Way Out #22: He Was Putting Payroll on Credit Cards: Then His Son Was Born Nine Weeks Early with Brian Best
entrepreneur Vanessa Jupe entrepreneur Vanessa Jupe

Way Out #22: He Was Putting Payroll on Credit Cards: Then His Son Was Born Nine Weeks Early with Brian Best

The scariest moment of Brian's life forced the ultimate realization: If your business completely relies on your physical time, it is a trap. Today, his business runs on recurring revenue so he can travel the country in an RV with his family. Learn how he built a business that can run without him on this week's episode of 101 Ways Out!

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Way Out #17: From Pastor to Serial Entrepreneur with Keith Davenport
entrepreneur Vanessa Jupe entrepreneur Vanessa Jupe

Way Out #17: From Pastor to Serial Entrepreneur with Keith Davenport

In this episode, we sit down with Keith Davenport, a man whose life is a masterclass in radical transformation. Keith went from growing up in a conservative evangelical household with a childhood calling to be a pastor, to ultimately leaving his faith to identify as a progressive atheist and political candidate. After experiencing severe burnout and untreated ADHD while managing crisis communications during the COVID-19 pandemic, Keith took a massive leap into serial entrepreneurship. We discuss how he acquired a beloved local coffee shop, launched a multi-six-figure consulting firm, and founded an HR tech startup. Ultimately, Keith shares how he redefined success entirely, choosing his mental health and his role as a husband and father over traditional corporate power.

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Way Out #15: From Startup Toxicity to Building a Balanced Life with Anna Duin
consultant (marketing) Vanessa Jupe consultant (marketing) Vanessa Jupe

Way Out #15: From Startup Toxicity to Building a Balanced Life with Anna Duin

Anna Duin spent 11 years doing marketing at startups — always doing the work of multiple people for the price of one. She navigated layoffs, negotiated flexible hours, and went through two terrifying years with a seriously ill child while her last company turned toxic. When she finally left, she didn’t have a plan. Just a conversation where she heard herself say: “I think I just have to build my own thing.” This is what happened in the year that followed.

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Way Out #6: She Left a "Good Enough" Marriage, Then Corporate: For a Camper Van and the Smokies with Taylor Surdyke
nomad Vanessa Jupe nomad Vanessa Jupe

Way Out #6: She Left a "Good Enough" Marriage, Then Corporate: For a Camper Van and the Smokies with Taylor Surdyke

On paper, Taylor Sordike had the American Dream: a husband, a suburban home, and a rising career in logistics. But deep down, she knew she was settling for "safety" rather than alignment. In this post, Taylor reveals how leaving a "good enough" marriage gave her the muscle memory to walk away from corporate life, buy a camper van, and follow her intuition to the Smokies. Her advice for anyone standing on the edge of a pivot? "Do it scared."

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