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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this monthly "Email Breakdown" episode, Liz Wilcox — the Fresh Princess of Email Marketing — shares her top-performing email from March 2025. With List Building Live and her Annual Pass sale both happening this month, Liz sent more emails than usual — and one simple message stood out above the rest. Spoiler: it's not fancy, it's not long, but it's proof that empathy, timing, and a little personality go a long way.
Episode HighlightsLiz's top-performing email: "Hit reply to this email."
Why this worked:
The numbers:
Bonus shoutout: an honorable mention email sent only to existing $9/month members encouraging them to upgrade to the Annual Pass.
Subject line: "Why I upgraded to the Annual Pass — straight from members."
65.8% open rate and 6.9% click rate.
This single segment generated nearly half of total sales from the campaign.
Why segmenting matters — even if Liz usually teaches it as a "2.0 strategy."
When it's easy to isolate a group (like current members), personalization can dramatically improve results.
Keep it human: Low-pressure, empathetic emails convert because they build trust.
Timing matters: Send relational emails at the end of a campaign to catch hesitant buyers.
Segment smart: Small, targeted messages can outperform full-list blasts.
Honesty sells: Transparency and relatability create lasting loyalty.
Measure what matters: A single thoughtful email can drive massive end-of-launch results.
Check out Liz's Email Marketing Membership here
Join the Email Sound Booth Facebook group here
Check out Liz's free welcome sequence here
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