How Tyler O’Shea Fixed His Deliverability and 2X’d His Open Rates

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