I spoke with Amy Rubenstein, CEO of Clear Investment Group, about how she built a thriving real estate platform by focusing on one of the most overlooked areas of the market: distressed C-class multifamily housing.

Amy didn’t come from institutional real estate — she taught herself everything from Excel to underwriting by reverse-engineering models, and built a company that now serves both high-net-worth and institutional LPs. Today, her firm consistently delivers 30%+ IRRs by stabilizing mismanaged assets and restoring them to market performance.

We talk about her journey from buying a single six-unit property to leading a vertically integrated investment platform, her thoughts on risk and inflation, why C-class housing remains resilient, and how she thinks about scaling her team and her impact.

Guest Bio:

Amy Rubenstein is the CEO and co-founder of Clear Investment Group, a real estate investment firm focused on distressed, workforce multifamily housing across the U.S. Under her leadership, Clear has grown from small syndicated deals to managing institutional capital and generating 37%+ average IRRs. She has over two decades of experience in real estate investing, is a self-taught operator, and remains deeply involved in every aspect of the firm’s strategy and execution.

Stay Connected:

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David Weisburd: @dweisburd

David Weisburd: https://www.linkedin.com/in/dweisburd/

Amy Rubenstein: https://www.linkedin.com/in/amy-rubenstein-a0514698/

Clear Investment Group: https://www.linkedin.com/company/clear-investment-group/posts/?feedView=all

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(0:00) Episode preview

(1:24) Management and tenant issues in distressed properties

(3:02) Amy Rubenstein's industry beginnings and real estate asset performance

(5:26) Forecasting interest rates and market conditions

(7:59) Interactions with LP base and institutional investors

(11:11) Institutional interest and tax benefits in C class real estate

(14:07) Essentials of being a successful GP

(17:09) Team management and the role of humility

(21:22) Delegation, high achievers, and trust

(24:19) Growth strategy and future business outlook

(26:07) Multifamily real estate and market volatility

(29:13) Investment lessons and self-taught skills

(33:06) Impact investing and ESG perspectives

(35:24) Closing remarks