He Lives Overseas, But His 3 Rentals Cash Flow While He Sleeps
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Dave, a U.S. diplomat stationed in Vienna, Austria, shares his journey from accidental landlord to building a multi-property real estate portfolio while managing investments remotely from overseas postings. Starting with a 440-square-foot co-op in New York City in 2005—purchased during law school with $125,000 in debt—Dave was forced to navigate ownership after being deployed abroad. He creatively solved the occupancy rule by having his sister move in, turning the property into a rental after five years. Despite a 12-year hiatus, he reignited his investing journey in 2017 after discovering BiggerPockets, which helped him overcome analysis paralysis. He then strategically acquired turnkey properties in Jacksonville, Florida, and Colorado Springs—markets he analyzed using diplomatic-style frameworks focused on long-term 'climate' trends like military presence, millennial migration, and Fortune 1000 company locations rather than short-term 'weather' data. His remote investing playbook emphasizes relationship-building with property managers, conservative financial modeling, and using a defined decision threshold to avoid over-analysis. Today, he manages three properties from Vienna, with a goal to grow to five or six properties before retiring from the State Department, seeking financial freedom through passive income and a stable 'forever home' for his family. The episode delivers actionable insights for long-distance investors, emphasizing the power of turnkey providers, the importance of vetting property managers through direct human contact, and the psychological shift from seeking comfort to building confidence in decisions. Dave’s story underscores that real estate investing is accessible even when you can’t physically visit markets, as long as you focus on sustainable systems, data-driven frameworks, and strategic partnerships. His experience proves that remote investing isn’t about perfection—it’s about consistency, relationship capital, and knowing when enough is enough.
Use 'climate' over 'weather' thinking: Focus on long-term trends (military presence, population growth, corporate HQs) rather than short-term market fluctuations.
Turnkey investments can be a strategic fit for remote investors—especially those with family or career constraints—when paired with strong due diligence.
Build human relationships with property managers and vendors; direct communication beats algorithmic platforms for trust and clarity.
Define your decision threshold: Stop gathering data when you have enough to make a confident call—don’t let analysis paralysis stall action.
Financial freedom for remote investors isn’t just about cash flow—it’s about stability, family continuity, and the ability to choose your next chapter.
The Accidental Landlord: From Law School Debt to a New York Co-op
“I was lucky because maybe this was a sort of foreshadowing to the skills I would learn as a diplomat, but I developed a very good relationship with the building management company.”
The 12-Year Pause: How BiggerPockets Ignited a Second Act
After a 12-year gap, Dave rediscovered BiggerPockets in 2011–2012, which helped him overcome analysis paralysis and develop a framework for remote investing based on long-term market trends.
The Remote Investor’s Playbook: Weather vs. Climate
“I think one of the ways you can think about it is trying to look at the climate rather than the weather, right? The weather is a daily occurrence. It's a snapshot in the now, whereas the climate is about certain trends...”
Turnkey Success: Jacksonville and Colorado Springs
“I'm very risk averse. So I'm rounding down a lot on the income. I'm rounding up a lot on the cost and I'm just making sure that that at least kind of hits that delta that I need.”
The Human Edge: Why Relationships Trump Algorithms
“Human to human relationships is still critical, I think, to being able to make judgment calls and make good decisions.”
“If you're doing anything of substance, anything that's new, anything that's pushing you outside of your normal boundaries... it is physically impossible to be doing something new... while also being comfortable.”
“I think one of the ways you can think about it is trying to look at the climate rather than the weather, right? The weather is a daily occurrence. It's a snapshot in the now, whereas the climate is about certain trends, certain data, certain pieces of information that while...”
“I would love to stop that. Not the public speaking. I enjoy that. But the moving for my kids' sake, they're now 12, 11 and 7. So they've had to leave friends and it does now.”
Hosts
Guest
BiggerPockets
organization
Dave
person
Co-op
other
Ashley Kerr
person
Colorado Springs, Colorado
place
Tony J. Robinson
person
Jacksonville, Florida
place
U.S. State Department
organization
Vienna, Austria
place
Fountain, Colorado
place
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