Getting Cut From My Baseball Team Led Me To Build A Blog For "Underdog" Stories

Published: February 22nd, 2022
Tyler O'Shea
Founder, Joker Mag
Joker Mag
from Philadelphia, PA, USA
started November 2017
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Hello! Who are you and what business did you start?

Hello! My name is Tyler O’Shea and I’m the founder of Joker Mag, a media platform for inspiring underdog stories in sports. Through original articles that celebrate the underdog mentality, our mission is to inspire athletes, coaches, and sports fans to conquer obstacles and overcome adversity.

We currently receive an average of 25,000 monthly visitors, which generates roughly $250 per month in revenue. But given the size of the market for this kind of content, I truly believe the sky is the limit.

The name “Joker Mag” comes from the site’s mascot, Joker, who is my family’s bulldog. He was the runt of the litter and my family picked him out after learning that he was the outcast that no one else wanted.

Joker has had a tough journey – overcoming two hip replacements, breathing problems, and various other ailments. Joker is a literal underdog in every sense of the word and represents everything we’re about.

In case you’re still wondering, he got his name from the black spot around his eye that’s reminiscent of the infamous Batman villain!


What's your backstory and how did you come up with the idea?

Getting cut from the baseball team in 7th grade was a turning point in my life. When the coach put the list of names on the board, I scanned it about ten times before realizing mine wasn’t there. I was smaller than the other kids but just needed an opportunity to prove myself.

It would have been easy to give up and move on. But instead, I promised myself I’d prove that coach wrong. 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 for inspiration.

Fast forward 10 years: I finished my senior season at McDaniel College being named Honorable Mention on the All-Conference team. I made it a whole lot farther than anyone ever thought I would. ​​I credit a lot of that success to the stories of those players I looked up to and admired.

After graduating from college, I launched Joker Mag. My mission is to share underdog stories that give people the same feeling I felt when I was that undersized ballplayer searching for hope and inspiration.


Take us through the process of designing your website.

Inspired by my new idea, I shared it with my closest friends and family. While they couldn’t understand what I was looking to build, they provided a lot of encouragement. I knew what I wanted, but I didn’t know where to start.

I connected with a family friend who worked at a design agency, and she offered to build the website pro bono. My only other startup costs were the logo design, hosting, and locking down my domain name.

While the first iteration of the website was being built, I started cranking out stories in Word documents and sending them over to the agency. We needed content on the site before launching to the public – and I was eager to get it going.

Describe the process of launching the website.

Our launch consisted of a single message pushed out on popular social media platforms (Facebook, Twitter, Instagram, and Snapchat).

In the early days, a basic website was all I needed – a place where I could write and publish new content. In the beginning, I published one new story per day for about 6 months straight. I even had a few college friends volunteer to write articles.

We were off to a good start – but at this point, I knew almost nothing about digital marketing and growing an audience online. I learned pretty quickly that friends and family are not your audiences – and they don’t understand (or care) what you’re building. You need to branch out, learn who your target market is, and figure out how to connect with them.


Since launch, what has worked to attract and retain visitors?

I’ve tried almost everything under the sun to grow our readership – Facebook/Instagram ads, podcasts, YouTube videos, newsletter promotions, and more. However, our most reliable growth channel is SEO. I’ve been able to parlay my self-taught skillset into an SEO career in the corporate world.

Funnily enough, the whole SEO thing happened accidentally. One day I was messing around in Google Analytics, and I noticed one of our articles getting way more traffic than the rest. “Where are all these people coming from?” I remember asking myself. Then I discovered there was a traffic source called “organic”, and I stumbled down the rabbit hole.

In the following months, I invested countless hours gathering all the information I could about generating organic traffic. I implemented everything I learned – some tactics worked, others didn’t. Now, my SEO philosophy boils down to: “a search engine friendly website is a user-friendly website”.

Thus, Joker Mag’s SEO strategy is all about nailing the fundamentals:

  • Reverse-engineering competitors’ content success
  • Thorough keyword research
  • Targeting low-competition terms we can rank for
  • Satisfying search intent
  • Creating high-quality, evergreen content that readers love

I’ve also put some effort into growing our Twitter following. This past October, I wrote several short Twitter threads to test out a new growth strategy.

With a small sample size – and different posting times – I saw mixed results. Some worked better than others, but our top-performing thread generated around 254,000 impressions.

While your brand can be unique, the way you distribute content doesn't have to be. You can take bits and pieces of what’s working and do it a little bit better.


Twitter is another growth lever I’d like to continue testing, but SEO takes the cake.

We retain readers through our monthly Underdog Newsletter, which receives new sign-ups every week with little effort.

How are you doing today and what does the future look like?

My #1 focus is on improving website traffic through SEO. This singular focus will increase revenue and generate more growth opportunities going forward.

As it stands today, our monthly traffic falls between 25,000 and 30,000 sessions per month – with a large portion coming through organic search. We currently generate revenue from the following sources:

In the future, I’d like to move into brand partnerships as our primary monetization method. Once our audience is large enough, I believe more brands will want to align themselves with our positive message. Long-term, my goal is to take this from a “niche site” to an established digital media brand.

Through starting the website, have you learned anything particularly helpful or advantageous?

My biggest mistake was splitting my focus and spreading myself too thin. I am pretty much a one-man team, and this is a side project. My time needs to be spent on tasks with asymmetric upside.

In the past, I was using my time to: produce a podcast, line up interviews, create Facebook ads, write a weekly newsletter, edit videos, and more. Now, I strictly focus on improving our SEO. This involves competitor analysis, keyword research, building content briefs, writing, and publishing content.

Whereas my previous tasks were “busy work” without a collective focus, my time is now spent building toward one specific goal.

What platform/tools do you use for your business?

What have been the most influential books, podcasts, or other resources?

Content Inc. by Joe Pulizzi taught me a lot about the how and why behind building a content-centric business. I also recommend checking out Aleyda Solis’ as well as the Ahrefs blog to learn the fundamentals of SEO.

I’ll also shout out Jake and Lim How Wei on Twitter – two sources of wisdom for SEO and blog growth.

Advice for other entrepreneurs who want to get started or are just starting out?

While your brand can be unique, the way you distribute content doesn't have to be. You can take bits and pieces of what’s working and do it a little bit better – format it differently, make it easier to understand, etc. This is how I’ve found success – I’ve taken other people’s (successful) processes and run them through the filter of my brand.

Are you looking to hire for certain positions right now?

I am! I’m currently looking to bring on a freelance writer for a part-time role. If you’re an experienced sports writer, or just have a passion for underdog stories, reach out to me on Twitter.

Where can we go to learn more?

If you have any questions or comments, drop a comment below!

Thank you, Starter Story, for this wonderful opportunity! I’ve been a loyal reader since the beginning, and am excited to share my story to hopefully inspire the next generation of entrepreneurs.

Tyler O'Shea, Founder of Joker Mag
Pat Walls,  Founder of Starter Story
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