In this episode of Weiss Advice, Yonah Weiss sits down with Rey, a former U.S. military officer turned multifamily real estate investor and fund manager. Since entering the space in 2016 and retiring from the Armed Forces in 2019, Rey has helped lead acquisitions of over $150 million in multifamily assets.
Rey is the Co-Founder and Senior Managing Principal of Stressless Capital Fund, a customizable real estate investment fund focused on helping investors participate in multifamily opportunities. He is also the bestselling author of “BLUF: The Bottom Line Up Front,” a guide designed to help passive investors better understand multifamily investing.
In this conversation, Rey shares how his military training shaped his investment philosophy, why he started as a passive investor before becoming a sponsor, and the critical lessons he learned raising capital and navigating changing market conditions.
Whether you're an experienced investor or someone curious about passive real estate investing, this episode breaks down the mindset, discipline, and strategy needed to succeed in multifamily real estate.
Key Topics & Timestamps
00:00 – Introduction
Yonah welcomes Rey to the show and introduces his background in multifamily investing and military service.
01:14 – Military Beginnings
Rey shares how joining the military at 17 shaped his discipline, leadership skills, and long-term career path.
04:43 – Learning the Business Through Passive Investing
Before leading deals himself, Rey invested as a limited partner (LP) to understand multifamily syndications and how deals are structured.
06:07 – Raising Capital and Stewardship of Investors
Rey explains the responsibility that comes with managing investor capital and the importance of trust in syndications.
08:32 – Market Shifts and Interest Rate Changes
How rising interest rates changed the multifamily landscape and how experienced investors adapt to new market conditions.
38:15 – What “Passive Income” Really Means
Rey breaks down common misconceptions about passive income and how investors should think about long-term wealth building.
40:40 – Where to Connect with Rey
Rey shares how listeners can learn more about his investing approach, consulting, and his book BLUF: The Bottom Line Up Front.
Connect with Rey here:
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