Podcast Summary: “Ask Us ANYTHING: Wake the Dead (Your Email List) ☠️… My Spirit Airlines Confession 😬🛫”

Podcast: Do This, NOT That: Marketing Tips with Jay Schwedelson
Host: GURU Media Hub
Episode: 446
Date: November 13, 2025

Episode Overview

This episode of "Do This, NOT That" is part of the recurring "Ask Us Anything" series, where host Jay Schwedelson tackles both a serious marketing query and a lighthearted, offbeat question. This week, Jay dives deep into winning strategies to "wake the dead" in your email list—reactivating contacts who haven’t engaged in over a year—by sharing actionable techniques based on tested behavioral science and real-world data. The episode closes with Jay’s enthusiastic confession about flying Spirit Airlines, bringing his trademark humor and authenticity to both marketing advice and life’s funny moments.

Key Discussion Points & Insights

1. How to Wake Up a Dormant Email List (00:58 – 10:23)

• Question from Jenny (Lake Placid):
  "We have a ton of contacts in our database who have not opened or clicked on an email in over a year. How do we wake the dead as we go into the end of year?" (01:32)

A. Secret Sauce #1: Letter Format Emails from Executives

• Timing: November 20 – December 20 yields highest impact.
• Open Rate Boost: "Letter format emails that actually come from a founder, a CEO, an executive director, or senior vice president, whatever, from November 20 through December 20 actually have a 40% higher average open rate than regular emails do."
  — Jay Schwedelson (02:11)
• Why it works:
  – More personal, feels exclusive.
  – “When you get this kind of letter format, email style email from somebody really important and they're saying, hey, we kind of want you back, we have this special thing for you. We missed you.” (03:39)
• Best Practices:
  – Use the executive’s name, not the brand, in the "from" field.
  – Subject line should acknowledge lapsed engagement (e.g., “A note from our founder” or “You disappeared, but I get it”).
• Big Brands Already Do This:
  – “Allbirds has letters coming from their CEO three or four times a year. Glossier has it coming from Emily Weiss.” (03:10)

B. Secret Sauce #2: Verification-Style Emails

• Verification Emails Defined: Designed to confirm the recipient’s interest or status.
• Open Rate Lift: "It lifts open rates by 27% on the consumer side and 31% on the business side." – Jay Schwedelson (04:20)
• Tactics:
  – Subject line example: “Are you still with [Company Name]?” (dynamically personalized)
  – Simpler variant: “Verify your active status.”
• Caveat: Be ready for a higher unsubscribe rate. "You're going to get a lot of people to wake back up, but you're also going to get a high unsubscribe rate because it's going to really annoy some people." (05:31)
• Consumer Brand Variation:
  – “Verify your VIP status”
  – “Still want free shipping?”
  – “Want to make sure”
  – These emails should come from the regular brand address, not executives. (06:02)

2. Ridiculous Question: Airline Preferences and Spirit Airlines Confession (10:24 – 15:13)

• Question from Tate (Los Angeles):
  "Jay, what is your favorite airline to fly?" (10:38)

Jay’s Spirit Airlines Journey

• Initial Perception:
  – “I used to avoid flying Spirit Airlines because I thought that Spirit was like some sort of inferior brand, that if I flew on Spirit, I wouldn't make it to my destination...” (10:50)
• Turning Point:
  – Needed to visit his son in New Orleans; Spirit was the only practical option.
• Outcome:
  – “Spirit is great. It is awesome. First of all, their planes look cool. They're yellow, and that looks cool. Second of all, I have gotten there multiple times. I'm still alive. That's a win. On top of that, they've been on time every single time. I have nothing but positive things to say about Spirit Airlines.” (12:00)
• Humorous Observation:
  – “I don't understand when people get on the plane and then...instead of going down the aisle, someone's making a hard left, and they're going, 'Hey. Can I use the restroom?' ...Like, what were you doing 10 minutes before this?” (13:08)

Notable Quotes & Memorable Moments

• On Personalization of Email Outreach:

  “The key thing there is the from name, though. That's what you really need to be considering.”
  — Jay Schwedelson (03:32)

• On Accepting Unsubscribes:

  “You just have to have a little bit of thick skin, knowing you're going to get some zingers of people saying, take me off your list.”
  — Jay Schwedelson (05:54)

• On Letting Go of Airline Stereotypes:

  “I'm here to report. I'm here to tell everybody, nobody cares. Spirit is great. It is awesome.”
  — Jay Schwedelson (12:00)

• Meta, Self-Referential Humor:

  “So what have we gotten out of this episode? Number one, send emails to people that have not been opening or clicking them. Good luck with that. Number two, fly Spirit Airlines. There you go. That's my commercial. Number three. Go to the bathroom.”
  — Jay Schwedelson (14:50)

Timestamps for Important Segments

| Timestamp | Segment | | ------------ | -------------------------------------------------------------------------------- | | 00:58–10:23 | Strategies for Re-engaging Dormant Email Contacts | | 02:11 | Secret Sauce #1: Executive Letter Format Email (40% open rate boost) | | 04:20 | Secret Sauce #2: Verification-Style Emails (27–31% open rate boost) | | 05:31 | Caution: Higher Unsubscribe Rates | | 10:24 | Ridiculous Question: Airline Preferences | | 12:00 | Jay’s Spirit Airlines Confession & Reassessment | | 13:08 | Humorous Take on Pre-Flight Restroom Behavior | | 14:50 | Jay's Summary of Episode Takeaways (Emails, Spirit Airlines, Bathroom breaks) |

Episode Tone & Style

Jay maintains a lively, conversational, and self-deprecating tone throughout the episode, blending tactical marketing wisdom with relatable, everyday humor. His direct style and willingness to poke fun at himself make the discussion both practical and entertaining.

Actionable Takeaways

• Test letter-style, executive “from name” emails between November 20 – December 20 to revive dormant subscribers.
• Run verification-style campaigns to dormant segments, but brace for higher unsubscribes—and be okay with that.
• Embrace new experiences and don’t write off brands (or airlines!) based on old biases.
• Add a touch of humor and human connection to marketing efforts and life in general.