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Hanging with Humans Podcast | Episode 26 | Jason Wheeler
Episode 26: "Modern day Robin Hood"
Jason Wheeler, (A fresh) 47
San Bernardino, Ca
Green River, Ut
Denver, Co
It all started with a missed flight and a lost wallet that brought me to meet the the professional gambler Jason Wheeler.
On an unexpected cross-country bus journey. What began as small talk between strangers quickly revealed an extraordinary connection—both of us were traveling to Los Angeles to visit our sisters, and go with them to watch Kendrick Lamar & SZA perform.
This chance meeting blossoms into a compelling two-part conversation spanning Utah to Denver, where Jason unveils his remarkable life story.
From his early days in Indianapolis' tough Haughville neighborhood, Jason reveals how he launched his first hustle in fourth grade. By seventh grade, he'd graduated to selling marijuana in Catholic school, leading to his first arrest.
Though basketball scholarships offered legitimate opportunities, Jason candidly admits, "I'm going to school for all the wrong reasons... I'm more about the hustle." While attending four different colleges and playing alongside future NBA stars, Jason continued building his enterprise.
After finding success as a mortgage broker until Obama-era regulations changed the industry, Jason entered what he calls the "scam game" operation that generated $10-15K daily.
At 40, Jason served his first prison sentence during COVID, where entrepreneurship continued with a lucrative K2 smuggling operation.
Now at 47, he's transformed his life with over 40 Airbnb properties and a powerful perspective: "I'm grateful for all the mishaps that I've had in my life. It kind of made me the person that I am."
The whole situation was an example of “everything happens for a reason.” Even if it was extremely stressful in the moments prior, I ended up making a friend and capturing a conversation with an authentic raw spirit of a human
Can’t wait to finish up the part 3 of the podcast when I link with him in Fl or Atl. But either way, I’m glad to have met you Jason, thank you for your time and your generosity. And thanks for keeping it a buck. 💯
Shout out to Quality Control Music.
https://www.instagram.com/jason.wheeler.297?igsh=a3A4bjAzMmlmdHdj
H.w.h.p. - Bringing authentic conversations that reveal the extraordinary journeys of people walking among us everyday.
Send us a text
Support the show
Contact & Info:
www.hangingwithhumans.com
https://poplme.co/hash/P5oM9JFj/1/dash
Support the Podcast:
https://gofund.me/2a99e9b7
Video Podcast :
https://www.YouTube.com/@hangingwithhumans
https://rumble.com/c/c-2507620
Social Media:
https://www.instagram.com/hangingwithhumans
https://www.tiktok.com/@hangingwithhumans
Thank you so much for taking the time out of your important life to listen, It means the world to me.
#HangingWithHumans #Podcast #HWHP
In honor of those who served our country. During times of peace and war. Those who gave the supreme sacrifice, Those still missing and those who came home both whole and broken.
In honor of those still fighting everyday to keep their head above water.
View all episodes
By H.W.H.P.Episode 26: "Modern day Robin Hood"
Jason Wheeler, (A fresh) 47
San Bernardino, Ca
Green River, Ut
Denver, Co
It all started with a missed flight and a lost wallet that brought me to meet the the professional gambler Jason Wheeler.
On an unexpected cross-country bus journey. What began as small talk between strangers quickly revealed an extraordinary connection—both of us were traveling to Los Angeles to visit our sisters, and go with them to watch Kendrick Lamar & SZA perform.
This chance meeting blossoms into a compelling two-part conversation spanning Utah to Denver, where Jason unveils his remarkable life story.
From his early days in Indianapolis' tough Haughville neighborhood, Jason reveals how he launched his first hustle in fourth grade. By seventh grade, he'd graduated to selling marijuana in Catholic school, leading to his first arrest.
Though basketball scholarships offered legitimate opportunities, Jason candidly admits, "I'm going to school for all the wrong reasons... I'm more about the hustle." While attending four different colleges and playing alongside future NBA stars, Jason continued building his enterprise.
After finding success as a mortgage broker until Obama-era regulations changed the industry, Jason entered what he calls the "scam game" operation that generated $10-15K daily.
At 40, Jason served his first prison sentence during COVID, where entrepreneurship continued with a lucrative K2 smuggling operation.
Now at 47, he's transformed his life with over 40 Airbnb properties and a powerful perspective: "I'm grateful for all the mishaps that I've had in my life. It kind of made me the person that I am."
The whole situation was an example of “everything happens for a reason.” Even if it was extremely stressful in the moments prior, I ended up making a friend and capturing a conversation with an authentic raw spirit of a human
Can’t wait to finish up the part 3 of the podcast when I link with him in Fl or Atl. But either way, I’m glad to have met you Jason, thank you for your time and your generosity. And thanks for keeping it a buck. 💯
Shout out to Quality Control Music.
https://www.instagram.com/jason.wheeler.297?igsh=a3A4bjAzMmlmdHdj
H.w.h.p. - Bringing authentic conversations that reveal the extraordinary journeys of people walking among us everyday.
Send us a text
Support the show
Contact & Info:
www.hangingwithhumans.com
https://poplme.co/hash/P5oM9JFj/1/dash
Support the Podcast:
https://gofund.me/2a99e9b7
Video Podcast :
https://www.YouTube.com/@hangingwithhumans
https://rumble.com/c/c-2507620
Social Media:
https://www.instagram.com/hangingwithhumans
https://www.tiktok.com/@hangingwithhumans
Thank you so much for taking the time out of your important life to listen, It means the world to me.
#HangingWithHumans #Podcast #HWHP
In honor of those who served our country. During times of peace and war. Those who gave the supreme sacrifice, Those still missing and those who came home both whole and broken.
In honor of those still fighting everyday to keep their head above water.