorter podcast episodes (e.g., 17-22 mins) outperform longer ones in downloads and algorithmic reach (21:26).
  • Break content into focused topics for more downloads and shareable segments (22:46).

6. Newsletter Hacks and Behavioral Psychology

• Time Framing:
  • Add “2 min read” to content blocks or pre-header to manage expectations, increase clicks (24:09).
• Visual Structure:
  • Avoid dense content blocks (>5 lines); break text into short, readable bites for higher click-through rates (25:09).
  • Outliers (like Morning Brew) can get away with longer blocks; most B2B brands cannot.
• Personality Section:
  • End each newsletter with a playful ‘since you didn’t ask’ segment—personal stories to build rapport, keep readers to the end (27:33).
  • “It makes everybody stay to the end. You have to give a reason for people to want to stay other than...sign up for my webinar.” — Jay (27:57)

7. Advanced Email Tricks

• White Space & Pre-Headers:

  • No pre-header + a short (≤3 words) subject line = white space effect = higher open rates (28:35).
  • Use ChatGPT to learn how to suppress pre-headers on your platform.

• Subject Line Graphics:

  • Don’t use generic headshots/unrecognizable speakers in webinar graphics. Only feature celebs/major draws (30:58, 31:05).
  • Use subject lines like “Gary Vee is here” if the guest is widely known (31:32).

• Pre-Header Continuation Words:

  • Starting pre-headers with “and,” “but,” or “plus” increases opens—these “continuation words” drive curiosity (36:02).

8. Email Engagement and Deliverability

• You’re Not Sending Enough Email:
  • Most B2B marketers under-send, fearing annoyance. The real problem is boring, unengaging emails (34:02).
  • Modern spam filtering is based on engagement, not trigger words. Low engagement means your sends go straight to spam.
• Friendly From Lines:
  • Vary your sender name with specifics (e.g., “ACME Live Event”) to break monotony (35:30).

9. The Reply Signal: The Ultimate Deliverability Hack

• Reply-to-Get Mechanic:
  • Instead of a link, prompt users to reply with a keyword (“reply ‘guide’”) to receive a resource.
  • Triggers the strongest engagement signal for inbox placement; increases response 3x vs. forms/landing pages (37:08).
  • "The number one way to stay in somebody’s inbox in perpetuity is to get them to reply to an email." — Jay (38:02)

Timestamps for Notable Segments

• Jay Explains the Virtual Event Business & Nicole Kidman story: 03:05–04:44
• The Fatal Flaw: Calling It a "Webinar": 05:47–07:06
• “Attend-to-Receive” Strategy (“bonus for live”): 07:44–11:46
• Why In-Person Events Will Outlast AI: 11:46–13:49
• The Power of Fridays & Sundays: 14:27–15:55
• Purpose-Driven Webinar Topics & Intent: 17:04–18:30
• Webinar/Podcast/Newsletter Length Psychology: 20:08–24:09
• Newsletter Visual Structure & Personality Section: 25:06–27:57
• White Space, Pre-Header, and Subject Line Tricks: 28:35–32:41
• Email Engagement, Deliverability & Friendly From Line: 34:02–36:02
• Reply-to-Get Resource Hack: 37:08–38:53

Notable Quotes

• On Virtual Events:

  “You want to show up and see what [Nicole Kidman] has to say. I think that's part of why people get virtual events wrong...” — Jay, 03:55

• On Webinar Language:

  “If you are actually calling it a webinar, you should stop listening to this podcast and go and change that.” — Jay, 05:47

• On B2B Email Timing:

  “Click through rates for business to business emails on Sundays is up like 60% year over year.” — Jay, 14:23

• On Email Frequency:

  “Believe it or not, you're not sending out enough email, which I know is going to sound the opposite of what every meeting you're sitting in.” — Jay, 34:02

• On Inbox Strategy:

  "The number one way to stay in somebody’s inbox in perpetuity is to get them to reply to an email that you send." — Jay, 38:02

• On Content Packaging:

  "Stop following everybody else's playbook and just look at it a little differently. And that's how you can win." — Jay, 06:58

Actionable Takeaways

• Replace "webinar" in all promotions—test “Live Insider Session”, “Live Panel”, etc.
• Always offer unique bonuses for live attendance, and be explicit on what’s needed to earn it.
• Don’t be afraid to withhold on-demand content; let FOMO drive real engagement.
• Test event and content email sends on Fridays and Sundays.
• Use odd, specific time allocations (22 mins) for webinars.
• Chop email, newsletter, and podcast content into smaller, more digestible chunks.
• Use personality and culture to hook your audience at the end of newsletters.
• Try subject lines with ≤3 words and no pre-header to create inbox white space.
• Trigger pre-headers with “and”, “but”, or “plus”.
• Encourage replies with “send ‘guide’ for resource”—skyrockets engagement and future deliverability.

Final Thoughts

This episode is a masterclass in ditching tired, status-quo marketing tactics in favor of creative, counterintuitive plays that drive real interaction and results. Jay’s advice is to experiment, stay focused on human psychology, and treat every piece of content—whether webinar, newsletter, or email—as a product with care for its packaging and delivery.