Facts

Who: Tyler O'Shea
What: Founder of Joker Mag – a media brand for underdog stories in sports
Format: Content & media · United States, English
Started: November 2017
Audience: 74,000 followers combined across all Joker Mag social channels
Promotion budget: More than $100/month
Income: Side income – grown from a few hundred dollars a month to now covering rent and utilities
Status: Active and growing
Channels: Search & AI traffic, text social media, offline & word of mouth, video platforms, own newsletter

The short version

What worked: Years of self-taught SEO built the foundation, but the real recent jump came from short-form video – daily posting for a month, with a handful of videos (including one about an NFL GM's career) driving most of the new followers and views.
The result: 45,000–70,000+ monthly pageviews depending on the sports season (peak: 82,302 in October 2025), 74,000 combined social followers, and enough revenue now to cover rent and utilities.
The catch: A 50+ episode podcast (2018–2020), built around guests he genuinely admired, turned into a huge time sink that never paid off – he eventually cut it.

Background

I got cut from the baseball team in 7th grade. The coach thought I was “too small.” Later that day, I made a promise to myself that I wouldn't quit. Instead, I found inspiration in the stories of undersized athletes who defied the odds – players like David Eckstein, Dustin Pedroia, and Tim Lincecum.

I read every story I could find, searching for inspiration and evidence that my dream was possible. I quickly found out about all the adversity those guys faced to get where they are today. Getting cut from the school team was just a small bump in the road. I discovered that I could use this 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 nation's oldest semi-professional baseball league. 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.

Starting point

My first 10 followers came from my own family (mainly my grandfather and my parents) and a few friends and college teammates. I was fresh out of college, and a few of those buddies ended up volunteering to write for me in those early days.

My first 100 followers came through SEO, which I stumbled into by accident. I checked Google Analytics one day and saw traffic coming from “organic search.” That led me down a rabbit hole of learning as much as I could about SEO and, eventually, growing the site to roughly 70,000 monthly pageviews mainly off the back of Google Search.

What worked

2017: Word of mouth, family, and friends. Trying to publish one article per day.

2018: First few hundred strangers visit the site from organic search (primarily Google).

2019: Learn as much as possible about SEO and start building search traffic.

2020–2025: More of the same. Eventually grow to 70K monthly pageviews through SEO and get accepted into an exclusive display ad network. Begin building an email newsletter and experimenting with social media.

March 2025: I publish my first book, The Underdog Mentality: Sports Stories That Will Change How You See the Game (and Yourself). It hits the top-10 in two Amazon Best Seller categories, surging past authors like Tom Brady, Bill Belichick, and Deion Sanders.

September 2025: I have an epiphany. Google is changing the SEO game faster than ever. There's still opportunity, but words on a page aren't enough to grow my brand anymore. I need to distribute my underdog stories in other ways. Go where my audience is. Let me test out short-form video in the simplest way I know how: talking to my camera. If it doesn't work, who cares? I'll figure out something else.

October 2025: I start posting short-form videos daily. A handful go crazy and drive most of the growth. I experience rapid social media growth through short-form storytelling videos, primarily on Instagram, Facebook, TikTok, and YouTube. Instagram grows from 1,463 followers to 19,100 followers in 30 days. TikTok grows from 110 followers to 1,945 followers. Tons of comments, DMs, and followers (including a few celebrities). Wow, this is fun. Where else can you get this many eyeballs in such a short time frame?

Present day: Still doubling down on cross-channel growth, with a focus on short-form video on social media. Website traffic is only down 7% year-over-year, but I've grown exponentially across socials, which has unlocked multiple new meaningful revenue sources, including: Facebook Content Monetization, YouTube Partner Program (AdSense for YouTube), brand sponsorships, organic book sales, and more.

What didn’t work

I started a podcast in 2018 and did 50+ episodes through spring of 2020. I met some amazing people and interviewed a childhood hero of mine (Jim “The Rookie” Morris), but it turned out to be a huge time sink. There was a massive time investment in sourcing guests, researching, prepping for interviews, conducting interviews, editing each episode, and promoting each episode. The payoff just didn't justify the effort. That said, once we are more established – and the effort makes sense from a business standpoint – I'd love to get back into interviewing guests in some capacity.

I never wanted to quit, as I've always felt that this is my life's work. My whole early life and baseball career led me to this stage of telling these underdog stories to inspire as many people as possible around the world.

That being said, I've had a ton of people express doubt – whether to my face, behind my back, or as anonymous commenters on my website. Joker Mag has been called some variation of a “silly little hobby” for almost a decade now. The revenue and, more importantly, the impact, beg to differ. I've gotten thousands of emails and hundreds of thousands of social media comments that share how much a specific story meant to someone, or impacted their lives in a positive way. One heartfelt comment means more to me than any dollar amount I've earned from this endeavor. The impact is what matters most, and it's what has kept me going in the face of failure and doubt.

The turning point

Pre-2020: Seeing that first visitor from Organic Search made the biggest impact over the next 5–6 years. It helped me establish a foundation, develop an initial audience, and build our first scalable revenue source (programmatic display ads).

Present day: That first short-form video that took off on social media (I believe it was about Howie Roseman's journey to becoming an NFL GM, which I posted in late September or early October of 2025) made me realize the growth that is possible outside of SEO. Yes, all algorithms are unpredictable and, many times, frustrating. But they can also be so incredibly rewarding. I've made the conscious decision to focus on algorithms that have the greatest upside in our present landscape. One well-optimized website article can bring me 5,000 new visitors per month, while one 60-second Instagram Reel can put me in front of 500,000+ new people overnight. SEO is limited by existing market demand. Email is limited by your existing subscriber base. Social media is only limited by your ability to push through the duds until you hit on a gem (and rinse and repeat). At least that's how I see it.

Audience

Most of my audience consists of US-based sports fans. More specifically, men who love watching Major League Baseball and/or the National Football League.

But in reality, I'm sharing these stories to inspire anyone going through a personal struggle in their own life. I try to tell the stories in a way that welcomes both non-sports fans, casual fans, and die-hards. There is a story for everyone. I pride myself on deep research, because you never know what specific detail of a story will resonate with someone.

Looking ahead

Revenue is up 56% in the first half of 2026 year-over-year. Our social following has exploded, up 173%, which tells me there is still a lot of revenue upside to capture. The more followers, views, and email subscribers we gain, the more interest we seem to get from potential sponsors. I've also received more inbound acquisition interest than ever, and as of today, our market value has doubled in the last 6 months alone.

What will work is consistently doubling down on building up our library of stories, repurposing them across platforms, and recycling them over time to grow our audience. The Morning Brew guys coined the “write, grow, sell” methodology, and I'm following that in my own way.

Practical takeaways

  • Track which channel is actually driving growth right now, and be ready to shift when its marginal return drops – SEO built the foundation for years, then short-form video reignited growth almost overnight.

  • A project can be personally meaningful and still not be worth the time – his podcast connected him with a childhood hero but never paid off, and he eventually cut it.

  • Years of consistent, unglamorous output (publishing new stories every week) made the later opportunities – sponsorships, a self-published book, a viral video – possible in the first place.

Tyler’s pitch

Joker Mag is your home for the best underdog stories in sports.

Website: jokermag.com
X (Twitter): OSheaSEO
Newsletter: newsletter.jokermag.com

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– Alex, tinyfound

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