If You Know You Know

In this episode of If You Know You Know, we sit down with Richard Dias from The Loonie Hour to talk money, the Canadian economy, real estate, investing, entrepreneurship and, of course, Montreal sports. Richard breaks down the money questions normal people actually want answered: Why is everything so expensive? Is a six-figure salary still a lot of money? Should you rent or buy? What are the bigge...

In this episode of If You Know You Know, we sit down with Montreal entrepreneur and hospitality veteran Dillon Griffin to talk about the restaurant business, Montreal nightlife, entrepreneurship and what it really takes to own and operate successful restaurants and bars. Dillon shares the realities of Montreal’s hospitality industry : restaurant costs, hiring great employees, interview red flags,...

In this episode of If You Know You Know, we sit down with Daniel Lo Manto, the man behind BOSSA and one of Montreal’s sandwich kings, to talk about what it really takes to build a restaurant brand from the ground up and grow it to five locations. Daniel gets into the side of the restaurant business customers rarely see: his biggest business mistake, why eating out has become so expensive, dealing...

Will Rossy, founder of Sprouht, joins If You Know You Know to talk about what he’s learned from having conversations with people from all walks of life and what actually makes a good life. Through Sprouht, Will has built an audience of millions and generated hundreds of millions of views by asking people meaningful questions about life, success, happiness, relationships, regret, money, and the adv...

Corey Shapiro, founder of Vintage Frames Company, joins If You Know You Know to talk about building one of the most recognizable eyewear brands out of Montreal and the unconventional path that got him there. Corey takes us back to the beginning, from getting his start in the sneaker industry to turning his obsession with vintage eyewear into a business that has built a massive celebrity network an...

Benji Greenberg spent years at Joe Beef before leaving to build Yans Deli. We talk about taking the leap, what it really takes to open a restaurant, Montreal food culture, Jewish deli traditions, business mistakes, crazy customer stories, and what actually happens behind the scenes in the restaurant world. If you know, you know.

On this episode of If You Know You Know, we sit down with Zach Macklovitch, one of the biggest names behind Montreal’s nightlife and cultural scene. Zach takes us inside the world of Montreal after dark from the legendary parties and unforgettable nights that helped put the city on the map, to wild stories involving Travis Scott, Tiësto, Kaytranada, A-Trak and more. We get into what makes Montreal...

Join us on this week's episode of If You Know You Know as Tory sits down with Olivia Smart, 4x Spanish National Champion, Spanish ice dancer, and 2022 & 2026 Winter Olympian. Olivia opens up about what it really takes to compete on the world's biggest stage, from the sacrifices behind the scenes to the pressure of performing at the Olympics. She shares the difference between ice dancing and fi...

Join us on this week's episode of If You Know You Know as Tory sits down with Montreal real estate mogul Tatiana Londono. With more than $5 billion in real estate transactions, Tatiana shares the remarkable journey behind building one of Canada's most recognizable real estate empires. She opens up about her upbringing, what inspired her to pursue real estate, the biggest risks she took to build he...

Join us on this week's episode of If You Know You Know as Tory sits down with Amanda and Bianca, the founders of Collecteur, the Canadian company revolutionizing the modern woman’s menstrual experience. From the realities of Canada’s women’s healthcare system to the controversy surrounding the Tampax lawsuits, this conversation dives into the questions every woman should be asking about the produc...

Join us on this week's episode of If You Know You Know as Tory sits down with Jordan Shore for an honest conversation about the food, content, and culture shaping two of Canada's biggest cities. Jordan shares his favourite restaurants in Toronto, how the city's food scene compares to Montreal, and whether Montreal still deserves its reputation as Canada's culinary capital. They also dive into the...

This week on If You Know You Know, we sit down with Julia Brownstein of the Brownstein family behind Browns Shoes, one of Montreal's most iconic fashion success stories. Julia shares what it was like growing up with the Brownstein name, being surrounded by fashion and entrepreneurship from a young age, and how her family's business grew into a Canadian retail powerhouse. We dive into Montreal's un...

In this episode, we sit down with renowned Montreal fashion stylist Cary Tauben to discuss his incredible career in the fashion industry and the stories that come with it. From his early days breaking into the business to becoming one of Canada's most recognizable stylists, Cary shares the lessons, risks, and opportunities that shaped his journey. We dive into some unforgettable moments along the...

In this episode, we sit down with Steve Marcone to talk about the reality of opening and operating restaurants in Montreal. From building concepts and creating experiences to the pressure behind running a successful spot, Steve shares what people don’t realize about the restaurant industry and the work that happens behind the scenes. We also dive into Montreal’s food scene, the challenges of the b...

In this episode, we sit down with Terry DiMonte to talk about his journey into radio, the evolution of broadcasting, and what it was really like building a career behind the mic. From the early days of getting into radio hosting to unforgettable celebrity encounters including meeting Elton John, Terry shares stories, lessons, and moments from a career that helped shape Montreal media. We also dive...

In this episode, we sit down with Chuck Hughes for a behind-the-scenes look at what really happens in the kitchen. From wild kitchen horror stories to the pressure of becoming a celebrity chef, Chuck shares the moments that shaped his career and the chaos that comes with it. We go back to how he got his start in the food industry, working his way up through the grind of restaurant kitchens, to bec...

In this episode, we sit down with Eva Alexopoulos as she opens up about her return to comedy and what it’s really like getting back on stage. From the nerves to the excitement, Eva shares what performing live means to her and how it feels stepping back into the spotlight. We also dive into how she first got started in comedy, including the story behind her very first stand-up gig and the moments t...

In this episode of If You Know You Know , we sit down with Jake Karls to talk about the real side of entrepreneurship, beyond the highlight reels. From building Mid-Day Squares from the ground up to navigating the pressures that come with growth, Jake opens up about the mindset it takes to keep going when things get tough. We dive into personal growth, the importance of therapy, and how to handle...

In this episode, I sit down with Brent Gilchrist to talk about his time in the NHL, what it was like playing in Montreal, and how life has changed since stepping away from the game.

In this episode, I sit down with Dom Cooks to talk about how he turned a passion for food into a full-time brand. We get into content creation, entrepreneurship, burnout, and what it really takes to grow an audience in today’s digital world.

In this episode, I sit down with Guy Carbonneau former captain of the Montreal Canadiens and Stanley Cup champion. Wetalk about what it’s really like playing in Montreal, one of the most intense hockey markets in the world. We get into leadership, the pressure of wearing the CH, and how the game has evolved from speed and conditioning to today’s style of play. We also dive into current hockey topi...

In this episode, we take a deep dive with Caroline Vreeland for an unfiltered conversation about fame, motherhood, and building your own identity in the age of Instagram and OnlyFans. We talk about trying for another baby, what it's actually like growing up with the “Vreeland” last name and Montreal hot spots. Caroline opens up about body shaming, internet criticism, and the pressure that comes wi...

In this episode of If You Know You Know, I sit down with Montreal love coach Kavita for an unfiltered, honest conversation about modern dating, red flags, and why ghosting feels like a full-time personality trait in 2026. We dive deep into what’s actually happening on dating apps like Hinge and Bumble, why so many people say they “aren’t ready for a relationship” but are still swiping daily, and h...

In this episode, I sit down with Benjamin Roy from Heated Rivalry to talk expectations vs. reality, what filming was really like, and how life changed once the show took off. We dive into behind-the-scenes moments, cast dynamics, recognition, and what the experience taught him plus a fun rapid fire featuring his Montreal hidden gems and coffee order.

In this episode, I sit down with Cathy Skinner, who many of you know from Below Deck. We talk about why she chose yachting, what working on yachts is actually like, and what reality TV looks like behind the scenes once the cameras are on and off. Cathy opens up about navigating social media and public attention, how quickly opinions become part of your everyday life, and what surprised her most ab...