One of Toronto's most well-known hoteliers, Steve Gupta, got his start in real estate by owning a different type of business that also provides a place for weary travelers to rest and be revived.

It led to a career with some interesting choices for an executive who, personally, has never been big on rest.

Gupta's career in real estate can be traced to 1978 when he purchased a car and truck stop in Port Hope, Ontario, about 110 kilometres east of Toronto, that was once a Texaco.

"I worked there seven days a week and traveled from Toronto. I was going back and forth. I was there every day by 6:30" a.m., said Gupta.

These days, as the founder and executive chairman of Gupta Group and Easton's Group, he oversees an empire that includes 19 hotels in Canada, with six under development, representing renowned brands such as Marriott, Hilton, IHG and Starwood.

While growing up in India, Gupta learned that there is no such thing as a day of rest.

"My father had a construction business, and there is no day off over there. The only day off was if it was raining," Gupta said.

His father didn't own real estate, but as a government contractor, he knew a few things about real estate that he passed on to his son.

Gupta landed in Canada in 1971, but because of a requirement to be in the country for one year to be licensed as a broker or agent, he decided the next best thing was insurance until he could start his real estate career.

He worked for an insurance company as he built up capital, again with little rest: "I was the top salesman in my first year," he said.

Thirty years after he bought the car and truck stop that came to be known as Easton's Service Centre, he sold the property in 2009, but the lessons from his entry into the real estate world are lasting.

"The truck stops used to be good [business] for Sunday night to Thursday. On Fridays and Saturdays, they were dead. So we created a blend for cars and trucks. It was good that if people missed an exit, they would actually come back" on the highway, he said.

Gupta wasted no time turning the centre around and, in his first few weeks of ownership, secured a meeting with the president of Texaco, who appointed him as the company's general manager for Canada.

The fledgling entrepreneur convinced Texaco to try a new payment system that was more convenient for trucking companies and offered greater rewards. He essentially created his own currency that drivers could spend at his stop.

"I negotiated a higher discount with Texaco. I took a risk and was rewarded, and so were my customers," Gupta said.

His workday started at 6 a.m. and every day from 10 a.m. to 2 p.m. he called trucking companies about his business plan to grow the stop to 200 employees.

Gupta doesn't think his story is much different from that of every successful entrepreneur.

"Entrepreneurs are born. They come wired up. Something clicks, and they take off like a rocket. I had the knowledge, the intellect, the passion to work hard and make things happen," he said.

Everyone in commercial real estate had to start somewhere. CoStar's First Job column explores where careers began.