This Past Weekend w/ Theo Von

#630 - Stephen Wilson Jr.

December 23, 2025

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  • Stephen Wilson Jr.'s career and perspective are deeply influenced by the sacrifices and legacy of his single father, a former boxer who prioritized fatherhood over his professional boxing dreams. 
  • The conversation explored the profound, often painful, process of grieving a parent, with Wilson Jr. noting that his father's final request to 'write a good song for me' catalyzed his current music career. 
  • Wilson Jr. shared vivid memories of growing up in Southern Indiana, detailing the cultural collision between the Midwest and the South, and his experiences in a highly religious environment that included witnessing dramatic spiritual events like exorcisms. 
  • Songwriting and stand-up comedy are viewed as the last bastions of authentic, passed-down storytelling in a culture increasingly lacking in genuine creativity. 
  • Stephen Wilson Jr. applies a scientific methodology, treating songwriting as research to detect truth and minimize personal bias when processing deep emotions like grief over his father's passing. 
  • Childhood experiences of fear, loss, and the need to maintain internal balance (like obsessive counting or quiet observation) significantly shape adult perspectives and creative processes. 
  • Stephen Wilson Jr. is focusing on improving his health and establishing a more consistent routine after feeling burned out from touring, which includes returning to MMA training. 
  • The conversation explored the concept that fear often stems from a lack of understanding, illustrated by Stephen Wilson Jr.'s childhood experience of overcoming fear while deer hunting in the dark. 
  • Stephen Wilson Jr. shared that his father's example taught him that being a good stepfather is demonstrated through consistent actions rather than spoken affirmations, a lesson he applies to his relationship with his stepson. 

Segments

ShipStation Advertisement Read
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(00:00:00)
  • Key Takeaway: ShipStation centralizes shipping tasks and offers rate browsing to find discounts up to 90% across over 200 carriers.
  • Summary: Small business owners require incredible drive to see their ventures thrive through incremental growth. ShipStation provides a centralized platform to manage shipping tasks efficiently. Its rate browser automatically secures the best shipping rates with discounts reaching up to 90%.
Introducing Stephen Wilson Jr.
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(00:01:13)
  • Key Takeaway: Stephen Wilson Jr., a musician from Southern Indiana, was nominated for CMA New Artist of the Year and has a new single, ‘Gary,’ out now.
  • Summary: Stephen Wilson Jr. is a musician and songwriter originating from Southern Indiana. He recently received a nomination for ‘New Artist of the Year’ at the CMAs. His current projects include the single ‘Gary’ and a sold-out spring tour.
CMA Nomination Reflection
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(00:02:23)
  • Key Takeaway: Being nominated for CMA New Artist of the Year was a significant, unexpected win for Wilson Jr. because his career path contradicted typical industry expectations.
  • Summary: Wilson Jr. was nominated for New Artist of the Year at the CMAs, an honor he did not expect to win. He felt that being nominated was a huge victory because, on paper, his journey contradicted industry norms. He was genuinely rooting for the other nominees, including Zach Top One.
Country Music Identity and Upbringing
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(00:03:24)
  • Key Takeaway: Wilson Jr. identifies as country due to his cultural upbringing in Southern Indiana, which involved listening to country and classic rock, and hunting/eating wild game for survival.
  • Summary: Wilson Jr. firmly identifies as country based on his culture and upbringing in Southern Indiana. His listening pedigree consisted of classic rock and country music, often heard in body shops. His family lived a very agrarian lifestyle, often hunting squirrels and rabbits as a cost-effective means of survival.
Father’s Legacy and Sacrifice
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(00:04:29)
  • Key Takeaway: Stephen Wilson Jr.’s father was a single parent, a Golden Gloves boxer, who balanced working multiple jobs with raising three children, even performing traditionally feminine tasks like curling his daughter’s hair.
  • Summary: The guest shared a photo of his father, Stephen Wilson Sr., who was a successful amateur boxer while raising three children alone. The father worked as a bus driver and in a body shop while training to be a professional boxer. Wilson Jr. recalls distinct memories of his father performing feminine care tasks for his younger sister despite having swollen eyes from sparring.
The Naming of Stephen Wilson Jr.
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(00:07:51)
  • Key Takeaway: Stephen Wilson Jr. was named after Stephen, the first Christian martyr, who was stoned to death, a fact Wilson Jr. humorously linked to his father’s potential state of mind at his birth.
  • Summary: The guest’s father was named after Stephen, the first Christian martyr, who was stoned for his faith. Saul (later Paul) oversaw the execution because he viewed Stephen’s preaching as blasphemous under the Jewish law at the time. Wilson Jr. noted that his father’s name choice might reflect a certain state of mind when he was born.
Religious Upbringing and Bible Study
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(00:11:37)
  • Key Takeaway: Wilson Jr. grew up in a Pentecostal Nazarene church environment, which involved ‘Holy Rolling,’ and he recently began attending a Bible study to learn more about biblical characters.
  • Summary: Wilson Jr. grew up in a religious environment characterized by Pentecostal Nazarene traditions and ‘Holy Rolling.’ He has recently started attending a Bible study for the first time to learn more about biblical stories. This background informs his discussions, such as the story of Stephen and Saul.
Midwest/South Cultural Collision
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(00:12:07)
  • Key Takeaway: Southern Indiana, where Wilson Jr. is from, is a cultural collision point where Southern accents and NASCAR viewing mix with Midwestern habits like putting noodles in chili.
  • Summary: The region of Southern Indiana is described as the place where the Midwest and South ‘chest bump.’ This results in a unique culture where people exhibit Southern traits but also adopt Midwestern culinary habits, such as adding noodles to chili. This area is identified as Jackson County, Indiana.
Apostolic Christian Church Memories
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(00:12:56)
  • Key Takeaway: Wilson Jr. recalls visiting an Apostolic Christian Church where community meals valued dessert highly, and women wore distinct, highly braided hairstyles.
  • Summary: Wilson Jr. visited an Apostolic Christian Church with his grandparents in Southern Illinois, noting the culture valued hard work and communal meals. Attendees felt shame if they could not finish the elaborate desserts made by skilled cooks. The women in this church culture typically wore their hair in one large braid and were very covered up.
Witnessing Exorcisms and Slain in the Spirit
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(00:14:34)
  • Key Takeaway: Wilson Jr. witnessed traveling evangelists cause people to be ‘slain in the spirit’ at his church, noting that while some theatrics were present, he believed some instances were genuinely real.
  • Summary: Wilson Jr. saw traveling evangelists hold revivals where people would be ‘slain in the spirit’ by being physically struck and falling down. He believes that while theatrics existed, God did show up in those moments, contrasting with his own experience of being tapped on the forehead without falling. He also recalled seeing grown men have demons cast out of them before lunch.
The Walk of Shame at Church
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(00:20:16)
  • Key Takeaway: After failing to be ‘slain in the spirit’ when an evangelist struck him, Wilson Jr. experienced a ‘walk of shame’ over the bodies of others who had fallen.
  • Summary: When the evangelist failed to make Wilson Jr. fall, he moved on, leaving Wilson Jr. standing while others lay ‘slain’ on the floor. Wilson Jr. had to walk over the bodies, which he described as the most shameful walk he has ever taken at church. Modesty cloths were used to cover women who fell, sometimes resembling actual window curtains with curtain rods still attached.
Childhood Peeping Tom Tendencies
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(00:23:04)
  • Key Takeaway: Due to a difficult home environment, a young Wilson Jr. developed a habit of watching neighbors through windows, seeking to absorb how other people lived normally.
  • Summary: As a child, Wilson Jr. was visually stimulated and used a step stool to watch people in their homes, sometimes asking for a ladder for Christmas for this purpose. He clarifies that he was not always looking for perverse things but enjoyed observing normal domestic life, as his own home environment was often aggressive and defensive. This behavior is framed as an early form of people-watching, which is common among future comedians and songwriters.
Father’s Sudden Death and Final Call
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(00:29:53)
  • Key Takeaway: Stephen Wilson Jr.’s father died suddenly from a pulmonary embolism at age 59, and Wilson Jr. said his final goodbye to him over the phone on the side of I-65 in Kentucky.
  • Summary: Stephen Wilson Sr. passed away seven years prior at 59 due to a pulmonary embolism, following a short period of declining health. Wilson Jr. received a panicked call and spoke to his father during the emergency room crisis while pulled over on I-65 in Kentucky to maintain cell signal. His father calmly told him, ‘I’m going, Stephen,’ and asked him to ‘write a good song for me’ before saying ‘I love you’ four times.
Catalyst for Music Career
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(00:36:31)
  • Key Takeaway: The final conversation with his father served as the catalyst for Wilson Jr.’s entire music career, providing the jet fuel to fulfill his father’s dying wish.
  • Summary: Wilson Jr. views the final conversation with his father as the catalyst for his career, providing the motivation to keep his father ‘alive’ through his music. He realized that fulfilling this wish also helped resurrect the memory of loved ones for other grieving audience members. The mission statement became keeping his dad alive by channeling that grief into his songs.
The Significance of ‘Stand By Me’
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(00:38:45)
  • Key Takeaway: Two weeks after his father’s death, Wilson Jr. played his arrangement of ‘Stand By Me’ at a festival in Deadwood, South Dakota, which was a pivotal moment where he felt his father’s presence and embraced his identity as an artist.
  • Summary: Wilson Jr. had been singing ‘Stand By Me’ privately for a year prior, haunted by its use in the Stephen King movie adaptation, ‘The Body.’ When he played it at the festival, he felt his father on his shoulders, confirming his path as an artist. This song, which his father had previously called his favorite, became central to his grieving process.
Father’s Favorite Song: ‘I’m a Song’
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(00:44:35)
  • Key Takeaway: Stephen Wilson Sr.’s favorite song written by his son was ‘I’m a Song,’ which he listened to repeatedly on his large T-Mobile Sidekick phone after Wilson Jr. played it at the Bluebird Cafe.
  • Summary: Wilson Sr. specifically told his son that ‘I’m a Song’ was his favorite song, recalling it from a performance at the Bluebird Cafe a month prior. Wilson Jr. was surprised because he wrote so many songs, but his father had recorded it on his large phone. Wilson Jr. sang this song at his father’s funeral, recognizing it as proof that he was capable of writing something great.
Idolize, Demonize, Humanize Dynamic
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(00:52:02)
  • Key Takeaway: The biological progression of a son’s relationship with his father moves from idolization in childhood to demonization in teenage years (to promote genetic diversity) before finally reaching humanization in adulthood.
  • Summary: The dynamic between fathers and sons follows a pattern: initial idolization, followed by demonization during reproductive years to encourage leaving the tribe for procreation. The final stage is humanization, where the son recognizes the father as just another human doing their best. This realization breaks down lingering anger and forces self-reflection on the son’s own responsibilities.
Evolution and Break
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(00:56:48)
  • Key Takeaway: The conversation pauses briefly to address abstract concepts like evolution before taking a short break.
  • Summary: The speakers briefly touch upon the concept of evolution and the feeling of suffering before deciding to take a short intermission. This segment is immediately followed by several advertisements for sponsors like Nordstrom Rack, Shopify, and Valor Recovery.
Midwest Nostalgia and Childhood Smells
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(01:00:36)
  • Key Takeaway: Childhood memories in small Midwestern communities are strongly linked to sensory details like the smell of grandmother’s curtains and hot tar roads causing ‘NAACP feet’.
  • Summary: Stephen Wilson Jr. recalls specific sensory details from his grandparents’ small town in Wyoming, Illinois, including the smell of gardens and hot summer roads. Running barefoot on hot tar roads resulted in a specific type of foot soreness referred to as ‘NAACP feet.’ These small-town experiences provided a sense of safety and a world that ‘made sense’ to him as a child.
Nostalgia and Hand Cream
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(01:02:00)
  • Key Takeaway: The prevalence of hand cream in the 1990s is humorously linked to women using it as an excuse to avoid kitchen duties.
  • Summary: The discussion moves to nostalgia, prompted by Stephen Wilson Jr.’s song ‘1994,’ leading to a memory of his mother’s cow skin rug. He recalls inhaling the scent of her hand cream, which he associates with his mother being momentarily unavailable. This leads to a joke about women using hand cream to avoid cooking with cast iron pots.
Storytelling vs. Digital Sharing
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(01:05:03)
  • Key Takeaway: The shift from physical exploration (looking under couches) to digital consumption has reduced the necessity and value of oral storytelling.
  • Summary: The lack of constant digital distraction in childhood forced kids to create their own stories by exploring their immediate environment, like looking under the couch. Storytellers were highly valuable because they were the primary source of new narratives, unlike today where information is easily shared via links online. Stand-up comedy and songwriting are now seen as the primary remaining forms of valuable, authentic storytelling.
Authenticity in Art and Business
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(01:08:00)
  • Key Takeaway: Authenticity in creative work requires grounding in genuine emotion and experience, which can conflict with commercial viability.
  • Summary: The speakers agree that finding what is real is difficult, and Stephen Wilson Jr. authenticates his music through personal experiences and emotions, making it hard to write for others. He notes that a major challenge was getting others to authenticate his emotions in his music, sometimes leading to songs being rejected because they didn’t fit the intended performer. This personal authenticity is contrasted with the perceived lack of creativity in places like Hollywood.
Science Methodology in Songwriting
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(01:15:56)
  • Key Takeaway: Stephen Wilson Jr. applied his food science background to songwriting, using the scientific method to process grief and test song hypotheses.
  • Summary: Stephen Wilson Jr. describes channeling his devastation after his father’s death into a four-year research process for his record ‘Son of Dad,’ using meticulous documentation. He treated song ideas as hypotheses, testing them in front of small audiences to gather instant feedback data, which is much faster than traditional scientific experimentation. This methodology helped him observe his pain objectively, treating science as a ’truth detection tool’ rather than an ideology.
Father’s Boxing Legacy
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(01:39:45)
  • Key Takeaway: Stephen Wilson Jr.’s father was inspired by Muhammad Ali and Rocky to become a boxer, developing his skills under trainer Champ Cheney.
  • Summary: Stephen Wilson Jr.’s father began boxing after being inspired by Muhammad Ali and the movie Rocky, initially fighting in tough man competitions. He later trained under Champ Cheney in Indianapolis, who taught him fundamental skills like footwork and head movement, transforming him from a tough brawler into a skilled fighter. The gym environment was intense, filled with cigar smoke, gambling, and sparring, where Stephen and his brother also participated in exhibition fights.
Childhood Fear and Awareness
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(01:29:27)
  • Key Takeaway: Growing up with an elderly father and a mother in danger fostered extreme awareness and a tendency to retreat or maintain internal balance through rituals.
  • Summary: Theo Von describes growing up in fear due to his sister’s illness and his father’s advanced age, leading to a constant expectation of loss. Stephen Wilson Jr. notes that his father would bring him to funerals, forcing an early confrontation with death, while Theo’s father would abandon him and his sisters at Burger King during funerals. This environment of instability caused both to develop heightened awareness and internal coping mechanisms, such as obsessive balancing rituals, to manage the uncertain world.
Fitness and Burnout Recovery
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(01:52:59)
  • Key Takeaway: Stephen Wilson Jr. plans to prioritize health and establish a routine, including returning to MMA training, after experiencing burnout from touring.
  • Summary: The guest acknowledged taking touring fitness for granted and intends to invest in having a trainer on the road in the future. He has previously taken MMA classes and feels he will get back into it this year. Establishing roots in places will help create a necessary system or pattern for consistent health focus.
UFC Performance Institute Visit
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(01:54:07)
  • Key Takeaway: Stephen Wilson Jr. trained at the UFC Performance Institute in Las Vegas with Brandon Jenkins and Forrest Griffin.
  • Summary: The guest visited the UFC Performance Institute after a show in Vegas and trained with Brandon Jenkins, noting the difference between boxing and MMA training angles. Forrest Griffin gave him a tour of the facility, which was described as having a surprisingly ‘dangerous’ lunchroom filled with highly capable individuals.
Meta Internal Research Controversy
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(01:57:53)
  • Key Takeaway: Unredacted court filings allege Meta shut down internal research that found Facebook use correlated with lower depression and anxiety after one week.
  • Summary: Internal research, codenamed Project Mercury, reportedly showed that users who deactivated Facebook for a week reported reduced feelings of depression, anxiety, and loneliness. Meta allegedly called off further work, claiming the findings were tainted by the existing media narrative, despite a staffer insisting the results were valid.
Australian Social Media Ban
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(02:01:08)
  • Key Takeaway: Australia implemented a social media ban for users under 16 starting December 10th due to concerns over design features and harmful content exposure.
  • Summary: The ban includes ten platforms like Facebook, TikTok, and X, aiming to reduce time spent on screens driven by platform design. A commissioned study found 96% of 10-15 year olds use social media, with seven out of ten exposed to harmful content, including misogynistic material and cyberbullying.
Family, Fatherhood, and Step-Parenting
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(02:03:57)
  • Key Takeaway: Stephen Wilson Jr. values his stepson’s calm constitution, which contrasts with his own chaotic upbringing, and learned effective step-parenting through his father’s actions.
  • Summary: The guest admires his stepson for being intelligent, collected, and ordered, qualities he did not grow up around. He learned from his own father, who was a stepfather, that love is shown through actions, not words, avoiding the common pitfall of telling stepchildren they are loved ‘just like’ biological children.
Fear, Understanding, and Life Chapters
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(02:07:24)
  • Key Takeaway: Fear is often rooted in a lack of understanding, and recognizing old emotional patterns allows for freedom from their influence.
  • Summary: Familiarity can breed contempt, creating a battle between love and negative feelings in close relationships. The guest used the analogy of being scared in the dark woods until the sun rose, showing that the environment didn’t change, only the understanding of it did. He hopes his journey through multiple life chapters inspires his nieces and nephews that they are not stuck in one identity.
Musical Performance and Grief
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(02:17:18)
  • Key Takeaway: Stephen Wilson Jr. performed his song ‘Gary’ and the deeply personal track ‘Grief is Only Love That’s Got No Place to Go.’
  • Summary: The song ‘Gary’ paints a picture of a fading, traditional working-class man struggling with change and stagnation. The song about grief emphasizes that the pain is a manifestation of love that lacks a current outlet, particularly referencing the loss of his father.