If You Know You Know | Podcast on RSS.com

If You Know You Know

If You Know You Know

by Victoria morton

Entrepreneurship Self-Improvement

Season 1

William Rossy on What People Get Wrong About Success & Happiness

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 advice they wish they knew sooner. After interviewing everyone from everyday strangers to high-level entrepreneurs, executives, creators, and fascinating people around the world, we wanted to know: What has Will learned from all of them? We get into how Sprouht started, the reality behind creating viral content, what millions of views actually mean, and how Will approaches strangers and gets them to open up on camera. He shares the biggest lessons and patterns he’s noticed after thousands of conversations including what successful people have in common, whether money actually makes people happier, the regrets that come up again and again, and what he now believes truly makes a fulfilling life. We also bring it back home to Montreal. Will shares his favourite hidden Montreal gems, the places he thinks deserve more hype, his relationship with the city, and how being from Montreal has influenced the person and creator he’s become. Plus, we talk about ambition, success, purpose, social media, building a community instead of just chasing views, the conversations that have stayed with him the most, and the advice he’s personally taken away from the people he’s interviewed. After spending years asking everyone else the big questions, this time Will Rossy is the one answering them. Watch the full episode of If You Know You Know with Will Rossy of Sprouht.

Corey Shapiro on Celebrity Clients, Dream Collaborations & Taking Risks

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 and put Vintage Frames on some of the biggest names in music and entertainment. We get into Montreal vs. Miami, his favourite Montreal restaurants and hidden gems, how relationships and networking helped shape his career, and why Elton John remains the ultimate dream collaboration. Corey also opens up about the side of entrepreneurship people don’t always see: the hardest moments of building his company, taking risks when there was no guarantee they would work, staying relevant as trends change, and what he would do differently if he were starting again today. Plus, we talk about celebrity stories, sneaker culture, personal style, Montreal’s influence on his brand, the evolution of Vintage Frames, what success actually looks like behind the scenes, and his best advice for anyone trying to build something of their own. If you’re into fashion, entrepreneurship, Montreal culture, celebrity stories, or just want to know how Vintage Frames became Vintage Frames, this episode is for you. Watch the full episode of If You Know You Know with Corey Shapiro.

Inside Yans Deli: Benji Greenberg on Leaving Joe Beef & Building His Own Restaurant

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.

Zach Macklovitch on Montreal Nightlife, A-List Parties and a $35K Mistake

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 truly special, why its nightlife has always had a culture of its own, and how the city compares to Toronto when it comes to clubs, crowds and going out. Zach also opens up about one of the biggest mistakes of his career, a mistake that cost him $35,000 and what he learned from it. Plus, he shares some of his most legendary DJ stories, how Montreal nightlife has changed over the years, what he thinks the city is missing today, and where he sees the future of Montreal nightlife heading. If you’ve ever wondered what really happens behind the scenes of Montreal’s biggest parties, this one is for you!

Tatiana Londono on her Biggest Regrets, Success & Building an Empire

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 her business, and how the power of social media and personal branding helped take her company to the next level. The conversation dives into the story behind her most expensive listing, a wild condo experience she'll never forget, the biggest regret of her career, what success truly means to her today, and the mindset that's guided her through decades of entrepreneurship. Tatiana also shares her favorite restaurants and hidden gems in Montreal, discusses leadership, building a winning team, and the lessons she's learned about business, money, and creating a life on your own terms. Whether you're an entrepreneur, interested in real estate, or simply looking for inspiration from someone who's built an extraordinary career, this episode is filled with honest conversations, practical advice, and stories you won't hear anywhere else.

Two Women Challenged a Billion-Dollar Industry

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 products they use every month. Amanda and Bianca explain why they created Collecteur, the importance of organic period products, and how education, transparency, and innovation are changing the future of menstrual health. They also open up about the truth behind building a startup, the challenges of launching a purpose-driven business, breaking into a competitive industry, and what it's really like being female founders in Canada. Whether you're curious about period care, entrepreneurship, or the future of women's wellness, this episode is packed with eye-opening insights and practical takeaways. If you care about your health, love supporting Canadian businesses, or want to hear the story behind a company that's challenging the status quo, this episode is for you.

JORDAN SHORE

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 realities of content creation, discussing what's real versus what's staged online and what it actually takes to build an authentic audience. Jordan also opens up about his upcoming projects, including his exciting collaboration with Hanna Puley, the costume designer from Heated Rivalry, and what’s next for him creatively. From hidden gems and social media to the biggest differences between Montreal and Toronto, this episode is packed with insights, laughs, and plenty of debate. If you love food, travel, content creation, and discovering the best spots in Canada, this episode is for you. Don't forget to like, comment, and subscribe for new episodes every week!

Julia Brownstein on Family Legacy, Shoe Trends & Building Relationships

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 unique sense of style, the fashion trends she loves, the ones she thinks should disappear, and how the city's fashion scene has evolved over the years. Julia also shares some of her favourite hidden gems around Montreal, the neighbourhoods she loves, and what makes the city such a special place to live and work. From family legacy and business to fashion, retail, and Montreal culture, this episode is full of great stories, insights, and plenty of laughs. Whether you're a fashion lover, entrepreneur, or simply someone who loves Montreal, you're going to enjoy this conversation.

Cary Tauben on Fashion Trends, Partying with Kate Moss & Building a Career

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 way including the time he accidentally screamed at David Beckham, partying with Kate Moss, and the shocking story of stolen goods right before one of his major campaign shoots. Cary also shares his thoughts on Montreal's evolving fashion scene, current trends, personal style, and what it really takes to stay relevant in such a competitive industry. If you love fashion, celebrity stories, entrepreneurship, and behind-the-scenes industry secrets, this is an episode you won't want to miss.

Steve Marcone on Inside Montreal’s Restaurant Scene & What People Don’t See

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 business, and some unforgettable moments along the way including Cole Caufield stopping by his restaurant to eat. Steve opens up about the highs, the stress, and what it really takes to survive and stand out in one of the city’s most competitive industries. If you love food, hospitality, entrepreneurship, and behind-the-scenes restaurant stories, this episode is for you.

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