Episode Description
(Watch the YouTube video of this episode here)
We've done 22 real estate deals since 2009. Rentals, flips, a syndication, land, storage units, co-living, a mobile home, and even a ground-up build. This episode, we ranked them all. Not just by returns. By what we'd actually do again.
We walk through every deal on the list: what we paid, what we learned, what went sideways, and what we'd change. The top deals share a pattern: they had great numbers AND something novel or interesting about the structure. The bottom deals? Either the money wasn't there, or operating them was just genuinely painful.
A few highlights: Deal #1 has generated a 141% return, and we haven't even sold it yet. Deal #22 was purchased for $1 and lost $13,500. Our primary home made the list at #9. And there's a mobile home story you'll want to hear.
Key Moments
- (00:00) Introduction
- (02:45) #1: Lyon Apartments (141% Return and Still Holding)
- (03:00) #2: Baker Tower (Syndication, Mixed-Use, Downtown Albany)
- (04:30) #3: Columbus Duplex (The Very First Deal)
- (05:30) #4: First Avenue Duplex
- (07:30) #5 & #6: Sunnyside Properties (Where the "Smell of Money" Paid Off)
- (09:00) #7: The Warehouses (First 1031 Exchange)
- (10:50) #8: 14th Street Co-Living House (15 Bedrooms, Hard Money)
- (11:30) #9: Our Primary Home Makes the List
- (13:10) #10: Land Flip in Indiana (Never Even Visited the Property)
- (15:30) #11 & #12: Two More Singles
- (18:30) #13: 11th Street Lebanon (First Full Flip, 10 Months, $100K in Repairs)
- (20:20) #14: James Storage Works (Storage + Apartment + Warehouse)
- (22:00) #15: Jackson Street Duplex (7 Years of Zero Maintenance)
- (25:00) #16 & #17: More Mid-Pack Deals Reviewed
- (27:50) #18: Verta Crossing Syndication (Passive Investment, Mixed Experience)
- (31:10) #19: Philomath Retail Building (Break-Even, Required Purchase)
- (32:30) #20: Sunnyside Land (Plans Fell Through, Now Selling)
- (33:20) #21: Thornton Lake Lot Split (Good for Investors, Painful for Us)
- (35:40) #22: The Mobile Home (Bought for $1, Lost $13,500)
- (37:30) Recap: What the Best and Worst Deals Have in Common
5 Key Lessons
- The deals you'd do again aren't always the highest-returning ones: James ranked by "awesomeness" — a mix of returns, novelty, and experience — which produced a different list than pure ROI would.
- Buying something for $1 doesn't mean it's free: The mobile home was acquired for a dollar and lost $13,500. The price paid at acquisition is almost irrelevant compared to what you spend after.
- Holding vacant land is a slow drain: Plans fall through. Opportunity cost accumulates. Sometimes the right move is just selling the land and redeploying the capital.
- The first deal is worth more than its returns: Columbus duplex sold for nearly double its purchase price after 12 years. But its real value was that it started everything else.
- The ranking exercise is useful even when it's uncomfortable: Forcing a bottom-to-top rank of your own portfolio reveals your real preferences, tolerances, and blind spots — things IRR spreadsheets can't show.
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Disclaimer
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