Careers Under Construction

Some of the hardest conversations Jamie Wilson has walked into have started with people yelling at him. His approach? Listen, understand where people are coming from, and find common ground.

He started his career as a teacher before becoming a U.S. Army Ranger, Treaty Commissioner, Deputy Minister, and eventually the first Indigenous Chair of the Manitoba Hydro board.

Today, he serves as VP of Indigenous Strategy, Research & Bus...

Three days after David Asper started practising criminal defence in Winnipeg, he was pulled into his boss’s office. Joyce Milgaard was sitting there. Her son David had already spent 17 years in prison for a murder he said he didn’t commit.

A six-year fight followed, culminating in an April 1992 Supreme Court of Canada decision. Later DNA testing confirmed another man was responsible.

After helping win Milgaard’s fre...

Krystyn MacKinnon started her career in banking at 19 and became an assistant branch manager a year later.

She went on to help launch a title insurance startup across Western Canada, lead 100% commission sales teams, and is now Principal at Colliers Project Leaders—with no technical background in engineering or project management.

In this episode of Careers Under Construction, Krystyn shares:

• The feedback that changed how sh...

Catch Fire Group helps mid-sized business owners sell the companies they’ve spent a lifetime building.

Gary Brownstone’s job is to help owners see their business the way a buyer does.Sellers look back at the sacrifices, risks and legacy they’ve built.

Buyers look at cash flow, growth and what happens when the founder leaves.

In this episode of Careers Under Construction, Gary shares:

• Why he never puts a price on...

Those little paint colour cards you flip through at the hardware store? There's a good chance they were made by one family right here in Winnipeg. The Duha Family.

Rick's first job in the family business was screwing posts into paint fan decks.

Now, a robot does it.

Rick isn't buying robots to replace his team. He's buying them to replace the repetitive tasks.

That's where people get AI wrong. It's not about replacing people — it...

Kyle Romaniuk is a serial entrepreneur who started selling T-shirts on consignment at just 10 years old before launching his own design agency straight out of Red River College.

That agency grew into Cocoon Branding, where he worked with brands like Red Bull and GoodLife Fitness. When COVID wiped out 80% of his agency's revenue, Kyle changed direction and launched FRAKXION.

In this episode of Careers Under Construction, Kyle shares:

In 2018, 20-year-old Hailey Dugay was sitting in the back seat of her boyfriend's truck, heading home with friends.

Earlier that night, Jesse Paluk had been involved in an altercation at a bar near Fraserwood. Later, when three vehicles approached on a gravel road, Paluk stood in the road holding a rifle and told William Comber to have his back.

What no one inside the truck could see was Comber standing off to the side. As Hailey's b...

Dale Weise was cut multiple times during junior hockey before going on to play 513 regular-season NHL games.

Today, he buys and grows established businesses in Winnipeg.

In this episode of Careers Under Construction, Dale shares:

• How getting cut built his determination
• The time he thought he made the Rangers, only to be cut two days before opening night
• How he recorded the fastest Gordie Howe hat trick in Philadelphia Flyers history
• ...

Jenna was studying to become a dentist when she watched an episode of Cake Boss and decided to make a cake just for fun.

She made it in the tiny apartment she shared with her twin sister Ashley. She was hooked right away. Then a competitor called the city on her. That push forced her to turn a hobby into a real business.

Today Jenna and Ashley run Jenna Rae Cakes:

• 4 locations and around 40 employees, heading into their 12th year
• ...

Jaime Mann believes one thing above all else: connection isn't soft, it's strategic.

As a keynote speaker, leadership coach and partner in a construction company, she blends psychology, leadership and a little sass to help people lead with more clarity, courage and confidence.

In this episode of Careers Under Construction, Jaime shares:

• Why connection is one of the most overlooked leadership skills
• What years of anxiety, loss and ...

In 2019, Jason Tyler McLean put a brand new gun in his mouth and pulled the trigger. It jammed. The odds of that happening are one in millions.

He woke up the next day, wrote himself a letter and made a promise he has kept ever since.

Long before he became a coach, Jason was just trying to make it through each day.

Drugs at 13. The streets of Winnipeg at 15. Gangs. A sales career that brought financial success, but not peace.

Then a t...

When Todd Burns took over his dad’s company in 2011, it was a one-man operation running out of a basement.

Today, Cypher Environmental sells green infrastructure products in more than 50 countries and Todd is on a mission to replace toxic road salts with better alternatives.

In this episode of Careers Under Construction, Todd shares:

• Why he refused to compete on price and focused on building better products
• How he spent seven...

Amanda Fiebelkorn didn't know what she wanted to do after high school, so she flew to Tahiti.

After six months of nannying and teaching English, she came home with a new mindset and a new direction.

Today, Amanda is the founder of The Social Manor, working with brands like Canon, Popeye's Supplements, Melted, Don's Photo and other local favourites.

In this episode, Amanda shares:

• Why she didn't wait for years of experience before s...

Three weeks after Nicole Dubé left CTV Morning Live, the role she had just left was eliminated.

She didn't know it was coming. She just knew it was time.

After 20 years in broadcast journalism, Nicole bet on herself and launched DUBÉ MEDIA, where she helps leaders communicate with clarity, whether it's on stage, on camera or in the conversations that matter most.

In this episode, Nicole shares:

• How “embarrassment resiliency&rdq...

Rob Tetrault spent over a decade chasing one number: $1 billion in assets under management.

When he finally hit it, he sat at his desk and felt nothing. No confetti. Just the realization that the goal he'd sacrificed so much for didn't change much.

Today, Rob is the founder of Tetrault Wealth Advisory Group, overseeing more than $1.2 billion in assets with a team of 16. But the story he shares in this episode is about much more than ...

It started with a beer ad during a Jets game.

Taiv co-founder & CEO Noah Palansky was at a bar when he noticed the TV was advertising a competitor’s cheaper pint. He realized restaurants had zero control over the screens on their own walls — and built a solution to fix it.

A few years later, Taiv is in over 5,000 locations across North America, with around 100 employees and more than $20 million USD raised. Noah made ...

Sandy Shindleman started with nothing and built one of Manitoba's largest privately-held real estate companies.

Today, Shindico Realty manages close to 200 properties and $3 billion in assets across Canada and the United States.

In this episode of Careers Under Construction, Sandy shares:

• The roles he played in the early days vs now
• Why he looks at how much he can lose, not how much he can make
• The 2019 stroke that forced him to re...

Most people don't bet their career on a city.Jim Ludlow did.As President of True North Real Estate Development, Jim has helped shape downtown Winnipeg — the MTS Centre, the return of the NHL, True North Square, and now the $1 billion redevelopment of Portage Place and the Bay.In this episode of Careers Under Construction, Jim shares:

• What it really meant to be "the first hire" at True North
• The Phoenix deal that almost happ...

Élise Page and Teri-Lynn Friesen met teaching at a local dance studio. One random conversation changed everything. Now they run Fête Ice Cream & Coffee, one of Winnipeg's most loved scratch-made ice cream shops.In this episode of Careers Under Construction, Élise and Teri-Lynn share:

• What Covid did to their numbers and their biggest lessons learned
• Getting into retail stores like VitaHealth
• The hardest parts of being young mot...