The Money Mondays

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.
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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.
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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.
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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/
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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.
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