Nate and I sat down for one of those meandering, no-rush conversations about what it’s actually like to live in Italy—not the Instagram version, but the messy, funny, frustrating, sometimes absurd day-to-day stuff. We talked about learning Italian (and butchering it along the way), the oddities of dining out, what it means to be a musician here, and how different the cultural wiring is compared to the U.S. There’s beer. There’s music. There are stories about language mishaps, the real cost of living abroad, and the weird, wonderful way Italy gets under your skin. If you’ve ever thought about moving here—or just want to know what it’s like beyond the vacation glow—this one’s for you.
Nate on Instagram: @bozemanateNate’s band: Kantner Brothers

📍 Mentioned in the episode:

Snack Bar Anna:https://share.google/N7VtUPbHbjDn8Vx02
Books that helped with Italian:Italian for Dummies: https://amzn.to/3LgyMWi
501 Italian Verbs: https://amzn.to/3JqV7Qq

Talking taxes in Italy is no picnic — especially if you're a foreigner trying to navigate the system. I sat down with Giovanni Cervini to dig into some of the stuff that trips people up the most: tax residency rules, what happens if you own property, double taxation headaches, remote work implications, and how all of it changes if you’re new to Italy. Giovanni laid out how the Italian system looks at fiscal residency (hint: it’s not just about where you sleep), how remote workers should plan ahead, and what incentives might be available if you’re relocating. If you’re thinking about moving here or already have, this is one of those areas where "I'll figure it out later" can get very expensive. The bottom line? Do your homework. Talk to professionals who know the system inside and out. And definitely don’t assume the rules will be the same as back home — they aren’t.If you want to get in touch with Giovanni directly, you can reach him through his firm, Studio Cervini-Grasselli: https://www.cervinigrasselli.com/cont...The information provided in this podcast is intended for general informational purposes only and does not constitute financial, legal, tax, or professional advice. No professional-client relationship is created by listening to or participating in this podcast. The views and opinions expressed are those of the individuals involved and do not necessarily reflect the views of any organizations they may be affiliated with. Listeners are advised to consult with qualified professionals for advice specific to their individual circumstances. The host and guests disclaim any liability for actions taken based on the content discussed.

In this episode, Erica gets real about what it’s like to pack up your life, move your family across the ocean, and start over in Italy. We dig into why they did it, the hoops they had to jump through for citizenship, and what it’s actually like navigating daily life, schools, and cultural differences with kids in a brand new country. Erica doesn’t sugarcoat the challenges, but also shares how rewarding it can be raising kids in a place where life moves differently. If you’ve ever dreamed about dropping everything and moving to Italy, this one’s for you.

You can find Erica on her website travelingmuggles.com or on instagram at @travelingmuggles

In this episode, I sit down with my friend Andreas to talk about what it’s actually like building a life—and a business—in Italy. We get into everything from cultural identity and language learning to the weird realities of Italian bureaucracy and what it takes to thrive here as a foreigner. We also dive into the cocktail scene, community-building, and how Italy’s approach to food, service, and even music (yes, metalheads exist here too) reveals a lot about the culture. It’s part travel story, part entrepreneurial therapy session—perfect if you’ve ever dreamed of doing something bold abroad.

And hey—if you’re in Perugia, check out Andreas’ bars: Dempsey’s and Marla. They’re worth your time.

In this episode, I talk with my friend and business partner, attorney Christina Prejean, about what it really takes to get Italian citizenship. Christina shares how her background—including time in the military and a serious travel bug—led her to dive into dual citizenship. We get into the nuts and bolts of the process, why an Italian passport is worth chasing, and how getting help from someone who actually knows what they’re doing can save you a ton of time and headaches. If you’re curious about claiming your Italian roots or just want a no-BS look at the legal side of living abroad, you’ll want to listen in.

If you’ve got questions about Italian citizenship, reach out to Christina at [email protected] and follow @becomeitaliani on Instagram.

Disclaimer: The content in this episode is for general informational purposes only and is not intended to provide specific legal advice regarding immigration, citizenship, visas, or any related matters. For advice tailored to your situation, speak directly with a qualified professional.

In this episode, I talk with Giulia Speziali—an Italian language teacher from Perugia—about everything from her time teaching in China to what makes Italian such a weirdly emotional language to learn and teach. We get into how people actually learn languages (hint: it’s not from grammar books), how TikTok is changing education, and why pronunciation trips people up more than anything. We also unpack Italian culture from both inside and outside—how Italians act abroad, what coffee means here, and why regional pride runs so deep. If you’ve ever tried learning Italian, taught a language, or just wondered what makes Italians tick, this one’s for you.

And if you’re looking to learn Italian with Giulia, check her out on Instagram at @italianocongiulia.

In this episode, I talk with Sonya about what it’s really like to move from Russia to Italy. We cover everything from language struggles to cultural curveballs—plus what surprised her most about Italians. We also dig into what it feels like to be an expat, the weird differences between life in the US and Italy, and how travel restrictions have shaped our lives in unexpected ways. Sonya shares some solid advice for Russians thinking about traveling or moving to Italy, and we both reflect on the weird privilege of being English speakers in a world that caters to us way more than most people realize.

In this episode, I sit down with my friend Cosimo Serpolla to talk honestly about life in Italy—what works, what doesn’t, and what people don’t tell you before moving here. We dig into cultural expectations, job market frustrations, how the experience differs if you’re LGBTQ+ or an expat, and why cities like Brussels keep pulling people away. If you’ve ever dreamed of living in Italy, this one’s for you—just don’t expect a sugar-coated fantasy. We’re talking about the real deal.