Why Veterans Are Made for Real Estate (And No One Tells Them)
Thu Feb 05 2026
Guests: Trey Stone & Ian Stapleton
Hosts: Markian Sich & Eric Upchurch
Real estate investor Trey Stone and digital entrepreneur Ian Stapleton reveal how they built massive wealth through multifamily investing, why veterans are uniquely suited for real estate, and how “unpopular” properties can become the safest and most profitable assets when operated correctly.
From turning around D-class neighborhoods to raising capital ethically, navigating risk, and building elite partnerships, this conversation goes far beyond typical real estate advice. It’s a raw, tactical breakdown of how wealth is actually built—through focus, courage, and execution.
Trey Stone is a veteran multifamily operator with 21+ exits and thousands of units, known for revitalizing distressed communities and creating forced appreciation at scale.
Ian Stapleton is a former Air Force officer turned entrepreneur who built a 25M+ subscriber digital media empire, now investing and partnering in large real estate deals.
They explain:
Why buying “nice” properties is often riskier than distressed assets How forced appreciation creates true downside protection Why veterans outperform in real estate investing How to vet partners—and why most people do it wrong The real role of risk, fear, and “being a little crazy” in success How real estate can transform entire neighborhoods, not just returns Why tax benefits exist—and what most investors misunderstand about them How focus beats diversification in every phase of businessChapters:
00:00 Intro
03:12 Ian’s path from the military to entrepreneurship
08:41 Why social media success wasn’t enough
12:56 How Trey and Ian partnered—and what made it work
18:44 Why most partnerships fail
24:31 The power of adding value before asking for anything
31:05 From single-family to multifamily at scale
38:22 The truth about D-class properties and neighborhoods
46:10 How forced appreciation really works
54:03 Why veterans thrive in real estate
01:01:44 Risk, fear, and making bold decisions
01:09:32 Tax benefits explained without hype
01:18:06 Focus vs diversification in investing
01:26:40 Lessons from 20+ exits and decades in real estate
01:35:12 Final advice for investors starting today
Connect with Trey & Ian
Want to learn more about Trey and Ian’s work or explore what they’re building? Connect with them here: TrackrecordassetsTrack Record Assets
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About Active Duty Passive Income (ADPI):
ADPI helps military members and veterans build wealth through real estate investing, education, and community—so they can achieve financial freedom after service.
👉 Subscribe for more conversations on real estate, investing, and life after the military.
Support the show
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Guests: Trey Stone & Ian Stapleton Hosts: Markian Sich & Eric Upchurch Real estate investor Trey Stone and digital entrepreneur Ian Stapleton reveal how they built massive wealth through multifamily investing, why veterans are uniquely suited for real estate, and how “unpopular” properties can become the safest and most profitable assets when operated correctly. From turning around D-class neighborhoods to raising capital ethically, navigating risk, and building elite partnerships, this conversation goes far beyond typical real estate advice. It’s a raw, tactical breakdown of how wealth is actually built—through focus, courage, and execution. Trey Stone is a veteran multifamily operator with 21+ exits and thousands of units, known for revitalizing distressed communities and creating forced appreciation at scale. Ian Stapleton is a former Air Force officer turned entrepreneur who built a 25M+ subscriber digital media empire, now investing and partnering in large real estate deals. They explain: Why buying “nice” properties is often riskier than distressed assets How forced appreciation creates true downside protection Why veterans outperform in real estate investing How to vet partners—and why most people do it wrong The real role of risk, fear, and “being a little crazy” in success How real estate can transform entire neighborhoods, not just returns Why tax benefits exist—and what most investors misunderstand about them How focus beats diversification in every phase of businessChapters: 00:00 Intro 03:12 Ian’s path from the military to entrepreneurship 08:41 Why social media success wasn’t enough 12:56 How Trey and Ian partnered—and what made it work 18:44 Why most partnerships fail 24:31 The power of adding value before asking for anything 31:05 From single-family to multifamily at scale 38:22 The truth about D-class properties and neighborhoods 46:10 How forced appreciation really works 54:03 Why veterans thrive in real estate 01:01:44 Risk, fear, and making bold decisions 01:09:32 Tax benefits explained without hype 01:18:06 Focus vs diversification in investing 01:26:40 Lessons from 20+ exits and decades in real estate 01:35:12 Final advice for investors starting today Connect with Trey & Ian Want to learn more about Trey and Ian’s work or explore what they’re building? Connect with them here: TrackrecordassetsTrack Record Assets Subscribe & Share About Active Duty Passive Income (ADPI): ADPI helps military members and veterans build wealth through real estate investing, education, and community—so they can achieve financial freedom after service. 👉 Subscribe for more conversations on real estate, investing, and life after the military. Support the show