Jerome Dwight

In this episode, we’re joined by Michael Yan, the founder and CEO of Simplify, an AI-powered hiring platform that is revolutionizing the job search experience. Michael has helped over 1 million job seekers streamline the application process using innovative technology.

As a Forbes 30 Under 30 honoree and Y Combinator alum, he’s building a company that’s rapidly growing and transforming the way job opportunities are matched with tal...

From 28 Stores to 30,000—But It Was Never About the Coffee.

I had the incredible privilege of sitting down with Howard Behar, former President of Starbucks and one of the driving forces behind its global transformation.
What made this episode truly special? We invited rising high performers from our BoomerangFX Toronto team to join the live taping. They listened in, asked powerful questions, and left inspired by a masterclass in lea...

From Humble Beginnings to Dragons' Den: The Unstoppable Journey of Manjit Minhas I had the incredible honor of sitting down with Manjit Minhas, one of Canada’s most successful entrepreneurs and a Dragon on the hit show Dragons' Den. Her story is nothing short of inspiring. Manjit’s journey is a testament to resilience, adaptability, and the power of grit. From working in her family’s liquor store at just 13 years old to bui...

In this episode of ChallengerX, I sat down with Brendan P. Keegan—a six-time President & CEO, business executive, and best-selling author—who has raised over $10 billion in capital and scaled a business from $500M to $2.5 Billion.

From his meteoric rise at Electronic Data Systems (EDS) as the youngest Chief Sales Officer in a Fortune 100 company to leading Merchants Fleet through a 5x revenue growth and eventual acquisition by ...

How do you take an idea from your apartment to a $100 million business? In this episode, I sit down with Neil Cuggy, Co-Founder & CEO of GoodFood, to uncover the journey behind one of Canada’s most successful online grocery and meal kit companies.GoodFood is a Canadian online grocery, home meal, and meal kit company that has redefined how people shop and eat. Built on a foundation of quality ingredients, sustainability, and giv...

In this episode, I had the incredible opportunity to sit down with Lexi Miles Corrin, the Founder and CEO of WAXON Laser + Waxbar, one of Canada's leading wax bar chains.

Imagine this: you're 25 years old, you've just signed a lease, built a business from scratch, and the night before opening… you’re sitting in an empty store thinking: “Who am I to do this?”

Lexi didn’t have a background in beauty. She didn’t have an...

What if we told you that traditional banks are falling behind, and blockchain technology is leading a financial revolution? In this episode, Julie Fellows and Gabby Kusz join us to unpack traditional finance and reveal how crypto, blockchain, and digital assets are changing the game!

- Why banks are failing to keep up with modern financial demands

- Why younger generations won’t tolerate outdated banking anymore

- Is crypto truly the...

From selling products out of their backpacks in college to running a multi-million dollar influencer marketing agency—Mat Micheli’s journey is nothing short of extraordinary.When Mat and his co-founder, Joe Gagliese, started Viral Nation, influencer marketing was still uncharted territory. But they saw an opportunity that no one else did—creators were driving massive engagement but weren’t making money.So what did they do? They too...

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 consumers a healthier choice. In thi...

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 Global Asset Management, one of Cana...

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 pain points in business: expense man...

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: ✨ Empowerment fuels creativity: Danie...

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 he navigated fierce competition, s...

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 embracing change and focusing on c...

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 leadership, trust, and building a purp...

"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 lessons on how ethical leader...

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. In this episode, Dr. Mulhollan...

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 100-year-old grandmother!
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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 navigated his early career in the...