What happens when your worst fear becomes your reality… and somehow becomes the launchpad for a popcorn empire?

In this powerful episode of Nightmare Success In and Out, Brent Cassity sits down with Emily O’Brien, founder of Comeback Snacks, to unpack how a honors grad from Canada went from international development and corporate sales… to being groomed by a boyfriend, caught smuggling cocaine back from St. Lucia, and sentenced to four years in a Canadian prison.

Emily shares the raw details of how quickly life can spin out of control, what it was like to be arrested at the airport, face her family in shackles, and navigate the Canadian prison system. She opens up about addiction, bad decisions, shame, and the brutal uncertainty of house arrest and sentencing.

But this isn’t just a story about a fall — it’s about a comeback. Inside prison, Emily started experimenting with popcorn recipes, listening to other women’s stories, and dreaming up a brand that would stand for second chances. That prison-born idea became Comeback Snacks — a popcorn company that now sells in over 1,200 retail stores, hires formerly incarcerated people, and uses bold flavors to spark conversations about redemption and prison reform.

From building a business out of a halfway house kitchen to speaking on stages, producing documentaries, and becoming a voice for fair-chance hiring, Emily proves that mistakes are universal — and so are comebacks. If you’ve ever wondered whether your worst decisions have to define you, this episode will hit home.

Listen in as Brent and Emily talk prison, purpose, entrepreneurship, Comeback Snacks, and what it really takes to rebuild your life after a conviction.

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