In this episode, I sit down with Tyler O’Shea, founder of The Underdog Newsletter, to break down how he turned around his declining open rates, overcame inbox placement issues, and built a smarter, more profitable email strategy using the Base Sending Segment method.
Whether you're a newsletter operator, email marketer, or media buyer—this conversation is packed with insights you can apply immediately.
🧠 What We Cover:
- The problem that nearly wrecked Tyler’s deliverability
- How Beehiiv flagged his list—and how he fixed it
- Why sending to your full list is a mistake (and what to do instead)
- How to build your Base Sending Segment
- Inbox recovery, smarter segmentation, and growth without risk
🎧 Listen, learn, and apply the exact tactics Tyler used to hit 55% open rates and scale without spammy tricks or cold blasts.
🔗 Subscribe for more episodes on email growth, deliverability, and newsletter strategy.
Mentioned in this episode:
📨 The Underdog Newsletter → https://newsletter.jokermag.com/
📥 AudienceBridge → https://www.audiencebridge.io/subscribe
𝕏 Chris Miquel → https://x.com/miqchris
𝕏 Tyler O'shea → https://x.com/OSheaSEO
Popular Podcasts
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
My Favorite Murder with Karen Kilgariff and Georgia Hardstark
My Favorite Murder is a true crime comedy podcast hosted by Karen Kilgariff and Georgia Hardstark. Each week, Karen and Georgia share compelling true crimes and hometown stories from friends and listeners. Since MFM launched in January of 2016, Karen and Georgia have shared their lifelong interest in true crime and have covered stories of infamous serial killers like the Night Stalker, mysterious cold cases, captivating cults, incredible survivor stories and important events from history like the Tulsa race massacre of 1921. My Favorite Murder is part of the Exactly Right podcast network that provides a platform for bold, creative voices to bring to life provocative, entertaining and relatable stories for audiences everywhere. The Exactly Right roster of podcasts covers a variety of topics including historic true crime, comedic interviews and news, science, pop culture and more. Podcasts on the network include Buried Bones with Kate Winkler Dawson and Paul Holes, That's Messed Up: An SVU Podcast, This Podcast Will Kill You, Bananas and more.
The Joe Rogan Experience
The official podcast of comedian Joe Rogan.