EP 264: What $250M of AUM Has Taught Drew Breneman About Real Estate Cycles

by | May 22, 2025

In this episode of the Gentle Art of Crushing It podcast, host Randy Smith interviews Drew Breneman, founder of Brennan, who has achieved significant success in real estate investment with a focus on multifamily properties. Drew shares insights on the current state of the real estate market, particularly contrasting the performance of the Sunbelt and Midwest regions. He discusses his early investments, the challenges faced in Phoenix, and the opportunities available in Chicago, including tax abatement strategies. The conversation emphasizes the importance of cash flow in investments and provides valuable resources for new passive investors.

Drew's Bio

-Started an internet business in high school. He saved all the money from it and acquired his first rental property at age 19 back in 2005.

-Founder of Breneman Capital

-Breneman Capital specializes in multifamily investing with a data-driven approach. The firm only invests in the best markets and submarkets within those markets. 

-Invested in a variety of geographies and asset classes: Multifamily in Madison, WI (2005-2007). Then industrial, office, and retail in Minneapolis St. Paul (2008-2012). Multifamily and mixed-use in Chicago (2013-today) before focusing on only multifamily in select submarkets in the Midwest (Chicago, Milwaukee, Madison).

-Acquired $250MM+ of investment property as key/sole GP.

-24%+ average realized IRR on investments sold

-14 deals have executed full cash-out refinances of all our initial equity

-Host of the Breneman Blueprint podcast

-Started out with a duplex and have worked my way up to $30MM+ deals.  All self-made starting from scratch – my parents are public school teachers, so didn't start with any capital of theirs or connections.

Breneman Capital: https://www.breneman.com/

Podcast: https://www.breneman.com/podcast

LinkedIn: https://www.linkedin.com/in/drewbreneman/

Chapters

[00:00] Market Overview and Current Trends

[05:09] Drew's Journey into Real Estate

[11:24] Exploring the Sunbelt and Its Opportunities

[16:04] Performance of Phoenix Assets and Future Outlook

[21:39] Chicago Projects and Tax Abatement Opportunities

[22:01] Chicago's Real Estate Appeal

[24:04] Investment Strategies in Chicago

[27:58] Understanding Cash Flow vs. Equity Multiples

[31:49] Educational Resources for New Investors

[35:26] Personal Insights and Future Aspirations

[37:53] outro 

RANDY SMITH

Connect with our host, Randy Smith, for more educational content or to discuss investment opportunities in the real estate syndication space at http://www.impactequity.nethttps://www.linkedin.com/in/randallsmith or on Instagram at @randysmithinvestor

Keywords

real estate, multifamily, investment strategies, passive investing, market analysis, tax abatement, cash flow, Chicago, Phoenix, Drew Breneman

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