Boston Barber Co. Owner Found His Calling Cutting Hair in Parents’ Fleet Street Basement

Robert Dello Russo today owns Boston Barber Co., with locations on Beacon Hill and in the North End, but he got his start as a barber by the time he reached his early teens, inauspiciously plying his trade out of the humble basement of his parents’ Fleet Street apartment.

The 44-year-old North End native started “fooling around” with barbering at about the age of 12 or 13, as he describes it, by cutting the hair of his friends and relatives who couldn’t afford a haircut. “Charging was out of the question,” he added.

Cutting hair came naturally to Dello Russo, he said, and before he knew it, he was as skilled as a professional barber.

“I had too many clients and was spending the whole day in the basement,” he said, “so it got ridiculous.”

By the age of 15 or 16, Dello Russo said he “started getting a little bit serious” and began charging $5 per haircut. 

His makeshift barbershop then consisted of a chair, which, he said, wasn’t even a proper barber’s chair, and he worked using a pair of cheap clippers he bought at CVS.

In time, however, Dello Russo acquired a professional barber’s chair and station for the space, and his father “indulged” him, he said, by outfitting it with a counter and a sink. He even had a TV and a small restroom down there for customers.

“It was like a little social club with barber’s chair,” he recalled.

Dello Russo called it the “Men’s Den” and even had business cards printed up (albeit on ordinary paper as opposed to on cardboard stock).

As supportive as his parents were of his business aspirations, they drew the line at allowing him to install a barber’s chair outside their home, Dello Russo said.

An ongoing joke around the neighborhood back then was that Dello Russo is in fact the fabled Demon Barber of Fleet Street from “Sweeney Todd: The Demon Barber of Fleet Street,” the 1979 Broadway musical that later spawned a 2007 film adaptation directed by Tim Burton.

“I did in fact grow up on Fleet Street my whole life,” Dello Russo said, “but not in London.”

By the time he reached his late teens, however, Dello Russo had all but abandoned barbering, which he then viewed as more of a pastime than as a possible profession. “In my basement, it wasn’t real,” he said.

Instead, he tried his hand as a carpenter and as an electrician, among other occupations, but nothing seemed to click for him.

It was then that Dello Russo began pursuing a career in barbering in earnest, eventually going on to graduate in 1996 from New England Hair Academy in Malden.

Afterwards, Dello Russo worked at a few barbershops, both in and out of the city, but all the while, he aspired to be his own boss.

“I had a vision about what kind of barbershop it would be,” Dello Russo said, “so I quit my job and started looking for a space in the North End.”

In 2007, Dello Russo opened his first barbershop (now called “Boston Barber & Tattoo Co.”) at 113 Salem St. with two barber chairs. He has expanded in that location every year since then to now include 12 barber’s stations and a full service café with an espresso bar, as well a tattoo parlor, which he opened in 2011 after building on an empty lot adjacent to his building.

While the addition of the tattoo parlor might seem like an odd expansion move for a barbershop, Dello Russo said it made a lot more sense to him than opening a tanning or nail salon there, as others had suggested to him.

“Everything else that popped up took away from the integrity of what I created,” said Dello Russo, whereas in contrast, tattoos are  “an art form that goes along with being a barber.”

In hindsight, Dello Russo said: “I wanted something that would be attractive businesswise and would get people talking, and it worked.”

The Salem Street barbershop expanded yet again in the fall of 2019 when Dello Russo took over the adjacent space previously occupied by North End Nails.

In 2011 – the same year he added the tattoo parlor to his Salem Street barbershop – Dello Russo purchased the Beacon Hill barbershop at 124 Bowdoin St.

Dello Russo walked up there during a snowstorm, hoping to get an audience with the owner, Peter Fenerlis, whom he’d never met before. On his person, Dello Russo had a Bill of Sale certificate he printed himself, as well as a backpack full of cash, he said, so the owner “would know [he] wasn’t joking around.”

Dello Russo’s overture was well received, and he walked out of there that day as the proud owner of his second barbershop.

As for expanding to Beacon Hill, Dello Russo said the decision was a “no-brainer” for him.

“We were the only barbershop on Beacon Hill for a long time,” he said, “so all anybody had to do was care and to make the place nice [to succeed].”

Owning the Bowdoin Street barbershop had also been a dream of Dello Russo’s since childhood when he would pass the Capitol Barber Shop at 124 Bowdoin St. on his way to the State House to visit father, also named Robert Dello Russo, who was then working as chief of staff for former Massachusetts Speaker of the House and State Rep. Sal DiMasi.  “I swore that one day I would own that shop,” he said.

The Bowdon Street barbershop has operated under several different owners since opening in 1922, and once counted John F. Kennedy, who, prior to reaching the White House, lived in an apartment upstairs, among its loyal patrons.

Today, both locations of Boston Barber Co. are regularly patronized by local elected officials, including Mayor Martin J. Walsh and Dello Russo’s childhood friend, State Rep. Aaron Michlewitz, who, in his 20s, lived a few doors down on Fleet Street from Dello Russo’s childhood home and began getting haircuts from him in the basement.

“I wanted to be supportive and help my friend out,” said Rep. Michlewitz, “and he gave a really good haircut. He was a natural in that sense, and I’ve been going to him ever since.”

In fact, Rep. Michlewitz said although he looks out the window of his State House office onto the Bowdoin Street barbershop, he still makes the trek to the North End to get his hair personally cut by Dello Russo, who works out of that location.

Upon moving into Beacon Hill, Dello Russo did his part to complement the adjacent State House, he said, by installing a gold-leaf painted sign with all gold accents, as well as white marble countertops that match the stone steps leading to the building. 

“I did my very best to uphold the style and integrity of the neighborhood,” he said.

Three years ago, the Bowdoin Street barbershop expanded when Dello Russo took over the space next door previously occupied by a dry cleaners, bringing the total number of barber’s stations at this location to seven.

While the pandemic hit his industry particularly hard over the past year, Dello Russo credits his “amazing staff,” including Nikki Medieros, his manager, and Steve Silver, his assistant manager, for their unwavering commitment to Boston Barber Co. throughout it all.

And as he celebrates his first decade on Bowdoin Street this year, Dello Russo is well aware of how far he has come from cutting hair in his parents’ basement.

“My goal was to become a staple in Beacon Hill,” he said, “and I sure hope I’m on my way to achieving it.”

For more information or to book an appointment at either Boston Barber Co. location, visit bostonbarber.com.