Bill Cummings built his billion-dollar fortune constructing commercial properties in the Boston area without ever borrowing a dime, so he knows how to create wealth on his own terms.
He has also learned to appreciate the qualities that one needs to succeed.
Like being frugal.
Eighty-six-year-old Cummings and his wife, Joyce, still clip coupons and fly coach, all because they get a kick out of saving a buck. “It’s fun,” he said.
“You build lifetime habits, and it doesn’t feel good to say, ‘I’m not going to do that anymore,’” Cummings told The Post.
By not owning a private jet or flying first class, Joyce made a new friend in 2017. She struck up a conversation with her seatmate on a flight home from St. Louis.
The woman was headed to Beantown because her son had just been drafted by the Boston Celtics.
And that’s how Joyce got to know the mother of Jayson Tatum. Now she’s the All-Star player’s biggest fan.
“I hear what Jayson did every night, and the next day, ever since,” said Cummings.
In order to get where he is, he tells people to “work hard and save your money. Don’t spend it. Many young people are not taught to save.”
Other tips are spelled out in his book, “Starting Small and Making It Big: Hands-on Lessons in Entrepreneurship and Philanthropy” (Cummings Foundation), which tells his story and offers advice from his decades of running a real estate business and a nonprofit foundation that has given away $500 million so far.
Here are the traits Cummings said are critical to getting a job and sustaining your career.
Show your drive
When evaluating prospective hires, Cummings focuses on a person’s level of determination, which he believes is the key to getting ahead: “Nothing is as important as hard work, desire, persistence and dedication. What idle pleasures are we willing to give up to achieve what we really want?”
He recognizes that distractions are tempting, and that everyone needs some downtime.
“But young people discover how much easier it is to watch the Patriots on TV than struggle to get paid for front-line work,” he said.
“All people have differing skills and abilities, just as we all have our unique flaws and shortcomings,” he writes in the book. “Work regularly at developing a system of strong values, even though we may regularly fall short of those values in our daily lives.”
One example from his own life: He pays his contractors, suppliers and his staff on time and wouldn’t dream of stiffing them.
“Some highly prominent business people have even bragged about [not paying] to show how smart they think they are,” he writes. He termed such practices “despicable.”
Be able to write well
His applicants must take an editing test, he said.
“It’s a densely written one-page letter with 35 mistakes in it. We want to spot it when we have a good writer. If somebody can express him or herself, if they can put their thoughts down on paper, they’re probably smart enough to do a lot of other things, too.”
No one has ever gotten a perfect score, but the top performer, Neil Swidey, worked for Cummings before becoming an acclaimed journalist at the Boston Globe and a best-selling author.
“Infinite curiosity about how things work will be a strong portent of creativity,” he writes.
Cummings launched his career after his dad urged him to buy a floundering fruit-juice company. Bill quizzed the owner about the operation, convinced him the company wasn’t worth much and bought it for $4,000.
“Dad was visibly pleased,” he recalled.
Cummings quickly turned it around, expanded sales into the dining halls at his alma mater, Tufts University, as well as at Harvard and other schools, and sold the firm for $1 million in 1970.
It was all the seed capital he needed to launch his development business.
“I never had to borrow to build,” he said.
Be a problem solver
Cummings believes that “the most valuable colleagues in any firm are typically those who quickly recognize problems when they occur, and then deal with them. Job candidates with curiosity and ingenuity can often do great work.”
During the early years of his company’s growth, Cummings drew criticism from a local paper. He felt the coverage was undeserved, so he started his own publication to provide a different perspective.
He put Swidey in charge, making it clear that the paper wouldn’t cover the owner’s interests or provide good p.r. He asked only that it do its best journalistically.
The weekly was a hit. In 1994, he sold it and two other community newspapers for $1 million.
Find joy in your work
“I loved what I was doing — opportunistically creating value and jobs — more than any financial return,” Cummings writes in the book, adding that people who throw themselves into something “merely for the money inevitably struggle to muster the requisite commitment.
“The secret of entrepreneurship is doing something you look forward to when you wake up in the morning. If you’re not going to really enjoy it, you’re doomed before you even start.”
Luck isn’t really luck, Cummings writes. “It’s being smart enough and prepared enough to recognize and take advantage of good opportunities when they come along.”