Jerome Dwight

Jerome Dwight
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Jerome Dwight

Welcome to The Challenger Mindset Podcast, the podcast spotlighting disruptors and innovators who are redefining the future of business. Hosted by Jerome Dwight—entrepreneur, business leader, and growth strategist—this podcast dives deep into the minds of trailblazers who embrace bold action, tackle tough decisions, and challenge the status quo. Join us for thought-provoking conversations on leadership, resilience, and the pivotal moments that drive transformation and success in today’s business landscape.

  1. Bankwyse CEO & Blockfills COO on The Future of Crypto & Digital Markets

    6 DAYS AGO

    Bankwyse CEO & Blockfills COO on The Future of Crypto & Digital Markets

    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! We discuss: - Why banks are failing to keep up with modern financial demands - Why younger generations won’t tolerate outdated banking anymore - Is crypto truly the future of finance, or just hype? The future of finance is digital. The question is, will banks evolve, or will they be replaced? What do you think—can traditional finance catch up, or is it already too late? Like, comment, and subscribe for more exclusive insights from industry leaders.

    37 min
  2. Viral Nation CEO Mat Micheli's $100M Influencer Marketing Agency

    FEB 18

    Viral Nation CEO Mat Micheli's $100M Influencer Marketing Agency

    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 took action. They cold-emailed every brand they could, secured their first $10,000 brand deal, and built what is now one of the world’s leading influencer marketing agencies. In this episode you'll learn How Mat & his co-founder turned a $50 influencer gig into a multi-million dollar empire.- The cold emails that landed their first big brand deal ($10,000!)- How COVID-19 became their biggest opportunity while others panicked- The #1 hiring mistake founders make—and how to build an all-star team- The future of social media marketing & influencers Mat’s story is proof that entrepreneurial success comes from courage, relentless execution, and the ability to pivot at the right time. The best ideas don’t win. The boldest actions do.

    29 min
  3. Disrupting the $20B Gum Industry with Clean Ingredients, PUR Company CEO Jay Klein’s Bold Revolution

    FEB 12

    Disrupting the $20B Gum Industry with Clean Ingredients, PUR Company CEO Jay Klein’s Bold Revolution

    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 this episode, we explore:✅ Why the gum industry has resisted clean alternatives✅ How Jay Klein built a challenger brand from scratch✅ The power of consumer demand in driving industry change✅ What every entrepreneur can learn from taking on billion-dollar giantsThis is not just a business story—it’s a revolution in clean consumer products. #GumIndustry #CleanLiving #ChallengerBrand #JayKlein #PURCompany #PURGum #Entrepreneurship #HealthyChoices #Disruptor #Innovation

    21 min
  4. From Torture Camps to Vice Chairman of CI Global Asset Management | Roy Ratnavel’s Unstoppable Rise

    FEB 5

    From Torture Camps to Vice Chairman of CI Global Asset Management | Roy Ratnavel’s Unstoppable Rise

    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 Canada's largest investment firms with over $130 billion in assets under management. Roy’s journey is the ultimate testament to resilience, grit, and the power of owning your destiny. In today’s episode of the Challenger Mindset Podcast, we dive into his incredible story—how he transformed unimaginable hardship into an unstoppable drive for success, the principles that guided him, and the mindset that helped him break through every barrier. 🔥 In this episode, you’ll learn: The traumatic events that shaped Roy’s life and leadership philosophy How he turned pain and loss into relentless ambition The secret principles that helped him stand out on Bay Street (Canada's Wall Street) Why "Communicate, Differentiate, Appreciate" became his personal success mantra His advice for young people facing adversity: "Take responsibility, control your input, and fight for every heartbeat." 📚 Check out Roy's bestselling book, "Prisoner 1056," where he shares the full story of survival, resilience, and triumph. Don't miss this inspiring conversation that proves no obstacle is insurmountable. 🚀 Subscribe to the Challenger Mindset Podcast and hit the notification bell to stay updated on our latest episodes!

    35 min
  5. How Float CEO Raised $70M from Goldman Sachs

    JAN 29

    How Float CEO Raised $70M from Goldman Sachs

    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 management. 🔥 Key takeaways from our conversation: ⚡ Speed wins. The fastest-moving companies out-innovate the biggest ones. 🎯 Customer obsession is the ultimate strategy. If customers love what you’re building, they’ll tell you exactly what they need next. 💰 Raising capital isn’t just about money. The right investors bring expertise, network, and alignment with your vision. 📈 Growth isn’t enough—it has to be sustainable. Rob and his team focus on profitable growth that delivers real value, not just vanity metrics. This isn’t just another fintech startup. Float is on a mission to take down the banks and put power back in the hands of businesses. And trust me—I’ve seen firsthand why so many companies (including mine!) are making the switch. #Fintech #Entrepreneurship #StartupGrowth #Leadership #ChallengerXPodcast #Saas #boomerangfx

    36 min
  6. Cirque du Soleil’s Blueprint for Success

    JAN 22

    Cirque du Soleil’s Blueprint for Success

    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: Daniel built Cirque's magic by trusting his teams and giving them the freedom to innovate within clear boundaries. 🎭 Reinvention is key: Every Cirque show is a testament to pushing boundaries and embracing new ideas. 🌍 Crisis as opportunity: During the pandemic, Daniel’s team launched "Cirque Connect," reaching 70M viewers globally and proving the power of adaptability. 📚 Leadership advice for CEOs: "Do your homework, understand your industry deeply, and then go big." This conversation is a masterclass for current and aspiring leaders, packed with actionable insights and behind-the-scenes stories from one of the most innovative brands on the planet. Connect with us Instagram - https://www.instagram.com/jeromedwightx TikTok - https://www.tiktok.com/@jerome.dwight

    25 min
  7. Inside the PayBright Story: From Startup to $340M Exit

    JAN 16

    Inside the PayBright Story: From Startup to $340M Exit

    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, scaled at lightning speed, and ultimately sold PayBright to Affirm for $340 million. Here’s what we cover: 💡 How Wayne identified and capitalized on a gap in Canada’s financial services 🚀 The pivotal moment that shifted PayBright’s focus to e-commerce and BNPL 🔥 Why speed and trust were critical to scaling PayBright in a competitive market 🤝 The story behind PayBright’s $340M acquisition by Affirm and what came next 🌟 Wayne’s biggest leadership lessons for entrepreneurs breaking into legacy industries Wayne’s journey is a must-watch for anyone looking to challenge the status quo, make bold decisions, and build something that lasts. 🎧 Tune in now to learn the strategies behind one of Canada’s biggest fintech success stories.

    32 min
  8. CFO of Knix on Disruption

    JAN 10

    CFO of Knix on Disruption

    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 customer needs. - The strategies behind Knix’s meteoric rise, from challenging conventional retail to scaling globally. - Why combining instinct with data is the key to staying ahead of the curve. - Garrett’s philosophy on anticipating change rather than reacting to it. - How finance leaders can challenge the status quo to become strategic drivers of innovation. Why Listen? If you’re a leader looking to challenge norms, make bold decisions, and create lasting impact, look no further.

    24 min
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About

Welcome to The Challenger Mindset Podcast, the podcast spotlighting disruptors and innovators who are redefining the future of business. Hosted by Jerome Dwight—entrepreneur, business leader, and growth strategist—this podcast dives deep into the minds of trailblazers who embrace bold action, tackle tough decisions, and challenge the status quo. Join us for thought-provoking conversations on leadership, resilience, and the pivotal moments that drive transformation and success in today’s business landscape.

Information

  • Creator
    Jerome Dwight
  • Years Active
    2024 - 2025
  • Episodes
    19
  • Rating
    Explicit
  • Copyright
    © Jerome Dwight
  • Show Website
    Jerome Dwight

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