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Private Equity Firm Invested Over $100,000 in Prison Training Program

Dropping Bombs · This Blue-Collar Business Prints Money (No One’s Talking About It) · June 5, 2026
Private Equity Firm Invested Over $100,000 in Prison Training Program
Dropping Bombs
Dropping Bombs
This Blue-Collar Business Prints Money (No One’s Talking About It)
"We needed like over $100 grand to kind of get the ball rolling here. And they cut the check. There was no arguing."
One Solutions ProWest, the private equity-backed parent company, immediately funded over $100,000 to launch the prison-to-workforce roofing program without resistance, according to program director Adam Chonier. The investment supports training infrastructure across 17 states and multiple prison facilities, representing an unusual corporate commitment to second-chance hiring at scale.

About this episode

Brad Lea interviewed Bob Schober, founder of a nine-figure roofing empire and viral philanthropist known as the Nine Figure Roofer, in a wide-ranging conversation focused on second-chance hiring and rehabilitating formerly incarcerated individuals through commission sales. Schober, a 28-year sober alcoholic who once lived homeless in a Volkswagen bus following the Grateful Dead, built a multi-state roofing operation later sold to private equity while retaining 20 percent ownership. The most newsworthy revelations centered on his Hustle 2.0 program, which trains prisoners via Zoom before release and has hired over 200 ex-convicts, six of whom earned over $600,000 each in their second year post-release. Adam Chonier, Schober's right-hand executive who served two six-and-a-half-year prison terms, joined by phone to detail how his division generated $37.7 million in sales last year with a team composed entirely of formerly incarcerated individuals, while disclosing his personal income exceeded seven figures. The program operates across 17 states through prison tablets using the Edovo app, offering a 12-point curriculum combining roofing sales training with character development. Schober also discussed his recent viral philanthropy, having given away approximately $100,000 in cash over three months while amassing 820,000 social media followers and 400 million views. The conversation explored broader themes of recidivism, the failures of traditional reentry programs, and why commission-based blue-collar work may be the most effective path to breaking cycles of incarceration. Schober emphasized that financial opportunity, not counseling or halfway houses, represents the real solution, and noted private equity firm One Solutions ProWest funded over $100,000 to launch the initiative without hesitation. The episode also touched on Schober's sales background, his Ferrari ownership, and his conviction that AI will not disrupt trades, making home services the 'new white-collar job.'

Key takeaways

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