The UpFlip Podcast

Updated: 24 Nov 2025 • 217 episodes
www.upflip.com

The UpFlip podcast is where you get to unravel how great businesses are built, how they are run behind the scenes, and how their success can be replicated. We feed on the idea that no matter what the circumstances are, the American Dream is still just around the corner. With over 150+ videos and 50 million views on YouTube, UpFlip has ignited the spark that rekindles the fire of entrepreneurship in its ever-growing 700K+ audience. Through this podcast, we aim at sharing practical nuggets of gold and brilliant advice with you by making knowledge more accessible. For more information about us and our services, please visit https://www.upflip.com.

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Teague Egan faced every founder’s nightmare: payroll was due, and a massive investment deal with General Motors was stalled. With his back against the wall, Teague sold his house for $2 million and wired the cash to his company just to stay alive. That "all-in" gamble paid off, securing the partnership and positioning

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Richard Gould went from a high school dropout to the founder of a blue collar franchise with over 20 locations. After buying a business from his mentor and quadrupling sales, he took a massive risk: selling everything to move to a new state with no connections. There, he rebuilt his empire from scratch, proving his sys

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Michael Sutton was a university student looking to pay tuition when he and a buddy spotted an overlooked problem: dirty grills. With zero experience and just pure hustle, they started knocking on doors. After landing five sales on their very first day, they hit a critical snag—they had no idea how to actually clean a g

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John Sampogna co-founded his digital agency, Wondersauce, at just 26, with the ambition to take on the giants of Madison Avenue. He spent five years grinding, building a stellar reputation, and scaling his team from two to 100 employees. But as the operational weight of payroll, HR, and collections threatened to pull h

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Chase Gallagher wasn't playing video games at 12. He was knocking on doors to build his lawn care hustle. A year later, he sold his dirt bike for a trailer. That relentless drive paid off: his side hustle has exploded into CMG Landscaping, a $1.5 million-a-year operation, with total ventures approaching $2 million annu

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Giuseppe Grammatico was living the life many dream of—a six-figure salary at JP Morgan. But with a five-hour daily commute and a baby on the way, he realized the "dream" was costing him the one thing that truly mattered: time with his family. He made the terrifying choice to quit his secure corporate job with no busine

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