Reluctant Billionaire w/ Andrew Cartwright

In this episode of  Money Mondays , Andrew Cartwright dives deep into how money actually works, not just on paper, but in the real world. Fresh off a trip to Peru, Andrew shares firsthand experiences that reveal how fragile, misunderstood, and uneven global currency systems really are. From damaged U.S. dollar bills being rejected overseas to the long-term impact of leaving the gold standard in 19...

Money Mondays is here, and we’re starting with a question that sounds simple… but can change your entire life:  Rich vs Wealthy. In this episode, Andrew Cartwright breaks down the  real distinction  most people miss: Rich  can be loud, flashy, and unstable Wealthy  is quiet, strategic, and built to last You’ll hear why  “true power is in distinctions”  and how small mindset shifts can flip your tr...

In this episode, Andrew walks through how he actually thinks and works day to day, from analog brainstorming with pen and paper to capturing every idea digitally and running it through AI tools like ChatGPT and Claude. He shares how his environment, routine, and creative process are intentionally designed to support problem-solving, long-term focus, and execution. The conversation expands into dis...

In this episode,  Andrew Cartwright  sits down with attorney  Ryan J. Umina  to explore how law, communication, and power shape the systems we all live inside. They break down why communication failures are at the root of so many legal and business problems, from broken vendor relationships to fragmented legal infrastructure. The conversation moves from real world business disputes into high level...

In this episode,  Andrew Cartwright  sits down with  Docs  for a raw, unscripted conversation about what it  really  takes to build something meaningful on YouTube. This isn’t about fake gurus, clickbait fame, or chasing viral moments. It’s about  showing up every day , doing the work, and building a  real community  that actually cares. They dive into: What authenticity really means in the creato...

🎙️  WELCOME BACK TO THE RELUCTANT BILLIONAIRE  — and if this is your first time, you’re in for a 🔥 deep dive. In this episode, we sit down with  Ben Thinking  —  certified personal trainer ,  powerlifter ,  endurance athlete ,  supplement formulator , and lifelong student of  human performance . What starts as a fitness story quickly turns into a masterclass on  how the body  actually  works . 💪...

In this episode, Andrew breaks down why he just made the largest single investment of his life into a startup he doesn’t control and why the product is completely free to use. Recorded live at the Las Vegas Convention Center , during one of the largest apartment and rental industry shows in the country, this conversation dives deep into  Magic Door , a property management platform built from  real...

In this episode, Andrew Cartwright sits down in Washington DC with Chairman Gonzales of the Caddo Nation for a powerful conversation about leadership, sovereignty, and rebuilding from the ground up. Chairman Gonzales shares what it was like stepping into office during a moment of total collapse with empty buildings no funding and a community in crisis. He explains how trust relationships and long...

A young investor started with  no money, four rentals, and zero credibility . Then he found a  38-unit property  that had sat on and off the market for  12 years , a building so bad banks refused to touch it: failed septic systems, collapsing collections, elderly owners, and endless fallout contracts. Because nobody else wanted it, he saw his shot. He approached the owners directly,  didn’t ask fo...

In this keynote from the White Label Conference, Andrew Cartwright breaks down one of the most powerful and overlooked business models:  white labeling , where you put your brand on proven back-end systems and let experts do the heavy lifting. Andrew shares how he started 32 companies, rebuilt entire neighborhoods, survived massive financial setbacks, and used white labeling to double his income a...

In this episode, Andrew Cartwright sits down with real estate investor and entrepreneur  Brian Davila , a self-made multimillionaire who went from addiction and failure to flipping success and financial freedom. They talk about real estate, resilience, the California market, immigration, politics, and what it really takes to rebuild your life. This one’s real, raw, and packed with insight.

In this episode of  The Reluctant Billionaire Podcast , Andrew Cartwright sits down with  Melissa Perlman , Founder & President of  BlueIvy Communications , to talk about the power of storytelling, public relations, and personal brand building in today’s fast-moving media landscape. Melissa shares how she built one of South Florida’s leading communications agencies, her approach to authentic l...

In this episode of  The Reluctant Billionaire Podcast , Andrew Cartwright sits down with  Gino Barbaro , co-founder of  Jake & Gino , multifamily investor, mentor, and author, to talk about the mindset, systems, and discipline behind building a $350 million real estate portfolio. From running a small family pizza restaurant for 20 years to teaching thousands how to achieve financial freedom th...

In this episode of  The Reluctant Billionaire Podcast , Andrew Cartwright sits down with  John Anderson , pro strongman, IFBB bodybuilder, world-traveled wrestler, and mindset coach, for an unfiltered conversation about discipline, consistency, and the mental edge it takes to build a life without limits. From overcoming childhood learning disabilities to becoming a world-class athlete, John shares...

In this powerful sit-down,  Andrew Cartwright  flips the script and interviews  Chris Smith  and  Paki Phillips , founders of  The Vegas Circle Podcast . They share how they turned their Midwest roots and real-estate hustle into one of Vegas’s most talked-about podcasts, built on consistency, culture, and authentic storytelling. From surviving censorship battles and industry double standards to bu...

At just 19,  Rachel Pizzolatto  has already conquered science, sports, and the spotlight — from  MythBusters Jr.  to modeling for  GUESS , inventing new technology, and training for the Olympics . In this episode of  The Reluctant Billionaire Podcast ,  Andrew Cartwright  sits down with Rachel to talk about balancing brains and beauty, going viral, handling hate, and chasing her dream of becoming...

In this episode, Andrew sits down with his longtime underwriting and M&A partner to break down  how business lending really works behind the scenes . They go deep into SBA rules, refinancing strategies, and the biggest mistakes entrepreneurs make when talking to banks. You’ll learn: How the new  SBA 7(a) refinance rules  actually work Why so many business owners are stuck paying  9%–10% intere...

In this episode, Andrew sits down with Jamaica—Bronx-born, cardiology practitioner, and member of the Origin of Opportunity community. She breaks down her journey from grinding multiple jobs to building  $15,000/month in passive income , and why her true financial freedom number is  $50,000/month . They unpack the real obstacles most high-performers face: ⏳  Time 💰  Capital 📉  Debt-to-income li...

$800K in 1,000 Square Feet In this episode, Andrew sits down with a fast-growing restaurant owner to break down the REAL numbers behind a successful food business. From a tiny  1,000 sq ft  location generating  $800,000 a year , they dig into overhead, margins, cost of goods, labor, and what it actually takes to scale. They walk through January numbers live on the phone, uncovering: • $40,000 reve...

In this episode, Andrew sits down with Australian psychologist and relationship expert  Meg Tuohy  for a powerful, honest conversation about the connection between  relationships, emotional safety, and your financial life . Together, they explore: How your personal relationships influence your success Why emotional safety is the foundation of growth The five qualities women find most attractive in...

#realestate #entrepreneur #wealth 🚀 Is real estate really as easy as it looks? In this episode, I sit down with Chris Cheff, a seasoned real estate investor, to break down the real risks and rewards of flipping houses, securing funding, and navigating today’s investment landscape. We cover:✅ The $2.2 Billion Ukraine funding & how it affects the economy✅ Gap funding, joint ventures, and the...

#business #entrepreneur #wealth What if I told you that the richest people in the world don’t network the way you think they do? 🤯In this episode of Reluctant Billionaire, I sit down with Jordan Hutchinson, the mastermind behind Jets & Capital, where he hosts high-level networking events that bring together millionaires, entrepreneurs, and investors.🚀 We cover:✅ How to network with high-net...

sat down with Greg Nathan to talk about an experience that changed his life forever. He was at the January 6th Capitol protest, and what happened next was something he never saw coming. From what started as a patriotic gathering to facing serious legal charges, jail time, and financial ruin, his story is a wake-up call for anyone who thinks this could never happen to them. We dive deep into what r...

#business #entrepreneur #wealth What if I told you there’s a device that can detect cancer BEFORE symptoms even appear? In this episode, I sit down with David Robb, who is working on groundbreaking technology that could change the future of health. We dive deep into how this device mimics a dog’s nose to detect cancer early, why early detection is the key to saving millions of lives, and the chall...

#entrepreneur #wealth Success isn’t just about money, it’s about resilience, mindset, and taking action. In this episode, I share my journey from being financially cut off at 12 to building multiple businesses and competing in Ironman. I open up about the struggles I faced, the power of mentorship, and the lessons I’ve learned through business and endurance sports. Whether you're an entreprene...