From Engineer to Real Estate Investor: How Harley Green Built a Life of Financial Freedom
Most people dream of escaping the 9-to-5 grind, but few actually make it happen. Harley Green did.
After spending 15 years as a software architect in the defense industry, he transitioned into full-time real estate investing, built a remote business, and now travels the world with his family.
On Engineer Your Success with Dr. James Bryant, Harley shared how he went from a corporate career to real estate entrepreneur, leveraged virtual assistants to scale, and designed a life of flexibility, freedom, and financial success.
From Engineering to Real Estate: The Turning Point
Harley’s career as a software engineer was stable and rewarding, but he knew one thing: working for someone else wasn’t the long-term plan.
💡 His first step? House hacking.
- He and his wife converted their basement into a rental unit, bringing in extra income while still living in the home.
- This low-risk strategy gave them their first taste of real estate investing.
- Soon after, they purchased a short-sale condo, kickstarting their rental property portfolio.
At first, the goal was simple: build wealth for the future. But they quickly realized that rental properties could replace their salaries—if scaled the right way.
Scaling Up: From Long-Term Rentals to Short-Term Success
Many investors start with long-term rentals, but Harley saw an opportunity in short-term rentals and Airbnb.
📍 The shift to short-term rentals came after a vacation in Myrtle Beach.
While browsing local listings, he and his wife realized the numbers made sense for Airbnb. They took the leap, purchased a two-bedroom condo, and immediately saw higher cash flow than their long-term rentals.
🚀 Why short-term rentals?
✔️ Higher monthly income compared to traditional rentals
✔️ More flexibility in pricing and guest stays
✔️ Ability to pivot based on market demand
The catch? It required more hands-on management.
That’s when Harley made a critical decision—to start outsourcing.
The Power of Delegation: How Virtual Assistants Changed Everything
Managing multiple properties, guest bookings, and maintenance became overwhelming. Instead of spending hours on admin tasks, Harley hired virtual assistants (VAs) to handle operations.
💡 How virtual assistants helped scale his business:
✅ Responding to guest inquiries and managing reservations
✅ Coordinating maintenance and cleaning teams
✅ Handling customer service and resolving issues
✅ Tracking finances and keeping records tax-ready
By outsourcing routine tasks, Harley was able to focus on growth, find new investment opportunities, and eventually transition into full-time real estate investing.
Building a Business That Runs Without You
With multiple income streams and a remote team in place, Harley and his family made a bold move in 2024:
🌍 Becoming digital nomads.
Now, they travel full-time with their three kids, spending 1-3 months in different countries while managing their business remotely.
📌 Key lessons from Harley’s journey:
✔️ Start small—your first investment doesn’t need to be huge.
✔️ Leverage outsourcing—you can’t scale if you do everything yourself.
✔️ Build systems—a business that runs without you gives you freedom.
✔️ Take action—opportunities come to those who move forward, not those who wait.
What’s Next for You?
Harley’s story proves that financial freedom isn’t just for the lucky—it’s for those who take action.
Whether you’re looking to start investing, scale a business, or free up time through delegation, the key is the same: build systems that let you focus on growth.
🎧 Want to hear the full conversation? Listen to Engineer Your Success with Dr. James Bryant on YouTube or Spotify.
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