We had the good fortune of connecting with Jonathan Pollock and we’ve shared our conversation below.

Hi Jonathan, why did you pursue a creative career?
Back in 2011, I left the corporate world and founded Ciao Andiamo–a boutique travel company specialized in insider journeys to Italy. After an MBA from Harvard Business School and 8 years in corporate America–with roles in finance, and marketing–I was ready for meaningful change. So, I gave my two weeks notice, and took a leap of faith on a passion project I hoped to evolve into a business that could withstand the test of time. My connection with Italy traces back to my high school days, when I first started learning Italian language. I kept up with it in college, and was inspired to study abroad in the small town of Sesto Fiorentino, just outside of Florence. The experience was transformational. I fell in love with all things Italian: the people, the culture, the natural beauty, traditions, and cuisine. Through the language, I connected with locals, immersed myself in the country, and did all I could to experience the real Italian way of life. This included extending my stay another semester and getting a job as a waiter at a restaurant in Florence’s historic center. After graduating college, I put Italy on the back burner, and took my first full-time job, working in finance for a Fortune 500 consumer packaged goods company. In my first years in the working world, I was successful and learned a lot, but was never fully satisfied. The son of two self-made entrepreneurs, I had caught the entrepreneurial bug, even as I found myself pulled along a more traditional career path. Some years went by, as I continued up the corporate ladder, expanding my resume of professional experiences and completing my MBA, all the while dreaming of one day venturing off and creating something of my own. Eventually it all clicked, and I saw a way that I could set out on an entrepreneurial endeavor, and tie it to my own deep-seated passion for Italy. And so, I launched Ciao Andiamo, with a mission to help others embark on authentic adventures through Italy and fall in love. It wasn’t an easy decision to leave a stable corporate career, and it certainly wasn’t on the shoulders of any fool-proof business plan that I expected to scale overnight. Making this business work was going to require some serious bootstrapping and grit, but I was convinced that diving in headfirst was the only way to transform a budding creative concept into something truly meaningful. I had faith that with a clear vision tethered to my own true north, with determination and the flexibility to adapt along the way, I could ultimately succeed. Corporate America would always be there, should I wish to return. But entrepreneurial, creative fulfillment would never come to fruition without that initial leap of faith. Now, in our 10th year of operation, I am proud to say that what began as a company of one, headquartered in the living room of my Manhattan apartment, today consists of a passion-filled team of partners and staff, spread across dual offices in New York and Italy. We have organized over 1,000 trips for some very happy travelers, transforming honeymoons, anniversary & birthday celebrations, family trips, solo adventures and group excursions into one-of-a-kind, authentic journeys. And we have done so with the highest level of care and integrity, always staying true to our roots and core mission of helping travelers discover Italy through local eyes, and fall in love.

What should our readers know about your business?
Ciao Andiamo first opened its doors in March of 2011, with a simple mission to help people fall in love with the beauty of authentic Italy. As a bootstrapped, non-financed operation that began as a team of one, I took a lean start-up approach, with a timeline of 6-12 months to test, learn, and identify where the real market opportunity would be. Part of this testing and learning approach was all about limiting upfront overhead, while offering a range of services that laddered up to the company’s core mission. At the time of launch, these services included food & wine events, conversational language lessons over wine & antipasti, and travel planning. While there was interest in food & wine events and laid-back language lessons, it became clear that in order to build a scalable venture and deliver on the company’s core mission in the most effective way, I would need to focus the endeavor on trip planning, with an emphasis on experiential travel led by Italian locals. Soon after Ciao Andiamo began, I met my eventual business partners Max Brunelli and Cristiana Chiacchierini, a husband and wife dream team, with years of experience in the Italian hospitality industry. Max and Cristiana were on their own parallel journey, looking to build something meaningful and lasting, with a shared vision and passion for authentic Italian adventures. We began to collaborate in curating all kinds of experiences for travelers, and it proved to be a perfect synergy. We got to work building our respective offices and teams, in New York City (where the focus would be on growth, trip planning, and client services), and in Umbria, Italy (where we would manage our invaluable relationships with carefully selected collaborators across Italy, oversee operations and bookings, lead insider tours, and closely look after all our clients during their travels). So began the next phase of Ciao Andiamo, and we slowly transformed what had begun as a small passion project into a dynamic business poised for smart growth. What sets Ciao Andiamo apart today more than anything is that we are mission-driven, and care deeply about authentic, immersive Italy travel experiences that delve into local culture & foster real connections. This shapes the services we provide, and the attention and care with which we look after our guests. I’ve learned lots of lessons along the way, and I’m still learning as I go. Perhaps the most important lesson I learned early on was the need to be willing and able to pivot. It’s all well and good to fall in love with your original business idea. But chances are, the most successful path forward won’t be “plan A”, or perhaps even “plan B or C”, so you have to learn to be adaptive. This means removing the blinders and (at least some of) the emotional attachment to “your baby”. Similarly, if you are looking to build a business that can grow and scale, you need to let go of control. That doesn’t mean you shouldn’t hold on tight to an anchoring vision and mission, and steer the company’s ship along the right path. But it does mean you have to loosen your grip on many (if not all!) aspects of the day-to-day, and trust in the people you bring on to the business. It’s a scary proposition, when you care so much and aspire for “perfection”. But letting go is what will ultimately set you free–your team, yourself, and your business–to achieve in ways that are truly transformational. There may be mistakes, and other team members may not do everything exactly as you yourself would have done, and that’s OK.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
I’m based in Manhattan’s West Village. I love it here because you get access to all the perks and energy of New York City, but with the charms of a European-style neighborhood oasis. There’s no shortage of amazing dining options, and I would definitely try to take a visiting friend to one of my favorite Italian spots (no surprise there): I Sodi or L’Artusi, and ask for a seat at the bar.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
I dedicate my shoutout to my parents, whose careers as self-made entrepreneurs proved foundational. In their respective professions of physical therapy/fitness and law, they created their own successful, lasting businesses, and instilled in me so many life lessons that inspired my entrepreneurial journey.

Website: www.ciaoandiamo.com
Instagram: www.instagram.com/ciaoandiamo
Linkedin: www.linkedin.com/company/ciao-andiamo
Facebook: www.facebook.com/CiaoAndiamo/
Youtube: https://www.youtube.com/channel/UCqKz4pnM-jpcuXFBzpvQpwQ
Other: https://www.tripadvisor.com/Attraction_Review-g672717-d14997170-Reviews-Ciao_Andiamo-Spello_Province_of_Perugia_Umbria.html

Image Credits
Ksenija Savic Photography

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