Podcast Summary: Do This, NOT That: Marketing Tips with Jay Schwedelson l Presented By Marigold

Episode Title: Ask Us ANYTHING: Best WIN-BACK Strategy? 📺TV Show Update!
Release Date: May 7, 2025
Host: Jay Schwedelson
Presented By: Marigold
Podcast by: GURU Media Hub

Introduction

In this special episode of "Do This, NOT That!", hosted by Jay Schwedelson, listeners are invited to engage in a dynamic Ask Us Anything session. Jay addresses both professional marketing queries and more lighthearted, personal questions, offering a blend of actionable strategies and relatable conversation. The episode is sponsored by Marigold, a leading relationship marketing platform.

Work Question: Crafting an Effective Win-Back Strategy

Timestamp: 00:00 - 15:30
Question From: William from Cleveland, Ohio

William’s Challenge: William seeks advice on launching a win-back email campaign targeting contacts in his database who haven’t engaged (opened or clicked) with emails in over a year. His concern is that more than half of his database falls into this inactive category.

Jay’s Comprehensive Response:

1. Timeliness is Crucial:

   • Quote: “Everybody waits way too long on their win back program. ... after 60 days pass and the person doesn’t open, click on one of your emails, over 70% of people will never open and click on one of your emails again.” (03:45)
   • Insight: Initiate win-back efforts much earlier than a year. Start at 30 days of inactivity and continue through 60, 90, and 120 days.

2. Structured Win-Back Timeline:

   • 30 Days:

     • Strategy: Intense, value-driven emails.
     • Example: Subject lines like “Three Things You Missed in the Last Two Weeks” or “In Case You Missed It, These Two Things Just Dropped.”
     • Purpose: Highlight the value the contact has missed, creating a sense of urgency and FOMO (Fear of Missing Out).

   • 60 Days:

     • Strategy: Emphasize potential mistakes in ignoring the engagement.
     • Example: Subject lines such as “Wait, Are You Still Here?” or “You Used to Love This.”
     • Purpose: Reinforce the importance of staying connected and the benefits they are missing out on.

   • 90 Days:

     • Strategy: Implement confirmation status sends.
     • Example: Subject lines like “CONFIRMATION: VIP Status Ending...” or “Are You Still in the Retail Industry?”
     • Purpose: Prompt recipients to confirm their interest by engaging, thereby filtering out truly disengaged contacts.

   • 120 Days:

     • Strategy: Go "nuclear" with drastic changes to re-engage.
     • Tactics: Change email send times, alter the sender's name from a brand to a personal name (e.g., “Alyssa from Brand”), and experiment with different content to capture attention.

3. Execution Tips:

   • Aggressiveness at Right Intervals: Jay emphasizes the importance of escalating efforts as inactivity persists.
   • Personalization and Variation: Adjusting email elements like send time and sender name can break the monotony and potentially rekindle interest.

Conclusion: Jay underscores that waiting a year to initiate win-back strategies is ineffective. Instead, marketers should implement a structured, timely approach starting at 30 days to maximize re-engagement rates.

Sponsorship Highlight: Marigold

Timestamp: 16:00 - 19:00

Jay takes a moment to acknowledge Marigold, the podcast sponsor. He shares his positive experience using Marigold’s platform for sending billions of consumer and business emails, praising its loyalty programs, inbox delivery rates, and superior segmentation capabilities.

Exclusive Offer:
Listeners receive 50% off the first three months by visiting JSchweddelson.com/emma.

Ridiculous Question: TV Show Recommendations

Timestamp: 19:10 - 25:50
Question From: Jackie from Fernandina Beach, Florida

Jackie’s Query: Jackie poses a whimsical question about Jay not watching what she considers the "best show on TV," leading into a broader discussion about Jay’s current TV show obsessions.

Jay’s Entertaining Response:

1. Current Shows:

   • Paradise (Hulu):

     • Description: A dystopian, end-of-the-world series starring Sterling K. Brown.
     • Jay’s Take: Highly recommends, highlighting Sterling K. Brown’s performance and noting the show’s renewal for a second season.
     • Quote: “If you've not tried that, it is great for loyalty programs … It’s a great, great show.” (22:30)

   • Love Hotel (Peacock):

     • Description: A reality dating show featuring stars from Real Housewives dating various men.
     • Jay’s Take: Praises it as a quality reality dating show, appreciated for its entertainment value.

   • Four Seasons:

     • Description: A show featuring Amy Poehler’s friend and Steve Carell from The Office.
     • Jay’s Take: Mixed feelings, finds it mildly depressing and is unsure about continuing to watch.
     • Quote: “It’s okay. It’s mildly depressing. I don't know if I recommend watching this show.” (24:15)

   • House Hunters:

     • Description: A long-running show where couples search for new homes, often with conflicting preferences.
     • Jay’s Take: Finds the premise strange and perplexing, having watched over 400 episodes without understanding the consistent outcomes.
     • Quote: “They pick the worst option possible. ... my ability to pick which one they're going to pick is at like a 19%. I'm terrible at it anyway.” (24:45)

2. Personal Anecdotes:

   • Jay shares humorous frustrations about remembering actors’ names and the inconsistencies in House Hunters, adding a relatable and lighthearted touch to the discussion.

3. Engagement Encouragement:

   • Quote: “If you leave this thing a review, you would be a really cool human being. I would really appreciate it.” (25:30)

Closing Remarks

Jay wraps up the episode by encouraging listeners to subscribe for more actionable marketing tips and to engage with the podcast through reviews. He also promotes GURU Media Hub’s free virtual marketing events, featuring top marketers like Daymond John and Martha Stewart.

Additional Resources:

• Subscribe for Updates: Ensure you receive the latest episodes each week.
• Virtual Marketing Events: Visit guruvents.com for access to exclusive, free marketing events.

Key Takeaways

• Win-Back Strategies:

  • Initiate engagement attempts much earlier than a year of inactivity.
  • Use a structured timeline with escalating strategies at 30, 60, 90, and 120-day marks.
  • Incorporate value-driven content, personalization, and confirmation tactics to maximize re-engagement.

• Effective Campaign Tactics:

  • Leverage FOMO and highlight missed value in communications.
  • Utilize confirmation status sends to determine active interest.
  • Experiment with different email elements to break through disengagement.

• Engagement Tips:

  • Encourage listener interaction through reviews and questions.
  • Provide exclusive offers and resources to add value to the audience.

• Entertainment Insights:

  • Balancing professional advice with personal anecdotes can create a more engaging and relatable podcast experience.

Notable Quotes:

• “After 60 days pass and the person doesn't open, click on one of your emails, over 70% of people will never open and click on one of your emails again.” (03:45)
• “Everybody's watched house hunters, like 400 seasons of it. But it's the strangest thing because the couple never is on the same page.” (24:30)

This episode of "Do This, NOT That!" offers valuable insights into effective win-back email strategies while providing an entertaining glimpse into Jay Schwedelson’s personal interests. Whether you're seeking to revitalize your email marketing efforts or simply enjoy a candid conversation about TV shows, this episode delivers both depth and personality.