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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Most people would’ve written me off.
I had a 1.6 GPA.
But underdogs don’t break — we build.
In this debut episode of The Underdog Standard, Andrew Owlett shares the raw, unfiltered story of how he went from being a 1.6 GPA kid to a first responder, to a Fortune 5 leader, to the CEO of multiple companies in real estate, luxury hospitality, and AI.
This episode is more than a story — it’s a blueprint for anyone who has ever been underestimated, overlooked, counted out, or told to "be realistic."
Andrew breaks down:
1) The 1.6 GPA that almost defined him
2) How firefighting became the foundation for elite leadership
3) The move into Fortune 5 and learning to operate under pressure
4) How real estate, hospitality, and tech unlocked true scale
5) The Underdog Standard Framework (Pressure → Systems → Resilience)
6) How underdogs can outperform pedigree every time
This episode reveals how resilience becomes wealth, how pressure becomes training, and how systems become leverage. If you’re reinventing your life, pivoting careers, stepping into leadership, or building something bigger than where you came from — this is your roadmap.
DM Andrew the word STANDARD for a private resource: The Underdog Playbook.
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