In this episode of the Big Mike Fund Podcast, host Mike Zlotnik sits down with Harvard-trained physician Dr. Jordan Romano to discuss his unique, hyper-local real estate investing thesis. While maintaining an active medical practice at Tufts Medical Center in Boston, Dr. Romano has spent over a decade quietly dominating a single, rural New England market by focus-targeting workforce housing.
Dr. Romano pulls back the curtain on how he identifies hidden value in properties that larger conglomerates overlook. He shares tactical insights on bypassing the volatile short-term rental market, navigating strict municipal zoning boards, and his exact blueprint for executing a highly profitable land subdivision play that essentially netted him a piece of downtown land for free.
What you will learn in this episode:
The Resident-to-Attending Pivot: How to successfully move capital out of restrictive academic retirement accounts and into physical, tangible assets via self-directed vehicles.
The Hyper-Local Advantage: Why deep geographic expertise in a single town outpaces trying to analyze macro-level national markets.
Zoning & Value-Add Playbook: The mechanics of converting single-family spaces into multi-family configurations, adding garage units, and working within Class B/C properties.
The Land Subdivision Framework: Step-by-step strategy for acquiring an oversized lot, renting the primary house to break even during approvals, and selling the structure while holding the remaining acreage with zero cost-basis.
AI Utility Auditing: How uploading property bills into AI engines can uncover immediate water mitigation and portfolio cost-saving strategies.
The Investor’s Mindset: Why playing the long game with active tenant screening and high-precision execution eliminates portfolio “cracks in the foundation”.
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Timestamps
0:00 – Welcome to the Big Mike Fund Podcast & Guest Intro
0:52 – Dr. Romano’s “Chapters”: Balancing Medicine at Tufts with Real Estate
1:50 – Transitioning Capital: Moving Academic Retirement Funds to Self-Directed Assets
2:36 – The Hyper-Local Thesis: Targeting Small Multi-Families in New Hampshire
3:59 – The Safety of Class B Workforce Housing (Nurses, Firefighters & Resident Docs)
5:40 – Navigating Coastal Markets, Capital Improvements, and Interest Rate Shifts
6:53 – Value-Add Execution: Splitting Layouts & Keeping Construction Pricing Fair
8:12 – The “Free Land” Strategy: How to Execute a Smart Downtown Subdivision
9:58 – NIMBYism Barriers & Why Dr. Romano Completely Avoided the Airbnb Trap
11:52 – Managing Expense Inefficiencies: Using AI to Audit & Mitigate Portfolio Water Bills
13:18 – The Long Game: Portfolio Foundations vs. High-Volume Scaling Pitfalls
14:58 – Channeling Sam Zell & Stan Druckenmiller: “Show Me the Deal” & Watching One Basket
19:09 – What’s the Endgame? Playing the Active Game vs. Retiring to a Beach
21:20 – Why Keeping Fiduciary Control Means Avoiding Unnecessary Partnerships
23:26 – Staying Grounded: Lessons from a Single Mother & Making a Local Impact
26:53 – Advanced Risk Reading: Top 3 Book Recommendations from Dr. Romano
28:26 – Outro & How to Book a Call with Dr. Romano
Connect with the Guest:
Connect with Dr. Romano:
Website: https://www.medicalexpertwitness.com/
Linkedin: 💼 https://www.linkedin.com/in/j-jordan-romano-5598144/
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LinkedIn: 💼 https://tempofunding.com/linkedin
Instagram: 📸 https://www.instagram.com/tempofunding
Email: 📧 mailto:invest@tempofunding.com
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