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. Cirque du Soleil’s Blueprint for Success

    5 DAYS AGO

    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
  2. 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
  3. 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
  4. People First, Coffee Second: Starbucks Legend Howard Behar

    JAN 3

    People First, Coffee Second: Starbucks Legend Howard Behar

    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 purpose-driven culture. We discuss: ☕ His humble beginnings as the son of immigrant parents and how they shaped his leadership style. 👥 Why empowering people by letting “those who sweep the floor choose the broom” is the key to organizational success. 📊 The limitations of data and why being present with your team is irreplaceable. 🌍 Taking Starbucks global while staying true to its core values. Whether you're a leader, entrepreneur, or someone striving to make a difference, this episode will inspire you to lead with heart, purpose, and integrity. Discover why trust and authenticity are the true drivers of success.

    39 min
  5. Ethics at Airbnb & Ebay with Robert Chestnut

    12/27/2024

    Ethics at Airbnb & Ebay with Robert Chestnut

    "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 leadership drives business success. From managing discrimination issues to creating policies that scale integrity during hypergrowth, Rob provides a roadmap for leaders to build companies that last. You’ll discover: - Why mission-driven companies always outperform profit-driven ones. - How to navigate ethical dilemmas in fast-growing businesses. - The critical link between purpose, trust, and financial success. - What every leader needs to know about AI’s impact on ethics and decision-making. Hit play to hear Rob’s unfiltered insights on why integrity is the new currency of success. Don’t forget to like, subscribe, and share your thoughts in the comments below!

    34 min
  6. Dr. Mulholland on Building Billion-Dollar Innovations

    12/18/2024

    Dr. Mulholland on Building Billion-Dollar Innovations

    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. Mulholland and I discuss: - The early days of aesthetic medicine and the rise of non-surgical treatments like Morpheus8 - How InMode became a global leader in energy-based medical devices - The BoomerangFX story: Our shared vision to create the most advanced practice management and digital marketing platform for private-pay practitioners - His insights on building a high-performing team, creating a patient-first experience, and driving retention in competitive markets - The future of aesthetic medicine and his latest innovations like the groundbreaking Quantum device Tune in to hear how Dr. Mulholland’s bold ideas and visionary leadership have reshaped the medical aesthetics industry, and how he continues to inspire doctors to build thriving practices.

    45 min
  7. Using AI to Fix a Broken Industry: How Pave Revolutionized Vehicle Inspections

    12/16/2024

    Using AI to Fix a Broken Industry: How Pave Revolutionized Vehicle Inspections

    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! Steve’s unique strategies for finding champion clients and scaling globally Tackling skeptics, scaling internationally, and staying ahead in the fast-moving AI landscape Steve’s vision for the future of AI in automotive, from predictive analytics to autonomous solutions If you’re excited about innovation, leadership, and the power of AI to transform industries, you need to listen to this episode.

    29 min
  8. John Ruffolo on Navigating Tech Cycles, Investing in Shopify, and Beating the Odds

    12/10/2024

    John Ruffolo on Navigating Tech Cycles, Investing in Shopify, and Beating the Odds

    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 1990s tech industry and spotted the potential of the internet revolution - His game-changing role in creating Omers Ventures and nurturing iconic companies like Shopify - Why understanding technology cycles is critical for successful investing and how his strategy evolved through market booms and busts - The personal resilience that carried him through a life-threatening cycling accident and inspired his return to lead Maverix Private Equity - John’s vision for Canada’s tech ecosystem and the steps needed to build more global success stories - Tune in to hear how John has combined innovation, determination, and leadership to redefine the rules of investing and build a legacy of transformation.

    47 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
    14
  • Rating
    Explicit
  • Copyright
    © Jerome Dwight
  • Show Website
    Jerome Dwight

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