If You Know You Know

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...

In this episode, I sit down with Lenny Lighter. A conversation that’s both personal and deeply rooted in Montreal history. Lenny ran one of the city’s most iconic restaurants, Moishes Steakhouse, carrying forward a legacy that spanned generations and helped shape Montreal’s food scene. We talk about entrepreneurship, leadership, and the responsibility that comes with running an institution. Lenny...

Today’s guest is Jon, the founder and owner of MobiSpaw, a startup that’s reimagining pet care on the go. As a true startup guy, Jon has taken a simple idea and turned it into a mobile service that makes grooming stress-free for pets and convenient for their owners. In this episode, we dive into his journey, from the moment the idea clicked, to building a business from scratch, the challenges he’s...

In this episode, we take it back to the beginning of Mandy’s, from a small local salad shop to one of Canada’s fastest-growing food brands. We talk about growth, staying true to quality, sourcing local ingredients, and what it really takes to scale a food business without losing its identity. We also dive into ingredient decisions behind the scenes, including the shift from canola oil to olive oil...

This week on If You Know, You Know, I sit down with Elana. The next generation behind Montreal’s legendary diner, Beauty’s. We talk about growing up inside an institution, the pressure of carrying a family legacy, the chaos of restaurant life, and the moments that shaped her work ethic. Nostalgia, honesty, and a whole lot of smoked-salmon energy. Listen now.

This week on If You Know, You Know, I’m joined by someone who needs no introduction, Harley Finkelstein, President of Shopify, longtime entrepreneur, and genuinely one of the most generous mentors in the business world. Harley doesn’t just talk about success he teaches it. In this episode, we dive into what it really takes to build and scale an iconic global brand, how to stay creative in a fast-c...

This week on If You Know, You Know, I’m chatting with the minds behind If Only Home. The Canadian home-bedding brand that's redefining comfort with conscience. 100% GOTS-certified organic, OEKO-TEX free-of-harm, and crafted in a family-run, Fair Wages™ facility, they’re not just selling sheets, they’re raising the bar for ethical luxury. We’ll talk about what makes them stand out in the crowded wo...

This week on If You Know, You Know, I chat with Julia Grandoni. Creator, businesswoman, and viral queen about what it really takes to turn social media into a full-blown career. From the chaos of influencer life to building her own company, Julia gets real about staying authentic in an industry built on filters. Expect laughs, honesty, and a little behind-the-scenes tea.

This week, I sit down with Anne-Sophie, the creative force behind Anso Atelier, a marketing agency that’s as strategic as it is stylish. From turning a passion project into a full-fledged business to leading a powerhouse team of women redefining brand storytelling, She shares what it really takes to build something timeless in an image-driven industry. We get into creativity, confidence, burnout,...

In this episode of If You Know, You Know, I sat down with wellness creator and entrepreneur Katherine Garbarino, the woman behind Girls Living Well for a real, no-filter conversation about the highs and lows of the wellness world. From her 500 days alcohol-free to her honest take on trends like detoxes, greens powders, and 5AM routines, Katherine opens up about what wellness actually looks. They d...

In this episode of If You Know, You Know, I sit down with Laura, the owner of Georges Laoun Opticien, a Montreal institution where eyewear meets art. From carrying on her family’s legacy to creating a space that celebrates design, individuality, and community, Laura shares the story behind the shop that’s become so much more than a place to buy glasses. We talk about entrepreneurship, self-express...