Jerome Dwight

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...

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. Fr...

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 La...

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...

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 tal...

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 Intro 2:26 Wh...

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...

In this episode, Alex Dogliotti, Chief Operating & Human Resources Officer (COO) of Mindvalley, shares how the company is redefining education and leadership in the age of AI. He explains why the future belongs to leaders who can bridge technology and people, and how he guides one of the world’s leading edtech companies, impacting 20 million learners across 135 countries With a community spann...

James Keyes has led two of the most recognizable brands in the world, 7-Eleven and Blockbuster, steering both through some of the most defining moments in modern business. At 7-Eleven, Keyes transformed a company buried in $4 billion of debt into a global brand. Through data-driven innovation and a relentless belief that “change equals opportunity,” he led the company’s IPO and 37 straight quarter...

Paul English is a tech entrepreneur, computer programmer, and philanthropist, Paul is best known as the Co-Founder and former CTO of Kayak, the travel search engine that redefined how millions book trips and later sold for $2 billion. Raised in a working-class Boston family, Paul learned early that limitations could be fuel for creativity. When his mother brought home a computer, he taught himself...

Julia Hartz didn’t plan to be an Entrepreneur, but she built one of the most influential platforms in the world of live experiences. As Co-Founder and CEO of Eventbrite, Julia turned a simple idea into a global business that, in 2024, powered 4.7 million events across 180 countries, connected 89 million monthly users, and sold 83 million paid tickets. Eventbrite sits at the intersection of digital...

Carl Gambino is the Founder and Principal of The Gambino Group, a leading luxury real estate firm with over $2B in lifetime sales across New York, Los Angeles, Miami, and the Hamptons. He represents world-renowned talent and investors, while also mentoring the next generation of real estate leaders. Born in New York City and raised in New Jersey, Carl grew up fascinated by architecture and real es...

In this episode, we sit down with Songe LaRon, the visionary co-founder and CEO of Squire, the world’s leading barbershop management and fintech platform. What began as a frustrating experience trying to book haircuts during his time as a corporate lawyer turned into a multi-national SaaS business now powering over 20,000+ barbers across the US, UK, Canada, and Australia. After graduating from Yal...

In this episode, we sit down with Allie Egan, founder & CEO of Veracity, a wellness brand transforming how we approach metabolic health, hormones, and beauty. With $14M in funding and a projected $20-30M in revenue by 2025, Allie is reshaping the health space with a personalized, science-backed approach. What I admire most is how Allie turned her own health struggles into a mission-driven bran...

In this episode, we sit down with Cameron Herold, a serial entrepreneur known for his rare ability to turn vision into repeatable, scalable systems. Over the course of his career, Cameron has built three companies that each surpassed $100 million in revenue and played a pivotal role in the branding, sale, and integration of more than 500 business locations. By the age of 42, he had helped engineer...

In this episode, we sit down with Peter Taunton, a self-made entrepreneur and the powerhouse behind Snap Fitness, one of the world’s largest wellness brands. From turning a struggling local gym into a 2,500+ location global franchise, Peter’s story is a masterclass in grit, leadership, and scaling smart without outside funding. Peter’s career spans over three decades—starting with humble beginning...

In this episode, we sit down with David Lui, a pioneering Canadian retail entrepreneur and the CEO behind the reinvention of Kit and Ace. From humble beginnings in Vancouver to leading some of the country’s most recognized fashion and lifestyle brands, David shares his remarkable journey of grit, vision, and reinvention. David’s career spans over three decades—from launching his first store at age...

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...

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...

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 liquo...

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 revenu...

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...

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 backgrou...

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...

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...