Running A Startup From Across The Globe: My Summer In Italy

You’ve heard about companies operating remotely or having satellite offices, but have you ever experienced it, toyed with the idea or are you just interested in getting the inside scoop? This blog post is all about my experience living and working abroad, finding work/life balance, cherishing cultural differences, key learnings, and takeaways for success. 

Austin and Angela at a WineSociety meeting in Paris
              Photo: WineSociety meeting in France 




This year, we were presented with a unique opportunity…

After running his company DotLoop, for over 12 years, my husband, Austin, decided it was time to step away. He deemed 2019 as his sabbatical year where he would check off a few bucket list items and plan his next big thing. It was important to me to be able to support him throughout this transition. Knowing it would be challenging, I asked myself a host of questions to weigh the pros and cons of this decision. I also felt as though I needed to seize the opportunity, as I didn’t want to regret letting this CHANCE pass us by.

Bucket List Item #1. Live abroad...and Italy was calling our name. 

The beautiful Val D'Orcia, a UNESCO world heritage sight

Going back to the moment Austin first proposed the idea to me, several questions obviously arose...What did this mean for WineSociety? How effective would I be by running the company from thousands of miles away and operating on a 6-9 hour time difference? How would the team react? What if there was an urgent situation I needed to be present for? How would this affect our team culture? We sat down together and walked through the challenges and opportunities for this venture.

Decision-making process...

STEP 1: Weigh the +’s and -’s

The best way to come to a decision is by first writing down all the pros + cons.. (I am a huge fan of whiteboards or giant size post-it notes

STEP 2: Discuss the risks and benefits of each, along with proposed solutions to the negatives. 

STEP 3: Propose the scenario and get objective third party opinions. 

STEP 4. Make an educated and well thought-out decision.

Knowing that WineSociety was already a remotely operated company - from across the country (me living in CA and most of my team in OH) gave me the confidence to be able to run it from across the globe. In reality, it was just a bigger time difference and a more expensive flight to get home if needed. I was fortunate to have a conversation with another CEO in our YPO chapter who had done the same thing a few years back, and he encouraged me by sharing his positive experience. In addition, we had just completed another canning run, so there would be no production and little vendor management needed while I was gone. Plus, being immersed in the “old world” of wine was definitely appealing and relevant to our business. I considered it an opportunity that I could not let pass by!

Angela at her desk

Company culture and communication are two of the most important things for a company’s success. However, it can be challenging when the team is dispersed. Creating connection and unity is key. 

Implement your plan  - here are 3 things I had in place before departing...

  • A clear strategy business plan with defined roles in place 
        1. A clearly stated company goal and plan to get there with weekly check- in’s and accountability metrics
        2. Clearly defined roles and responsibilities for each person to reach that goal  = less confusion
  • Delegate and empower
        1. Set parameters and empower your team so members don’t have to ask permission for everything
        2. Being physically out of the office allows and encourages team members to have more ownership.
  • Use tools and technology to help stay connected and organized
        1. Daily communication, collaboration and check in’s with Slack, GDrive and Dropbox
        2. Weekly All Hands (We call ours “All Smiles”) with mandated video conferencing
    Angela, Austin and Paris the dog on a trans-Atlantic flight

    Bon Voyage! 

    Armed with a few Italian lessons under our belts, outreach to set up a few meetings in Europe, a solid communicated plan and focus for WineSociety and our affairs in the States in order, we were on our way to the adventure of a lifetime. With only a carry-on each and our little Yorkie, Paris, we boarded our flight to Europe, excited for our immersion into the Italian culture. 

    Angela enjoying morning coffee on the Italian terrace with laptop

    First things first! 


    One of the benefits of being in Europe is that half the world is asleep and offline until about 2 pm… that means almost 6 hours of precious uninterrupted time! The first thing I did was make time for myself and other activities that I enjoyed like running and cooking. Reflecting back on a post I wrote for Sunday Forever’s How I Sunday Issue, I realized that I had fallen back into the 100% work grind where I didn’t allow any time for self-care. 

    Tools and Processes for success

    Time blocking is key, and when used properly, can allow for the best time management and a healthy work-life balance. It is important to treat a time block to work-out just as you would a meeting. Both are equally important, and allowing time for exercise will enable you to do better work throughout the day. 

    I used my early mornings to start the day with an espresso while watching the sunrise (quiet, mindful time), followed by blocked time for a podcast, project or preparation for upcoming meetings. Then, depending on the day, I would head to the local market to pick up fresh produce, plan dinner or research a cool town to explore that evening. 

    Angela and Paris on a morning run through the hills of Tuscany

    By 11am I would be off on a run, then we would prepare our favorite lunch (caprese salad with italian burrata cheese - so simple and delicious.). I would then shower and be ready to join my team online by 2pm. It was like I had two days in one! Having these mornings helped me have a better mindset, feel more energized and enabled me to better plan my time. 



    The azure waters of the Tyrrhenian Sea surrounding the isle of Capri on the Amalfi Coast

    You don’t have to work 24/7 to be successful!

    Vacation? Does that word even exist in a start-up? LOL! After a year and a half of 12+ hour days, eating, sleeping and breathing all things WineSociety, a weekend to recharge was definitely overdue. (Notice I said weekend, LOL!) One thing that always slips when you're dedicated to your job is your self-care, it's almost as though stepping away from work constitutes failing or slacking off. It's a strange but very common mindset that most entrepreneurs and self-employed people feel. This is why when I checked in with myself, I realized, actually, the whole theory is reversed - more self-care equals a healthier working habit and life. So, (starting with baby steps) I dedicated one weekend to completely disconnect, and accompanied by friends, we embarked to one of my favorite places...the island of Capri

    Step out of your comfort zone and challenge your fears!

    Angela and Austin white water rafting with friends

    Before this trip, if you would have asked me to list one thing that I would never do… it would have been white water rafting! I don’t know why, but I have always been scared of rushing down rapids with the chance of falling out and getting stuck under the raft or getting hurt on the rocks. Somehow, my husband and some of our local friends convinced me to try it! I was so nervous that morning and contemplated bailing, but faced my fears, zipped up my wet suit and boarded our raft. I was so grateful for our guide who was funny and awesome at leading our team through the rapids. Humor can definitely make any situation lighter.  After our second set of rapids, I realized that white water rafting was actually pretty fun and not that scary! Conquering one of my fears felt so amazing, and is good to remember for any challenge in life.


    Angela and Austin spending time with friends at the Monteverdi Culinary Academy in Castiglioncello del Trinoro

    Great minds think alike

    We soon discovered that we were not the only ones who decided to spend some time in Europe over the summer. We ended up seeing more of our friends there than we did back in the States! Every two weeks or so, it seemed we were either traveling or hosting friends that just happened to be in town. Quality time with family and friends was another thing that had slipped this past year. That’s what I love about the Italian culture --  family, food + wine, art and music are top of mind and naturally bring people together.  Being reminded of that and taking time to slow down from my busy city life was just what I needed.

    A change can do you good.

    This change of pace really allowed me to look at situations more openly and from a birds-eye view. Having the uninterrupted time to strategize and ultimately make a few key decisions for the company, was space I didn't know I even needed! It also got me back on track to living a well balanced life where self care, family + friends and work all have a place in my day. 

    A close up shot of a vine growing in Tuscany

    Un bicchiere di vino della casa, per favore. 

    Being in the wine industry, I of course felt like I was in heaven having access to wines like Rosso di Montalcino, Chianti and Brunello on a daily basis. But what I really love + respect is that in Tuscany, their house wine (vino della casa) that is offered around 5 euro/carafe can sometimes be better than most $20-$30 bottles of wine here in the states! The carafe was an inspiration for selecting our 500mL cans (1 carafe = 500mL, the perfect amount to share) and the notion of vino della casa + our appreciation for great quality wine was another inspiration for WineSociety - having a great go-to wine on hand for any occasion! In meeting with several winemakers and restaurant owners, it was reinforced that quality is key in Italy. For a lot of wineries, if they have a bad year, they will not even produce wine. I cherished the time spent learning firsthand more about Italian wines and the passion behind them. 

    Tuscan sunset illuminating an al fresco dinner table

    Having been home for over a month now, and looking back on my experience, I am filled with gratitude for the opportunity to live abroad and even more grateful to be able to share my experience with you. Things happen for a reason and FATE will always lead you in the direction you are meant. 

    Secondly, I can safely say it was much-needed time to seek clarity and focus along with future growth opportunities. It took me away from being in the grind 24/7, to having a few hours of the day for much needed self-time. It was a bit of a change coming back home, but I feel so much more inspired, energized, and ready to jump back into the day-to-day.

    So after experiencing the operation of my company from abroad, I can tell you that for me it was a CHANCE worth taking and a decision I would not take back. Even though it had its challenges, the outcomes, learnings, and experience outweighed them and I am now in a better position to take the steps necessary to move the company forward!

    Angela on the hilltop in Tuscany

    Cheers to where FATE leads you!


    Enter to Win the travel sweepstakes presented by WineSociety to Burgundy, France

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