The Money Mondays

Dan Fleyshman

“The Money Mondays” is primed to be a global brand in the business space, focusing on investments, cash flowing businesses, side hustles and visual acts of charity. Viewers will be able to learn from experts, win weekly prizes and participate in charity efforts in an “MTV Cribs” style setting. Many episodes of the podcast will be recorded with Celebrities, influencers & athletes inside of their homes, studios & headquarters. Hosted by Dan Fleyshman, the youngest founder of a publicly traded company. Dan has Angel invested in 43 companies and spoken at over 250 business industry events.

  1. 4D AGO

    Why Most People Aren’t Built for CEO Pressure (And That’s Okay) 💼 E162

    In this week’s episode of The Money Mondays, Dan Fleyshman sits down with Eric Spofford and Justus Parmer for a fast-paced, money-focused conversation built around the show’s three pillars: how to make money, how to invest money, and how to give back.Eric shares his journey from addiction and rock bottom to building a real business that scaled to hundreds of employees and ultimately sold for $115M—then breaks down the real mechanics of creating “sellable” companies: EBITDA, multiples, reducing key-man risk, building leadership teams, SOPs/KPIs, and what the exit process actually looks like from banker to data room to LOI and due diligence.Then Justus dives into how he thinks about investing with an “edge,” why he’s focused on American industrial assets and long-term infrastructure plays, how AI is impacting decision-making, and why the “butterfly effect” of giving back matters more than people realize.As always, keep in mind—this episode might not just be for you. It could be the one you send to a friend who’s trying to scale, raise money, invest smarter, or build something real. Get a free sales and marketing audit from my team. We'll find where you're leaking revenue and tell you exactly what to fix → danhighlevel.com 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/

    1h 6m
  2. FEB 23

    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?

    1h 5m
  3. FEB 16

    Money Talks: Terrence J Breaks Down Wealth, Real Estate, and Giving Back 💵 E160

    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

    33 min
  4. FEB 2

    Daniel G + Coach Stormy: Make It, Invest It, Give It Away 💰 E158

    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-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 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

    43 min
  5. JAN 26

    From TV Mogul to CEO: Joey Carson’s Blueprint for Scale 📈 E157

    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 coachable Joey’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 people Legacy, 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

    40 min
  6. JAN 19

    Bootstrapping to $100M: How Josh Snow Took on Colgate & Crest 🪥 E156

    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

    29 min
  7. JAN 5

    You Deserve to Be Rich with Earn Your Leisure’s Rashad Bilal 🏝️ E155

    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=1 Dan Fleyshman, The Money Mondays Learn more here: https://themoneymondays.com Watch all the podcast episodes: https://youtube.com/playlist?list=PLs0D-M5aH-0IOUKtQPKts-VZfO55mfH6k Let’s Connect... Website: https://themoneymondays.com Podcast: https://podcasts.apple.com/us/podcast/the-money-mondays/id1663564091 Twitter: https://twitter.com/themoneymondays LinkedIn: https://www.linkedin.com/company/the-money-mondays/about/ TikTok: https://tiktok.com/@themoneymondays FB: 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

    43 min
4.5
out of 5
438 Ratings

About

“The Money Mondays” is primed to be a global brand in the business space, focusing on investments, cash flowing businesses, side hustles and visual acts of charity. Viewers will be able to learn from experts, win weekly prizes and participate in charity efforts in an “MTV Cribs” style setting. Many episodes of the podcast will be recorded with Celebrities, influencers & athletes inside of their homes, studios & headquarters. Hosted by Dan Fleyshman, the youngest founder of a publicly traded company. Dan has Angel invested in 43 companies and spoken at over 250 business industry events.

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