7 min 12 sec

Harvard Med School Program Manager Gets Paid to Travel to Italy

After yearning to spend more time back in her homeland, a med school program manager creates a side hustle centered around Italian food and culture.
Customer Service Food Service Tourism Travel

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What It's About

A profitable side hustle that celebrates Italian culture and helps a Boston woman revisit her roots.

Business Model
Skills Required
Coordination & Researching
Profit Potential

Words of Wisdom

Francesca’s “Aha!” moment came when she looked back at all of the free advice she’d given out over the years. She’d shared her family’s authentic Italian recipes with her friends, helped them book entire holidays and taught countless people about Italian culture. So, she asked herself the all-important side hustle question, “Can I charge for this?”

A side hustle should be something that you look forward to—not just tolerate. And some of the best side hustles we've featured on the show start out as something they do for fun. Is there something that you love doing that would make for a good side hustle?

Fun Fact

As a native Italian in Boston, Francesca started her side hustle as a way to travel back to Italy more frequently. This permits her to organize a few week-long tours, make connections by building private trips and helps with her constant craving for Italy! She is also a great cook, so she teaches Italian cooking at the adult education centers as well as private classes in her own home.

If you think limiting your travel business to one country could be a little too niche, you’d be wrong. Around 48.6 million tourists visit Italy every year. That’s 10 million more people than live in California!

Notes from Chris

Episode 171

Francesca Montillo's side hustle was 20 years in the making. Ever since she left high school, she dreamt of starting her own travel business and sharing a small pizza-slice of her native Italy with the world. But instead of following her dream, Francesca opted for what she thought was the safe option.

After 20 years of waiting for the right time, she decided to finally go ahead and start her business anyway.

Putting a basic website online that she called The Lazy Italian, she wrote about her experiences, holidays she’d planned and recipes she loved to cook. She made sure to mention she was the real Italian deal, too.

Right now Francesca is making an average of $500 a month through her side hustle, although this number can get a lot higher when she’s got a big tour to work with.

Francesca’s ultimate goal now is to turn this side hustle into her full-time work in the next one to two years, and she plans to start promoting her tours to bigger groups. She also wants to stop running stateside cooking classes (no matter how fun they are) and instead turn her attention to writing a Lazy Italian Cookbook.


  • Lazy Italian Culinary Adventures:Book your own all-inclusive Italian excursion on Francesca's website!
  • ServSafe:The online certification course Francesca took so that she could teach her cooking classes

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


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Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! ✈️

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Quote of the Day
"At first when I saw my competition it was upsetting, but then I realized that I was comparing my 'Chapter 1' to someone else's 'Chapter 15 or 20'—they had been in the business longer and yes, were doing better, but I was comparing apples to oranges."
—Francesa Montillo #SideHustleSchool

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To infinity and beyond,

Chris Guillebeau