We recently connected with Tyler O’Shea and have shared our conversation below.
Tyler, so good to have you with us today. We’ve always been impressed with folks who have a very clear sense of purpose and so maybe we can jump right in and talk about how you found your purpose?
In 7th grade, I got cut from the school baseball team.
It sounds like a little thing now, but back then, it was devastating. I still remember standing in that locker room, scanning the list of names ten times before realizing mine wasn’t there.
As the other kids high-fived and congratulated each other, I slipped out the side door.
With tears in my eyes, I walked down the hallway, staring at the lockers and wondering what just happened. I pulled out my cell phone and called my dad to pick me up.
To this day, my dad still talks about pulling up to the front of the school to find me sitting by myself, with a distressed look on my face.
I didn’t realize it then, but this pivotal moment led me to my life’s purpose.
The coach didn’t think I was good enough – even just to wear the team jersey and sit on the bench.
But the truth is, I was smaller than everyone else on the field.
The bat was too heavy for me, and I had to take a crow hop from shortstop to make the throw to first base.
With that reality, it would have been easy for me to give up on baseball for good. But on that day, something clicked inside of me.
Instead of quitting, I promised myself I’d prove that coach wrong. And everyone else who ever doubted me.
I started looking up to undersized athletes who defied the odds. Guys like David Eckstein, Tim Lincecum, and Dustin Pedroia.
I read every story I could find, searching the deepest corners of the internet for inspiration – evidence that my dream was possible.
After hours of staring at the desktop computer screen, I uncovered all the adversity those guys faced to get where they are today.
In the grand scheme of things, getting cut from the school team was just a tiny bump in the road.
I discovered that I could use this small setback to my advantage.
Fast forward 10 years.
I finished my senior season at McDaniel College being named Honorable Mention on the All-Conference team. The following summer, I was voted MVP of the Delco League – the oldest semi-professional baseball league in the nation.
I made it a whole lot further than anyone ever thought I would.
In addition to my family – who supported me in every way possible – I credit a lot of that success to the stories of those players I looked up to.
The underdogs who beat the odds.
They carved out a path for me to follow and provided inspiration that kept me going.
So after college, I launched Joker Mag – a media brand dedicated to inspiring underdog stories in sports.
As more people started reading the website, I grew a small following on social media and built a loyal subscriber base on my Underdog Newsletter.
And in March of 2025, I published my first book, The Underdog Mentality: Sports Stories That Will Change How You See the Game (and Yourself).
The early rave reviews proved something I’ve believed since I was a kid – these stories matter.
We all need a little extra fuel to push forward when the odds are against us.
At the end of the day, my mission is simple: To share underdog stories that give people the same feeling I felt when I was that undersized ballplayer searching for hope, inspiration, and proof that my dream was possible.
Like my mom always told me, you can do anything you set your mind to. Sometimes, we just need a little extra push.
And that’s why I’m so passionate about sharing these stories with the world. It’s my life’s purpose to inspire others.
Let’s take a small detour – maybe you can share a bit about yourself before we dive back into some of the other questions we had for you?
I’m the founder of Joker Mag, a digital media brand dedicated to the best underdog stories in sports.
It all started with my own journey – getting cut from my middle school baseball team, feeling like I wasn’t good enough, and searching for inspiration from pro athletes who beat the odds.
Their stories fueled me to keep pushing forward, and I eventually played college baseball, where I finished my senior year being named an honorable mention on the All-Conference team.
After graduation, I realized that the mainstream sports media overlooks a lot of the same kinds of stories that inspired me as a young athlete. That’s why I launched Joker Mag: to create a home for the best sports stories you’ve never heard and inspire people to chase their own dreams.
Today, my work reaches thousands of readers through The Underdog Newsletter, a free weekly email highlighting the most inspiring stories in sports.
Recently, I took the next step by publishing my first book, The Underdog Mentality: Sports Stories That Will Change How You See the Game (and Yourself). In its first few days, it cracked the top 10 in two Amazon Best Seller categories, ranking ahead of books written by Tom Brady, Bill Belichick, and Deion Sanders.
What excites me most is growing Joker Mag into a sustainable media company, amplifying even more incredible stories, and building a tight-knit community of readers who believe in the power of The Underdog Mentality.
I’m always looking for new ways to scale the brand, collaborate with like-minded people, and continue growing our community of readers.
If you had to pick three qualities that are most important to develop, which three would you say matter most?
Looking back on growing my media brand, the three most important qualities have been passion, consistency, and grit. In my experience, if you’re missing one, you will have a hard time finding success.
You need to have a passion for whatever you’re building because, without it, you’ll lose the excitement. If it’s not fun for you, then you won’t stay consistent.
You need to be consistent because nothing worth having is built overnight. Building a media business is not like building a house – it’s like building a skyscraper. It takes years of laying the foundation, forming the structure, and grinding through the unglamorous work that no one sees.
You need grit to stay consistent through all of the inevitable ups and downs that will come your way. Growth is never linear, no matter what social media influencers say. There are always lull periods and times when you’ll feel like giving up. You need the tenacity to stick with it and keep plowing forward, no matter what obstacles are in your way.
As one of my role models, Arnold Schwarzenegger, once said, “There is no such thing as overnight success. The joy is in the doing.”
Thanks so much for sharing all these insights with us today. Before we go, is there a book that’s played in important role in your development?
There have been a few, but the one that sticks out the most is “The ONE Thing: The Surprisingly Simple Truth About Extraordinary Results” by Gary Keller.
For years, I split my focus across multiple ideas and the latest trending business ideas on Twitter. It was a mistake that cost me years of progress.
But after reading “The ONE Thing”, I decided to zero in on what I believe is my true purpose: sharing underdog stories that inspire others.
Since narrowing my focus on my “one thing” and attacking it consistently, I’ve made incredible progress. My website traffic has grown from a few hundred pageviews to over 50,000 pageviews per month. My newsletter has grown to over 21,000 subscribers, and I just published my first book, which peaked in the top 10 on two different Amazon Best Seller lists.
Had I kept splitting my focus between multiple ideas, I never would’ve accomplished any of these things.
Contact Info:
- Website: https://jokermag.com/
- Instagram: https://www.instagram.com/jokermaghq/
- Facebook: https://www.facebook.com/JokerMag
- Linkedin: https://www.linkedin.com/in/tylersoshea/
- Twitter: https://x.com/OSheaSEO
so if you or someone you know deserves recognition please let us know here.
