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 culture and real-world connection. Helping creators and communities bring online connection into real-world belonging.Starting her career in television, Julia learned the power of storytelling — a skill she later used to build culture, inspire teams, and connect millions around the globe. Alongside her husband and co-founder, Kevin Hartz, and their technical co-founder, Renaud Visage, Julia bootstrapped Eventbrite from scratch. Building a platform that empowered anyone to turn an idea into an event, making it faster and easier than ever before.Then came 2020. The world went quiet — concerts, festivals, and conferences disappeared overnight. Eventbrite’s business stopped instantly, and Julia was suddenly faced with a challenge that tested everything she’d built. Through data-driven decisions, empathy, and an unwavering focus on her mission, she led Eventbrite back to growth.Today, Eventbrite is tracking—and powering—the cultural shifts redefining how people connect, play, and recharge. Julia continues to lead the future of human experiences — where AI enhances creativity, and Gen Z’s demand for authentic experiences is driving the next wave of live engagement.For leaders navigating change, Julia’s journey is proof that clarity, adaptability, and belief in people - can turn disruption into opportunity.We cover:- How to rebuild and refocus when your business model breaks- Why clarity and empathy are critical to resilient leadership- Lessons on scaling culture, systems, and global reach- The evolving role of AI and human creativity in business growth- How to stay grounded while leading through uncertainty// LINKS //Instagram https://www.instagram.com/jeromedwightxYouTube https://www.youtube.com/@jeromedwightxTikTok https://www.tiktok.com/@jerome.dwightSpotify https://open.spotify.com/show/47yRU8VeRXZjvwwbS2CWgn?si=TFWYhoKYRziQbTjaXjuOjw&nd=1&dlsi=1ae5fe7561434a39#JuliaHartz #Eventbrite #ChallengerX #ChallengerMindset #Entrepreneurship #Leadership #Resilience #Innovation #FutureOfWork #JeromeDwight
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 estate. His journey wasn’t linear — he faced challenges early on, but used them as fuel to reset, refocus, and rebuild.
From walking dogs in Los Angeles to closing his first $6M real estate deal, Carl turned small opportunities into career defining moments. By combining relentless work ethic with an obsessive drive to learn the market, he quickly built credibility and earned the trust of clients at the highest level.
Carl’s story is more than a career highlight reel — it’s a lesson in resilience, belief, and the power of relationships. His journey shows that success doesn’t come from shortcuts, but from the willingness to bet on yourself, keep learning, and never stop moving forward.
We dive into Carl’s story of hard work, key turning points, and the mindset that keeps him growing. Proof that belief and resilience drive lasting success.
We cover:
- The role of mindset, discipline, and daily habits in building success
- Why relationships and discretion matter most in high-stakes business
- How knowledge and preparation create confidence before experience
- Lessons for entrepreneurs on pushing through setbacks and seizing opportunity
// 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
#CarlGambino #GambinoGroup #ChallengerX #ChallengerMindset #LuxuryRealEstate #Hollywood #Entrepreneurship #CEOInsights #Resilience #Startup #Founder #Mindset #Leadership #BusinessGrowth #RealEstate
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 Yale and launching his career in M&A law, Songe left behind the security of the corporate world to solve a problem nobody else was looking at. Alongside his co-founder, he built Squire from the ground up—bootstrapping early growth, running their own barbershop to understand the customer, and eventually raising $165 million in venture capital.
Today, Squire is not just a booking tool—it’s a fully integrated operating system and fintech engine helping barbershops run more efficiently, grow faster, and stay financially empowered.
But behind the product is a deeper story—one about bold pivots, overcoming rejection, and why customer obsession is still the most powerful growth strategy in business.
We cover:
- How solving his own pain led to a billion-dollar opportunity
- The leap from Yale Law to barbershop entrepreneurship
- The brutal Series A journey: 59 rejections and 1 life-changing “yes”
- Why every founder needs to live inside their customer’s world
If you’re building a vertical SaaS company—or chasing an opportunity in an overlooked market—Songe’s story is a playbook in grit, intuition, and scale.
// 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
#challengerx #jeromedwight #songelaron #squire #fintech #startuplife #founderstory #barbershoptech #verticalsaas #entrepreneurship #customerobsession #startuplessons #scalingtech #ycombinator #growthmindset #blackfounders #ceomindset #leadership #buildinpublic #startupgrind
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 brand. From her journey into functional medicine to empowering others to take control of their health, she’s changing the game.
Before launching Veracity, Allie was the CEO of Cynthia Rowley, doubling revenue in just two years. She also worked at Estée Lauder, leading top brands like Tom Ford and La Mer.
We dive into how Allie scaled Veracity from scratch, her journey from fashion CEO to wellness founder, and her 3 tactical tips for early-stage CEOs.
// 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
#Entrepreneurship #Wellness #Health #Founder #Growth #Business #Leadership #Veracity #Startup #ChallengerX #Veracity #AllieEgan #JeromeDwight
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 one of the most admired franchise scale-ups in business history. As COO of 1-800-GOT-JUNK, Cameron led the company’s growth from $2 million to $106 million in just six years—expanding into four countries and 330 cities, scaling to 3,100 employees, and earning over 5,200 media placements, including a feature on Oprah.
Today, he’s a top-rated international speaker (550+ events, 26 countries) and the founder of COO Alliance, the world’s leading peer network for second-in-command executives.
But behind the metrics is a deeper story—one about operational excellence, leadership under pressure, and what it really takes to build companies that last.
We cover:
- The real emotional cost of entrepreneurship—and how to survive it
- His philosophy: “People by day, paper by night” (and why it works)
- The 3 flywheels that powered 1-800-GOT-JUNK’s hypergrowth
- Why culture beats strategy—and how to build a team that scales
- The mindset of a COO: why every great CEO needs a “Cameron”
If you’re serious about building a business that lasts—one with strong systems, a winning culture, and leadership that multiplies—Cameron’s story shows you how to do it.
// 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
#challengerx #challengermindset #jeromedwight #cameronherold #1800gotjunk #entrepreneurship #leadership #scaling #growth #operations #culture #strategy #franchise #systems #businessowners #executivemindset #founders #startups #visionaries #highperformance
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 beginnings in a small town, working in his father’s grocery store, and later taking over a bankrupt health club at just 22. With no plan B, he built everything from the ground up. A simple, no-frills gym model that prioritized unit economics, customer relevance, and operational excellence—and scaled it into a global empire.
In this episode, Peter shares the mindset, principles, and tactical decisions that fueled his growth. He offers real-world insights that go beyond theory—from building teams that go all-in, to making hard pivots when a business starts losing momentum.
We cover:
- How to spot opportunity when it whispers—not knocks—and act decisively
- The blueprint for scaling from 1 gym to 2,500+ with lean, no-frills systems
- Why leadership is about culture, clarity, and helping your people grow
- How to pivot a stagnating business by staying relevant and cutting the noise
- Why grit and accountability are the real unfair advantages in business
Whether you're building from scratch, turning around a struggling operation, or scaling to your next level—Peter’s story is packed with hard-earned wisdom to help you navigate the path with clarity, resilience, and real-world strategy.
// 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
#ChallengerX #ChallengerMindset #PeterTaunton #SnapFitness #LiftBrands #Entrepreneur #Leadership #Founder #Startup #Resilience
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 17, to having 12 stores across the country, to holding executive roles at Esprit, Sportchek, Marks, and Canadian Tire -- and now, as co-owner of Kit and Ace and Mastermind Toys, he’s shaping a new era of Canadian retail alongside Joe Mimran—anchored in innovation, technical fashion, and operational excellence.
In this episode, we cover:
- Fax, Grit & Vision: How a cold pitch by fax at age 17 launched David’s retail empire.
- Failing Forward: Losing his supply chain overnight—and why stepping back was the smartest move.
- The Reinvention of Kit and Ace: Building technical fashion that’s trend-aware but timeless.
- Leadership in Action: What it really means to be the "Chief Everything Officer."
David’s story is one of courage, reinvention, and relentless belief in possibility—perfect inspiration for emerging CEOs, founders, and anyone pursuing bold growth in competitive industries.
// 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
#Leadership #Retail #Entrepreneurship #Fashion #KitandAce #MastermindToys #CanadianBusiness #StartupStories #Resilience #Persistence #Innovation #Growth #Vision #Strategy #Founder #CEO #CanadianRetail #BrandBuilding #Ecommerce #Grit #Inspiration
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 opportunities are matched with talent. Backed by prominent investors such as Soma Capital, Hypen Capital, and Craft Ventures, Michael is creating waves in the HR tech space.
In this episode, we cover:
- From Frustration to Innovation: Michael’s journey from struggling job seeker to creating Simplify, helping millions.
- Rapid Iteration & Feedback: Key lessons learned from early challenges and driving growth.
- Securing Funding: Michael’s path to funding from Y Combinator and George Ruan through persistence and storytelling.
- AI’s Impact on Work: How AI is reshaping job searches and why human creativity remains vital.
Michael’s journey from a Stanford dorm room to building a company that has helped millions of job seekers is one of true entrepreneurial spirit. His insights on leadership, innovation, and the future of AI in the workplace will inspire anyone looking to make a meaningful impact.
#Leadership #Innovation #Entrepreneurship #AI #Startups #Tech #Careers #JobSearch #Founder #CEO #YC #Funding #Growth #Vision #Impact #Hiring #Product #Strategy #Persistence #Success
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 left inspired by a masterclass in leadership.
But Howard didn’t talk about coffee. He talked about people.
Leadership. Culture. Purpose.
His philosophy—rooted in servant leadership, emotional intelligence, and culture-first thinking—is what really scaled Starbucks into the global powerhouse it is today.
My favorite takeaways:
This episode isn’t just a story about Starbucks. It’s a road map for anyone building something that matters—with values, vision, and heart.
#Leadership #ServantLeadership #Starbucks #ChallengerMindset #BoomerangFX #ChallengerXPodcast #HowardBehar #TeamCulture #PersonalGrowth #HighPerformance
From Humble Beginnings to Dragon's 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 Dragon's 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 liquor store at just 13 years old to building a $200+ million dollar brewery and distillery, Manjit faced countless obstacles — and always turned them into opportunities. Here are some takeaways from our conversation:- Early Lessons: Manjit learned essential business skills working in her family’s liquor store, which set the foundation for her future success.- Calculated Risk: She combines research, data, and gut instinct to make informed decisions and manage risk.- Dragon's Den Insights: Investors bet on people, not just products. Manjit looks for passion, clarity, and execution in a pitch.- Saying Yes to Opportunity: Manjit embraces new challenges, from philanthropy to military involvement, always learning along the way.In this episode, we learned that with the right mindset, there is no limit to what you can achieve — even if the odds are stacked against you.// LINKS //Instagram https://www.instagram.com/jeromedwightxYoutube https://www.youtube.com/@jeromedwightxTikTok https://www.tiktok.com/@jerome.dwightSpotify https://open.spotify.com/show/47yRU8VeRXZjvwwbS2CWgn?si=TFWYhoKYRziQbTjaXjuOjw&nd=1&dlsi=1ae5fe7561434a39#Leadership #Entrepreneurship #DragonsDen #Business #Philanthropy #SuccessStory #Mindset #BusinessGrowth #ChallengerX #JeromeDwight
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 revenue growth and eventual acquisition by Bain Capital and Abu Dhabi Investment Authority (ADIA), Keegan’s leadership journey is anything but ordinary.
Now, as an acclaimed author of Dare to DISRUPT and The FUD Factor, Brendan reveals how fearless thinking and decisive action can turn adversity into opportunity.
This is a must-watch for anyone who cares about leadership, creating a legacy, and making a lasting impact.
// 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
#CEO #Leadership #BusinessGrowth #Entrepreneurship #Innovation #CapitalRaising #Disrupt #GrowthMindset #Scaling #Startups #BillionDollarBusiness #BrendenKeegan #ChallengerXPodcast #challengerX
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 ingredients, sustainability, and giving back, the company has grown into a powerhouse in the online grocery and meal kit space.Neil didn’t just see an opportunity—he created one. Before online grocery delivery was a thing, he and his co-founder built GoodFood from the ground up, solving a problem no one else dared to tackle. But it wasn’t easy. From rapid scaling challenges to the harsh realities of entrepreneurship, Neil shares the unfiltered truth about what it takes to build, survive, and lead in a competitive industry.In this episode, we dive into:- How Neil and his co-founder spotted a market gap before anyone else- The real struggles of scaling fast, hiring right, and staying ahead of the competition- Why hiring for hunger beats hiring for experience every time- The future of GoodFood and how they’re staying ahead of industry giants like Amazon and Whole FoodsThis conversation is more than just a business success story—it’s a masterclass in vision, resilience, and strategic execution. Neil breaks down the highs and lows of scaling a company, the mindset shifts that separate good entrepreneurs from great ones, and how to future-proof a business in an ever-changing industry. Like, comment, and subscribe for more conversations with the world’s top business minds.// LINKS //Instagram https://www.instagram.com/jeromedwightxYoutube https://www.youtube.com/@jeromedwightxTikTok https://www.tiktok.com/@jerome.dwightSpotify https://open.spotify.com/show/47yRU8VeRXZjvwwbS2CWgn?si=TFWYhoKYRziQbTjaXjuOjw&nd=1&dlsi=1ae5fe7561434a39#StartupSuccess #Entrepreneurship #BusinessGrowth #GoodFood #Leadership #MealKits #Disruption
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 background in beauty. She didn’t have any experience in running a retail space. But she had a vision — and she took action despite the fear. Fast forward to today, WAXON has grown to over 25+ locations across Canada and is entirely powered by female franchise owners.
In our conversation Lexi opens up about:
- The self-doubt she faced the night before opening her first location (and why most entrepreneurs quit right there).
- Her secret to hiring a team that stays for over a decade in a high-turnover industry.
- How she scaled from 1 location to 25+ without compromising quality.
- Why most women struggle to build businesses — and how to break through that barrier.
- Her best advice for anyone sitting on a business idea but afraid to start.
Lexi also dives into work-life balance as a mom of four, how she stays mentally strong, and why taking small, consistent actions is the real secret to building something big.
Timestamps:
0:00 - Intro: How Lexi Built Wax On at 25
3:45 - How Lexi got into the business
6:55 - Lexi's Early Influences
8:00 - Early years of business and Waxon
10:30 - Navigating hiring and company culture fit
16:00 - Biggest challenges for female entrepreneurs
19:50 - How to keep focus and mentally tough in business
23:00 - Advice for female entrepreneurs who are early in their career
25:35 - What's next for Lexi?
// 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
#challengermindset #jeromedwight #challengermindsetpodcast #waxon #waxonlaser #waxbar #leximilescorrin #founder #startup
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 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.
// LINKS //
Instagram https://www.instagram.com/jeromedwightx
Youtube https://www.youtube.com/@jeromedwightx
TikTok https://www.tiktok.com/@jerome.dwight
#challengermindset #jeromedwight #royratnavel #challengermindsetpodcast #motivation
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.
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
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:
📚 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!
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
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
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.
