New York state prisoners competed in a "Shark Tank"-style pitch competition -- here's the winning idea

Defy Ventures robert cassatoSarah Jacobs/Business InsiderThe winner of Defy’s competition, Robert Cassato, pitched a business for bringing personal trainers directly to users.
  • Defy Ventures is a nonprofit that helps prisoners start businesses while they’re still incarcerated.
  • The six-month course culminates in a “Shark Tank”-style pitch competition that puts inmates before executive volunteers.
  • At the most recent competition, held in a New York state prison, the winning idea paired personal trainers with clients in an Uber-like business model.

About two hours north of Manhattan, in a sparse room filled with 25 high-powered executives, Robert Cassato delivered his three-minute pitch smoothly and confidently from the stage.

With a thick Brooklyn accent, Cassato dove into the particulars of Homebody Fitness, an on-demand personal training service that allows people to ping nearby personal trainers.

“It’s Uber for fitness,” Cassato, 44 and a licensed personal trainer, told the room.

Hustling the right way

The idea was strong enough to win the Defy Ventures business pitch competition, held among Wallkill State Prison inmates participating in Defy’s “CEO Of Your New Life” program. The program helps convicts use their penchant for hustling in productive and legal ways, Defy founder and CEO Catherine Hoke said.

Cassato was one of 50 “entrepreneurs-in-training” (EITs) pitching that day. The 25 executives were volunteers acting as a judging panel for the pitches, which ranged from apparel companies to drone fleets designed to identify and help repair crumbling infrastructure.

Cassato’s idea earned him an IOU valued at $US500, which Defy will give to him once he is released. (His parole hearing will be held in June of 2018.) The top five ideas all earned similar IOUs, with second place winning $US400, third place $US300, and so on.

Defy Ventures Inc 3670Sarah Jacobs/Business InsiderRobert Cassato is announced the winner of Defy’s business pitch competition.

The EITs spent at least six months developing their ideas from scratch. During weekly meetings, the men practiced their pitches on one another and offered feedback on the presentation. Some decided to collaborate and cross-promote, with one inmate featuring his designs for clothing line in another inmate’s youth magazine.

Cassato, a former loan officer, said he practiced five or six days a week for the last six months to hone the pitch to perfection.

“The class at night is two hours, but on top of that I would go back to my cell and spend another couple hours on it,” he told Business Insider. “So I was putting about three, four hours a night into this.”

Defy ventures catherine hokeSarah Jacobs/Business InsiderDefy Ventures Founder and CEO, Catherine Hoke.

What is Defy?

Hoke, who founded Defy in 2010, started the nonprofit to give people like Cassato a second chance at professional success. Within three years, roughly 68% of all US prisoners will reoffend at some point. Over the company’s seven-year run, Hoke said Defy’s recidivism rate was just 3.2%; its employment rate was 95%.

Inmates who join Defy’s program receive MBA-like training from executives whose responsibility it is to help EITs see the potential in their ideas. The volunteers also act as lifelines when the thought of starting a business from scratch seems too daunting. And since Defy tries to rehabilitate the whole person, the organisation also offers parenting education and life coaching.

It’s not the only program of its kind, though it may be the largest. In California, The Last Mile helps inmates start their own tech-focused businesses through coding and entrepreneurship programs. The Last Mile was launched in 2014 in San Quentin Prison.

One drawback of both is that prisons forbid access to the internet, so the men may be missing out on valuable information related to market and product research. This is especially true for men serving long prison sentences; someone who has been in prison for the last 15 years, for example, probably doesn’t have much exposure to smartphones.

A lasting reputation

To date, Defy has enlisted 4,400 executives to mentor approximately 3,600 EITs around the US. It’s held 15 competitions so far with 10 more planned. The Wallkill class was the first in New York State.

In his acceptance speech, Cassato credited Coss Marte, former Defy participant and current CEO of prison-style bootcamp ConBody, as his main inspiration for sticking with the program. In the beginning, he said he had little interest. Quickly, the camaraderie of the fellow EITs helped him realise the value of seeing it through.

“Anybody’s gonna look you up online these days and say ‘I don’t know if I’m gonna do business with this guy,'” Cassato said. “But being part of Defy, they might look you up now and say ‘You know what, this guy is rehabilitated. I think he deserves a second chance, and I think I’m definitely gonna do business with him.'”

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