Jodi Koskella never planned to work in Silicon Valley. She certainly never planned to launch a vegan shoe company, write a book about business failure, or leave a successful corporate career to start over in Florence.

And yet that’s exactly what happened.

In this candid conversation, Jodi shares her remarkable journey from Minnesota to Silicon Valley, through the dot-com boom and bust, into entrepreneurship, and ultimately to Italy. Along the way, she learned that success is rarely linea, and that some of life’s most meaningful opportunities emerge from unexpected setbacks.

We talk about the realities of startup culture, the pressures of corporate America, the loneliness that can accompany professional success, and the moment she realized she needed a different life. Jodi also reflects on the rise and fall of her vegan shoe company, the book she’s writing about that experience, and why she believes we need more honest conversations about failure.

We also explore the challenges and rewards of building a new life abroad, finding community in Florence, and embracing reinvention at every stage of life.

This is a conversation about resilience, friendship, creativity, and the courage to choose a path that feels true, even when it doesn’t make sense on paper.

If you’ve ever questioned your career, dreamed of making a major life change, or wondered whether it’s too late to start over, this episode is for you.

Biography

Jodi Koskella spent twenty years in Silicon Valley marketing, working through startups and enterprise technology companies, most of the time wishing she was somewhere else. Years ago she co-founded a Made in Italy vegan shoe company with a dear friend as a way to escape the cubicle blues, and fell in love with the design world and Italy along the way. After a roller coaster adventure with shoes, she returned to Silicon Valley just long enough to pay off her company debts while plotting her next move, which turned out to be relocating to Florence, Italy. She is currently consulting in marketing and fashion design, while continually deepening her long-term relationship with Italy.

https://www.linkedin.com/in/jodi-koskella-b63b1/

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Podcast Producer: Andrew Niklas Curtis

Recording and post-production Lorenzo Maiani, Faminore Sound Agency