Linda Hewlett

Real Estate Investor

Linda Hewlett has been a prolific investor and leader in the Boston, Massachusetts real estate sector since 1989. Over the course of her career, she has cultivated a portfolio of more than 50 rental properties and commercial real estate investments that continues to grow in value, and she is always looking for opportunities to expand it further.

Linda was born and raised in Salem, Massachusetts, a small community known for its infamous witch trials in the 17th Century. After a brief stint at Carnegie Mellon University in Pittsburgh, Pennsylvania, Linda transferred to the Massachusetts Institute of Technology in Cambridge, Massachusetts, whereupon she immediately fell in love with nearby Boston, the city which she would later adopt as her permanent home. During her time in university, she worked as an assistant clerk treasurer to help cover tuition, the cost of textbooks, and everyday expenses.

Although her initial interest was in finance, Linda Hewlett was introduced to real estate investment while helping some friends find living spaces to rent and buy while still in school. On the strength of the resounding success she found acting on behalf of her friends, after graduation, she made the decision to pursue a career in real estate full time. Since then, she has not looked back. Linda credits her innate love for people and her passion for her profession for her many notable achievements.

Where did the idea for your career come from?

I was still in university when a few friends first enlisted my help to find somewhere for them to live. They were a few years ahead of me in school. Having graduated and recently become engaged, they were looking to find a good spot in the Boston area to start a life together. Knowing I had a knack for sniffing out a good deal, they thought to approach me, and I was more than happy to oblige. It took me less than a week to find an ideal property for them—and it was a steal! After that, I suppose word made its way around campus, because before I knew it, other friends and acquaintances started asking for my help finding rental units and reasonably-priced houses for purchase. At a certain point, it occurred to me that real estate investment might be my future. I’m so glad I pursued it. I love it so much.

What does your typical day look like and how do you make it productive?

After sleep and some early morning exercise, my typical day begins with opening my smartphone and laptop to scour the city for good real estate deals. If I find something intriguing, I will look into it further. A lot further. If a property really jumps out at me, I might even spend a few hours researching it. However, that does not happen every day. On days when I’m not knee-deep in property analysis, I will tend to my portfolio by checking the market forecasts, crunching data sets, and monitoring my investments. I tend to stop around 6 pm and eat dinner. After that, I make sure to allot some time for family and recreation. Work isn’t everything, after all.

How do you bring ideas to life?

I’m a big proponent of envisioning the outcome you want before setting about working on an idea. I believe in the power of optimism and positive thinking. Employing techniques like that can do nothing to hinder and everything to help with the execution of any enterprise.

What’s one trend that excites you?

I’m excited by the trend of professionals who have been working remotely since the onset of the COVID-19 pandemic leaving large cities to live in small towns, villages, or even the countryside. It’s prompting some interesting developments in the real estate market and creating some brand new avenues for opportunity.

What is one habit of yours that makes you more productive as an entrepreneur?

I sleep for a minimum of seven hours each and every night. For me, that is the perfect amount of rest to maintain productivity without fatigue or loss of mental processing power. Anything less, and I notice a decline in my daily work performance.

What advice would you give your younger self?

If I could go back in time and give my younger self some advice, it would be to make sure to enjoy youth. Once you enter the professional world, there is precious little time to enjoy yourself the same way you can before graduating from university.

Tell us something that’s true that almost nobody agrees with you on.

The Boston Red Sox will win the 2022 World Series. I don’t think a lot of people would agree with me about that, but I have faith. Go Sox!

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Be organized. Keep meticulous records, especially when it comes to debts, assets, taxable earnings—anything that has to do with finance. There are literally dozens of instances in the past when doing so has saved me from serious consequences. As an added bonus, keeping organized records ultimately saves time. Instead of wasting half an hour digging through a stack of documents in search of a specific piece of paper, with the aid of a solid filing system—and all you need to make one is a cabinet, some folders, and some labels—the same task can be completed in less than a minute.

What is one strategy that has helped you grow your business?

I use a strategy that combines careful analysis with patience. I research every property that I’m interested in very intensely, and then I wait until the price is right to make an offer. It’s a little bit more complicated than I’m making it out to be here, but boiled down to its base elements, that’s the strategy that has brought me so much success with real estate investment. It’s how I built such a profitable portfolio.

What is one failure you had as an entrepreneur, and how did you overcome it?

I’ve made one or two investments that turned out to be lemons, especially early in my career. I dealt with these problems by selling them off at no gain to myself or even a modest loss, and then resolving to delve deeper into research before purchasing anything else. Although I only made this particular mistake once or twice, I believe that I am the better investor for having learned this difficult lesson.

What is one business idea that you’re willing to give away to our readers?

I think that a business retrofitting houses with solar panels, updating heating and cooling systems to consume less power, and installing other green technology could do very well in today’s real estate climate. There are all kinds of tax breaks and incentives available to people who make their properties more energy efficient, so creating a company that specializes in that field could grow very fast.

What is the best $100 you recently spent? What and why?

This is a bit of a boring answer, but I paid off some credit card debt. I always make sure to pay off my cards each month in full in order to avoid incurring the high interest rates associated with carrying a balance. Due to my background in finance, I’m well aware of the awesome power of compound interest. Lenders love it—and justifiably so. Borrowers, however, should fear it.

What is one piece of software or a web service that helps you be productive?

I use Zillow all the time. It is, in my experience, the best overall app for scouting new real estate listings.

What is the one book that you recommend our community should read and why?

I wholeheartedly recommend The Millionaire Real Estate Investor by Gary Keller. Anyone who wants to make a career out of investing in property can benefit from the wisdom that book contains.

What is your favorite quote?

“Real estate cannot be lost or stolen, nor can it be carried away. Purchased with common sense, paid for in full, and managed with reasonable care, it is about the safest investment in the world.” — Franklin Delano Roosevelt

Key Learnings:

  • Be organized and keep meticulous records. The advantages of doing this are too numerous to list.
  • Before making a major purchase, such as a piece of real estate, research it thoroughly. Find out every bit of information you can. Once you are satisfied, look at the market and figure out how it ought to be valued. Then, be patient; wait for the optimal time to buy.
  • Pay off your credit cards or any other high-interest debt as soon as possible to avoid incurring compound interest on the principal borrowed.