Building in Sicily: Startup Dreams and Sacred Days

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

More episodes of Becoming You Podcast

Explore listener stats, chart rankings, contacts and more on the Becoming You Podcast podcast page.