Society

Formerly Homeless Roofer Now Gives Away $100,000 in Three Months

Dropping Bombs · This Blue-Collar Business Prints Money (No One’s Talking About It) · June 5, 2026

Dropping Bombs

This Blue-Collar Business Prints Money (No One’s Talking About It)

"December 4th, as I was telling you earlier, is when I did my first video that I posted up. Probably given out $100 grand, and there's over 400 million views. And there's 820,000 subscribers across all the channels."

Bob Schober, who once lived in a Volkswagen bus following the Grateful Dead and struggled with addiction, revealed he has given away approximately $100,000 in cash over three months while building 820,000 social media followers and generating 400 million views. The former door-to-door salesman turned nine-figure roofing CEO now carries $6,000 to $7,000 in cash weekly to distribute directly to struggling individuals in stores like Goodwill.

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

Schober revealed six formerly incarcerated individuals on his roofing team each earned over $600,000 in their second year after prison release.
Adam Chonier, who served two six-and-a-half-year prison terms, now runs a roofing division that generated $37.7 million in sales with earnings exceeding seven figures personally.
The Hustle 2.0 program has hired over 200 ex-convicts who have purchased homes and reunited with families, accessible via Edovo app on prison tablets.
Private equity firm One Solutions ProWest funded over $100,000 to launch the prison training program across 17 states without resistance.
Schober gave away approximately $100,000 in cash over three months, building 820,000 social media followers and 400 million views in the process.
One friend who served over 20 years in prison earned $30,000 in his third month selling roofing door-to-door.
Schober, a 28-year sober alcoholic, previously lived homeless in a Volkswagen bus and sold t-shirts following the Grateful Dead before entering sales.