040: How To Start A Travel Agency (Jon Pollock)

Jon Pollock

Italy. It’s a place that is on high on most people’s bucket lists. And if it’s a country you’ve always wanted to explore then this is your show! Jon Pollock, founder and owner of Ciao Andiamo, has created a business based on giving tourists an authentic and personalized tour of Italy.

In today’s show we talk about where the idea for his business came from, how it has evolved, and what Jon did in preparation of starting this business as well as how he navigated those first few years in the trenches. Join us for all of this, and so much more in the 40th episode of How’d You Get Into That?.


Jon Pollock didn’t grow up dreaming of taking people around Italy on their own customized tours. Born and raised in Long Island, he wasn’t sure what he wanted to be as a child. In high school, he took Italian because he was interested in languages. He soon grew to love Italian and continued to study it in college.

That love of the language led him to live abroad for a semester. Having fallen in love with the Italian culture, Jon stayed on for awhile longer after his semester was over. He took a job as a waiter in Milan to get away from the tourists and really immerse himself in the culture and to connect with the Italians in a more everyday kind of way.

Even after he moved back to the States and had completed his undergraduate degree (he studied Business and Economics), Jon knew he wanted to take his passion for Italy and somehow translate it into his working life. He worked in a few corporate settings before settling on B school. He saw earning an MBA as a way to connect with others and see what else was out there in the business realm. Soon he was intrigued by entrepreneurism and took a position with a start up between his first and second years of B school.


  • What driving at night has to do with achieving your dreams.
  • If not now, when? Jon answers…
  • Why and when you should scrap Plan A.
  • How long did it take for Ciao Andiamo to be profitable?
  • Why it’s okay for your vision to change.
  • Who to listen to and when, according to Jon.
  • And so much more!

After his second year of B school, he went to back to the corporate setting but had a role that was fairly entrepreneurial and allowed him to learn a tremendous amount. He was still cultivating his idea for an Italy-related business while with the firm, so he stayed with them for four years while he was gaining business experience and honing his business idea. Jon didn’t want to have one foot in the firm and one foot out, so he also saved up a nest egg that would allow him to take the leap in one fell swoop.

Initially the concept of his business was centered around a few different avenues; he wanted to take people on their own personal Italian excursion but also he wanted to teach people the language through conversation over antipasti and wine. He also saw an opportunity to host authentic Italian food and wine nights to show people what Italy is really like, before they even arrived.

Despite caution from family friends, after about four years Jon went full speed ahead and left his corporate position to create Ciao Andiamo. The first few years were challenging, he quickly used up his nest egg and had to find creative ways to keep his business afloat. But even in those lean early days, he was incredibly grateful to be bringing his dream to life. Through those difficult times one of the biggest lessons he learned was, there never really is the perfect time to start a business so it’s best to just go for it!

And go for it he did. Since starting his company, Ciao Andiamo has evolved into a travel boutique that creates customized trips around Italy based on your interests and their secrets. They make sure your trip to Italy is an authentic one with local flavor. Most of his clients are honeymooners and small groups, but his company will provide customized trips for anyone.

Please join me in thanking Jon for sharing his knowledge biscuits with us today. After listening, I know you’ll want to pack your suitcase and head to the beautiful country that is Italia, taking Jon’s wisdom with you along the way! We appreciate you being here with us and we’ll see you on the next episode of “How Did You Get Into That?”. 

Tweetable: “My initial mission was to connect people to Italy.” Jon Pollock


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