
Building in Sicily: Startup Dreams and Sacred Days
From Becoming You Podcast by Rebecca Cafiero
November 17, 2025 · 38 min
About this episode
Rebecca shares her experiences of moving to Sicily, launching a startup, and the personal growth that comes with it.
Welcome back, or "ciao amici"! In this deeply personal catch-up episode, I'm pulling back the curtain on the last 90 days, an adventure that's included moving the entire family (and dog!) to Sicily for a sabbatical AND launching a beta product, PitchWell. It's been a time of immense "good and growth, the hard and the holy". I'm sharing what it's really like to live abroad past the "vacation phase", navigate being a beginner again, and build a startup from Sicily. This episode is part travel diary, part startup update, and all about what happens when you say yes to the things you "can only imagine". In This Episode, I Share: The launch and growth of PitchWell, the AI-powered visibility platform, and what it was like to ship the next version from Sicily. The "good" of living in Italy: increased family time, daily walks, and dinners together. An update on learning the language (I've graduated from survival A1 to elementary A2!). How this adventure is building "chosen resilience" for the whole family, instead of resilience that comes from trauma. A story about my nine-year-old son's newfound confidence and a rainy crepe adventure. The "growth" (or hard parts): the mental load, the…
People in this episode
Host: Rebecca Cafiero
Topics covered
- startup
- travel
- family
- resilience
- language learning
- personal growth
Keywords
- Sicily
- PitchWell
- startup
- family
- resilience
- language learning
- personal growth
Mentioned in this episode
Products: PitchWell
Places: Sicily, Italy
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