Jerome Dwight

Jerome Dwight
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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. DEC 5

    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

    39 min

  2. NOV 7

    Mindvalley COO: How AI Is Transforming Leadership, Education, and Culture | Alex Dogliotti

    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 spanning millions, Mindvalley’s mission has always been clear: to unlock human potential through transformational education. But as AI reshapes industries, Alex explains how Mindvalley is evolving—blending technology, emotional intelligence, and purpose-driven systems to build the future of learning. Alex discusses what he calls “The Future Human”—where mindset, technology, and health converge to help people live longer, smarter, and more fulfilled lives. He dives into how AI is disrupting traditional education, why emotional learning still matters, and how leaders can integrate AI without losing the human element that drives connection and culture. For founders and executives, this episode is a roadmap for future-proofing your organization—where innovation isn’t just about adopting new tools, but reimagining how humans and AI can grow together We cover: - How Mindvalley evolved from an education company to a transformation platform - Why AI will reshape learning, leadership, and HR as we know it - How to train AI as if it were part of your team—not a replacement for it - How to balance technological progress with human connection // 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 #AlexDogliotti #Mindvalley #AILeadership #FutureOfLearning #Transformation #DigitalLeadership #ChallengerX #Innovation #FutureHuman #BusinessStrategy #AIMindset #OrganizationalDesign #FounderMindset #LeadershipEvolution #HumanPotential

    21 min

  3. OCT 17

    Kayak Founder & CTO: The Future of Tech, AI, and $2B IPO - Paul English

    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 to code.After several early ventures, Paul co-founded Kayak with Steve Hafner, determined to simplify online travel. Despite early challenges and setbacks, their relentless focus on product quality and user experience turned Kayak into a billion-dollar success. The company went public in 2012 with a $1.2B IPO, and was later acquired by Priceline for $2B.Yet for Paul, the true reward wasn’t wealth — it was seeing his team win and using that success to fuel something bigger.Today, he channels his energy into philanthropy and innovation — building schools in Haiti, leading homelessness initiatives, supporting mental health programs, and launching an AI institute to empower the next generation. His mission now is to use technology and empathy together to create lasting human impact.Paul believes AI will shape the next great revolution, and that leaders must guide it with creativity, ethics, and heart.His journey proves that success isn’t about exits or valuations — it’s about how you use what you’ve built to serve others.We cover:- How Paul turned early struggles into lifelong motivation- The lessons behind building and scaling Kayak to a $2B IPO- Why leadership starts with honesty, vulnerability, and team trust- How philanthropy fuels long-term purpose and fulfillment- The evolving role of AI in business, education, and human potential// 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#PaulEnglish #Kayak #ChallengerX #ChallengerMindset #Entrepreneurship #Leadership #StartupJourney #AI #Innovation #Philanthropy #Resilience #JeromeDwight

    30 min

  4. OCT 10

    Eventbrite Founder & CEO: Shaping the Future of Human Connection - Julia Hartz

    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

    39 min

  5. SEP 25

    Luxury Real Estate Mogul behind Hollywood’s $2B Celebrity Deals - Carl Gambino

    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

    32 min

  6. SEP 17

    Squire Founder & CEO: From Lawyer to Building a $750M Barbershop SaaS Company - Songe LaRon

    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

    38 min

  7. SEP 8

    Veracity CEO: From Harvard to Health Care Revolutionary - Allie Egan

    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

    27 min

  8. AUG 22

    The COO's Playbook: Building Three Companies to $300M - Cameron Herold

    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

    34 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
    35
  • Rating
    Explicit
  • Copyright
    © Jerome Dwight
  • Show Website
    Jerome Dwight