Jerome Dwight

Jerome Dwight

By Jerome DwightBusinessEntrepreneurship
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Jerome Dwight episodes

  • 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.

    33 min
  • 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
  • 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.

    40 min
  • 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!

    35 min
  • 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
  • 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
    • 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
    • From Setbacks to Olympic Glory: Sarah Wells' Story

      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 entrepreneurs across North America. 

      In this episode, Sarah and I explore: 

      • How her experiences with rejection and injury shaped her approach to overcoming obstacles 

        • The importance of creating psychological safety in teams to foster innovation and risk-taking 

          • Lessons in goal-setting and redefining success for long-term growth 

            • How self-doubt and imposter syndrome mirror the challenges faced by entrepreneurs and leaders 

              • Building a culture of resilience within organizations to drive impact 

                • Tune in to discover how Sarah’s Olympic mindset can inspire you to challenge limits, reframe failure, and find opportunities in adversity. 

                28 min
              • Small Town, Big Success: Talon Maningas' Aesthetic Revolution
                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 trauma surgery to aesthetics and building a thriving practice in a small town - Wh...
                36 min
              • A CFO’s Guide to Transforming Business, Melanie Pump
                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 of the CFO- Melanie’s approach to managing risk, financial stabil...
                22 min

              About Jerome Dwight

              From the publisher's feed

              Welcome to The Challenger Mindset Podcast, the podcast spotlighting disruptors and innovators who are redefining the future of business.