Why Tyler O’Shea Invested His Entire Acquisition Budget Into beehiiv Boosts

Situation:

Tyler O’Shea launched Joker Mag in 2017 to tell inspiring underdog stories in sports. As the brand grew, he expanded into The Underdog Newsletter to create a more direct and owned channel with his audience. With 50,000+ monthly pageviews and 14,000+ newsletter subscribers, the newsletter became both a content hub and a traffic funnel for his website.

Challenge:

Early growth via Facebook ads brought in low-quality leads, leading Tyler to clean his list manually. He struggled with cost-effective acquisition that ensured real engagement. With a full-time job and limited bandwidth, he needed a tool that could bring in the right audience without draining resources or time.

Solution:

Tyler migrated to beehiiv for its creator-focused tooling and embraced:

Boosts as his primary acquisition strategy, now his biggest subscriber driver
Segmentation to improve deliverability and personalization
Ad Network to begin monetizing organically through aligned sponsorships
He now uses Boosts to reach highly targeted audiences, resulting in open rates of 57% and CTRs of 15–20%, while also receiving replies from readers that build 1:1 connections.