Real Estate Underground

Mastering Short-Term Rentals and Affordable Housing with Denis Shapiro


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What would it take to transform your career from a federal government employee to a successful real estate entrepreneur? Meet Dennis Shapiro, the managing partner of SIH Capital Group, who unveils his journey and the strategies that led to his remarkable success. Inspired by "Rich Dad Poor Dad," Dennis shares how he transitioned from stock picking to managing multifamily properties and ultimately, developing hospitality and affordable housing business lines. Learn about the crucial role of specialized teams and strategic partnerships that have been pivotal to Dennis's achievements.

Ever wondered how to manage short-term rentals under stringent local regulations? Dennis offers a behind-the-scenes look at managing hospitality properties on the Jersey Shore, including the innovative Surf Village project, which revitalized nine bungalows into a branded experience. He also provides a deep dive into affordable housing investments through Low-Income Housing Tax Credits (LIHTC), illustrating how his strategy maximizes returns on properties nearing the end of their compliance periods. Real-life examples from Pennsylvania and Virginia showcase the practical applications and potential market transitions.

Discover the keys to personal and professional growth as Dennis emphasizes the importance of networking, mentorship, and continuous learning. He shares how small daily habits can accumulate into significant achievements, his newfound passion for CrossFit, and insights from his book, "The Alternative Investment Almanac." The episode wraps up with a fascinating story behind Dennis's unique name, adding a personal touch to this information-packed conversation. Don't miss out on these valuable insights into real estate investment and personal development from an industry expert.

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Additional Resources:

  • Clark St Capital -> Passive real estate investments for busy business owners and executives
  • Elevista -> AI SaaS for real estate investors
  • Clark St Academy on YouTube -> Learn how to invest in real estate

Social Media:

  • LinkedIn -> Ed Mathews (President at Clark St and Elevista)
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Real Estate UndergroundBy Ed Mathews

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