Passive Real Estate Investment | Casmon Capital Group | United States

Investing in Distressed Assets with Amy Rubenstein, Ep. 604

Amy Rubenstein, CEO of Clear Investment Group and Partner at Windy City RE, commands a formidable presence in the real estate investment realm, having overseen transactions exceeding half a billion dollars since 2005. Hailing from Chicago, Amy is an alumna of Brandeis University, graduating Cum Laude. With two decades of experience in real estate, she holds licenses in California and Illinois, strategically leveraging her expertise across diverse markets. Clear Investment Group’s expansive portfolio spans distressed multi-family complexes nationwide, showcasing Amy’s adeptness in creative structuring and asset revitalization, optimizing financial performance across multi-family, retail, and office sectors.

Beyond her business acumen, Amy is a committed philanthropist, notably in the Arts and Education sectors. As the Artistic Director of Windy City Playhouse, an acclaimed non-profit theater company in Chicago, she spearheads immersive theatrical productions, co-creating hits like “Southern Gothic” and “A Recipe for Disaster” alongside celebrity chef Rick Bayless. Amy’s multifaceted contributions reflect her unwavering dedication to both business excellence and community enrichment.

In this episode, we talked to Amy about what is a distressed asset, the cautionary measures to take, the origins of these assets, how she sources the opportunities she finds, and much more.

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Distressed Assets;

01:54 Amy’s background;

04:08 What is a distressed asset;

09:42 An insight on cautionary measures to take with Amy’s approach;

19:04 The origins of these properties/assets;

24:15 How Amy sources the asset opportunities;

26:16 Round of insights

Announcement: Download a Sample Deal package here.

Round of Insights

Apparent Failure: Trying to support herself with a career as an actor.

Digital Resource:

Most Recommended Book: The Ideal Team Player.

Daily Habit: Walking to work every day.

#1 Insight for investing in distressed assets: Accepting that the market changes rapidly and one cannot withhold all the information, therefore asking for help and questions is the key to overcoming daily challenges.

Best place to grab a bite in Chicago, IL: Bloom & Planta.

Contact Amy: Website:

Thank you for joining us for another great episode! If you’re enjoying the show, please LEAVE A RATING OR REVIEW,  and be sure to hit that subscribe button so you do not miss an episode.

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