Roger Andrews never thought of himself as a salesman, and when he was younger he even thought sales was a necessary evil. That attitude flipped 180 degrees when he got into real estate a decade ago and started pitching other investors to buy into the properties he was accumulating.

“If I’m selling something of value and if I’m providing somebody a chance to profit, while I’m making a profit, then that’s a good thing,” he said. “‘That's capitalism, right?”

Andrews found success in a world that was far from his career as an illustrator, where he has built a business that has some major corporations as clients, including the giant toy maker Hasbro.  

It was not a path he imagined as a young artist. “I was the guy who spent my time drawing comic books,” he said.  

After high school in his home town of New Bedford, Mass., he went to the Butera School of Art in Boston, originally to train as a sign painter. But then was awarded a scholarship to study commercial art. 

“I was very fortunate — it rerouted the trajectory of my entire life,” Andrews said. “I became known for doing illustrator work because I had a visual style.”

A few years into his art career, first as an illustrator at Hill Holiday in Boston and then as the proprietor of Roger Williams Illustration, he realized he wanted another way to make money. 

“I said to myself ‘let me find something that has income while I’m sleeping,’” he said. “Let me do the real estate thing. I had owned my own home so I knew the value of building equity.”

He read some books about real estate investing and he was off to the races.

“I liquidated my 401k and bought my first property in 2017 in New Bedford,” Andrews recalled. “I bought a three-family with an FHA (Federal Housing Authority) loan with 3.5 percent down.” 

He bought that first multifamily for $265,000 and “held it for 3-4 years and then took the profits to buy another property.” LIke many investors who sell, he adds: “I should have held on to it.”

“The freelance entrepreneurial spirit — I always had that — I was working for agencies all over the world, I did a lot of work in New York and LA,” Andrews said.

He had taught at Butera and one of his students who had started working at Hasbro connected him and he did illustrations for table top games like Clue, Risk and Operation. 

Meanwhile, on the real estate side he plunged in, buying properties remotely as far north as Maine and as far south as Georgia. (He lives in Westport, MA.)

“I threw myself into the fire. I made every single mistake you can make as a landlord, dealing with lead, dealing with tenants, dealing with lockouts,” Andrews said. “It wasn’t fun, but you know everybody wants to maximize cash flow.”

He had watched his grandparents manage their own three-family, the equity they later used to pay for their elder care. “I got to see that process — the rent collection, the clogged toilets …” so the idea of managing property was not foreign to him. “I’ve had a flood, fire, there was a murder, you name it — everything has happened. I’ve had properties seized by the city, I've had evictions.”

At his apex in 2021, Andrews owned 144 units in 42 buildings with various partners, thinking he was on his way to 1,000 units, but he has pulled back in the last couple years and now has five buildings. He was heavily invested in Rumford, Maine, a city that was hit hard by a flood in December of 2023.

“A lot of people left and the people who stayed couldn’t leave and the quality tenant pool diminished,” he said. “There were a lot of property management challenges. I'm 4.5 hours away and I can’t manage the managers. They were not being as responsive to me and the tenants and it became more problematic than I wanted it to be.”

There was also a lot of maintenance that came with owning older buildings, including new roofs and heating systems, which impacted profitability.

“If I had to do it again i’d look for newer construction,” he said. “Right now I feel like I have armor and I know where to buy, what to buy and how to stress test.”

For those who are thinking of getting into real estate, or growing a portfolio, Andrews has these words of advice: “A lot of it is not being so risk averse. You have to absorb that risk and you have to be OK with it.”

What is your special real estate superpower?

Probably capital raising. It’s a skill that I never knew I had because I was always a shy kid. I was never the captain of anything … Then I realized I had courage. I had the ability to raise capital, whether it was privately from individuals, or working with companies, or banks and credit unions. The ability to talk to someone and give them a reason to invest in something. I never knew I had that ability.a

What was the hardest lesson you learned early on in your real estate journey, and how did you overcome that and persevere?

I think the hardest lesson was learning that you can’t do it all. When you self manage you can’t be the guy — when you first start out you want to save money and get every bit of cash flow then you realize you don’t want to be the guy settling disputes between tenants or going door to door to collect rents or shovel snow out the driveway. So I hired a property manager to solve that problem. 

What advice would you offer to somebody looking to get into real estate or grow a portfolio?

The number one thing to do, and I learned this through trial by fire, is to have significant reserves. Keep some capital on the sidelines. I would highly recommend that when you enter the first property, if it’s $200,000 for the first property, I would have $100,000 in reserve. You never know when you are going to have a roof leak or an issue with the heating system. You never know when you are going to have a tenant who is going to trash a unit and you are going to pay $35,000 to renovate.

Among the strategies a property owner could pursue — long-term rental, mid-term rental or short term, (Airbnb), co-living — what works best for you, and why?

For me it's been long term, it’s the least trendy, but it’s the most stable over time. I don’t think people are going to be as transitional over time. With AI and robotics coming, jobs are going to be harder to come by and people are going to need places to stay for decades. Long term is the path. My longtime girlfriend has been going with Airbnb, and it’s been driving her crazy.  

Higher property taxes and insurance premiums are pushing up escrow costs, another barrier to affordability for a battered U.S. housing market, according to a recent report from the housing data analytics firm Cotality. Previously affordable states in the Midwest and South are facing the highest increases, with average payments up 45% nationally over the last five years and over 50% in states like Nebraska, Kansas, and Wyoming. “Rising escrow costs are a growing financial burden,” said Cotality principal economist Archana Pradhan. “This financial strain can deter many from entering the housing market … At the same time, existing homeowners are getting squeezed, especially those who are on fixed incomes or tight budgets.”

California’s push to allow the construction of multi-story buildings near major transit stops is approaching crunch time and some cities are starting to look to delay implementation. SB 79, which goes into effect on July 1, permits mid-rise, multi-family housing  of up to nine stories) within a half mile of transit stop of light rail, heavy rail, and bus rapid transit. Los Angeles put off compliance for now last month when the city council opted to overhaul its zoning map to buy it more time to plan for these developments. Smaller municipalities with fewer professional planners and resources, may be forced to accept the requirements of the state law, while others may try to resist following it altogether.

Goodbye to Britain’s architectural tradition of grand halls with towering arched panes of glass, Georgian townhouses with their sash windows and charming Tudor cottages with their diamond casements. Today, new construction must accommodate the reach of a small, older woman. The British Standards Institution recommends that windows in new buildings should accommodate 95% of the U.K. adult population and Scottish guidelines say they “should be cleanable from inside by 95% of the elderly female population, without the need for stretching.”  It’s another example of overregulation in the U.K., critics say, where the end result will be ugly and ill-proportioned buildings. “You won’t get any attractive buildings by following the regulations,” Stephen Bayley, chairman of the Royal Fine Art Commission Trust, told the Wall Street Journal. “It is difficult to execute such a thing with aesthetic finesse,” 

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