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Toni Jacaruso’s “Fired to Inspired” Multi-Million Dollar Entrepreneurship

Once upon a time, there was a tenacious woman who got fired from a job she hated. THANK GOD!

My entrepreneurial journey did not start with a desire to “be my own boss” or “follow in my parents’ footsteps.” Like most things in my life, I entered into entrepreneurship by happenstance, or by God’s grace, depending on your view of the world.

I first became an entrepreneur when I was 12, although I didn’t recognize it at the time. I started babysitting, and soon was babysitting every weekend. I began to realize some things about my business. Of course I didn’t have these words to describe it, but I recognized that my service was in high demand and that I needed to figure out how to scale and handle revenue displacement. I gathered all of my babysitting friends to present an opportunity:  I’d line up babysitting jobs based on their availability, handle all the collections, take a 20% commission, and give them the rest in cash – guaranteed. Within the first quarter, I had 3 contractors working for me. I had 5 more in the first year. Within 3 years, I had made enough money to buy a waterbed (a coveted luxury item at that time in cold Minnesota) and my first car (a very used Datsun 280ZX). By age 16, I was sick of dealing with labor issues, had a disdain for collections, and experienced my first case of burnout.

Since I was then old enough to get “a real job,” I went to work as a night auditor at a large Holiday Inn in downtown Minneapolis. Little did I know this would be the beginning of a lifelong career in the hotel industry. Two years later, I moved to Oklahoma City for college and got a job as a front desk agent at an Embassy Suites. I quickly developed aspirations of being promoted to sales manager, primarily because salespeople didn’t have to wear a uniform or a nametag! #biggoals

My entrepreneurial traits were already in full force by then, such as a disregard for rules, ignoring roadblocks, and a high tolerance for risk. I approached the director of sales at the hotel and asked if she would be willing to allow me to work in the sales office as the secretary (that’s what they were called in the 90’s) while the current sales secretary was out on maternity 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. This is an example of another trait I share with many fellow entrepreneurs: “Fake it until you make it”. Or as I like to say now, “Sell it and then figure it out.”

I continued my hotel journey for the next 20 years advancing my career with each new job. 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 and problem to problem, I didn’t take time to realize that I was miserable, that my life was out of balance, and that the company’s core values were not even close to my own.

While that company did an amazing job at managing the financial performance of hotel assets, they failed miserably at building optimal performance in their people. They saw human assets as dispensable. They managed with fear, withheld information, set ambiguous goals, and operated with the overall mindset of “what have you done for me lately?”

To be fair, many of my peers and colleagues were thoughtful, creative and kind. The company culture fostered selfish, egotistical and arrogance rewards. When they fired me, I was stunned to realize the immediate relief I felt. That’s how I knew I had been on the wrong path for a long time. As I drove away, I vowed I would never work with people I didn’t respect and care about again.

I used my time off to start meditating and journaling again. I connected with people I love. I heard myself laugh for the first time in months.

A few weeks later, I boarded a plane to visit my mom in St. John, USVI, since family was another thing I’d been neglecting. I found myself with a 4-hour layover for plane changes in San Juan, Puerto Rico, with lots of time to think. Suddenly a lightbulb went off. I felt a creative spark flickering that had been dormant for the past several years. I didn’t have any paper, but I did have a stack of American Airlines napkins. I plopped down on the carpet in an empty gate area and started writing feverishly. After an hour, my hand was sore, my hair was a mess, and before me was a beautiful airplane napkin mosaic consisting of 3 sections:  things I love to do, things I like to do, and things I will never do again!

The things I loved to do involved sales, hotels, travel and mostly, people. I realized my passion isn’t necessarily about the job itself; it’s about the people with whom I got to do the job. I immediately started drafting a business plan that was a list of 20 people that I loved and respected who worked in the hotel industry. It didn’t hurt that many of them were in positions of influence at Fortune 500 hotel companies.

When I returned home, I bought a new cell phone and started at the top of the list. I explained what had happened and did the bravest thing I had ever done – asked for help. The 3rd person on the list invited me to fly to Memphis the next day to participate in a think tank with a group of hotel executives. He told me, “I can’t pay you, but I can give you access to people who can.”

I signed my first deal at that meeting – a 4-month project for $50K. Not a bad first gig. I had never heard the word “bootstrapping” at that point, but that’s exactly what I was doing.

I took advantage of every interaction I had during that assignment and was able to obtain several more projects, one of which was a contract to conduct sales training 8 days a month making $200 an hour. I found that I was made for that job! More self-discovery: I never knew that I had a passion for inspiring others.

My biggest break came from a piece of business that I won that was a project beta-testing remote hotel sales support for Hampton Inn hotels. Hampton awarded us 20 hotels and a check for $250K. I hired a team of 4 people to help. We soon expanded the business outside of Hilton. Today, my company represents 56 hotel brands, supports 900+ hotel properties, and has 150 employees who have all passed my key interview criteria:  Do they have the experience needed to do the job exceptionally well? And would I go on vacation with them? Our revenues grew to $18 million in 2019, we have ranked on the Inc. 5000 list of Fastest Growing Private Companies in America for the past three years and this year ranked in the Inc. 5000 Best Workplaces.

Our company has been built on 3 driving principles: do what you love, with people you love, and help others. 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. I expect that our growth trajectory will continue, but even in these uncertain times, I’m not worried.

If this company doesn’t work out, I still have 17 people left to call.

Much love,

Toni Jacaruso

June 6, 2020