Reluctant Billionaire w/ Andrew Cartwright

Hosted by Andrew Cartwright

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Jun 2026

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About the show

Are you a Reluctant Billionaire? Discover the blueprint to achieving success and scaling your business on Reluctant Billionaire with Andrew Cartwright. Dive into strategies for business, loans, grants, and investing. expanding your customer base, and fostering long-term loyalty. Join Andrew Cartwright, a founder of 32 startups, in 17 Industries, 17 acquisitions, and 5 exits. Uncover insights from his experience as an investor, author, public speaker, actor, and content creator. Learn from Andrew's failures on the journey towards a $1 billion net worth. Seen: A&E, CBS, NBC, ABC, FOX, CNN

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60 recent

September 4, 20261 hr 34 min

THE PRICE OF SUCCESS with Andrew Cartwright

Andrew Cartwright sits down for a wide-ranging conversation about business, leadership, entrepreneurship, technology, community, and the ideas shaping the future. From building stronger business communities and recognizing individual strengths to storytelling, AI, personal experience, competition, collaboration, and what effective leadership actually looks like, the conversation moves beyond simple business advice into a much bigger discussion about how people think, communicate, and create opportunities. It’s an unscripted conversation filled with different perspectives, personal stories, disagreements, humor, and lessons learned through real-world experience. Whether you’re an entrepreneur, business owner, investor, or simply interested in how successful people approach challenges and opportunity, this episode offers plenty to think about.

September 3, 20261 hr 20 min

AI, Business & What It Takes to Win with Andrew Cartwright

In this episode of The Reluctant Billionaire, Andrew Cartwright sits down with Justin for a wide ranging conversation about business, AI, capital, entrepreneurship and what it really takes to execute. They break down the idea behind a results driven business boot camp, why accountability matters, how founders should think about partnerships, branding and access to capital, and how AI is rapidly changing the way businesses are built. Andrew also shares lessons from decades of building companies, lending, real estate and investing while looking at where technology and the creator economy may be heading next.

August 31, 202644 min

YouTube Took Everything: Andrew Cartwright on Big Tech, AI & Digital Freedom

Andrew Cartwright sits down with Justin for a wide-ranging conversation about what happens when creators build their businesses on platforms they don’t control. Andrew shares the story of losing his YouTube channel after years of building thousands of videos, the personal and financial impact that followed, and why he believes creators need a clearer path to restoration when platforms shut them down. They also get into creator mental health, social media algorithms, AI, Big Tech, autonomous vehicles, corporate power, and the growing importance of digital access. The conversation eventually turns toward the future of technology, ownership and upward mobility, and why Andrew believes access to capital and opportunity could become even more important as AI and automation reshape the economy. #AndrewCartwright #JustJustin #YouTube #BigTech #AI #CreatorEconomy #Entrepreneurship #Technology #Business #SocialMedia

June 3, 202657 min

The Power Hour: Real Estate Opportunities & Thinking Bigger

Andrew Cartwright shares exciting news about an upcoming trip to Richard Branson's private Necker Island, where he'll be speaking alongside high-level entrepreneurs and investors. The conversation then shifts into real estate, distressed assets, creative deal structuring, investor relationships, and why Andrew believes some of the biggest opportunities in commercial property could emerge over the next few years. From buying islands and beachfront properties to finding the "red truck" motivation behind every deal, this episode is packed with real-world investing insights and entrepreneurial thinking.

May 15, 202640 min

From Economic Collapse To Building A $100M Tech Company

What does entrepreneurship look like during economic collapse? In this episode, Andrew sits down with Gerson Gómez, founder of Ridery, one of Venezuela’s fastest-growing mobility and tech companies. From hyperinflation and $30 monthly salaries to building a company generating tens of millions in annual revenue, this is an incredible story about resilience, adaptation, startups, leadership, and opportunity during one of the most difficult economic periods in modern history. The conversation covers Venezuela’s recovery, building Ridery, startup culture, Amazon’s business philosophy, entrepreneurship under pressure, AI, scaling companies, resilience, family, self-development, and why curiosity may be one of the most important traits an entrepreneur can have. An inspiring conversation about persistence, vision, and building something meaningful when the odds are against you.

May 1, 202628 min

The Truth About Success Nobody Wants to Hear

Most people are chasing success the wrong way. They want the outcome without the process. The result without the failures. The identity without the growth. In this conversation, Andrew Cartwright breaks down what it actually takes to build something real—why failure isn’t optional, why most advice out there lacks depth, and why letting go of who you’ve been is the only way to become something more. This isn’t surface-level motivation. This is real-world experience from someone who’s built businesses across multiple industries and understands what actually works. If you’re tired of fake advice and want something real, this is it.

April 28, 202635 min

Take Control of Your Credit - Jimena Cortes

In this episode, Andrew Cartwright walks through a practical way to improve your credit score without relying on expensive credit repair services. He sits down with a credit expert to break down how credit actually works, what impacts your score the most, and how small changes in timing and payment strategy can make a massive difference. From understanding credit utilization to knowing when to pay your cards, this masterclass focuses on giving you control instead of guesswork. They also cover tools that help track your credit, identify what is hurting your score, and take direct action to fix issues, including dispute options, score tracking, and identity protection. If you have ever felt stuck with your credit or unsure how to improve it, this episode gives you a clear path forward with real examples and actionable steps.

April 21, 202631 min

Entrepreneur Talk with Founders of EBkicks

Andrew Cartwright sits down with real entrepreneurs who built something from nothing and turned passion into profit This episode is about what actually works not theory not fake gurus not people talking without experience From sneaker culture to building a product now sold in major retail stores this conversation breaks down the real process starting small learning the game creating your own brand and scaling it step by step They get into trust why it matters more than anything in business how most people miss opportunities right in front of them and why execution always beats talking If you want to turn what you love into something real this is the blueprint raw practical and proven

April 17, 202649 min

A&A Show: Gender, Discrimination, Masculinity & Femininity

In this episode, Andrew Cartwright and Ana dive deep into polarity, psychology, and the balance between masculine and feminine energy . From childhood conditioning to modern workplace dynamics, they explore how identity is shaped, suppressed, and expressed over time. This is not just a surface-level conversation. It’s about self-awareness, relationships, business, and understanding human behavior at a deeper level . They break down: • How early experiences shape identity • The concept of masculine and feminine energy in relationships and business • Why people present a “representative” version of themselves • The reality of gender expectations in today’s world • How balance leads to success, connection, and growth At its core, this episode is about understanding yourself and others without judgment and why open conversations matter more than ever. Listen in and challenge the way you think.

April 14, 202654 min

How the Wealthy Actually Think About Money and Risk

In this episode, Andrew sits down with a private, high-level investment professional to break down what really matters when it comes to managing money. They dive into trust, fiduciary responsibility, and how top firms evaluate investment opportunities at scale. From identifying market inefficiencies to understanding risk, team structure, and repeatable processes, this conversation gives a rare inside look at how serious capital is actually deployed. Beyond investing, they explore the biggest mistake most people make with money. Behavioral decisions, poor financial habits, and short-term thinking often destroy long-term wealth. The discussion highlights why many investors underperform and how a disciplined, long-term approach can change everything. If you want to understand how professionals think about money, risk, and building lasting financial stability, this episode delivers real insight without the noise.