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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:
By Kevin Bupp4.8
674674 ratings
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:

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