Receiverships, gut rehabs, and family legacy collided to shape Michael Root’s rise in Chicago real estate. In this episode, he shares how he scaled from inherited rentals to complex multifamily deals fueled by trust, operations, and bold decision-making. Hit play and discover how he turned legacy buildings and court cases into a winning strategy.

Key Takeaways To Listen For

• How coffee shops and street art led them to their first winning market
• What hundreds of court-appointed properties taught them about scaling
• From flips to full-scale multifamily: how their buy box leveled up
• The five deals he regrets walking away from and the mindset lesson inside
• Why property management is the foundation most investors skip

Resources/Links Mentioned In This Episode

• The Rising by Larry Silverstein | Kindle and Hardcover
• Circuit Court of Cook County

About Michael Root

Michael Root is Co-Partner at Root Property Group, a full-service real estate firm specializing in investment, management, and renovation throughout Chicago. With over 20 years of experience, he has played a key role in the company’s growth, strategic direction, and acquisitions, helping scale the firm to over $160 million in assets under management. In 2024 alone, under his leadership, the team added 100 units to their portfolio and achieved an impressive 82% lease renewal rate across their properties.

Connect with Michael

• Website: Root Property Group
• LinkedIn: Michael Root

Connect With Us

If you’re looking to invest your hard-earned money into cash-flowing, value-add assets, reach out to us at https://bobocapitalventures.com/.

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