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The Money Mondays

The Money Mondays

How Real Estate & AI Tech Are Creating Millionaires: Lessons from Gary Lipsky & Douglas James

Aug 4, 2025 · 47m

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On this episode

About this episode

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…