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Basketball

He Bet on Himself

Nov 8, 2026

•

6 min read

He Bet on Himself

How a mix of cockiness & confidence took him further than all 30 teams expected...

Tyler O'Shea
Tyler O'Shea

Football

30 Minutes of Sleep

Nov 1, 2026

•

7 min read

30 Minutes of Sleep

He showed up at a college prospect camp right after a 10-hour overnight shift at an Amazon warehouse. And it changed his life...

Tyler O'Shea
Tyler O'Shea

Football

Meat, Milk, and Spaghetti

Oct 25, 2026

•

6 min read

Meat, Milk, and Spaghetti

He chopped wood, flipped tires, and power-cleaned 100-pound tanks on his way to the league...

Tyler O'Shea
Tyler O'Shea
He Lost His Only Offer

Oct 18, 2026

•

7 min read

He Lost His Only Offer

How a 150-pound college freshman made it to the NFL...

Tyler O'Shea
Tyler O'Shea

Football

He Changed His Stars

Oct 11, 2026

•

7 min read

He Changed His Stars

And made an unlikely position change to make it to the league...

Tyler O'Shea
Tyler O'Shea
He Finds Joy in Pain

Oct 4, 2026

•

7 min read

He Finds Joy in Pain

And "meaning in suffering" while staring down a Stage 4 cancer diagnosis.

Tyler O'Shea
Tyler O'Shea

Football

He Wasn't Invited

Sep 27, 2026

•

8 min read

He Wasn't Invited

But he became a secret weapon anyway...

Tyler O'Shea
Tyler O'Shea
He Lied His Way to the League

Sep 20, 2026

•

9 min read

He Lied His Way to the League

A little white lie changed the course of his life...

Tyler O'Shea
Tyler O'Shea

Football

He Emailed His Way to MVP

Sep 13, 2026

•

8 min read

He Emailed His Way to MVP

He sent 1,000 emails hoping for just one yes...

Tyler O'Shea
Tyler O'Shea
One Leg, Zero Limits

Sep 6, 2026

•

7 min read

One Leg, Zero Limits

His secret? Keeping his "head in the clouds"

Tyler O'Shea
Tyler O'Shea

Baseball

He Was "Terrible"

Aug 30, 2026

•

9 min read

He Was "Terrible"

He "couldn't play." But he made it happen anyway...

Tyler O'Shea
Tyler O'Shea

Baseball

He Signed for $1

Aug 23, 2026

•

9 min read

He Signed for $1

Meet the real-life (baseball) version of The Waterboy...

Tyler O'Shea
Tyler O'Shea
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The Underdog Newsletter

The Underdog Newsletter

The best sports stories you've never heard & powerful lessons from underdogs beating the odds.

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