Matthew Cox | Inside True Crime Podcast This CEO Took On Jeter & Wes Watson And Got Rich Doing It | AG Gregoroff
Dec 12, 2025
AG Gregoroff, a former county-jail inmate, shares his incredible journey from a chaotic upbringing in San Diego to becoming the entrepreneur behind Toehold flip-flops. He discusses the harsh realities of prison life, including racial segregation and survival strategies. AG reflects on his path through odd jobs, military contracting, and discovering leatherwork. He also critiques current prison influencers, emphasizing authenticity. With a focus on craftsmanship and innovative marketing, he reveals how his past shaped his business mindset.
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Violent Rural Childhood
- AG Gregoroff describes growing up in rural Northern San Diego County surrounded by migrant communities and gang violence.
- He recounts childhood scenes of shootings and a man bleeding to death on his porch that shaped his early worldview.
FBI Raid, Asset Forfeiture, And Reprieve
- AG tells the story of his uncle's property being raided by multiple federal agencies for suspected meth production.
- He explains being arrested, held, taking plea deals, and later having the case dismissed after his uncle sued for asset forfeiture.
Time In The Hole
- AG recounts long stints in solitary confinement and