The Money Mondays

3d ago

In this episode of Money Mondays, Dan Fleyshman sits down with real estate entrepreneur John Gafford to talk about making money, smart investing, and giving back with purpose. John shares how he built Simply Vegas into the largest luxury real estate brokerage in Las Vegas and breaks down lessons from his bestselling book Escaping the Drift. This episode delivers practical insights on real estate, personal responsibility, and building wealth that truly lasts.---John Gafford is a real estate entrepreneur, author, speaker, and podcast host. He is the founder of Simply Vegas, the largest luxury real estate brokerage in Las Vegas, selling more million-dollar homes than any other firm in the market. With over 20 years of experience in real estate and business, John is known for building vertically integrated companies, high-performance teams, and purpose-driven organizations.John first gained national attention as a contestant on The Apprentice, where he was famously fired on live television. He is the author of Escaping the Drift, a bestselling book focused on personal responsibility, leadership, and reclaiming control over your life. He also hosts the Escaping the Drift Podcast, where he shares real-world lessons on business, investing, and personal growth.---Like this episode? Watch more like it 👇Building a Billion-Dollar Platform Across Law, Healthcare & AI w/ Sean Callagy 💰 : • Building a Billion-Dollar Platform Across ... The New Definition of Wealth: Strong Body, Strong Mind, Strong Family w/ Steve Eckert 💪: • The New Definition of Wealth: Strong Body,... How One Man Went From Prison to Building a Fitness Empire (REDCON1) | Aaron Singerman 💪 : • How One Man Went From Prison to Building a... The Best Stock Market Lessons I Ever Learned (Life Changing) 📈 E106: • The Best Stock Market Lessons I Ever Learn... Watch ALL Full Episodes Here: • The Money Mondays Podcast - FULL EPISODES Access a 30 day free trial of GoHighLevel: https://gohighlevel.com/fleyshman ---The Money Mondays is a business podcast here to teach you how to make money, invest money, and donate money by showcasing some of the world's most successful people and how they do the same. Hosted by serial entrepreneur Dan Fleyshman, the youngest founder of a publicly traded company in history, this money podcast gives you an exclusive behind the scenes look at how the wealthiest celebrities, entrepreneurs, athletes and influencers make, invest and donate money.If you want to learn more business and investing while you work to improve your financial life, you're in the right place! Subscribe: / @themoneymondays Dan Fleyshman,The Money MondaysLearn more here: https://themoneymondays.com Watch all the podcast episodes: • The Money Mondays Podcast - FULL EPISODES Let’s Connect...Website: https://themoneymondays.com Podcast: https://podcasts.apple.com/us/podcast... Twitter: / themoneymondays LinkedIn: / about TikTok: / themoneymondays FB: / the-money-mondays-110233585203220

Dec 8

In this special episode of Money Mondays , we hit pause on “how to make and invest money” and go all-in on the third pillar: how to give it away. Dan records live from Tampa in the middle of the 12th annual World’s Largest Toy Drive —a 10-city, 17-day marathon of giving that started 12 years ago with just eight volunteers wrapping toys on the floor. You’ll hear how Trina’s Kids Foundation grew from a small local effort into stadium-level events at places like BMO Stadium, Allegiant/Raiders Stadium, American Dream Mall, and the Miami Heat Arena , powered by semi-trucks of toys, strategic partners, and a relentless focus on efficiency and impact. Dan breaks down the real numbers behind the toy drive, how he negotiates with suppliers to stretch every dollar, and why he’s obsessed with proving to major brands and billionaires that philanthropy can be run like a high-performance business. But this episode isn’t just a highlight reel—it’s a playbook . Dan walks you through exactly how you can: Host your own toy drive, food drive, or local fundraiser in your city Use your business ecosystem —vendors, clients, employees, partners—to fuel charity work Eliminate friction in donations (from PayPal and wire to Bitcoin) Turn volunteering into a core part of your family or company culture Use social media the right way so your posts about giving create a massive butterfly effect instead of looking like a humblebrag You’ll also hear the origin stories of campaigns like the $100 Tipping Club and “Two Years Too Long” clothing drive, and how simple ideas—shared publicly—have inspired thousands of people around the world to copy and scale them. If you’ve ever thought, “I want to do more, but I don’t know where to start,” this episode will give you the mindset, the mechanics, and the motivation to launch something of your own—whether you have money to donate or just time, energy, and a phone.

Dec 1

In this episode, today’s guest Travis Chappell, @travismakesfriends , shares his journey from aspiring pastor to door-to-door salesman, and eventually to becoming a leading figure in the podcasting industry. He talks about building his network from scratch, why relationships fuel his work, and how podcasters can make money whether through sponsorships, affiliate deals, or their own products.Travis Chappell is the founder and CEO of Guestio, and the host of the podcast Travis Makes Friends (formerly known as Build Your Network). Travis today is known not just for his podcasts, but for helping people build meaningful networks, get access to high-caliber interviews, and grow their presence through proper connections.Like this episode? Watch more like it 👇"Podcasting is the ULTIMATE Networking Tool" - Sean Kelly 📡 : https://youtu.be/TBNtCDP6EU8Christian DelGrosso & Marshall Sylver's Social Media SUCCESS & Building WEALTH 📈 : https://youtu.be/h6ToLKH7Y5QHow the Next Million-Dollar Brands Are Built (And What It Takes to Lead Them) 🧠: https://youtu.be/jhrIhfCbugYWhy Most Influencers Fail (And How Kellan Ness Blew Up Instead)🔥: https://youtu.be/KTBu_A9Cl0MWatch ALL Full Episodes Here: https://www.youtube.com/playlist?list=PLs0D-M5aH-0IOUKtQPKts-VZfO55mfH6k---The Money Mondays is a business podcast here to teach you how to make money, invest money, and donate money by showcasing some of the world's most successful people and how they do the same. Hosted by serial entrepreneur Dan Fleyshman, the youngest founder of a publicly traded company in history, this money podcast gives you an exclusive behind the scenes look at how the wealthiest celebrities, entrepreneurs, athletes and influencers make, invest and donate money.If you want to learn more business and investing while you work to improve your financial life, you're in the right place! Subscribe: https://www.youtube.com/@themoneymondays?sub_confirmation=1Dan Fleyshman,The Money MondaysLearn more here: https://themoneymondays.comWatch all the podcast episodes: https://youtube.com/playlist?list=PLs0D-M5aH-0IOUKtQPKts-VZfO55mfH6kLet’s Connect...Website: https://themoneymondays.comPodcast: https://podcasts.apple.com/us/podcast/the-money-mondays/id1663564091Twitter: https://twitter.com/themoneymondaysLinkedIn: https://www.linkedin.com/company/the-money-mondays/about/TikTok: https://tiktok.com/@themoneymondaysFB: https://www.facebook.com/The-Money-Mondays-110233585203220/

Nov 25

On this episode of The Money Mondays , Dan Fleyshman sits down once again with entrepreneur and investor Matt Morgan , known for building over $1B+ in cannabis companies and now operating as a high-level investor across crypto, tech, AI, and real estate. They break down the three pillars of the show— how to make money, how to invest money, and how to give it away —through raw, honest advice on fear, risk, lifestyle creep, and long-term wealth building. Matt dives deep into Bitcoin, liquidity cycles, AI’s impact on the global economy, the blockchain revolution , and why volatility is actually a gift for early adopters. They also explore longevity, biohacking, and why freedom—not cars, watches, or houses—is the ultimate luxury . This is a fast-paced, insight-packed episode for anyone serious about leveling up financially, investing smarter, and preparing for a world transformed by AI, crypto, and extended human lifespan.

Nov 17

In this episode of Money Mondays, Dan Fleyshman sits down with Steve Eckert, Marine Corps veteran, peak-performance coach, and longtime Operation Blacksite instructor. Steve reveals how discipline, leadership, family values, and daily habits create real wealth not just financially, but mentally and physically. Steve Eckert is a Marine veteran, coach, speaker, and the embodiment of everyday discipline. With years of uninterrupted training alongside his wife and kids, Steve teaches the power of consistency, accountability, and living a life your children want to follow. At Operation Blacksite, he helps families and individuals develop confidence, capability, and mental toughness for today’s world.Like this episode? Watch more like it 👇Building a Billion-Dollar Platform Across Law, Healthcare & AI w/ Sean Callagy 💰 EP144: https://youtu.be/HEyjoJSrIgQWhy So Many Millionaire Athletes Lose Everything (and How to Avoid It) 🏋️‍♂️ EP143: https://youtu.be/tPObh6_bMCwThe Best Stock Market Lessons I Ever Learned (Life Changing) 📈 E106: https://youtu.be/wkJ-YVzSrjsHow One Man Went From Prison to Building a Fitness Empire (REDCON1) | Aaron Singerman 💪 EP140: https://youtu.be/9p4dpUEEFDIWatch ALL Full Episodes Here: https://www.youtube.com/playlist?list=PLs0D-M5aH-0IOUKtQPKts-VZfO55mfH6k---The Money Mondays is a business podcast here to teach you how to make money, invest money, and donate money by showcasing some of the world's most successful people and how they do the same. Hosted by serial entrepreneur Dan Fleyshman, the youngest founder of a publicly traded company in history, this money podcast gives you an exclusive behind the scenes look at how the wealthiest celebrities, entrepreneurs, athletes and influencers make, invest and donate money.If you want to learn more business and investing while you work to improve your financial life, you're in the right place! Subscribe: https://www.youtube.com/@themoneymondays?sub_confirmation=1Dan Fleyshman,The Money MondaysLearn more here: https://themoneymondays.comWatch all the podcast episodes: https://youtube.com/playlist?list=PLs0D-M5aH-0IOUKtQPKts-VZfO55mfH6kLet’s Connect...Website: https://themoneymondays.comPodcast: https://podcasts.apple.com/us/podcast/the-money-mondays/id1663564091Twitter: https://twitter.com/themoneymondaysLinkedIn: https://www.linkedin.com/company/the-money-mondays/about/TikTok: https://tiktok.com/@themoneymondaysFB: https://www.facebook.com/The-Money-Mondays-110233585203220/

Nov 10

In this special episode, Dan Fleyshman sits down with three guests, Raul Villacis, founder of The Edge men’s empowerment movement, and the Chapman Brothers, Aaron and Eric, who recently collaborated on a thought-provoking and visually stunning new book. Together, they share insights on entrepreneurship, financial discipline, personal growth, creativity, and giving back.---Raul Villacis is the founder and CEO of The EDGE Program, a movement helping high-performing businessmen find purpose, discipline, and clarity in every area of life. Before leading thousands of men around the world, he was one of them, a man who had achieved success on paper but felt empty inside.---Aaron J. Chapman is a veteran of the real estate finance industry, speaker, and author, while Eric J. Chapman is a professional illustrator and fine art painter. Their latest collaboration showcases the intersection of entrepreneurship, art, and personal growth reminding listeners that true wealth lies not just in money, but in meaning, impact, and legacy.---Like this episode? Watch more like it 👇Building a Billion-Dollar Platform Across Law, Healthcare & AI w/ Sean Callagy 💰: https://youtu.be/HEyjoJSrIgQHow One Man Went From Prison to Building a Fitness Empire (REDCON1) | Aaron Singerman 💪 : https://youtu.be/9p4dpUEEFDITurning Setbacks Into Millions: Tim Storey & Natasha Graziano On Making, Multiplying & Giving Money: https://youtu.be/Stbx6c5bawIFrom Mowing Lawns to Madison Square: The Grind to Pro | Andre Berto 🥊 : https://youtu.be/INn4jL1iRR4Watch ALL Full Episodes Here: https://www.youtube.com/playlist?list=PLs0D-M5aH-0IOUKtQPKts-VZfO55mfH6k---The Money Mondays is a business podcast here to teach you how to make money, invest money, and donate money by showcasing some of the world's most successful people and how they do the same. Hosted by serial entrepreneur Dan Fleyshman, the youngest founder of a publicly traded company in history, this money podcast gives you an exclusive behind the scenes look at how the wealthiest celebrities, entrepreneurs, athletes and influencers make, invest and donate money.If you want to learn more business and investing while you work to improve your financial life, you're in the right place! Subscribe: https://www.youtube.com/@themoneymondays?sub_confirmation=1Dan Fleyshman,The Money MondaysLearn more here: https://themoneymondays.comWatch all the podcast episodes: https://youtube.com/playlist?list=PLs0D-M5aH-0IOUKtQPKts-VZfO55mfH6kLet’s Connect...Website: https://themoneymondays.comPodcast: https://podcasts.apple.com/us/podcast/the-money-mondays/id1663564091Twitter: https://twitter.com/themoneymondaysLinkedIn: https://www.linkedin.com/company/the-money-mondays/about/TikTok: https://tiktok.com/@themoneymondaysFB: https://www.facebook.com/The-Money-Mondays-110233585203220/

Nov 4

In this inspiring episode of The Money Mondays , host Dan Fleyshman sits down with serial entrepreneur, speaker, and visionary Sean Callagy, a legally blind attorney on the verge of becoming the first self-funded unicorn founder with a billion-dollar valuation based on EBITDA. Sean shares how he went from broke and going blind to running a portfolio of thriving companies, including Callagy Law , Callagy Recovery , and the cutting-edge ActEye AI platform, all driven by his mission to elevate human potential through integrity and influence. Together, Dan and Sean dive deep into: ✅ Building multiple 8- and 9-figure businesses with integrity and heart ✅ Why influence is the only human attainable superpower ✅ How to scale teams using the “three loyalties” framework ✅ The future of AI and why Sean believes it can change the world for good ✅ Real talk on money, lifestyle creep, and living below your means ✅ The mindset behind sustainable giving and purpose-driven leadership Sean also shares powerful insights from his work with Tony Robbins , lessons from overcoming blindness, and the philosophy that drives his “Unblinded” movement, proving that success isn’t about what you see , but what you believe .

Oct 27

In this episode of The Money Mondays podcast, Dan Fleyshman sits down with Chip Paucek to discuss the challenges and opportunities faced by professional athletes after retirement. Chip shares how his organization, ProAthlete Community (PAC), described as “YPO for pro athletes” helps athletes transition from sports to successful careers and investments through mentorship, education, and connection. The conversation dives deep into the mindset shifts needed to thrive beyond the spotlight, from financial literacy to finding purpose through charity and community building.Christopher J. Paucek also known as "Chip Paucek" is the co-founder and CEO of ProAthlete Community, an organization designed to support professional athletes in unlocking their long-term potential. Before founding PAC, Chip was the co-founder and CEO of 2U, one of the world’s largest online education companies, which he took public and grew to nearly a billion dollars in revenue. With decades of entrepreneurial experience, Chip is now dedicated to empowering elite athletes to channel their discipline and drive into new ventures, education, and philanthropy after their playing careers end.Like this episode? Watch more like it 👇UFC Michael Chandler & CEO Wes Watson Talk MONEY 💸: https://youtu.be/e2J-QZU3cQE7x Mr Olympia Flex Lewis & Bedros Keuilian's TOP MONEY TIPS 💪: https://youtu.be/LAA-OsePAOQMowing Lawns to Madison Square: The Grind to Pro | Andre Berto 🥊 : https://youtu.be/INn4jL1iRR4NFL Player Turned Real Estate Investor & CEO of RepeatMD w/ Larry English & Phil Sitter 💵 : https://youtu.be/Gk07Zz56MFgWatch ALL Full Episodes Here: https://www.youtube.com/playlist?list=PLs0D-M5aH-0IOUKtQPKts-VZfO55mfH6k---The Money Mondays is a business podcast here to teach you how to make money, invest money, and donate money by showcasing some of the world's most successful people and how they do the same. Hosted by serial entrepreneur Dan Fleyshman, the youngest founder of a publicly traded company in history, this money podcast gives you an exclusive behind the scenes look at how the wealthiest celebrities, entrepreneurs, athletes and influencers make, invest and donate money.If you want to learn more business and investing while you work to improve your financial life, you're in the right place! Subscribe: https://www.youtube.com/@themoneymondays?sub_confirmation=1Dan Fleyshman,The Money MondaysLearn more here: https://themoneymondays.comWatch all the podcast episodes: https://youtube.com/playlist?list=PLs0D-M5aH-0IOUKtQPKts-VZfO55mfH6kLet’s Connect...Website: https://themoneymondays.comPodcast: https://podcasts.apple.com/us/podcast/the-money-mondays/id1663564091Twitter: https://twitter.com/themoneymondaysLinkedIn: https://www.linkedin.com/company/the-money-mondays/about/TikTok: https://tiktok.com/@themoneymondaysFB: https://www.facebook.com/The-Money-Mondays-110233585203220/