3) Please tell us about your entrepreneurial journey. What are some achievements and highlights from your career?
After building several successful neighborhood businesses, I was finally old enough to get “a real job.” I went to work as a night auditor at a Holiday Inn in downtown Minneapolis. I quickly developed aspirations of being promoted to sales manager, primarily because salespeople didn’t have to wear a uniform or a nametag!
My entrepreneurial traits were already in full force by then, such as a disregard for roadblocks and a high tolerance for risk. I approached the Director of Sales at the hotel and asked if she would allow me to work in the sales office while the current salesperson was out on leave. She scrutinized me for a moment and then asked, “Can you type?” I replied with one word: “Yes.” She acquiesced, offering me the temporary position and telling me that I would be expected to start on Monday. It was Thursday. After work that day, I jumped in the car and raced to the community college to enroll in a typing class so that I could learn to type over the weekend.
My hotel journey continued for the next 20 years. I held positions at the director level for some of the largest hotel franchise companies in the world, culminating in my last job as the Vice President of Sales for a hotel management and asset company with annual revenues close to a billion dollars. Unfortunately, I hated the work. I was running so fast from project to project, problem to problem, I didn’t realize I wasn’t happy. My life was out of balance and the company’s core values were not close to my own. When they fired me, I was stunned by the immediate relief I felt.
A few weeks later, I boarded a plane to visit my mom in St. John, USVI. I found myself with a 4-hour layover in San Juan. With that time to think, a creative spark flickered that had been dormant for the past several years. I plopped down on the carpet in an empty gate area and started writing feverishly on a stack of airplane napkins. An hour later, my hand was sore, my hair was a mess, and before me was a beautiful napkin mosaic consisting of 3 sections: things I love to do, things I like to do, and things I will never do again! And just like that, Jacaruso Enterprises was born.
I am grateful for the people who choose to work for me and who foster a culture of mutual respect. I am humbled by our success. For the last 4 years, Jacaruso Enterprises has been on the Inc.5000 list of fastest-growing private companies. In 2019, we worked with 68 different hotels brands, supported over 900 hotels in North & South America, employed over 150 people and topped annual revenue of over $18 million. In 2020, we were ranked in the Inc.5000 Best Workplaces and were recognized by CEO World Awards, Corporate Excellence Awards, various associations as well as peers from the largest hotel companies in the world.