If You Know You Know

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 topics, including 3-on-3 overtime, the Canadiens’ goalie situation, and where the game is headed.

Plus, a Montreal rapid fire to close it out.

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 with being labeled a "nepo baby." We also get honest about money including the reality of earning on OnlyFans, financial independence, and breaking stereotypes around women monetizing their image online.

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 how to spot emotional unavailability before you waste six months in a situationship. If you’re dating in Montreal (or anywhere, honestly), this one hits.

This episode also features real viewer call-ins asking for advice on situationships, mixed signals, first date confusion, and “what does this text actually mean?” energy. And of course, we break down Netflix dating shows like Love Is Blind as our unofficial case studies on modern relationship chaos. It’s funny, a little savage, very honest, and packed with real dating advice you can actually apply.

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 about seeing herself on screen. We also touch on personal loss, grief, and growth. Including what helped her through the hardest moments and how she protects her mental health now.

This is an honest, balanced conversation about career, visibility, and where Cathy is at today, plus a fun rapid-fire round you won’t want to miss.

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 shares the real story behind how Moishes began, what it was like stewarding a restaurant with decades of history, and the decision to eventually move on.

We also dive into his current chapter as the owner of Prime. What starting again looks like after legacy, the lessons he carried forward, and where he is today as an entrepreneur.

This episode is about legacy, evolution, and knowing when it’s time to build something new.

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 faced along the way, and what’s next for MobiSpaw!

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, and how making thoughtful choices like these plays a role in building a brand that lasts.

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.