Championing Underdog Stories in Sports

Welcome! Today we delve into the inspiring journey of Tyler O'Shea, the creative mind behind The Underdog Newsletter. Tyler's passion for sports and underdog stories has captivated over 11,000 subscribers, offering weekly doses of motivation and resilience through his unique storytelling.

👋 Meet Tyler: The Underdog Advocate

Tyler O'Shea's journey began with his own underdog story. As a former undersized baseball player, Tyler found inspiration in the tales of sports underdogs like Tim Lincecum, which ultimately led him to create The Underdog Newsletter. This weekly email, dedicated to inspiring sports stories, has grown from a personal passion project into a beacon of hope for many.

💡 The Genesis of The Underdog Newsletter

Launched on November 21st, 2017, The Underdog Newsletter has its roots in Tyler's personal experiences and his desire to share the powerful stories of sports underdogs. With over 50,000 monthly pageviews on its parent website, JokerMag.com, the newsletter reaches out to a growing audience every Sunday, sharing tales of triumph against the odds.

🧭 Mission and Vision

Tyler's mission is simple yet profound – to inspire and show the possibilities in the face of adversity through storytelling. The newsletter targets sports enthusiasts, students, athletes, and coaches, weaving narratives that resonate deeply with their experiences and aspirations.

♟️ Content Strategy and Engagement

Tyler's writing process is meticulous and driven by his deep passion. Depending on the sport the season is in, he carefully selects underdog stories from a rich collection of over 400 narratives he’s come across, ensuring each edition is both timely and timeless. His research-intensive approach involves delving into various sources to bring each story to life, aiming to leave a lasting impact on his readers.

From ideation to editing, it takes him at least 5 hours to write a single edition, which only speaks on the high standard he has for the quality of the product he sends out to his subscribers each week.

📈 Growth and Milestones

Tyler's journey from 0 to over 11,000 subscribers is a story of persistence and innovative strategies. Initially relying on organic growth, he later embraced paid advertising, particularly Facebook Ads, to widen his audience reach. This approach, coupled with a strong online presence, has been pivotal in the newsletter's growth.

The initial climb to 1,000 subscribers was a very slow, organic process, fueled by consistent publishing, social media engagement, and personal outreach.

Transitioning from 1,000 to 10,000 subscribers marked a shift in momentum, achieved from February to December of 2023 through a combination of cold outreaches to Twitter and LinkedIn followers and paid advertising. Particularly Facebook Ads, where he developed a following of over 12,000, after iterating and finding what type of content worked for him on that platform.

💰 Monetization

Tyler is in the process of diversifying the newsletter's revenue streams. He plans to incorporate a mix of:

•  🤝 Sponsorships

• 🧲 Affiliate marketing

• 🖥️ Display ads

• 🧢 Branded merchandise

Without a formal sales background, he relies on learning through action, gathering leads via Twitter shares and cold outreach. His vision is to create lasting partnerships with sponsors who are keen to grow alongside the newsletter.

Tyler is laser-focused on building and deepening the bond with his newsletter audience. It's about laying down a strong, trust-filled foundation today to support the big dreams he has for tomorrow. He's looking forward to evolving his brand into something even more impactful, with a community that's in for the ride.

⚙️ Behind the Scenes – Operational Insights

Despite assistance from freelance contributors, Tyler maintains a hands-on approach to ensure the quality of his content. His focus on quality over quantity, combined with a keen eye for effective storytelling, forms the backbone of The Underdog Newsletter.

To cultivate trust and engagement, he places immense value on the welcome email, envisioning it as the start of a meaningful relationship with subscribers. He believes in delivering substantial value immediately, rather than requesting further actions like asking for clicks or replies.

Tyler also perceives the proliferation of AI-generated content as an opportunity to highlight any newsletter's authentic, emotionally resonant stories that resonate with readers on a personal level.

📝 Founder’s Advice

Tyler emphasizes the importance of perseverance and authenticity in the newsletter journey. His advice for fellow newsletter creators is to stay true to their vision and be patient.

He cautions against taking every influencer's advice as the absolute truth and instead advocates for personal experimentation. This story is a testament to the power of resilience and the impact of genuine, human-centric storytelling in the digital age.

✌️ Goodbye

The Underdog Newsletter is more than just a weekly email; it's a source of inspiration and a testament to the human spirit. His dedication to sharing underdog stories in sports not only entertains but also motivates his audience, proving that with determination and passion, any challenge can be overcome. It was a pleasure learning about his story.

You can find him on Twitter where he’ll be happy to connect with anyone looking to share insights.