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Michael appears in the Top 100

People in Real Estate magazine

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Dellaquila Property Management Inc.

Michael Dellaquila

Winston Churchill said, “Some people dream of success while others wake up and work.” It is an axiom that is easily attributable to Michael Dellaquila, founder and CEO of Dellaquila Property Management Inc., for his is a career path that was carved out methodically, traversed purposefully, and tended carefully. He was not born into a dynasty of business tycoons. He was not heir to a fortune. And there most was certainly no silver spoon that fed him the promise of prosperity. Rather, his is the quintessential American success story, one that saw him rise from humble beginnings as a car salesman to a real estate titan with a portfolio of approximately $20 million and growing. But Michael, himself, will tell you that his success didn’t happen overnight. It took years of hard work and determination—and an unbridled passion for real estate.

In the 1990s, Michael was a middle-class college student whose grandfather owned a small auto dealership on leased land. When he retired, Michael’s father, Frank, who had served as vice president of Farmingdale College, bought the company and the land as well. When Michael graduated with a business degree, instead assuming a role in the family business, he got a job selling cars at a different dealership. “My father told me to go out and get a job on my own. He wanted me to learn, not hand me a career,” he recalls.

Michael lived in a small apartment, earning just $36,000 a year, always putting money to the side. At just 21 years old, he took out a loan and purchased his first property valued at $79,000, then turned it into a rental property. And although he was still selling cars, with this, Michael’s rise had modestly begun. After joining the family business sometime later, he and his father began acquiring properties together while expanding the business to five locations. At the same time, Michael continued to pursue real estate independently. Then in 2008, he and his father sold the dealerships to a large public company, but they made the shrewd decision to maintain ownership of the land and lease it to the new owners. Michael stayed on to manage the five dealerships for three years, and eventually bought his father’s shares in the remaining buildings and land—which he still owns to this day. By 2012, he had acquired five rental properties on his own valued at $3 million, generating him enough income to live. He left the auto industry, and the rest, as they say, is history. Today, as the leader of a thriving real estate firm, Michael’s upward ascent continues, born from a long-ago dream that he refused to let go of.

The Top 100 Magazine spoke with Michael to learn more about his transition to real estate and how Dellaquila Property Management is evolving.


Michael, what kind of properties do you invest in?

In the beginning, I was doing a lot of fix-and-flips, which was a tremendous amount of work, but I wanted to get more involved with commercial, income-producing properties. The flips and residential projects were full of headaches such as evictions, which is not what I wanted to do. Then I discovered a niche in triple-net-leases, which are basically leases with big corporations such as Walgreens, Dunkin’ Donuts, and other big corporations. They are called “triple-net” because they’re exclusive of expenses, which means the rent may be a little bit lower, but you get guaranteed rent from the companies, even if the site closes. Currently, I own properties leased by an auto franchise, drugstores, such as Walgreens, and other large investment-grade corporations, which makes my real estate investments much more secure than privately owned businesses.

What factors make you unique in your investment strategy?


First and foremost, I don’t carry heavy debt, as other investors do. I pay off our assets quickly and if I finance, I never borrow more than 50% of the property’s value. By using these strategies, I’ve built a strong portfolio of holdings, in complement of the revenue streams from those holdings. The reason I don’t like to assume more than 50% debt is in case of a market correction. I always want to have equity in the property in case it must be sold.


What do you enjoy most about your work? What drives you?


Making the deal is always a thrill. It’s not just about the money, it’s the satisfaction that comes from negotiations and strategizing. I’m creative by nature, but I’m also a salesman at heart, so I still get excited with every deal. I’m also an investor in businesses, which is not only rewarding, but aids in marketing the company as well. What really drives me is being able to use my experience and knowledge as a successful investor myself to help so many other investors prosper, and most recently, I’ve been working together with entrepreneurs and business owners to help bring their amazing ideas to life.


What do you consider to be your greatest accomplishments?


First on that list would have to be purchasing a Walgreens. I don’t think I ever imagined that I’d own a multimillion-dollar property outright, with no debt. Also, selling the family dealership to a public company was quite an achievement. On a personal level, my greatest rewards come from engaging within the community. I volunteer as much as possible, and I coach youth sports, something that I started doing 14 years ago for my son’s team. I think my favorite award is the one I received for Volunteer of the Year from the local Boys and Girls Club.


Lastly, Michael, you have some very interesting and energetic hobbies. Can you tell us about them?


I am a blue belt in Brazilian Ju Jitsu. I am also an amateur boxer and have fought at the master’s level and in some charity boxing matches. Additionally, I teach people about fitness, and when I’m not challenging my body, I exercise my sense of humor as a stand-up comedian as well as some life, career, and business coaching on the side and on my social media and YouTube channel.


Michael is a licensed real estate agent, holds a bachelor’s degree in business marketing, and is pursuing an MBA from Suny Old Westbury. 




Michael Dellaquila

CEO/Founder, Dellaquila Property Management Inc.

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