Entrepreneurs Exposed

Andrew Blackmon co-founded The Black Tux after a frustrating tux rental before his own wedding, and has since grown it into a nine-figure menswear company serving around 2 million customers. In this conversation, originally recorded for Shopify Masters, Andrew pulls back the curtain on the hidden complexity behind the brand, from in-house dry cleaning and tailoring to custom reservation technology. He also shares what it was like to lead hundreds of employees in his late 20s, how therapy made him a better CEO, and why he once gave 10,000 customers his personal cell phone number. Learn more about your ad choices. Visit megaphone.fm/adchoices

Bryan Gelman built Albert Gelman Inc. from a basement into a leading insolvency and restructuring firm, and in 25 years he's sat across the table from thousands of business owners at their lowest point. In this episode, he shares the messy, behind-the-scenes reality of building a company, what the current real estate downturn means for owners and lenders, and the patterns he's seen in why businesses fail and why some come back stronger. His core message for any founder: financial trouble doesn't have to mean the end, as long as you catch it early. Learn more about your ad choices. Visit megaphone.fm/adchoices

From aerospace engineering to helping build Rhode, Versed, and Merit Beauty, Melanie Bender has spent her career inside some of the biggest names in modern beauty. Now she's the Founder and CEO of Lore, a fragrance brand built on a philosophy that flips the usual playbook — define your beliefs first, build the brand world second, and let the product come last. In this episode, Melanie shares how that approach took Lore from 150 to over 250 Sephora doors in just months, why she believes luxury today is a feeling and not a price point, and what a decade of operating experience taught her about knowing when a brand is actually going to work. Learn more about your ad choices. Visit megaphone.fm/adchoices

Ronan Levy has spent his challenging entire industries. After beginning his career as a corporate lawyer, he went on to build companies across medical cannabis, psychedelic therapy, consumer health, and now functional beverages—often entering markets years before they became mainstream. Along the way he's helped build and exit multiple companies, taken a psychedelic medicine company public on the NASDAQ, co-authored The Ketamine Breakthrough, and become one of the most recognizable voices at the intersection of innovation, wellness, and regulation. Today, he's the Co-Founder of Fun Loving Company, whose first product, Misdemeanor, is trying to redefine what a social drink can be. Ronan joins me to discuss building businesses in controversial industries, navigating public perception, why success doesn't solve your problems, and what he's learned after several entrepreneurial ventures. Learn more about your ad choices. Visit megaphone.fm/adchoices

Gail Kasper left college with two thousand dollars, no job, and no car — and started answering phones sixteen hours a day. Today, she trains Fortune 100 companies. Gail is also a two-time TEDx speaker, TV host, Author, and creator of Cockatoo Selling, a real-time sales system — and SAD-T, a framework for staying in logic under pressure. Today we're getting into how sales has changed, whether something customized can scale, her stint on the Apprentice, and much more. Enjoy! Learn more about your ad choices. Visit megaphone.fm/adchoices

Today is my conversation with Zechariah Thomas, founder and CEO of Swift Hockey. A former competitive hockey player, Zechariah saw firsthand how expensive the sport had become for families. So at just 19 years old, he set out to challenge some of the biggest brands in hockey by building high-performance equipment at a more accessible price point. Since then, Swift Hockey has sold tens of thousands of sticks, generated millions in sales, secured a deal on Dragons' Den, expanded across North America, and earned Zechariah a spot on the Forbes 30 Under 30 list. In this episode, we discuss the rising cost of youth hockey, why participation is declining, what it takes to build a challenger brand in a category dominated by giants like Bauer and CCM, and how Zechariah is using entrepreneurship to make the game more accessible for the next g Learn more about your ad choices. Visit megaphone.fm/adchoices

Saud Juman's journey spans three very different chapters. In his early 20s, he built a business in the nightclub world: one that, on the surface, looked like success, but came with real risk, misalignment, and consequences he didn’t anticipate. At 25, he made a defining decision to walk away, moving back into his mother’s basement searching for a different path. That path became PolicyMedical—a healthcare technology company he built from scratch, scaling it over nearly two decades to serve millions of patients across North America, before a successful exit. And now, a third chapter—stepping into professional sports, serving as President of a Canadian Elite Basketball League team.In this episode, we talk about those transitions; what it means to walk away, rebuild, scale, and ultimately “own your exit” at every stage of life and career. Learn more about your ad choices. Visit megaphone.fm/adchoices

Today is my conversation with Kevin Gould, co-founder of Glamnetic, previously recorded for Shopify Masters. We cover the real story behind Glamnetic’s growth—from scaling to $50 million, hitting a plateau, and what actually broke inside the business during that phase. Kevin walks through the pivot from lashes to press-on nails, why it worked, and how they rebuilt the company to cross $100 million.Enjoy! Learn more about your ad choices. Visit megaphone.fm/adchoices

Brad Bradford is the City Councillor for Ward 19, Beaches–East York, and a mayoral candidate in 2026. In this episode, Brad unpacks what’s really happening in Toronto today. From a worsening housing crisis to some of the worst congestion in North America, declining transit safety, and rising concerns around crime and community well-being.  Brad shares his perspective on what’s broken at City Hall, where policy and execution are falling short, and what it will take to restore momentum in one of the world’s most promising cities. This is a candid discussion about housing, infrastructure, safety, and the future of Toronto’s economic and entrepreneurial ecosystem. Learn more about your ad choices. Visit megaphone.fm/adchoices

Julianne Costigan is the Founder & CEO of Costigan — a styling and personal branding company built on one powerful idea: style isn’t about clothes, it’s a leadership strategy. Over the past 15 years, Julianne has styled more than 300 women across industries like law, medicine, tech, finance, and media. Her work reframes personal style as a tool for confidence, visibility, and influence — helping women (and men) show up with intention in every room they enter, not just on the big stages. In this episode, we explore the evolution of her business, the psychology of executive presence, early lessons that shaped her craft, and why everyday moments—not just high-stakes ones—define your personal brand. Learn more about your ad choices. Visit megaphone.fm/adchoices