Some conversations stay with you long after they are over. This is one of them.

Kim Mason is someone I deeply admire for her intelligence, her humanity and the way she makes everyone in her presence feel heard and seen. She dreamed of becoming an anthropologist and journalist, but a summer job at RBC changed everything. Almost four decades later, she holds one of Canada's most senior banking positions.

But our conversation isn't really about her career. It's about the paths we walk in life—some we choose and others that seem to choose us.

Kim opens up about saying yes to the unexpected, balancing work and family, and how the people closest to her encouraged her to embrace a career-defining move. We explore why empathy can't be performed, what listening reveals that numbers can't, and how thoughtful advice can change lives.

I close with the advice I give anyone seeking direction in their career: how to find your passion and pursue it. It begins with the four rewards we seek from our work—and why some matter more than others.

When my 90-year-old mother-in-law moved into our home earlier this year, caregiving became deeply personal. Seeing the stairs, stubborn jar lids, fear of falling and loss of independence through her eyes changed how I understood aging, dignity and love—and inspired this conversation.

Millions of people in the middle of their own lives suddenly become caregivers. Most arrive untrained, unprepared and too often unsupported, yet they keep showing up because love asks them to.

Few understand that journey more deeply than Amy Coupal, CEO of the Ontario Caregiver Organization. As a child, Amy helped care for her brother, who lived with cerebral palsy. Years later, she walked beside her mother through cancer and palliative care. Today, she helps her father navigate life in his late eighties, holding their ordinary moments close because she knows their time together is not unlimited.

Amy gives voice to the exhaustion, guilt, anticipatory grief and invisible mental load carried by caregivers. Leanne Kaufman, President and CEO of RBC Royal Trust, then explains how honest conversations and thoughtful planning can answer some of caregiving's hardest questions before a crisis makes them urgent.

This is a deeply personal story—but it is also one that may profoundly affect any of us as our lives, and the lives of those we love, unfold.

Aaron Bethune lives his life. Musician. Writer. Strategist. Mountaineer. Seeker. Philosopher. Promoter and Publisher. His approach is one we can all learn from.

So many words of wisdom to take away: 'I like to get to the corner to see what's next before deciding to go forward or change lanes.'

Or

Success is not always the award, the applause, or even the destination.

Sometimes success is freedom.

Sometimes it is presence, being in the present.

I hope you take away as much as I did from Aaron Bethune.

Canada Day is more than flags and fireworks. It is a reminder that this country was not inevitable. It was imagined into being by people who chose union over drift and compromise over collapse.

My guest is JDM Stewart, author of The Prime Ministers: Canada's Leaders and the Nation They Shaped. James brings history to life by showing us Canada's prime ministers not as saints or villains, but as flawed, ambitious, and consequential leaders who shaped the country we inherited.

We talk about Macdonald, Laurier, Borden, Mackenzie King, Pearson, Louis St. Laurent, the two Trudeaus, Quebec, Western alienation, sovereignty, and why too many young Canadians know more about American presidents than the leaders who built, bruised, defended, and reimagined Canada.

This is not a history lesson. It is a Canada Day wake-up call. If we don't know how Canada was made, how can we understand what is at risk?

I close the show with my thoughts on what Canada and Canadians must do for us to remain strong and free.

To purchase J.D.M. Stewart's book: https://a.co/d/09mFoxzX

My guest today is Tim Moore, a serial entrepreneur with immense character. Tim's upbringing included failing a few grades, studying to become a priest, then becoming a teacher and eventually a truck driver. His life changed when he bought a secondhand pickup truck, covered it with a tarp, placed a newspaper ad, and started a moving business charging seven dollars an hour.

From there, he built AMJ Campbell into Canada's largest moving company, then Premier Executive Suites and many more ventures across real estate, storage, mortgages, hospitality, and more.

But that is his resume. This conversation is about something deeper.

Tim talks about fear as a warrior emotion, humility as a superpower, manners as a business strategy, and why the way you treat people is the true measure of success. He understood early that a move is never just boxes and furniture. It is people trusting you with their memories, their stress, their hopes, and their next chapter.

Later in the show, Kim Mason, Executive Vice President and Head of Private Banking at RBC, joins me to talk about Tim and what it means to stand beside entrepreneurs not only when things are going well but also when everything is on the line.

Tim is a fantastic storyteller with many career and life lessons.

To buy Tim's book: How I Made It: Secrets of a Self-Made Multi-Millionaire

https://www.indigo.ca/products/how-i-made-it-secrets-of-a-self-made-multi-millionaire?variant=46831238414546

Happy Father's Day.

Did your father ever try to bottle liquid manure, only to watch it explode in the sunlight while sitting in a store window display?

Did he ever bet the family's fortune on a machine he believed could extract gold from sand?

Did he buy horses before figuring out where to keep them, then decide the house would do?

Did he lose the rent, the car, the business, and occasionally the plot, but somehow never lose his love for his children?

Welcome to the unforgettable world of Dacker.

In my Father's Day special, I sit down with Lori Thicke, author of Dreamer's Daughter: Surviving My Childhood and Raising My Father.

Lori was only ten when her mother left. From that moment on, she and her younger brother Brad were raised by their father, a war veteran, salesman, dreamer, schemer, serial entrepreneur, and eternal optimist.

Dacker's ideas were often outrageous. His timing was questionable. His plans were usually missing a few important pieces. But his love for his children was never in doubt.

Lori's story takes us from Kirkland Lake to Paris, from childhood chaos to a life of purpose, including her role in helping create Translators Without Borders. Along the way, she searches for understanding of her father, her mother, her childhood, and ultimately herself.

This is a Father's Day episode with houses burning down, a car taking out three brand-new yachts, the Count and Countess of Albania staging a coup from Dacker's kitchen, plenty of humour, and a whole lot of heart.

Because sometimes the most imperfect fathers leave behind the most unforgettable stories and the most unquestionable love.

And at the end of the episode, I offer a personal tribute to my own dad, and to all fathers, the ones who are here, the ones we miss, and the ones who did their best with what they had.

To buy Dreamer's Daughter: https://www.indigo.ca/products/dreamers-daughter-surviving-my-childhood-and-raising-my-father

Not long ago in Canada, who you loved could cost you everything.

Betty Baxter knows this because it happened to her.

Betty was an elite athlete, an Olympic captain, a pioneering coach, and one of the rare women leading at the highest levels of international sport. Her athletes trusted her. Her program was working. Her future was bright.

Then, on a cold November night in 1981, Betty was told to drive to a roadside motel between Ottawa and Montreal. Inside, three of the most powerful men in Canadian volleyball were waiting. They did not ask about her athletes, her results, or her vision.

They asked one question.

"There are rumours that you are gay. Do you deny that?"

Betty's answer was stunning in its courage. "I am the same person I have always been."

Soon after, Betty was pushed out of the sport she loved.

But this is not only a story about prejudice, power, and what was taken from her. It is also a story about what Betty did next.

She became an activist, a human rights advocate, a builder of community, and a champion for women in coaching, fairness in sport, and every person who has ever been told they do not belong.

Betty's story reminds us that Pride began as courage. As risk. As people standing up when standing out could cost them everything. This is Betty Baxter's story - and it matters.

And stick around as I then chat with Eric Turner and Isadore Chung about Pride, belonging, representation, and why respect must be more than words on a page.

To buy Outspoken - Betty Baxter's book: https://five.libsyn.com/show/episodes/new

Robin Devine has spent her life knocking on doors, sometimes literally, and finding opportunity on the other side. Raised by her grandmother, Robin learned early that hard work, honesty, courage, and instinct could take you places credentials could not.

As a little girl, she sold lilacs and rhubarb door to door. As a young woman, she walked into an advertising agency with no portfolio, no experience, and talked her way into a job. By twenty-three, she was selling Checker automobiles out of a broken-down garage, turning old taxis into reverse status symbols.

What follows is a remarkable conversation about grit, reinvention, and seeing value where others see nothing. Her energy and passion are contagious as she shares her life story from advertising to automobiles, from Expo 86 to Canadian Tire, from Russian generals to Bestselling Books, Food banks, Shelters, and a Canada Watch she proudly markets with proceeds helping those in need.

This episode is timeless.

It is about agency and refusing to wait for permission.

You can also help support Canada's Food Banks and Shelters, by purchasing a special edition Canadian Watch. https://www.timeisticking.ca/