The Money Mondays
The Money Mondays
Dan Fleyshman
How Real Estate & AI Tech Are Creating Millionaires: Lessons from Gary Lipsky & Douglas James
47 minutes Posted Aug 4, 2025 at 1:45 pm.
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In this powerhouse episode of The Money Mondays, Dan Fleyshman brings together two incredible entrepreneurs who are reshaping the way people build wealth, invest capital, and give back.• Gary Lipsky, founder of Break of Day Capital, shares how he went from producing indie films and running youth programs to managing $100M+ in real estate assets. He breaks down real estate syndications, how to spot red flags, and why passive investing is one of the smartest wealth plays for busy professionals.• Douglas James, a Navy veteran turned tech founder, walks through his evolution from lead generation agency owner to co-creator of LeadFi, a cutting-edge platform using proprietary data and AI to supercharge high-ticket sales. He opens up about losing 8 figures, hitting rock bottom, and rebuilding with faith, focus, and purpose.In this episode you’ll learn:• Why hands-off real estate investing creates true freedom• How to evaluate IRR, cash flow, and cap rates in deals• The power of AI and real-time data for qualifying leads• What both men teach their kids about charity and legacy• Why neither plans to hand over massive wealth to their children without preparationFrom real estate to revenue tech, this episode is a blueprint for how to make, grow, and give money, with purpose.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/