Getting to Know You: Linda Hewlett, Real Estate Investor

Originally hailing from Salem, Massachusetts, Linda Hewlett is a professional real estate investor now based out of Boston.

After high school, Linda enrolled in Carnegie Mellon University in Pittsburgh, Pennsylvania, but transferred to the Massachusetts Institute of Technology (MIT) in Cambridge, Massachusetts midway through her undergraduate degree. Upon settling in at MIT, she immediately became smitten with neighboring Boston, its people, and its unique culture, even taking a job as an assistant clerk treasurer in the city in order to help pay for her school expenses. Boston made a lasting impression on Linda, and as time went on, she grew more and more attached to the place the locals call ‘Beantown,’ and eventually resolved to make the city her permanent home.

Linda Hewlett studied finance in university, excelling in her courses and planning to pursue a career in that field after graduation. However, a favor asked by some friends during her senior year at MIT made her question that choice. Looking for an appropriate place to live and start a life together, a couple that Linda was well-acquainted with approached her for help with house hunting one day, knowing that she had a knack for uncovering good deals. Harboring a secret interest in real estate for as long as she could remember, Linda agreed eagerly, and found the couple a suitable and well-priced home within just a few days. Closing the deal seemed to come naturally to Linda, and on top of everything else, she found it fun. Indeed, the whole experience prompted her to rethink her career path, and that very same week, she made the decision to become a professional real estate investor.

Since 1989, Linda Hewlett has been a fixture of the Boston real estate investment community. She now boasts a robust and balanced portfolio, featuring over 50 rental properties and commercial real estate investments, and she is always looking to add to it. A humanitarian at heart, she cites an innate love for people and a passion for her chosen vocation as the reasons for her success in the real estate sector.

What do you currently do at your company?

Put simply, I buy properties. Sometimes I develop them, thereby increasing their value. When that process is complete, I either sell them for a profit or hold on to them as long-term investments. To give an example for each instance, I once bought a vacant lot for a certain amount of money, and then spent the next few months building a structure fit for a commercial venture on top of it. I had electrical and plumbing infrastructure installed. I made sure it was zoned correctly. In the end, I sold that property to regional restaurant chain that wanted to open a new location in that specific area of the city, and made a tidy amount of money by doing so. The restaurant is still there. From what I understand, it’s thriving. By contrast, I purchased a small apartment building some years back, made some cosmetic and structural improvements to it, and hired a property manager to deal with the tenants. But I’ve held on to that property to this very day, and it has returned a nice profit for me every single year.

What was the inspiration behind your business?

Ever since I was a little girl, I’ve been interested in houses and buildings. There was even a time when I flirted with the idea of becoming an architect. I put all that aside when I started my post-secondary education, though, opting instead to study finance. I thought that would give me a more stable future. What changed my mind about the idea of real estate investment as a career was an encounter I had shortly before graduation. Some friends of mine asked for my help in finding a decent place to live in the city, knowing that I loved that sort of thing. I agreed, of course, and found the resulting hunt to be not only exciting, but fulfilling, as well. I think it took me all of three days to find them their dream starter home. It was then that I experienced a ‘eureka’ moment about my career path. Although I didn’t really want to be a realtor, I thought that my training and background in finance would qualify me to be an excellent real estate investor.

What defines your way of doing business?

The first descriptor that leaps to mind is ‘research-intensive.’ I conduct a lot of research on any property that interests me. Beyond checking all the usual online reference tools, I mean. I’ll head down to the country clerk’s office and analyze the original blueprints. If the building in question is inhabited, I’ll question the current occupants—whether they’re residential tenants or business owners—about its history and soundness. I also have an extensive network of real estate experts and city officials that I routinely consult before making an offer. The expertise and insight that they provide is invaluable to me. Some people might think operating this way is overkill, but I find it to be extremely effective. I like to know everything about what I’m investing in.

What keys to being productive can you share?

I find my productivity is often tied to my physical well-being. It stands to reason that if I’m not feeling my best, I won’t perform my best professionally. So, I try to eat healthy. Recently, I’ve cut out refined sugars—unless it’s someone’s birthday and there’s a cake, or it’s some other special occasion like that—and I’ve really noticed a positive difference. I also make sure to sleep for a minimum of seven hours each night. I find that it’s much more difficult to crunch numbers if I’m fighting off drowsiness.

Tell us one long-term goal in your career.

I would like to have 75 quality properties in my portfolio before entering into semi-retirement. At that point, I would like to manage my assets while sitting on a beach somewhere in the Caribbean, soaking in the sun and sipping on maitais.

What would you tell your younger self? 

I would tell my younger self to go with your gut. You’re fascinated by buildings and properties, so why not just embrace it? No matter what you tell yourself, real estate investment is your future. I’d also suggest to young Linda that it might be wise to start setting aside some money for investment sooner rather than later—maybe that way she and I could move my semi-retirement to the Caribbean forward by a few years.

What’s the most valuable lesson you’ve learned through the course of your career?

When I bought my first used car, my parents imparted a valuable lesson: Always check under the hood and always kick the tires. It’s sort of a folksy way of saying ‘don’t just take the seller at their word,’ and it is excellent advice. It applies to many other situations besides buying a used car. It applies to business ventures and business partners alike, or any major purchase. It’s the reason I conduct so much research before making an offer to buy a property or agreeing to put up cash for a joint investment.

What advice would you give to others aspiring to succeed in your field?

First, when faced with the prospect of investing a large amount of money, there is no such thing as too much research. Second, don’t get too fixated on squeezing as much profit out of a deal as you can. There are other important things in life besides money. Family and friends are important. Maintaining good health is important. Recreation is important. Too often in the real estate investment community, people become a bit warped in their quest for profit.

What are some of your favorite things to do outside of work?

For physical activity, I love hiking and bicycling. For nights with my family, nothing beats a good board game. When I’m alone, I like to read crime novels and watch romantic comedies. As I’ve intimated in some of my other answers, I always have one eye fixed on a Caribbean island, either vacation-wise,  or with respect to my forthcoming semi-retirement.

What are a few influential books you’ve read and/or websites you keep up with that you’d recommend?

Regarding real estate investment, I would definitely recommend The Millionaire Real Estate Investor by Gary Keller. I learned an incredible amount of useful information from that book. If anyone out there is just interested in some compelling reading, I would recommend Josephine Tey’s The Daughter of Time for fiction and Truman Capote’s In Cold Blood for non-fiction.