Olafson is the youthful entrepreneur behind a hot new cottage development at Lake Manitoba Narrows, where he has sold almost 290 lots in just nine months.
But he recently let slip that one of his buyers is none other than mega-celebrity James Gandolfini, who played the role of mob boss Tony Soprano on the hit TV series The Sopranos.
Not only is Gandolfini one of today's biggest stars, famous for playing a gangster who hired hit men to take care of characters who crossed him, he is also one of the most private and publicity shy actors and rarely grants interviews.
"I don't know if he would be too happy if a lot of people knew," said Olafson, when approached with the news tip that Gandolfini bought a cottage lot from him.
Too late, Chad.
Other members of Gandolfini's family were actually first to discover this provincial gem where Lake Manitoba bottlenecks like an hourglass, 200 kilometres north of Winnipeg. Two other members of the actor's family bought their properties first.
Gandolfini's brother-in-law, Eddie, used to visit Lake Manitoba Narrows Lodge, owned by Olafson's family, to hunt. He became good friends with Chad, 32. The brother-in-law and Gandolfini's sister, Joanna, even attended Olafson's wedding. "They both flew down from Manhattan," said Olafson.
This was before hit series The Sopranos began in 1999, starring New Jersey-born James Gandolfini.
"(Eddie) said to me that his brother-in-law was a struggling actor, so if you're ever in New York, maybe he can get you in to see something," said Olafson.
"(Gandolfini) had been in a couple of things by then but nothing famous. He was in the movie True Romance. Then he just got super famous super fast."
Olafson, who grew up on an Interlake cattle ranch his father, Blair, still runs, has visited the Gandolfini family in New York. "We went to see (Broadway musical) The Producers -- James took us to that -- and he said let's go for drinks after."
So they went to none other than famous New York landmark Sardi's Restaurant in Times Square. "It was funny. We walked out of Sardi's and right next to (Gandolfini) was this 80-foot poster of him in Times Square. I said to him 'that must make your head feel pretty big, eh man?' "
What did he say? "Aw, nothing. He jokes about how I say 'eh?' all the time."
The last time Olafson and his wife, Brandee, visited New York, he talked to Gandolfini beforehand by phone. "He said, 'Anything you want in New York, you just name it.'" Olafson didn't want to impose on his friend but mentioned it had always been a dream of his to see Saturday Night Live.
"He got us front-row tickets," said Olafson. They met Gandolfini later for dinner at a Manhattan restaurant the actor co-owns.
"He couldn't do anything with us afterward because he was busy, but he gave us his limo for the rest of the night. We just had his chauffeur drive us around Manhattan all night. It was great."
Gandolfini looked at properties in Montana before deciding to buy in Lake Manitoba Narrows. Olafson said Gandolfini hasn't fished or hunted there but likes snowmobiling, boating, riding around on ATVs, "and getting away. He's actually pretty quiet."
Olafson asked if there was any way to suppress news of Gandolfini's interest in the area. Gandolfini has managed to visit without fanfare in the past. "He likes coming out because not too many people know about the place. If people know about it too much..."
However, that kind of news is unlikely to stay secret for long.
Olafson's cottage development is also not well-known. He bought 720 acres -- including a mile of shoreline on the west side of Lake Manitoba, south of the Narrows bridge -- for $2.3 million last December. He immediately began clearing land and build roads.
The lots are not on Laurentian rock, or on sandy Lake Winnipeg shoreline, like many Manitoba cottages. The shoreline can be marshy and the lake is known more for fishing than other recreation.
But when Olafson put his lots up for sale on the market in Alberta, they took off.
"I went to the Home Expression Show in Edmonton," he said. "They sold like crazy. I sold 20 lots a day for a week, 150 lots in one week. It was just ridiculous.
"So many people from Alberta are originally from Manitoba. They move out to follow the oil money. Now they don't want to live there."
About 85 per cent of the 290 lots sold so far have gone to Albertans.
"In Alberta, it's $1 million to live on a lake and the lake is a slough, from what everybody tells me."
Olafson added: "We've got a pretty nice place up here, you know. Albertans tell us that all the time. Manitobans are kind of spoiled and don't always appreciate what we have."
The first four cottages are under construction. Olafson is also building a $2-million golf course. Lakefront lots sold for $55,900, golf course lots for $42,900, and backlots for $25,900. Forty remain but most are backlots.
One appeal to Albertans is that he places no time limit on when owners have to build cottages. That makes them easier for people to buy for retirement.
Many people see the Narrows eventually transforming dramatically from a sleepy sport fishing community to a cottage and even a retirement community.
"I'd like to see it in another 50 to 100 years," said longtime resident John Johnson. "People start retiring there and next thing you know it's another Gimli."