Jerome Dwight

Jerome Dwight
  • 3.0 (3)
  • Entrepreneurship
  • Updated Semiweekly

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. 1d ago

    Canadian Investment Legend: Building a Global Empire From Nothing | Michael Lee-Chin

    From arriving in Canada with nothing... to building one of the country's most iconic investment empires.In this episode of ChallengerX, I sit down with Michael Lee-Chin, entrepreneur, investor, and philanthropist, to unpack the mindset behind building wealth, creating lasting businesses, and thinking decades ahead of the crowd.From AIC Limited to Portland Holdings, Michael has spent a lifetime making bets others weren't willing to make. We get into conviction investing, long-horizon thinking, and why he's now turning his attention to advanced nuclear technology and its potential role in the fight against cancer.We get into the thinking and principles behind his extraordinary journey: Building wealth without a head startThe investment philosophy that changed everythingWhy most people never create meaningful wealth—and how to think differentlyTaking calculated risks when others won’tLegacy, purpose and what Michael is building next// LINKS // Instagram / jeromedwightx Youtube / @jeromedwightx TikTok / jerome.dwight A rare conversation on ambition, legacy, and building for the long term.#ChallengerX #MichaelLeeChin #entrepreneurship #leadership #investing #PortlandHoldings #longtermthinking #healthcareinnovation #financialsuccess

  2. Jun 17

    Reebok Co-Founder: Building a Legendary Brand That Took On Nike & Adidas | Joe Foster

    From the family workshop in Bolton... to building a brand that took on Nike and Adidas and won. In this episode of ChallengerX, I sit down with Joe Foster, the co-founder of Reebok, the entrepreneur who turned a small northern-England shoemaker into one of the world's leading sportswear brands, to unpack the mindset behind building a global name from almost nothing. From walking away from his family's footwear business to riding the 1980s fitness boom all the way to outselling Nike in the U.S., Joe shares the entrepreneurial lessons behind brand-building, competition, scaling, and resilience.This episode dives into:- Building a category-defining global brand- Competing against entrenched giants and winning- The branding instincts that beat bigger budgets- Seizing a cultural moment like the fitness boom- Scaling something personal into a worldwide business- The resilience required to build something enduring // LINKS // Instagram / jeromedwightx Youtube / @jeromedwightx TikTok / jerome.dwight A powerful conversation on entrepreneurship, ambition, and creating a brand the world never forgets.#ChallengerX #Entrepreneurship #Leadership #Sportswear #Branding #Founders #BusinessGrowth

  3. May 30

    Restaurateur & Dragon: Building One of Canada’s Most Iconic Restaurant Brands | Vikram Vij

    From bringing Indian cuisine into Canada’s cultural spotlight… to building one of the most recognizable restaurant brands in the country.In this episode of ChallengerX, I sit down with Vikram Vij, the chef who helped redefine how Canada experiences Indian food, entrepreneur, restaurateur, and former Dragon on Dragons’ Den, to unpack the mindset behind building Vij’s into a cultural phenomenon.From redefining Indian cuisine in North America to creating lineups around the block with no reservations, Vikram shares the entrepreneurial lessons behind brand-building, authenticity, scaling, and leadership.This episode dives into:- Building a category-defining restaurant brand- Turning culture into competitive advantage- The business psychology behind hospitality- What Vikram looked for as a Dragon investor- Scaling without losing authenticity- The resilience required to build something enduringA powerful conversation on entrepreneurship, identity, and creating experiences people never forget.// LINKS // Instagram / jeromedwightx Youtube / @jeromedwightx TikTok / jerome.dwight #ChallengerX #Entrepreneurship #Leadership #Hospitality #Restaurants #Founders #BusinessGrowth

  4. May 25

    NASA Engineer: Reinventing Photography for the Digital Age | Eric Fossum

    What if one invention quietly changed the way the entire world sees itself?In this episode of ChallengerX, Jerome Dwight sits down with Prof. Eric Fossum, the NASA engineer and inventor of the CMOS image sensor, the breakthrough “camera-on-a-chip” technology now powering billions of smartphones, webcams, medical devices, and automotive systems worldwide.From his years at NASA’s Jet Propulsion Laboratory to co-founding Photobit and transforming modern imaging forever, Eric shares the untold story behind one of the most impactful technologies of the digital era. 0:00 – Intro 3:23 – From curiosity to changing the world 4:36 – The early years that shaped an inventor 6:02 – NASA's impossible ask: shrink the camera, save the mission 8:34 – The "camera-on-a-chip" moment that rewired modern life 11:50 – Going all in: the Photobit gamble 17:00 – Did Eric know he was building the future? (And how he protected it) 20:58 – Startup to exit: hard-earned lessons from the trenches 22:40 – Where innovation and AI collide next 24:34 – The next frontier in imaging tech 28:34 – Advice every innovator needs to hearEssential viewing for academics, operators, and founders navigating innovation.// LINKS // Instagram   / jeromedwightx   Youtube    / @jeromedwightx   TikTok   / jerome.dwight   Spotify https://open.spotify.com/show/47yRU8VeRXZjvwwbS2CWgn #ChallengerX #EricFossum #NASA #Innovation #Technology #Entrepreneurship #AI #Engineering

  5. Mar 27

    Syntilay CEO: How AI Is Changing Product Design | Ben Weiss

    What happens when AI, besides assisting creativity - starts designing the product?In this episode of ChallengerX, Jerome Dwight sits down with Ben Weiss, Founder & CEO of Syntilay, to explore how AI is reshaping footwear design, brand building, and the future of physical products.From using generative AI and 3D printing to rethinking how products get made, Ben shares how he’s building at the intersection of technology, fashion, and entrepreneurship. He also opens up about turning a cold message into a mentorship with Reebok co-founder Joe Foster.0:00 – Intro2:20 – How Ben Weiss Discovered AI in Footwear Design4:38 – Inventing a Whole New Category7:43 – Outplaying the Competition in a Crowded Market9:56 – From Cold Message to Mentor: Meeting Reebok’s Joe Foster12:00 – The Power of Cold Calling and Discipline14:11 – Spotting When You’re on to Something Big16:26 – The Future of AI in Footwear19:01 – Overcoming Setbacks and ChallengesEssential viewing for founders, executives, and operators navigating growth. // LINKS // Instagram / jeromedwightx Youtube / @jeromedwightx TikTok / jerome.dwight #ChallengerX #ChallengerMindset #Leadership #Entrepreneurship #BusinessGrowth #OperatorMindset #ExecutiveLeadership #ScalingUp #TeamExecution #GrowthMindset

  6. Feb 23

    BILL CEO: The Hardest Part of Building BILL Was Becoming the Leader It Needed | René Lacerte

    In this episode, we sit down with René Lacerte, founder and CEO of BILL, the financial automation platform serving hundreds of thousands of businesses. What started as a bold idea to fix broken, manual financial workflows has grown into a company generating around $1.5B in annual revenue with a market cap of roughly $5B. René shares what it really means to carry CEO responsibility at scale. He talks about why even top leaders need CEO coaches, how culture becomes your true competitive edge, and how to balance patience with urgency. As he puts it, “The best ideas always seem obvious in hindsight.”0:00 Intro2:27 The Problem That Sparked BILL6:30 What Made You Actually Take the Leap?9:53 How BILL Survived — and Won — in a Tough Market13:32 The Hardest Leadership Lessons17:05 Scaling Strategy: Playing the Long Game23:42 Why Culture Decides the Outcome27:24 Speed vs. Impatience: A Founder’s Dilemma36:01 How Will BILL Be Remembered?Essential viewing for founders, executives, and operators navigating growth. // LINKS //Instagram / jeromedwightx Youtube / @jeromedwightx TikTok / jerome.dwight Spotify https://open.spotify.com/show/47yRU8V...#Renélacerte #Bill #fintech #FutureOfWork #leadership #leadershiptraining #ChallengerMindset #AI #TechLeadership #ScalingUp #BusinessGrowth #OperatorMindset #TeamExecution #JeromeDwight #challengerx #motivation

  7. Feb 11

    Altair Former COO: Scaling a $10B Tech Company Through 35 Acquisitions | Stephanie Buckner

    How do you scale a tech company from $3.6B to nearly $10B and lead 35+ acquisitions without breaking the organization?In this episode of ChallengerX, Jerome Dwight sits down with Stephanie Buckner, former COO of Altair Engineering and now Co-Founder of Escape Investment Management, to unpack the real operational, leadership, and M&A lessons behind hyper-growth in deep tech.0:00 Intro2:26 What drew you to the world of tech?4:40 Navigating your early career6:07 Returning to Altair and the path back8:58 The major transformational milestones at Altair15:26 The North Star priorities that guided your leadership18:17 What you looked for when building your leadership team20:30 Managing the exit to Siemens23:08 What led you to become an investor28:37 Your strongest convictions when evaluating investments30:44 The KPIs companies should focus on34:00 Lessons for the next generation of leadersEssential viewing for founders, executives, and operators navigating growth. // LINKS //Instagram / jeromedwightx Youtube / @jeromedwightx TikTok / jerome.dwight #Stephaniebuckner #Altair #engineering #FutureOfWork #leadership #leadershiptraining #ChallengerMindset #AI #TechLeadership #ScalingUp #BusinessGrowth #OperatorMindset #TeamExecution #JeromeDwight #challengerx #motivation

  8. 12/05/2025

    Asana COO: Transforming the Way Companies Operate | Anne Raimondi

    In this episode, Anne Raimondi, COO of Asana and a seasoned operator across companies like eBay, SurveyMonkey, Zendesk, and Guru — breaks down what it really takes to lead teams and build products in a world being reshaped by technology. Anne didn’t begin her career in tech. She found her way into the industry by solving real operational problems inside a retail company, and that experience shaped how she thinks about technology today: as a tool that should make people more effective, not overwhelmed. From scaling eBay during its explosive growth, to defining product-led culture at SurveyMonkey, to transforming customer experience at Zendesk, Anne shares the lessons she’s carried across decades of building, leading, and operating inside some of the most influential companies of the last twenty years. Now as COO of Asana, she’s helping redefine how teams work in an era where AI, automation, and collaboration tools are changing expectations faster than ever. In this conversation, Anne breaks down: - The mindset shift leaders need as work becomes increasingly tech-enabled - Why companies must remove friction — not add complexity - How to build teams that stay innovative as organizations scale - Why your product is your brand (especially as customer expectations accelerate) // LINKS // Instagram https://www.instagram.com/jeromedwightx Youtube https://www.youtube.com/@jeromedwightx TikTok https://www.tiktok.com/@jerome.dwight Spotify https://open.spotify.com/show/47yRU8VeRXZjvwwbS2CWgn?si=TFWYhoKYRziQbTjaXjuOjw&nd=1&dlsi=1ae5fe7561434a39 #AnneRaimondi #Asana #FutureOfWork #Leadership #ChallengerMindset #AI #TechLeadership #ScalingUp #BusinessGrowth #OperatorMindset #TeamExecution #JeromeDwight #ChallengerX

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Ratings & Reviews

3
out of 5
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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 - 2026
  • Episodes
    43
  • Rating
    Clean
  • Copyright
    © Jerome Dwight
  • Show Website
    Jerome Dwight