#935 Multifamily in Transition: Strategies for Today's Market with Gary Lipsky episode artwork

EPISODE · Aug 18, 2025 · 29 MIN

#935 Multifamily in Transition: Strategies for Today's Market with Gary Lipsky

from Real Estate Investing for Cash Flow with Kevin Bupp

Gary Lipsky is the president of Break of Day Capital, an investment firm that specializes in multi-family real estate in Arizona. Gary brings a 20+ year track record in the real estate space and has completed more than $300M of transactions over his career. Gary is also the host of the Real Estate Investor Podcast, where he interviews industry experts to provide broad range education to investors. He is also the best-selling author of Best in Class, founder of the Asset Management Summit, and a guest speaker featured at many prominent conferences. Connect with Gary: breakofdaycapital.com  Highlights: 02:55 – How Gary's entrepreneurial roots and first house hack in Los Angeles planted the seed for a multifamily career. 04:10 – Current challenges in Arizona 06:00 – Why today's market offers opportunity 09:50 – Outsourcing property management 12:45 – Experimenting with AI for investor communications, research, marketing 19:00 – The capital raising challenge 21:10 – Advice to LPs: focus on the operator's track record and discipline   Quote: "If a deal sounds too good to be true, it probably is. Don't chase IRR or bonus depreciation—chase a good operator, and everything else will work out."   Recommended Resources: Accredited Investors, you're invited to Join the Cashflow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! If you're a high net worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, go to InvestWithKB.com for opportunities to invest in real estate projects alongside Kevin and his team.  Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast.

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#935 Multifamily in Transition: Strategies for Today's Market with Gary Lipsky

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