Risk, Ruin & Bloody Good Stories | Jess Kelly - 1023 episode artwork

EPISODE · Jun 14, 2026 · 45 MIN

Risk, Ruin & Bloody Good Stories | Jess Kelly - 1023

from Roll With The Punches · host Tiffanee Cook

Jess Kelly is one of those humans who walks into a room, says hell yes before she’s fully qualified, figures it out on the fly, and somehow makes the rest of us feel a little braver for existing near her. In this episode, we talk about business, risk, failure, family, starting again, and what happens when the thing you’ve poured everything into comes crashing down. Jess and her husband spent years building a prefab housing business with a huge vision, a tiny budget, and a whole lot of guts. Then, after years of pushing, pivoting, borrowing, sweating, hoping, and believing, they had to make the brutal call to put it into voluntary administration. But this ain't no doom and gloom chat... Not even close. Jess talks about owning the narrative, choosing family in the middle of the chaos, writing her way through the mess, and why everything is either good news or a good story if you’re willing to look at it through the right lens. We also get into imposter syndrome, shame, the weird freedom of having nothing left to lose, and why curiosity might just be the thing that keeps us moving when life goes full catastrophe mode. Honestly, Jess is a bloody weapon. Funny, honest, optimistic without being fluffy, and wildly refreshing. This one is a big, warm, slightly chaotic permission slip to take the risk, tell the truth, and give the thing a crack before you’ve got the shiny website, the perfect plan, or any idea what the hell you’re doing.   SPONSORED BY TESTART FAMILY LAWYERS Website: testartfamilylawyers.com.au TIFFANEE COOK Linktree:  linktr.ee/rollwiththepunches Website: tiffcook.com  See omnystudio.com/listener for privacy information.

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Risk, Ruin & Bloody Good Stories | Jess Kelly - 1023

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This episode is 45 minutes long.

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This episode was published on June 14, 2026.

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Jess Kelly is one of those humans who walks into a room, says hell yes before she’s fully qualified, figures it out on the fly, and somehow makes the rest of us feel a little braver for existing near her. In this episode, we talk about business,...

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