Jerome Dwight

Think gum is harmless? Think again. For years, the $20 billion gum industry has been packed with artificial chemicals, synthetic ingredients, and aspartame—until one entrepreneur decided to change the game.💡 Meet Jay Klein, CEO & Founder of PUR Company, who dared to challenge Big Gum with a clean, chemical-free alternative. His mission? Reinvent gum with simple, natural ingredients and give c...

At just 17 years old, Roy Ratnavel was a prisoner of genocide, trapped in torture camps during Sri Lanka’s brutal civil war. He lost everything—his freedom, his homeland, and nearly his life. But against all odds, he survived, escaped to Canada, and started over from nothing. From working as a janitor, he climbed his way up through the ranks of Bay Street, eventually becoming Vice Chairman of CI G...

In this episode, I had the privilege of sitting down with Rob Khazzam, CEO & co-founder of Float, to talk about what it really takes to build a business that challenges giants, rewrites the rules, and refuses to take no for an answer. Rob’s journey is relentless—from launching Uber in Eastern Europe to fighting through obstacles and raising $70M from Goldman Sachs to fix one of the biggest pai...

In my latest podcast episode, I had the privilege of sitting down with Daniel Lamarre, former CEO of Cirque du Soleil, who shared his incredible journey and leadership wisdom. From navigating the financial crisis and COVID-19 to scaling Cirque into a global entertainment icon, Daniel's story is one of resilience, innovation, and vision. Here are a few standout insights that stuck with me: ✨ E...

What does it take to disrupt Canada’s financial giants, create a new market, and lead a company to a $340 million acquisition? Meet Wayne Pommen, the mastermind behind PayBright, Canada’s first buy-now-pay-later (BNPL) company. In this episode of ChallengerX, Wayne shares the inside story of how he turned a small healthcare lending company into a game-changing e-commerce powerhouse. Discover how h...

What does it take to disrupt the status quo in industries steeped in tradition? Garrett Dennie, CFO of Knix, has spent his career doing just that. From revitalizing legacy retailers like Sears and Rexall to driving innovation at Knix, Garrett shares how challenging norms leads to breakthrough success. Together, we talked about: - How Garrett disrupted traditional models at Sears and Rexall by embr...

What happens when a leader focuses on people over profit? Howard Behar, former President of Starbucks International, transformed the company into a global cultural phenomenon by living out his simple yet profound belief: “We’re not in the coffee business serving people; we’re in the people business serving coffee.” In this episode of ChallengerX, Howard shares timeless lessons on servant leadershi...

"If you think integrity is optional, you’re already falling behind." At least, that’s what Rob Chesnut, former Chief Ethics Officer at Airbnb and author of Intentional Integrity, believes. In this episode of Challenger X, Rob joins Jerome Dwight to reveal why integrity isn’t just about doing what’s legal—it’s about doing what’s right. Drawing from his time at Airbnb and eBay, Rob shares powerful l...

Dr. Stephen Mulholland, world-renowned cosmetic surgeon and co-founder of BoomerangFX, has spent his career revolutionizing aesthetic medicine and empowering physicians to thrive in private practice. From pioneering non-surgical treatments to creating billion-dollar companies like InMode, Dr. Mulholland’s journey is a testament to innovation, resilience, and the power of challenging the status quo...

Steve Southin, co-founder and co-CEO of PAVE, is redefining what’s possible in the automotive world. With groundbreaking AI technology, PAVE is transforming vehicle inspections, bringing unmatched accuracy, consistency, and speed to an industry ripe for disruption. In this episode, Steve and I explore: How PAVE replaced traditional inspections with cutting-edge AI that anyone can use... even his 1...

John Ruffolo, one of Canada’s most influential tech investors and founder of Maverix Private Equity, has spent his career shaping the future of innovation. From building Omers Ventures into a venture capital powerhouse to backing global successes like Shopify, John’s journey is a masterclass in resilience, foresight, and challenging the status quo. In this episode, John and I discuss: - How John n...

Sarah Wells, Olympian and founder of the Believe Initiative, brings a wealth of insights about resilience and leadership that resonate far beyond the track. Her journey from being cut from every high school sports team to competing at the Olympics is a masterclass in grit and perseverance. But it’s her ability to turn setbacks into stepping stones that has inspired business leaders and entrepreneu...

Dr. Talon Maningas reveals how he built a world-class cosmetic surgery practice in Joplin, Missouri, overcoming challenges in a small town to become a leading figure in aesthetic medicine. From embracing innovation with cutting-edge technology to mentoring the next generation of surgeons, Dr. Maningas shares the key principles that fueled his success. In this episode, we cover: - The journey from...

Melanie Pump, CFO, business leader, and author of Detox: Managing Insecurity in the Workplace, joins me to share her insights on leadership and the evolving role of the CFO. We chat about navigating the complexities of corporate finance, managing risk, and aligning financial strategy with business growth, as well as the emotional side of leadership. Together, we talked about: - The evolving role o...

Sanjay Singhal, author and founder of Audiobooks.com, built his career challenging conventions and embracing failure as a tool for growth. From his rise in tech to a public exit with Audiobooks.com, and now as an advocate for mental health and psychedelics, Sanjay has reshaped his own life while disrupting industries along the way. Together, Sanjay and I discussed: How Sanjay's personal battles wi...

Rosa Hoffmann, CEO of DecisioningIT, has built her career redefining the rules of business. As a female CEO in a male-dominated industry and an early adopter of AI, Rosa has shaken up the auto-finance industry with innovation and sheer determination. Together, Rosa and I talked about:- How DecisioningIT leverages predictive AI to reshape automotive lending- Rosa's insights on navigating a male-dom...

Today, we’re excited to welcome Dan Park, co-founder of Clutch.ca and a visionary entrepreneur transforming the way Canadians buy and sell cars. Before launching Clutch, Dan led Uber Eats Canada, gaining invaluable insights on scaling disruptive business models and breaking through barriers. Drawing on those experiences, he set out to challenge the automotive industry by building Canada’s first fu...