Jordan Belfort Trained an AI to Sell Like Him 🤖 E161

On this episode of The Money Mondays Podcast, Dan Fleyshman sits down with Jordan Belfort (The Wolf of Wall Street) and Hollywood super-connector Gavin Navarro for a rapid-fire masterclass on the three Money Mondays pillars: how to make money, how to invest it, and how to give it away.Jordan breaks down what really holds people back from earning more: it’s not just “mindset”—it’s missing skills, missing mentorship, and not putting in the reps. He shares why sales is the ultimate life skill, how to treat rejection as a numbers game, and why top performers don’t waste time trying to “convert” hard no’s.Then Gavin pulls back the curtain on turning relationships into real opportunities—without becoming the person who pitches everyone every day. He explains how to bring deals to high-profile people the right way, how to filter constant incoming pitches, and how he built a career by being the guy who can connect the right people in the right cities at the right time.On the investing side, Jordan shares his long-term approach (including S&P 500 and Bitcoin), while Dan lays out his 40/40/20 framework for balancing low-risk stability, medium-risk growth, and high-risk “shots at glory.” They also explain why businesses like beverages can require serious capital even when demand is booming.Finally, they talk about why charity matters—not just for optics, but for trust, culture, and legacy—and Dan closes with his signature question that always gets a different answer: what percentage of your net worth should go to your family?

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!In this episode, Dan sits down with Terrence J—host, actor, producer, and investor—to unpack the business side of building a career in entertainment and turning that momentum into real wealth. Terrence shares the hustle story behind landing 106 & Park (including the bold move that changed everything), why he chose to pivot to E! News at a peak moment, and how he learned to protect his brand by only saying “yes” to opportunities that align.Then they get straight to the money: Terrence breaks down how he accidentally fell into real estate through his first home purchase, how he evaluates investments (including restaurants and operator-led businesses), and why financial literacy is the difference between keeping wealth and losing it—especially for athletes and creators. They also talk mentorship, long-term planning (trusts, life insurance, and protecting family), and why giving back becomes even more important as your life and priorities evolve. The AI inside HighLevel is booking 250,000+ appointments every month without a human touching it. Voice AI answers missed calls and schedules meetings. Conversation AI handles lead follow-up 24/7. Over 2 million businesses run on this platform. Try it free for 14 days → danhighlevel.com/ai

On this episode of Money Mondays, Dan Fleyshman brings the show’s core theme—how to make more money, save more money, and invest more money—to life with Fanbasis founder/CEO Yash Daftery and Founders Club co-founders Chris Meade (CROSSNET) and Aaron Spivak (Hush). They dive into practical ways creators and internet entrepreneurs can turn audiences into real revenue through digital products, smarter payments, and higher AOV, plus what it really takes to build a high-trust founder network that unlocks better relationships, deals, and opportunities. You’ll also hear Dan’s takes on investing discipline, evaluating opportunities, and giving back in ways that create visible, meaningful impact.If you're still answering every call yourself or letting leads slip through the cracks, check out HighLevel's AI. Voice AI that picks up when you can't and books appointments on the spot. Conversation AI that nurtures and converts leads around the clock. This is what I use. Try it free → danhighlevel.com/ai

This week on Dan Fleyshman’s Money Mondays, Dan delivers a two-part episode that hits the show’s core pillars: how to make money, how to invest money, and how to give it away to charity.In the first half, Daniel G breaks down what actually creates consistent sales results—especially for women. He explains why women often have a natural advantage (listening, empathy, intuition), how those same strengths can turn into “kryptonite” when perfectionism and overthinking take over, and how to sell with confidence by focusing on the outcome your product creates. Daniel also shares a clear framework for getting paid to speak by becoming known for one thing, how to choose the right offer based on track record and ethics, and why every early “no” is simply feedback that sharpens your script.In the second half, Dr. Coach Stormy Wellington gets real about what holds people back from earning more—fear, doubt, insecurity, procrastination—and what separates average reps from true superstars in direct sales: self-worth, discipline, community, and an obsession with transformation. She also talks candidly about learning investing the hard way, why she prefers proven operators with a track record, and why giving back isn’t a flex—it’s a responsibility tied to purpose and legacy.Like this episode? Watch more like it 👇Watch ALL Full Episodes Here: https://www.youtube.com/playlist?list=PLs0D-M5aH-0IOUKtQPKts-VZfO55mfH6kThe 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/I put together a free audit for my audience. My team will analyze your business, find where revenue is slipping through the cracks, and give you a specific action plan. Ads, funnels, sales, automations, whatever's broken, we'll find it. Claim your free audit → danhighlevel.com

Joey Carson returns to Dan Fleyshman’s The Money Mondays for a fast, no-fluff conversation on the three core pillars: how to make money, invest money, and give it away, with real operator perspective from a CEO who has built and scaled across entertainment and business.Joey breaks down his 30-year career in TV and film, from leadership at Fox to running Bunim Murray Productions (think The Real World era) and turning a creative shop into a scalable studio with process, departments, and repeatable development systems.He also shares what it actually takes to leave a “safe” job, why he prefers uncertainty (because it creates unlimited upside), and how to know when you are stagnating.From there, Dan and Joey get tactical:How to bring a money-making idea to your boss without bruising ego (and why you need data plus a real plan)Why mentorship changes everything, and the number one trait that predicts success: being coachableJoey’s take on investing early vs. later, and Dan’s “Four Horsemen” framework for vetting deals (CEO, accountant, lawyer, and a domain advisor)A grounded approach to philanthropy: give where you can verify impact, stay close to the mission, and focus on actually helping peopleLegacy, family, and stewardship: Joey’s clear answer on wealth transfer: “All of it.”Bonus: Joey’s best advice for surviving today’s nonstop outrage cycle: observe, do not engage, and always ask: “What is the point?”If you are building a career, scaling a company, deciding what to invest in, or trying to stay focused while the world screams for your attention, this episode is a practical reset.Share this episode with a friend who is ready to level up their income, their decision-making, and their discipline.HighLevel just dropped AI tools that are changing how businesses operate. Voice AI answers your missed calls and books appointments for you. Conversation AI follows up with leads 24/7. Last month their AI booked over 250,000 appointments on autopilot. See what it can do for your business → danhighlevel.com/ai

Josh Snow built Snow Oral Care by doing what most entrepreneurs won’t: taking on the household-name giants head-on—and bootstrapping his way to nine figures in sales. In this special Money Mondays episode (recorded during the $100M Mastermind experience), Josh breaks down how to win shelf space against “the whole aisle,” why adversity can become your superpower, and what really makes a brand pop when customers walk past Colgate and Crest.He also goes deep on celebrity partnerships (what founders should know before chasing big names), shares his blunt investing filter (“don’t do it” unless you can stomach the loss), and explains how to choose philanthropy that actually means something instead of checking a box. And of course—he answers the signature Money Mondays question with an answer you won’t forget.Want the systems to turn these lessons into booked calls and consistent revenue? If you’re ready to automate follow-ups, capture leads, and keep your pipeline moving without living in your inbox, check out GoHighLevel—the all-in-one platform for CRM, funnels, email/SMS, calendars, and automations.Most businesses are leaking revenue and don't even know it. That's why I'm offering a free personalized audit from my team. We'll dig into your business and show you exactly where you're losing money and what to fix next. No AI fluff, real analysis. Get yours free → danhighlevel.com

Dan Fleyshman sits down with Rashad Bilal, co-founder of Earn Your Leisure, to break down the three pillars of Money Mondays—how to make money, invest money, and give it away—through the lens of building one of the most impactful finance media brands in culture. Rashad shares the mindset behind You Deserve to Be Rich—why believing you’re worthy of wealth is often the first (and missing) step to actually building it. He and Dan get practical on when to start investing (as soon as you have discretionary income), how to think about emergency funds, and why money sitting idle gets quietly eaten by inflation. They also go behind the scenes on Invest Fest’s growth—from a business “festival” concept to a 25,000-person experience—and why relationships are still the ultimate ROI. Finally, Rashad talks lifestyle creep, modern content mega-deals, and why giving back is a core part of building real wealth.Like this episode? Watch more like it 👇Watch 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/I use HighLevel to run my entire backend, and their AI features are insane. Voice AI that answers missed calls and books appointments. Conversation AI that's booking 250,000+ appointments a month on autopilot. Chatbots, workflow automation, all built in. Try it free for 14 days → danhighlevel.com/ai

In this episode of The Money Mondays Podcast, Dan Fleyshman sits down in Las Vegas with Bradley Sugars, founder of ActionCOACH, one of the world’s largest business coaching organizations operating in 85+ countries and responsible for billions in client revenue.Brad shares decades of hard-earned wisdom on what truly separates struggling operators from successful business owners. From why most entrepreneurs stay stuck doing $20/hour tasks to how real wealth is built through systems, coaching, and accountability, this conversation pulls back the curtain on money, mindset, and scale.They dive deep into:Why business coaching delivers a 6–7x ROI and how to know if you’re actually coachableThe difference between being a great operator vs. a true ownerWhy “how” kills most goals — and what to focus on insteadHow to think about investing once you’ve made money (businesses, real estate, and rules)Why talking about money openly is essential — especially with friends and familyThe real purpose of wealth, legacy, and giving backBrad also breaks down his philosophy on goal-setting, investing only where you’re an expert, and why most people would rather look rich than be rich. This is a masterclass in business thinking, long-term wealth, and building a life that actually feels successful.If you want to make more money, invest smarter, and understand wealth at a deeper level, this episode is required listening.Like this episode? Watch more like it 👇The New Definition of Wealth: Strong Body, Strong Mind, Strong Family w/ Steve Eckert 💪 : https://youtu.be/snsag2gHgp8Why Most People Never Build REAL Wealth (and How to Change That) 💵 : https://youtu.be/T1zhRFPdhzITurning Setbacks Into Millions: Tim Storey & Natasha Graziano On Making, Multiplying & Giving Money: https://youtu.be/Stbx6c5bawIBuilding a Billion-Dollar Platform Across Law, Healthcare & AI w/ Sean Callagy 💰: https://youtu.be/HEyjoJSrIgQWatch 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/Want to know what's broken in your business? I'll have my team audit your ads, funnels, sales calls, automations, or offer structure for free. We'll find the leaks and tell you exactly what to fix. Claim your free audit → danhighlevel.com

In this episode of Money Mondays, Dan Fleyshman sits down with entrepreneur and educator Troy Millings to talk about building businesses, smart investing, and creating generational wealth. Troy shares how he built Earn Your Leisure into a multi-million-dollar brand and breaks down lessons on financial literacy, mentorship, and making an impact through live events like Invest Fest. This episode delivers practical insights on investing, entrepreneurship, and giving back with purpose.Troy Millings is an entrepreneur, educator, and founder of Earn Your Leisure, a multi-million-dollar brand focused on financial literacy, investing, and entrepreneurship. He hosts the Market Mondays podcast and produces Invest Fest, a live event connecting investors, entrepreneurs, and creators. Troy is known for helping people build wealth, make informed financial decisions, and create lasting impact.Like this episode? Watch more like it 👇The New Definition of Wealth: Strong Body, Strong Mind, Strong Family w/ Steve Eckert 💪 : https://youtu.be/snsag2gHgp8Why Most People Never Build REAL Wealth (and How to Change That) 💵 : https://youtu.be/T1zhRFPdhzITurning Setbacks Into Millions: Tim Storey & Natasha Graziano On Making, Multiplying & Giving Money: https://youtu.be/Stbx6c5bawIBuilding a Billion-Dollar Platform Across Law, Healthcare & AI w/ Sean Callagy 💰: https://youtu.be/HEyjoJSrIgQWatch 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/If you want an all-in-one platform for marketing, CRM, texting, email, and booking, go to https://gohighlevel.com/fleyshman

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.comWatch all the podcast episodes:    • The Money Mondays Podcast - FULL EPISODES  Let’s Connect...Website: https://themoneymondays.comPodcast: https://podcasts.apple.com/us/podcast...Twitter:   / themoneymondays  LinkedIn:   / about  TikTok:   / themoneymondays  FB:   / the-money-mondays-110233585203220   Most businesses miss over half their phone calls, and 80% of those people never call back. HighLevel's Voice AI fixes that. It answers every call you miss, talks to your customers, and books appointments automatically. Their AI handled over a million calls last month alone. Try it free → danhighlevel.com/ai