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If You Know You Know: Daily Summaries Delivered
by Victoria morton
Unfiltered conversations with entrepreneurs, creators, and rule breakers. This is where business meets real life. Raw stories, real lessons, and the mindset behind extraordinary success.
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- 4 days ago39 min
Daniel Lo Manto on 5 Locations, Big Mistakes & Bigger Lessons
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 with difficult customers, fake Google reviews, and the realities of growing without losing what made BOSSA special in the first place. Of course, we talk food too. Daniel breaks down what actually makes the perfect sandwich, shares one of his favourite Montreal hidden gems, and tells us which Montreal spot is currently inspiring him. From sandwiches and scaling to mistakes, money, customers and Montreal’s food scene, this episode goes way beyond what’s between two slices of bread. Watch the full episode of If You Know You Know now.
- 1 weeks ago29 min
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.
- 2 weeks ago55 min
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.
- Aug 19, 202628 min
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.
- Aug 12, 20261h 5m
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!
- Aug 6, 202651 min
Olivia Smart on The Reality of Life as an Olympic Athlete
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 figure skating, how much Olympic athletes actually make, the biggest mistake people make when chasing success, how she found her way into elite sport, and why mental health and stronger support systems for athletes are more important than ever. This is an honest conversation about resilience, ambition, and what success really looks like when the cameras stop rolling. If you've ever wondered what life is truly like as an Olympian, this episode is one you won't want to miss.
- Jul 30, 202655 min
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.
- Jul 16, 202644 min
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.
About If You Know You Know
Unfiltered conversations with entrepreneurs, creators, and rule breakers. This is where business meets real life. Raw stories, real lessons, and the mindset behind extraordinary success.
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