The artifacts of a nearly century-old family firm decorate Thomas Bosley’s real estate headquarters in Davisville Village. There’s a portrait of a venerable looking William H. Bosley, the company’s founder, framed pictures of the sons and grandson who followed in his footsteps, and the vintage shingle that announced the firm’s birth in 1928.

In a conference room, a wall is covered with certificates from a trade that for residents of cities with vertiginous property prices can become an unhealthy obsession. They honour the Bosley name across the decades as presidents of both the Toronto Real Estate Board (TREB), which William helped found in 1920, and its national analog.

Tradition can be stifling. But there’s nothing of the stuffy scion in Thomas Bosley, the 68-year-old grandson of the company’s founder. He likes to keep things light, and his employees seem happy to oblige.

“Make sure you get a picture of his socks,” a receptionist shouts as Bosley poses for a Star photographer. Bosley immediately hikes up his pant legs and reveals black socks with big white polka dots and a splash of red up the heel. “I buy them for my management team,” he says, smiling.

Bosley has the relaxed satisfaction of a self-made man in the twilight of his career. Despite its deep roots, W.H. Bosley and Co. was drowning in debt when Thomas took it over in 1985. He turned it around by focusing almost exclusively on residential property sales, and by training real estate agents who last year made $1.3 billion worth of property transactions under his company’s banner.

“My business philosophy is have fun and make money,” says Bosley, president and broker of record of the rechristened Bosley Real Estate Ltd.

The golf clubs and balls in his office on Merton St. make that clear enough. He putts them down stairs, along hallways and eventually to the basement during the office “tournaments” he organizes. “We have prizes.”

Another habit is to rise from the desk that once belonged to his late father and look out the window. He sees across a driveway and into the main office space of a separate building, which is also part of his headquarters. By eyeing the agents at their desks, and the cars in the company parking lot, he gets a good idea of who is around making deals.

“One day, I looked out at the office there and my No. 1 sales agent mooned me,” he says. “How many companies can you do that to the president?”

Bosley expects the good times to keep rolling, and rising prices so far prove him right.

There were 101,299 homes sold in the GTA in 2015, a 9.2-per-cent increase compared to 2014, according to the Toronto Real Estate Board.

The GTA’s sales growth continued this year. In February, 7,621 homes were sold, 21.1 per cent more than in February 2015. The average selling price for all homes rose 14.9 per cent in the region year over year and hit $685,278. In Toronto, the average price of a detached home stands at $1,211,459. “Buying intentions are strong for this year as households continue to see home ownership as an affordable long-term investment,” said TREB president Mark McLean, who is also a manager at Bosley, in a February statement.

Affordable isn’t the word most buyers would use. There are recurring questions about the market’s stability, given growing household debt and the certainty that interest rates will one day increase. Tom Bosley dismisses the fears. Toronto has all the attractions of an international city, he says. Even people who once fled to the suburbs want back in.

He sees a lack of supply as a key source of climbing prices. Land for single-family Toronto homes is growing scarce. At the same time, fewer people can afford to move, for example, from semi-detached homes to detached ones. More people stay put, supply remains low, nerve-racking bidding wars break out and prices keep going up.

“I’ve got three people looking for semis in North Toronto,” says Bosley’s daughter, Christan, an agent with the firm, “and I can tell you there has not been a livable one on the market in the last four months that’s sold for less than $1.1 million. It’s crazy.”

Residential properties weren’t part of the business plan when Bosley’s grandfather opened his shop on Adelaide St. in 1928. The company managed commercial properties.

Homes became part of the portfolio in 1953, when William’s sons, Raymond and Murray, bought the company. Even then, much of the business involved buying out homeowners or landowners to assemble large tracts of land for clients with big plans. They assembled land for the building of Toronto City Hall, the downtown Bank of Nova Scotia and the Ford plant in Oakville.

Thomas Bosley, Raymond’s son, joined the business in 1968. He started as an appraiser of commercial properties. He hated the work. It was all facts and figures with little human interaction. He wasn’t crazy about his salary, either, just $5,000 a year.

In the mid-1970s, Bosley cut a deal with his father: he would give up his salary, move to the Yonge-Lawrence office, and live strictly off commissions he made on house sales. In his first month, he earned $12,000.

“That’s when I went, ‘Now I know what this is about,’” he says.

By 1983, the company had 300 salespeople in nine offices in the GTA. But branches outside Toronto were bleeding. Perhaps incredibly for a real estate company, it owned none of the buildings that housed its branches. And a bank loan without collateral was impossible.

Bosley went to his father and uncle with an ultimatum of sorts. He would buy the company by paying off its debt. If they refused, he would strike out on his own.

“My uncle, who basically ran the business, recognized that I was the general manager of the residential division and if I left everybody left with me,” Bosley says. “And so they got their act together and that’s how I ended up buying this.”

Today, Bosley Real Estate owns all but one of the buildings that house its seven branches — five in Toronto, one in Jordan (near St. Catharines) and another in Niagara-on-the-Lake.

Some 250 real estate agents work as independent contractors, with no benefits, under the Bosley banner. They pay a sliding percentage of their property transactions to the company — the more they make, the less they pay. In return they get the backing of a full-service company, including receptionists, in-house mortgage brokers and an eight-week training course. Agents who do little business eventually get “a nudge out the door,” Christan says.

Last year, Bosley realtors were involved in the buying or selling of 1,500 properties.

“My retirement is guaranteed,” Bosley says.

The perils of being the boss’s daughter

It goes without saying that the continued existence of family-owned firms, no matter how successful, depends entirely on offspring. Nine years ago, Thomas Bosley decided to test the intentions of his.

His wife’s son from a previous marriage worked on Bay Street and made clear his career wasn’t in real estate.

Bosley’s daughter, Christan, was in university, thinking of possibly becoming a lawyer and majoring in psychology and criminology — “perfect for a real estate agent,” her dad says.

“My dad tricked me,” says Christan. “He told me he was selling the company to Royal LePage and I had such a strong reaction that I thought I’d better take my (realtor’s) licence. To this day, I’m sure he was just testing me.”

By the time Christan started selling real estate in 2007, her mother, Ann, had been company vice-president for 14 years. Ann and her husband made sure Christan paid her dues.

“So, because I’m the boss’s daughter, what did they do? They made an example of me: I had to sit in the middle of the floor with 25 other agents, listening to me make cold calls,” Christan says, referring to the pitching of services to randomly called homeowners.

“I’m 22 years old, I’m nervous making cold calls in the first place; now I have to do it with 25 people watching me. It was pretty brutal. But, you know, you get used to it,” she adds, as her father chuckles.

Christan is now one of the company’s top realtors. She recently teamed up with another realtor and they share commissions for all new clients equally. But success has not made life at the office any easier as the boss’s daughter.

“Social relationships with your colleagues don’t happen, ever,” she says. “Everybody looks at you very differently and you have to work that much harder to prove the fact that you’re successful because you’re successful and not because Mommy and Daddy hand you leads.”

Christan, who has a broker’s licence, wants to one day take over the company. But her father’s real intentions, despite the test he threw at her, remain a mystery.

“He’s so cagey,” she says, sitting at a conference table with her parents. “Try to find out what he’s going to do with this company — cagey, cagey, cagey.”

Ann, at 65, is slowly relinquishing her duties and spending more time at her vacation home in South Carolina. But Thomas is harder to pin down, suggesting at one point that he will let go of the reins, but adding at another, “I don’t think I will ever retire.”

In any event, Ann says, Christan isn’t ready because she has yet to manage one of the company’s branches. “The salespeople,” Ann adds, “would very quickly lose respect for her: ‘Wait a minute, kid, what branch did you manage?’”

“It’s kind of funny that she talks like this,” Christan replies. “We have this argument frequently because our (company) general manager actually disagrees with your comment.”

There’s also the chance a rival company will make Bosley a buyout offer he can’t refuse.

“I get approached all the time,” he says. “But no one has wanted to write a cheque yet, so there’s really no consideration of it.”

Christan says she won’t begrudge her parents if they decide to cash in on the company they built. Besides, she doesn’t expect life at the top will be easy, no matter how healthy the family firm is today.

“There’s an immense amount of pressure, being the fourth generation,” Christan says. “Do I want to take it over and tank it in the next five years? No. I mean, there’s a lot of pressure!”

A Bosley family tree

• William H. Bosley was born in 1889 in Somerset, England. He came to Toronto at 23 and worked in the CP Railway yards for $40 a month. In 1920, he helped set up the Toronto Real Estate Board and, later, the Ontario Real Estate Association. His company, founded in 1928, was for decades based at 27 Wellesley St. E. In WWII, he was a special adviser on land acquisitions for the Defence Department. He also chaired the Toronto Harbour Commissioners (now PortsToronto). He died in 1965.

• Murray Bosley, William’s eldest son, was born in 1915. A story in the Toronto Daily Star called him the “youngest realtor in Canada” when, at 14, the Toronto Real Estate Board made him a member. He was an executive with a Crown corporation that built affordable housing for war workers and veterans, before serving as an artillery officer in Europe. He and his brother, Raymond, bought his father’s real estate company in 1953. In the early 1970s, he campaigned to save Union Station. He died in 2013.

• Raymond Bosley was born in 1921. He served as a lieutenant in the Second World War, became president of the Toronto Real Estate Board in 1958 and, later, president of the family firm. “He taught me compassion and ethical dealing,” says his son, Thomas. Raymond died in 2013.

• Thomas Bosley, 68, won’t say how big the debt was when he took over the family firm in 1985. He bought his first home in 1976 for $56,000, with a $1,000 down payment, then renovated it himself and sold it nine months later for $65,000. He bought and sold eight more homes for a profit before marrying and settling into a North Toronto home for 26 years.

• Ann Bosley, 65, began at Bosley Real Estate as a receptionist. She married Thomas in 1983, went on to build the company’s most successful branch and set up the training course for new realtors. She has been president of both the Toronto Real Estate Board and the Canadian Real Estate Association. “The better the sales agent, the easier they make it look,” she says. “So you are constantly fighting clients who think your job is a piece of cake.”

• Christan Bosley, 30, is the mother of a 14-month-old boy. Her husband is an appraiser of commercial properties at a different firm. She got her first taste of real estate during her final year at Western. “I was lucky enough to have an inheritance and I figured I could be immature and go to Europe and blow it and have the time of my life, or I could save my sanity and move out,” she says, laughing. “So I bought a condo.” Three properties later, she lives near her parents in North Toronto.