#187: Listen to This When You’re Feeling Like an Underdog

Welcome back to Good People, Cool Things! Bananas to think we're kicking off the SEVENTH season of this show. We're starting this season off in style with a true underdog story — or, more accurately, many underdog stories!

After being cut from his 7th-grade baseball team, Tyler O’Shea has always found inspiration in athletes who have succeeded against the odds. That drive led to both a collegiate career on the diamond and the founding of Joker Mag, a digital media platform dedicated to inspiring underdog stories in sports.

We’re chatting about how niching down has helped Tyler grow Joker Mag, why he’s found tremendous value in hearing from his audience, and his favorite recent underdog stories.

Special shout-out to One Hit No Wonder for supporting the show! If you dig this podcast, you'll enjoy that one, too.

Highlights of the conversation

  • Tyler’s origin story for creating a media brand about underdog sports, which started when he was just 13 years old. (2:50)

  • How niching down has helped Joker Mag’s traffic and why there’s still more to go. (4:58)

  • Stories that have surprised Tyler and why his audience is a great source of inspiration for future content. (7:35) 

  • Some growth tactics that have helped grow the brand and some that haven’t panned out as well. (10:25)

  • A surprising look at heights and weights of the athletes in different sports, particularly the Premier League. (13:13)

  • What Tyler has learned about SEO and how he’s navigated Google’s Helpful Content Update. (17:46)

  • A look inside Tyler’s newsletter content creation process. (23:47)

  • A bold sports prediction from Tyler — it didn’t pan out, but I still liked it! (27:34)

  • Tyler’s top three recent underdog stories. (28:42)

Where to find Joker Mag

Visit Joker Mag to learn more and sign up for the Underdog Newsletter.

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#188: Listen to This While You Hiss Your Sibilants

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#186: Listen to This While Doing Something That Brings You Joy