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.

Results:

• Acquired 2,000+ subscribers via Boosts alone
• Achieved 57% open rates and 15–20% CTR from Boost-acquired leads
• Turned beehiiv into his main growth and monetization engine
• Tyler's beehiiv website ranks #1 on Google search