Starting a family office sounds like something reserved for billionaires, but the truth is the “family office mindset” kicks in way earlier than most people realize. If you are sitting on a meaningful liquidity event, a paid off asset, or even a few million in deployable cash, you are already in the zone where strategy matters more than hustle. The problem is most investors hit that point and keep buying deals the same way they always have, reactive, scattered, and without a real portfolio blueprint. That is how wealth gets built, and quietly leaks.
What separates families who compound for generations from those who stall out is not access to deals. It is structure. How you hold assets, how you protect them, how you finance them, and how you balance stability with upside. The goal is not just to grow your net worth. It is to build a machine that preserves it, produces cash flow, and stays aligned with what your family actually wants long term.
In today’s breakdown, we cover:
• How family offices really structure ownership and liability
• The portfolio mix that keeps cash flow steady while still creating growth
• Why single tenant net lease can act like “bonds” inside your CRE strategy
• How to think about debt relationships, 1031 timing, and long term holds
If you are serious about turning a strong balance sheet into lasting generational wealth, this is where the game changes.
Let’s dive in.
Sponsored by www.CRECentral.com
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Starting a family office sounds like something reserved for billionaires, but the truth is the “family office mindset” kicks in way earlier than most people realize. If you are sitting on a meaningful liquidity event, a paid off asset, or even a few million in deployable cash, you are already in the zone where strategy matters more than hustle. The problem is most investors hit that point and keep buying deals the same way they always have, reactive, scattered, and without a real portfolio blueprint. That is how wealth gets built, and quietly leaks.
What separates families who compound for generations from those who stall out is not access to deals. It is structure. How you hold assets, how you protect them, how you finance them, and how you balance stability with upside. The goal is not just to grow your net worth. It is to build a machine that preserves it, produces cash flow, and stays aligned with what your family actually wants long term.
In today’s breakdown, we cover:
• How family offices really structure ownership and liability
• The portfolio mix that keeps cash flow steady while still creating growth
• Why single tenant net lease can act like “bonds” inside your CRE strategy
• How to think about debt relationships, 1031 timing, and long term holds
If you are serious about turning a strong balance sheet into lasting generational wealth, this is where the game changes.
Let’s dive in.
Sponsored by www.CRECentral.com
340. This 34-Year Old Built $500M of Real Estate - Here's How
The Commercial Real Estate Investor Podcast
40 minutes 7 seconds
1 month ago
340. This 34-Year Old Built $500M of Real Estate - Here's How
Most people think real estate is all about luxury condos and chasing the biggest margins. But what if you could build a portfolio that actually makes a difference—while still making a solid return?
In this episode, I sit down with Evan Holladay, founder of Holladay Ventures, who has already developed over $500 million in affordable and workforce housing across the Southeast. His mission? To create 100,000+ units of housing that teachers, nurses, and service workers can actually afford.
We cover:
How Evan got started in real estate after nearly becoming a doctor
The first deals that gave him confidence (and the ones that almost fell apart)
The biggest lesson he’s learned about picking partners and capital sources
Behind the scenes of Stonebridge Lofts—a 311-unit Nashville project backed by Amazon’s $2B housing fund
Why affordable housing isn’t what you think (and why families making up to $80K qualify in Nashville)
How to structure deals that balance mission and margin without sacrificing returns
Whether you’re a developer, investor, or just curious about how real estate can be a force for good, this conversation will change how you think about building wealth and building communities.
Sponsored by www.CRECentral.com
The Commercial Real Estate Investor Podcast
Starting a family office sounds like something reserved for billionaires, but the truth is the “family office mindset” kicks in way earlier than most people realize. If you are sitting on a meaningful liquidity event, a paid off asset, or even a few million in deployable cash, you are already in the zone where strategy matters more than hustle. The problem is most investors hit that point and keep buying deals the same way they always have, reactive, scattered, and without a real portfolio blueprint. That is how wealth gets built, and quietly leaks.
What separates families who compound for generations from those who stall out is not access to deals. It is structure. How you hold assets, how you protect them, how you finance them, and how you balance stability with upside. The goal is not just to grow your net worth. It is to build a machine that preserves it, produces cash flow, and stays aligned with what your family actually wants long term.
In today’s breakdown, we cover:
• How family offices really structure ownership and liability
• The portfolio mix that keeps cash flow steady while still creating growth
• Why single tenant net lease can act like “bonds” inside your CRE strategy
• How to think about debt relationships, 1031 timing, and long term holds
If you are serious about turning a strong balance sheet into lasting generational wealth, this is where the game changes.
Let’s dive in.
Sponsored by www.CRECentral.com
