Zen and the Art of Real Estate Investing with Jonathan Greene

135: Finding Real Estate Success by Building Real Connections with Denis Shapiro


Trusting what you see investors doing on social media can be tempting, but looks can sometimes be deceiving.

On this episode of Zen and the Art of Real Estate Investing, Jonathan interviews Denis Shapiro, Managing Partner of SIH Capital Group. Denis began investing in real estate in 2012. Over the years, he has created a diversified portfolio that includes ATM funds, mobile home parks, life insurance policies, tech startups, and industrial property. Denis is also the author of The Alternative Investment Almanac: Expert Insights on Building Personal Wealth in Non-Traditional Ways.

Jonathan and Denis begin their discussion by delving into Denis’s early exposure to real estate with the book Rich Dad, Poor Dad, and why it didn’t stick the first time around. They cover the lessons he’s teaching his kids about money using Monopoly, why he loves having a diversified portfolio, and what types of affordable housing he prefers. Denis explains how he finds off-market deals in the affordable housing space, the three asset classes he loves the most, and why private lending is an integral part of the three pillars of his business. You’ll hear why creating relationships is crucial to his business model rather than leaning on reputation, why taking actionable steps matters when introducing yourself to other investors, and the value of knowing your skillset and having a basic knowledge of terminology at your disposal. Finally, Denis emphasizes being cautious when choosing syndications to invest with and knowing what uncomfortable questions to ask.

Denis’s career is centered on relationships and trust, which continues to help his business scale and thrive.

In this episode, you will hear:

  • Denis Shapiro’s early exposure to real estate investing and his pivot from a career in government to real estate investing
  • What Monopoly is teaching his kids about real estate investing
  • The lessons he’s trying to teach his kids about money and why having money doesn’t necessarily make you rich
  • Why Denis loves being diversified with his investments
  • His first property and some of the big lessons he learned from it
  • The importance of having a team in place to help manage affordable properties at scale
  • The types of affordable housing Denis prefers, and the barrier of entry red tape creates that you won’t find in commercial real estate
  • Finding off-market deals in the affordable housing space
  • The three asset classes Denis loves the most and why he stays focused on those
  • Private lending and what makes it an attractive pillar in his business model
  • Creating relationships with other investors and building trust instead of basing a business deal on reputation
  • Learning to ask the right questions as a new investor
  • Taking actionable steps when you’re working on building relationships with people you want to work with
  • Why knowing your skillset and some industry terminology can improve how you relate to those you want to learn from and work with
  • What you can learn from LP investors and being careful when choosing syndications
  • Denis’s advice for not becoming too dependent on track records and knowing what uncomfortable questions to ask

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If you enjoyed this episode, we’ve created a PDF that has all of the key information for you from the episode. Just go to the episode page at to download it.

Supporting Resources:

SIH Capital Group –

SIH’s YouTube channel –

SIH Capital on Facebook –

SIH on Instagram –

Connect with Denis Shapiro on LinkedIn –

Find SIH Capital on Twitter/X –

Website –

YouTube –

Instagram –

Instagram –

TikTok –

Zillow –

Bigger Pockets –

Facebook –

Email –

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