Pondering Pennies

Pondering Pennies

Two brothers Dempsy and Rae talk about their week and whatever interests them.

Episodes

July 7, 2025 52 mins

In episode 66 of Pondering Pennies Dempsy and Rae face off in another round of who knows who better. However, this time its a fight to see who is the better brother as they try to answer questions about their sister. 

 

Code "PonderingPennies" in the checkout screen at liquid IV or Blend Jet for 20% off all items site wide. 

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In episode 65 of Pondering Pennies Dempsy and Rae see who knows who better!

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In episode 64 of Pondering Pennies Dempsy and Rae discuss work, the musk/trump fall out, protests in LA and the upcoming NFL season. 

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In episode 63 of Pondering Pennies Rae and Dempsy discuss the WNBA and Rae trying his hand as a gym influencer to secure free supplements and clothing.

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In episode 62 of Pondering Pennies return guest and friend Cortes comes on the podcast to discuss the latest political tensions between the United States and Mexico. 

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In episode 61 of the Pondering Pennies Podcast Rae and Dempsy discuss Rae's relationship updates, Dempsy building a fence, and latest pop culture T.V shows. 

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In episode 60 of Pondering Pennies Rae and Dempsy jump back on reddit this time to explore the sub reddit "Am I The Ass Hole".

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In episode 59 of Pondering Pennies Dempsy and Rae talk about what annoys them in episode 3 of Grind my Gears. 

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I episode 58 of Pondering Pennies Rae and Dempsy discuss Rae recent work travel, the Buffalo Bills, and the pain of being forced to attend sibling sporting events from their childhood. 

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March 3, 2025 65 mins

In episode 57 of Pondering Pennies Otto and Dempsy discuss Otto's recent ventures to Italy, the buffalo bills, Robert Kennedy Jr. and the recent Trump, Zelenskyy pres. conference. 

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In episode 56 of Pondering Pennies Dempsy and Rae explore the subreddit Am I Overreacting. After reviewing some of the posts Dempsy and Rae ask themselves "are we the baddies?".

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February 3, 2025 55 mins

In episode 55 of Pondering Pennies Dempsy and Rae speak to Cam. Cam is enrolled for his PHD in Systems Neuroscience.  

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January 20, 2025 61 mins

In episode 54 of Pondering Pennies Dempsy and Rae speak with Chris about his lived experience dealing with anxiety and OCD. After finding success in recovering with alternative therapy options Chris went on to establish his own alternative therapy practice. 

 

Chris's social can be found below:

https://www.pathtoinnerwellness.com/

https://www.instagram.com/pathtoinnerwellness/

https://www.youtube.com/@pathtoinnerwellness

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January 6, 2025 67 mins

In episode 53 of Pondering Pennies Dempsy and Rae speak with Charlie. Charlie is a first time surrogate living in Canada. Charlie is a self described birthmom, parent and soon to be surrogate mother. 

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In Episode 52 of pondering pennies Dempsy and Rae discuss two years of running the podcast, Their discontent with taxes and Rae order himself a new Tesla to kick of 2025. 

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In episode 51 of Pondering Pennies Dempsy and Rae play 1 Truth 2 Lies, Who will win the battle for the ages? Listen to the end to find out!

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In episode 50 of pondering pennies Dempsy and Rae discuss Dempsy's recent string of good luck and Rae ponders purchasing a Tesla Model 3. 

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November 11, 2024 72 mins

In episode 49 of Pondering Pennies Dempsy and Rae speak with Claire. Claire is apart of the Roman Catholic faith attending mass daily in her local community and working toward becoming a Extraordinary Minister of Holy Communion and speaks to Dempsy and Rae about balancing her faith and being a transgender women. 

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October 28, 2024 44 mins

In episode 48 of Pondering Pennies Dempsy speaks with Ashton about being a nudist in Oklahoma. 

 

Ashtons socials can be found at;

https://youtube.com/@justaloadofash?si=FZYTmhG_rXQa8rme 

 

https://www.tiktok.com/@justaloadofash?_t=8qsiN95JuOY&_r=1

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October 14, 2024 91 mins

In Episode 47 of Pondering Pennies Dempsy and Rae talk to Annie. Annie grew up as a third generation cult member. Annie ended up leaving the ministry (cult) in 2010. Annie shares background with us about the cult and some life experiences of grow up in such an organization. 

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